Reorienting Pliancy’s Brand Identity

Brands are always evolving—and Pliancy is no stranger to reinvention. We look back on our brand update, six months later.

Kyle Barber

Creative Lead

If I asked you to dress exclusively in your wardrobe from 10 years ago, how would you feel? Would the clothes fit you well? Would they match your current style, size, habits, or environment? Would they make you feel your best?

Like the clothes we wear, brands are a reflection of identity. They are always evolving—and Pliancy is no stranger to reinvention.

We got our start in 2008 as TSG, an accurate but plain initialism that stood for “Technology Strategy Group.” In 2017, we underwent a full rebrand to Pliancy, with an aesthetic and verbal identity that more clearly reflected our relationship-focused, tech-forward approach to IT. In June 2023, we brought our third iteration to life with a redesigned website, expanded palette, updated logo, and more.

From an outside perspective, a new website and a brand refresh can seem like a single event: one day, and everything changes. In reality, it’s a months-long process that both starts long before and extends far beyond launch day.

Business & Brand Growing Together

“Is rebranding really necessary?” you might ask. A brand is a point-in-time expression of a business: its philosophy, its history, its trajectory, and more. Some of those facets will stay the same; many of them will change over time.

Compared to 2017, Pliancy is a drastically different company. Our headcount has increased by leaps and bounds, our service offerings have expanded, and we now serve clients across the country. We were also operating in a rapidly changing IT landscape. Five or ten years ago, just having a cool brand presence was enough to set you apart, but we needed something more. It was time for our branding to reflect the size, scope, and capabilities of Pliancy as it exists today.

People-Informed Design

We didn’t wake up one morning and throw everything out the window, of course. Like any major project, we began with an internal audit. I interviewed key stakeholders to get their insights on how our brand impacted their roles and professional relationships—but I also met with anyone else who would volunteer, no matter where their position or tenure. If we claim to be a people-centric organization, then that has to be the bedrock of everything we do. An expression of our company’s identity can’t be driven solely by leadership alone. It belongs to all of us.

Conversations with colleagues from all corners of the company gave me a full-spectrum understanding of how people saw our brand, their favorite and least favorite elements, content wishlists, and other observations. Everyone had drastically different ideas of what our refreshed brand and website should encompass, shaped by their individual responsibilities and relationships.

I ended up with multiple massive spreadsheets of comments describing what people wanted the brand to be or do. We couldn’t implement everything (and not just because some opinions were completely at odds with others), but that feedback shaped the first iteration of the website’s new architecture. It directed our conversations about what we needed the updated branding to accomplish and helped us keep all perspectives in mind.

Pliancy, Unbounded

To design our next evolution, we partnered with Overline, who has walked with us through many phases of Pliancy from our early growth to now. (Read more about our collaboration.) 

An early and obvious goal was to maintain continuity with our existing elements and language. We didn’t want to abandon everything that had gotten us to where we were. Not only would that alienate clients and colleagues, but it would also render our old assets completely useless.

Digital assets tend to persevere—for better or for worse. We wanted to make sure that if you saw an old Pliancy deck from four years ago, it would still be recognizable as the same brand.

We call our logo the Occam, a tribute to Occam’s razor, to represent our pursuit of the simplest, most elegant solutions. That concept is a core part of Pliancy’s DNA, therefore we knew the idea of the Occam wouldn’t change, nor would we depart from our signature purple.

To reflect our relentless pursuit of less—less complexity, less obfuscation—we eliminated the border around our mark for a cleaner aesthetic and a more powerful impact at small sizes. Like the next evolution of Pliancy, the new Occam is free and unbounded, embodying the dynamism of our future trajectory. We also enriched the purple color to make it more dynamic, a change we carried throughout our expanded, updated palette.

This was a step-up evolution, not a drastic change. We weren’t trying to change the direction of the company or distance ourselves from an earlier version of Pliancy. Our brand evolution simply needed to match the evolution of our business. In tandem, our website needed to move from ambiguity to clarity.

It has been years since we were a Palo Alto-based company with a single-digit headcount. But if you visited our website in May 2023 and were greeted with a photo of the Golden Gate Bridge—one that hadn’t changed since 2017—you might think we serve Bay Area clients only. At the same time, the language around our services was cryptic and obfuscated what clients could expect day-to-day.

Pliancy now has six offices in four states, serving clients from coast to coast. To unhook ourselves geographically, we introduced intricate 3D renderings from artist Bryan Barger, adding dimension, motion, and wonder to our assets without referencing specific regions.

These striking visuals encapsulate the transformative magic of Pliancy’s tech-enabled professional services. We highlight transparency with glass & light textures; automation and iteration with repeated movement; and knowledge with an internally lit core to represent the way that our knowledge powers everything we do. Paired with transparent explanations of our services and approach, the new site and related assets now possess a more straightforward expression of Pliancy’s offerings and ethos.

Brand Beyond Launch Day

Any brand adjustment, whether it’s a full identity change or a refresh, has three phases: planning, design, and rollout. Our third phase began with our website launch, the biggest (and most public) part of the rebrand—but that was only the beginning.

Our initial audit outlined a list of about 20 assets that would need to be updated: email signatures, deck templates, social media, the usual. While we knew the list wouldn’t be exhaustive, we thought we’d be close. In practice, the real scope dwarfed our initial list.

Think about all the places your logo appears: throughout your intranet, in your HRIS platform, as part of your Slack theme, on your two-factor authentication screens, in your training modules, on company Zoom backgrounds… Six months later, we’re still finding places to update.

Why do small updates matter? If updating a brand is updating your wardrobe, these details are akin to your accessories. Belts, socks, hats, bags, pins, and patches—these are the difference between wearing an outfit and styling one. It may feel like an endless (and thankless) task, but every instance contributes to brand cohesiveness and brand strength.

Brand as Culture, Culture as Brand

The silver lining to making a million minor updates: it’s a team effort. We didn’t have to hunt down every instance for ourselves; in many cases, it came to us. In the course of their work, colleagues across the org found things we’d missed and made the effort to flag them, reflecting the signature Pliancy drive to make things better, in ways large and small.

Pliancy is unique in the way that everyone (or almost everyone) actually cares about or has interest in our brand. Everyone knows that we use it to put our best foot forward from the beginning. It’s a big part of our culture. We don’t send out messy pitches or ugly proposals. We don’t just plaster our logo on a 5¢ ballpoint pen and call it swag. When it comes to brand, we don’t phone it in.

Your company might also have an environment where brand resonates—or maybe not. If you’re finding it’s an uphill battle, here are a few strategies that work for Pliancy.

Brand Context & Education

To maximize buy-in and familiarity, branding should be part of the conversation from the start. During their first two weeks, new Pliancy employees attend multiple onboarding meetings to teach them about the company. We dedicate an entire meeting to our brand history, its role, and why it’s important, sharing our thought process and intent.

Internal Consistency

Employees should be able to recognize their company’s branding immediately. To do that, they need to see it consistently. We brand as much employee communication as possible: all hands meetings, slide decks, internal event flyers, employee handbooks—just to name a few. It’s not a low-lift endeavor, but it’s an investment we make in order to equip team members to act as brand stewards. If they can identify our brand right away, it means they’re more likely to notice when something is off-brand.

No Task Too Small

For the group in charge of branding—whether that’s your Creative department, your Design squad, your Communications team, or your Marketing arm—no task should be too small. As the primary person responsible for visual branding updates, I’m not above any little thing. If I have to sit and swap logos in 50 different places, I consider that a good use of my time. I want to show my colleagues that branding work matters to me. And not only does it matter to me, but it matters so much to me that I want it to matter to them, too.

Change & More Change

At Pliancy, branding is about more than just looking good (though we like when things look good, too). It’s a way for us to express who we are, how we work, and what we value.

We know this won’t be the last iteration of Pliancy. Change is the only constant, after all. So no matter how we change, we’ll be prepared to meet our future selves wherever we’ll be: with a new shape, a new size, a new color—whatever we need.

Stepping Stones or Stumbling Blocks: IT Certifications & Your Knowledge Journey

When it comes to proving your IT mastery, there’s no silver bullet—but certifications still have a purpose.

Nicholas Thomas

Infrastructure Projects Manager

Like the choice of Google Workspace versus Microsoft365 or the debate of how a VLAN differs from a subnet, IT certifications are divisive. For some, they’re a hard-earned symbol of new knowledge. For others, they’re the bare minimum to be a hirable candidate. For still others, they’re merit badges, obtained just for show.

There’s no shortage of online discourse about certs: “Do IT certifications matter” returns 99 million Google search results. “Are IT certifications important”: 374 million results. “IT certifications benefits”: 353 million results. “IT certifications cons”: 868 million results.

My stance? IT certifications are not the be-all, end-all way for a person to prove their knowledge or advance their career. But just as one should use the right tool for the right job, IT certs have a valuable place in the industry as a launchpad for early professionals. 

What Are IT Certifications?

If you’re reading a blog post on an IT company’s website, you probably already know what a certification is (and you probably have a couple, too). For those who don’t, IT certifications are credentials awarded to individuals who have demonstrated their knowledge of a particular aspect of technology, typically by passing an exam. 

Certifications from vendor-neutral organizations cover universal foundations and fundamentals that aren’t restricted by product or platform. For those exams, it doesn’t matter how Amazon or Google or Microsoft does something; individuals need to know the underlying principles behind the technology.

These vendor-neutral certifications give you an opportunity to see what companies across the field do, their strengths, and their weaknesses. This helps you keep a pulse on industry leaders and challengers, which is key information for an IT consultant looking to keep their clients on the bleeding edge.

Vendor-specific certifications validate knowledge within particular products, often diving deeper into step-by-step processes versus methodology or approach. Vendor-specific certifications aren’t just limited to big names like Cisco and Microsoft.

More and more companies have begun offering specific certifications for their products, which has flooded the certification “market,” to some extent. For some organizations, vendor-specific certifications are a requirement to be able to sell or work on a product/service and inspire folks to continue their learning journey. Of course, this is a double-edged sword and can lead to gamification or other divisive means. (We’ll come back to that.)

Certifications As My IT Stepping Stones

My learning journey in this field included a course of study in computer science, but my industry experience would be refined with certifications. I started small with CompTIA’s A+ exam pathway. I read the book, took a practice test, and saw that this applied field of support and critical thinking was definitely the right choice for me to pursue.

I’m also a goal-motivated person, so the looming exams kept me attentive and engaged. They expanded my knowledge and helped me see how vast the world of IT, with its many specializations, could be.

For me, these certifications functioned the way they were intended: they attested to a baseline level of knowledge in a particular topic or product. They got me noticed, and they got me in the door. But once I was there, I saw a darker side of things.

Playing the Certification Game

I interned and eventually began working full-time at a traditional MSP (managed services provider) where getting a raise meant you had to obtain a new certification. Many factors can impact compensation and career advancement, and earning an industry certification is a valid consideration.

But at this organization, it was the only consideration—above job performance, billables, and operational efficiency. (Thankfully Pliancy doesn’t operate this way, but I would come to find that this mindset isn’t uncommon among MSPs.)

Employees adjusted their behavior accordingly. I’m sure some genuinely sought and absorbed new information, but many gamified the certification process, ignoring calls and tickets in favor of cramming exam materials. The knowledge itself didn’t matter; the exams were merely means to an end.

Some people became excellent test-takers who could parrot knowledge, but the problem started when they were given tasks and tickets to handle that should have been within their skill set… at least according to their credentials.

One particular memory stands out to me: I received a call from an overnight technician with several Microsoft certifications, Exchange being one of them. He told me that the Spam Filter was spooling emails and that the Exchange database was dismounted.

Naturally, to avoid suggesting something he’d already tried, I asked what he had done so far to diagnose or resolve the problem. He said his first step had been to call me.

It was immediately apparent that he didn’t have a great sense of how to troubleshoot Exchange, regardless of what the certifications implied.

The takeaway: certifications are not necessarily the best (and certainly not the only) way to sift out who’s experienced and who’s not.

Inside the Exam-Creation Machine

There’s no magic way to weed out professional test-takers from those with practical skills. Every test is different, and they change over time, but there is one that I can speak to from personal experience.

Earlier this year, I was invited by CompTIA (Computing Technology Industry Association, the largest vendor-neutral credentialing program for technology workers) to contribute to the next iteration of the Cloud+ certification exam. Over three days at their global headquarters outside of Chicago, Illinois, our motley group of SMEs—from Google, Amazon, Microsoft, Backblaze, and more—was trained in CompTIA’s exam writing methodology and learned the test’s objectives before getting to work creating questions.

Our goal was to create material that was applicable across any cloud environment and rooted in practical experience, not rote memorization.

I’m grateful to have been part of the chorus giving the test a dose of reality; to say, here’s what I experience in my work, here’s what people will likely encounter, and here’s how you could test those scenarios.

Writing and reviewing material was a collaborative process. Like a writer’s workshop, we would unpack why a question was a good test of knowledge or why another didn’t meet the test guidelines. It was our responsibility to put current, applicable questions forth. (We’ve all taken outdated tests that have made us shake our heads and think, ‘What year is this from?’) The experience hammered home that technology is ever-evolving and ever-changing—so technology exams must, too.

Certification Commodification

Certifications are changing, but not always for the better. As certifications have proliferated, they’ve become increasingly commoditized. What’s to differentiate one from another—except that maybe you got one for a steal on Black Friday? (Yes, there are Black Friday sales for certification courses.)

There are also free certifications, but you know what they say: if something is free, you’re the product. Displaying a badge from a lesser-known platform on your resume, on your LinkedIn profile, or in your email signature is free marketing. In cases like these, it’s in a company’s best interest to award certificates to as many people as possible.

All of this begs the question: What is the true value of an industry certification?

One Size Fits… Some

Examining certifications in a vacuum—trying to paint them as inherently good, bad, useful, or useless for everyone—misses the point. Instead, we should consider what people are trying to achieve and whether industry certifications can meet that need.

✅ Jump-Starting Your IT Journey

As a new professional or a career changer, hands-on experience isn’t always possible. Pursuing certifications can demonstrate your performance against an established standard. Instead of just saying you’ve “always been good with technology,” passing scores on foundational exams can substantiate those claims—to an extent.

✅ Exploring New Concepts

Studying for an exam is a convenient way to discover whether you have an affinity for a specific topic. If you’re part of a small team or at a siloed company, studying for exams and/or creating an experimental lab environment of your own might be the only way for you to gain exposure to the more specialized or advanced facets of IT.

🟨 Advancing Your Career

At a company where certifications are the only way forward, you may have no choice but to play the game, get the badges, and check the boxes. But speaking broadly, certifications are not a silver bullet for compensation and career progression. Mid-career professionals and beyond can demonstrate their skills and knowledge through real-world experience, portfolio work, and other concrete projects, rather than solely through certifications. Certs become a factor, but not the factor. 

❌ Proving Technical Mastery

From my CompTIA experience and in my personal philosophy, passing an exam is not automatic proof of being an expert. Our north star for test material was, “Would someone with 2 to 3 years’ experience know how to handle this?” Certifications show proficiency, not mastery. It’s equally important to note that someone can possess mastery of a skill but not have an associated certification, the same way not everyone needs a college degree to succeed.

IT Certifications & You

And so, reader, where does this leave you? There’s no cut-and-dry answer—but maybe you saw that coming. For better or for worse, it depends on who you are and what you want to accomplish.

Industry certifications are a tool. Tools help you build, but they don’t tell you what to build—or how, why, or when. You’re wielding the tool. You get to decide.

Keep Reading

Making Equity a Reality: A Brief Primer

Curious about offering employee equity, but not sure where to start? This primer offers a bird’s-eye view.

Michelle Bakula

VP of Finance

No matter how young or old your company is, creating an employee option pool is a major undertaking. Employee equity will look different at every company, and the structure of your equity plan may change over time.

Looking to grant equity options to your team? Most people mentally file equity under “Finance,” but it’s largely a legal process involving copious paperwork and precise documentation. You’ll need to partner with a corporate attorney when you’re ready to take the leap.

Until then, this primer offers a basic overview and reflects our experiences creating employee equity long after our founding. For further reading, there are plenty of in-depth references online, such as this guide from Gusto.

Skip to:

1. Designing an Equity Pool
2. Corporation Type
3. Equity Management
4. Valuation
5. Grant Details
6. Internal Launch
7. Equity Maintenance

1. Designing an Equity Pool

Depending on the structure of your business, the owner(s)—who are often founder(s)—will need to decide how many shares they are willing to allocate to an employee equity pool. Market data can help guide this determination. Looking forward, the pool should be large enough to accommodate anticipated headcount growth.

2. Corporation Type

To offer options, companies must have a certain corporate structure (usually C corporations). Your legal counsel can advise whether changes need to be made to your corporate structure and how these changes may impact the rest of your business.

3. Equity Management

While it is technically possible to manage your equity documentation with something as basic as spreadsheets, licensing an equity management platform will simplify the end-to-end process for both you and your employees. Your legal advisors can help guide you through selecting a platform, setting it up, and making adjustments during major events (such as fundraising).

4. Valuation

Any business offering equity, whether to employees or investors, needs a 409A valuation to establish the value of the business. This valuation is valid for 12 months and sets the strike price, or exercise price, for options or shares granted during that period.

To obtain a 409A, you must provide financial statements, forecasts, company background (management structure, ownership structure, history), industry information, and more to a valuation partner. The goal of providing this info is to help the valuation partner find comparable companies to benchmark against. You may also have the opportunity to supply a list of publicly traded companies that you consider appropriate comps.

Your valuation should match your expectations for your business. When your valuation partner returns the 409A, you have the right to discuss adjustments before approving the final version.

5. Grant Details

It’s time to outline the specifics of the grants you will offer to employees: number of options, vesting schedules, cliffs, exercise periods, and so on. While some parameters are more common than others—such as a 4-year vesting schedule with a 1-year cliff—these decisions should be governed by your internal discussions and the specifics of your company and your culture. Because employee stock options are part of compensation, compensation benchmarking data can be useful in your decision-making process.

6. Internal Launch

At this stage, your employee equity plan should be ready to roll out. Equity is an exciting concept. It’s also complex and often misunderstood. Your internal launch should include educational resources, both live and asynchronous, to help your team understand what their grants mean, what they need to do, and why it matters.

Because exercising options can have significant tax implications, we always encourage our team members to consult with a financial advisor when making individual equity decisions.

7. Equity Maintenance

As time goes on, your equity plan may be affected as you scale or from events like fundraising or acquisition. From an accounting perspective, option grants must be recognized on an ongoing basis as internal expenses (stock-based compensation expenses) based on the grants’ value, plus associated tax implications.

Finally, you will need to obtain a new 409A annually or after a material event, such as a fundraise. Each valuation will establish a new fair market value for existing options and the strike price for newly issued options.

This primer merely scratches the surface; it is simplistic by design. The road to establishing employee equity can seem daunting, but like any big project, it’s a matter of breaking it down into manageable pieces.

The goal of this primer is to provide a bird’s-eye view of where to start and where to go from there. With the support of your advisors and team members, you’ll dive deep into the details at each stage.

When you reach the end, you’ll have accomplished something that could potentially change the lives of your employees. And no matter what happens, that’s an achievement in and of itself.

Ed. note: Organizational equity plans and policies should be designed in consultation with legal counsel. Equity choices on an individual level should be made with input from a qualified financial advisor.


This is part IV in a series of short essays on employee equity at Pliancy: why we choose to offer it, how equity reflects our efforts, what it means to employees, and how to make equity a reality.

Part I

From Sole Ownership to Shared Ownership

Part II

In Pursuit of Shared Ownership

Part III

The Promise & Potential of Employee Equity

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The Promise & Potential of Employee Equity

While offering equity is an org-wide pursuit, its potential impact is hugely personal. Dive into an employee perspective on equity and how equity reflects the Pliancy ethos.

Peter Radonich

Regional Associate Director, East Coast

Pliancy partners with ambitious companies tackling important problems, particularly those at the start of their journeys. It’s the caliber of these clients that drew me to Pliancy in the first place.

We’re proud to support clients who have gone public or been acquired for millions (or even billions) of dollars, and I’ve seen firsthand how benefitting from equity can change employees’ lives.

But it’s not only our clients who are aiming high. Pliancy is, too. From the day I joined Pliancy, there’s one message that has stayed constant:

We’re trying to create something that we feel is important; something that will be of value not only to us, but to the world.

Working in IT can be a hard lifestyle, especially when you’re just starting out. It’s like being a 21st-century carpenter. It’s a trade. If we can improve even one facet of the IT services industry, it will help the future generations of folks who pursue this work.

Offering equity stock options to employees isn’t common in this field, and it’s just one way we are trying to change the landscape of this industry.

Pliancy is showing its peers and competitors that there is a different way to do this work and still be successful.

You can create a positive place to work, you can treat people well, you can give them room to grow, you can show them in creative ways that they are valued, you can invite them on the journey—and still be a stable, profitable business.

There’s no rule saying that Marcus had to give up shares to create an employee option pool. He had sole ownership of Pliancy and, frankly, he could have kept it that way. Instead, his decision is a reflection of Pliancy’s ethos to put people first, even when it’s not easy.

Stock options don’t guarantee anything, especially for a company at our stage. But that’s a beautiful thing to me.

It’s a powerful gesture that says, “We’re building something. We’re aiming to be part of something. We intend to grow to a point where this symbolic offering becomes worth so much more, and we’re going to do it together.”


This is part II in a series of short essays on employee equity at Pliancy: why we choose to offer it, how equity reflects our efforts, what it means to employees, and how to make equity a reality.

Part I

From Sole Ownership to Shared Ownership

Part II

In Pursuit of Shared Success

Part IV

Making Equity a Reality: A Brief Primer

Keep Reading

In Pursuit of Shared Success

When we build together, we build better. Employee equity reflects the work it takes to get there.

Jasmine Francis

VP of People

Equity is a long-term incentive that recognizes the material impacts of employees at a growing company. It rewards the determination required to turn a pile of parts into a well-oiled machine. Instead of rehashing how equity improves retention and motivates employees, let’s do something different. Lace up your running shoes—we’re going for a jog.

Treadmills vs. Trails

At a traditional company, working can be like a treadmill. (And no, I’m not about to condemn all work as a rat race.) Treadmills are consistent. You know what you’re getting; you can set your speed, distance, incline, and intervals.

Because you’re indoors, you’re protected from the elements, so you can run in any weather or at any time of day. But even if you run a full marathon on that treadmill, the view that greets you will be the same one you’ve stared at the whole time.

At a growing company, working is more like a trail run. You’re learning the route in real time. You don’t choose when the trail goes uphill and when it goes downhill. If it’s raining, you get wet. If the trail is washed out, you have to find your own way.

Through all this, trails give you the excitement of discovery. There’s always the potential for something unexpected around the next bend. The view at the end, you hope, will be spectacular.

Neither of these options is inherently better than the other. You might like both; you might like neither. The difference is in the experience.

Building Pliancy Together

Though Pliancy has been in business for over a decade, we still operate with a startup mindset as we scale and mature our operations. We’re in the nitty gritty. If there’s a tree blocking us, we roll up our sleeves, push it out of the way, or find a better way around. Most importantly, we make sure the path is clear for the runners who come after us.

At Pliancy, individuals at every level have incredible autonomy and high impact potential. Our team members shape the services we provide, the way we offer those services, the products we select, and the internal processes that keep us… well, running.

Equity As a Tangible Reward

Equity options are a pledge we make to our employees that despite the growing pains, and despite the fact that things sometimes feel hard, everyone will have the opportunity to share in our success in a tangible, financial way.

That will take patience. It will take grit. But if we work together long enough, and if we push ourselves far enough, we can go the distance. When we take in that stunning vista at the end of the trail, we’ll enjoy it as a team.


This is part II in a series of short essays on employee equity at Pliancy: why we choose to offer it, how equity reflects our efforts, what it means to employees, and how to make equity a reality.

Part I

From Sole Ownership to Shared Ownership

Part III

The Promise & Potential of Employee Equity

Part IV

Making Equity a Reality: A Brief Primer

Keep Reading

From Sole Ownership to Shared Ownership

Discover why our founder wanted to give every Pliancy employee the opportunity for shared ownership.

Marcus Olson

Founder & CEO

In 2022, Pliancy rolled out equity option grants for all full-time employees. Offering equity stock options for an established, bootstrapped company required months of coordination across our leadership, finance, people, and business operations teams.

Why did we commit hundreds of hours to this endeavor? Because we believe we’re building something remarkable, and we want to give everyone the chance to feel a sense ownership in what we’re creating together.

Offering employees equity in Pliancy has been a goal of mine for years. Once we hit six or seven employees, we weren’t just another boutique firm of IT consultants. Our trajectory shifted toward something much bigger and more capable.

I knew one day I wanted every team member to be able to share in that success—the way I hadn’t at previous companies.

Before founding Pliancy, I was an early hire at a startup. I was the only employee in tech ops and administration, building and managing critical systems, but equity was never on the table. It wasn’t just that I was not offered equity; I was never educated on what equity was, why it mattered, and what it could mean for me.

When the company was acquired, the founders were happy (of course), yet there was no material impact on my life. It wasn’t until many years later that I truly understood equity and its potential.

After leaving that startup, I moved out to California. I happened to be sitting in my buddy’s bar on an unremarkable afternoon when, suddenly, a crowd of people flooded in, whooping, hollering, obviously excited about something big. It turned out that YouTube’s office was across the street. The year was 2006, and they’d just been acquired by Google.

All these people were celebrating because they’d taken a chance on building something revolutionary; thanks to their equity, it had paid off.

The energy in that room was unlike anything I’d seen before. At the surface, there was pure excitement. But beneath that was triumph, relief, satisfaction, unity… the feeling of a long exhale after years of commitment. I decided if I was ever in the position to offer employees that opportunity, I would do it.

Now that we’ve (finally) made equity a reality, my goals, the company’s goals, and our employees’ goals feel more aligned than ever.

We all have skin in the game, and we’re going after bold, ambitious things. I’m grateful to have everyone along for the ride.


This is part I in a series of short essays on employee equity at Pliancy: why we choose to offer it, how equity reflects our efforts, what it means to employees, and how to make equity a reality.

Part II

In Pursuit of Shared Success

Part III

The Promise & Potential of Employee Equity

Part IV

Making Equity a Reality: A Brief Primer

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How to Center Employees in Your Onboarding Process

Onboarding can be a nightmare for employees. It doesn’t have to be—if you remember who you’re building for.

Tiffany Kress

Senior People Partner

I have a recurring nightmare. I’ve arrived on campus for the first day of school, equipped with a new backpack and a pristine collection of color-coordinated folders. Yet instead of enjoying the crisp fall breeze and the electric aura of possibility, I have a feeling of dread.

I know I’m meant to be here, but I don’t know where to go, or even what classes I’m taking—which means I probably haven’t done my summer reading, either. I soldier on with neither map nor schedule, and more worries appear. That hallway doesn’t look familiar. That stairwell isn’t where it should be. Where’s my locker? What’s my combination? Does this school even have lockers?

Perhaps you’ve had a similar nightmare: finding yourself on stage with no idea what your lines are, or showing up to class after skipping the crucial step of getting dressed. Even worse, perhaps you’ve lived through a scenario like this.

This is exactly how we don’t want employee onboarding to feel. 

In this essay, I will… discuss why onboarding matters, how we approach onboarding at Pliancy, and how you can assess your own process.

What Your Onboarding Says About You

It’s been well-documented that a high-quality onboarding process has concrete benefits, like improved productivity, shorter ramp-up times, better retention rates, and higher employee satisfaction. And, of course, there are plenty of intangible advantages, such as a sense of belonging, a strong connection to organizational values, and a better understanding of company culture. (If you don’t believe us, take it from the SHRM Foundation, Forbes, Harvard Business Review, Bamboo HR, and Zenefits.)

Regardless of whether you subscribe to the intrinsic or extrinsic value of onboarding, one fact remains true: first impressions are everything, and onboarding is one big first impression.

Consider your onboarding experience and what it says about you. How often do new hires experience system access issues? How many new hires don’t have their computer set up on day 1 or delivered on time? When 9 a.m. on start day rolls around, is it clear what they’ll be doing for the first hour, the first day, and the first week?

Whether your new hires realize it or not, the employee onboarding experience gives them critical information about your company:

– Does this company care about its employees?
– Do they value employees’ time?
– Is the company thoughtfully prepared for projects and events?
– Do teams have organized workflows and processes?
– How does the company record and share information?
– How well do teams communicate and collaborate?
– What kinds of infrastructure exist for employees?

New employees should never feel like lost students wandering the halls. Instead, onboarding should be built around their experience. The process should anticipate needs, feel seamless to the employee, and strike a balance between automation and human support.

Onboarding at Pliancy

When I started working at Pliancy in 2021, it was the most organized onboarding process that I’d ever experienced. The company had built a strong foundation of knowledge sharing, live meetings, and thoughtful details. I was impressed—but that doesn’t mean it was perfect. It’s only in retrospect that I can see we had, and still have, so much room for improvement.

My experience was the result of years of iteration. It’s changed in big ways and small ways since my first day, and it will continue to change in the future. That’s the Pliancy way.

Embracing Iteration in Onboarding

Case in point: a few years ago, we licensed a platform that, among other things, helped guide new hires through their onboarding tasks. Over time, other teams moved away from using this tool. During a periodic review of resources, we realized that we were paying thousands of dollars a year for something that new hires would utilize for a few weeks, and then never log in again. It didn’t enhance the employee experience enough to move the needle.

So we pivoted. We adapted our onboarding checklist and workflow for a platform that was already standard for every employee, meaning the licensing costs were already accounted for. Plus, every employee would continue to interact with that platform regularly during the course of their work, rather than learning a system they’d only use for a month.

Yes, we blew up a process we’d worked hard on. Some may have seen it as a step backward. But in the same way you sometimes need to drop a class that isn’t serving you, we needed to drop that initial solution to realign with the bigger picture: optimizing the employee experience.

Building an Employee-Centered Onboarding Experience

There is no Platonic ideal of an onboarding experience. It’s impossible to prescribe a perfect and universal set of systems or steps, and I’d be wary of anyone claiming they can. Instead, I’ll share the basic components that guide our approach to employee-centered onboarding.

Each section also includes questions to help you evaluate your own onboarding process. You can revisit this assessment as you work toward your ideal onboarding state—just like we continue to do.

Balancing Knowledge & Connection

I think of onboarding as having two sides: knowledge and connection.

Knowledge refers to what new hires need to know: company policies, SOPs, expectations, and so on. It also includes what we, as employers and onboarders, need to know in order to build the best process possible.

Connection refers to the social and emotional aspects of a job: how new hires interact with others and how they feel about the company, their team, and their work.

Our onboarding elements fall into these categories:

Knowledge

– Pre-Boarding
– Self-Service Resources
– The Roadmap
– Feedback

Connection

– Stewardship
– Cultural Immersion
– The Human Touch

📓 Pre-Boarding: Summer Prep

Imagine the chaos that would ensue if teachers and administrators started prepping for the school year on the first day of school. Working closely with managers, onboarding planning should start long before the employee’s arrival. There must be definitive answers on what hardware, software, and permissions the employee requires, plus the logistics of getting them what they need (physically or virtually) before their start date, and instructions for getting started.

Ask yourself:

– Do you have a final checklist to ensure the necessary components are in place?
– What systems does the employee need access to, and what is the process for granting access?
– Who is responsible for pre-start logistics, such as laptop setup, delivery, and office access?

🍫 Self-Service Resources: The Campus Vending Machine

Everyone processes information at their own pace. Some people absorb and digest everything fully the first time. Some may want to skim a collection and return to specific resources when they’re needed. Others may only search for information if and when they encounter a roadblock. Regardless of learning preference, a comprehensive collection of self-service resources can cut down on unresolved issues and delayed answers. This can take the form of a knowledge base, a shared drive, or an intranet. Wherever you keep your information, make sure it’s easily accessible and logically organized.

Ask yourself:

– Is your information stored and organized in a public place?
– How do new employees know where and how to access this information?
– Who monitors the accuracy and currency of this archive?

📍 The Roadmap: The Syllabus

A syllabus tells you more than what to expect from a class; it lays out what the teacher expects of you. Supplying an onboarding roadmap makes it easier to track progress, eliminates ambiguity, and gives new hires the chance to ask questions about the road ahead. Our road map outlines weekly expectations for what they should be learning, doing, or billing.

Ask yourself:

– Do your new hires know what is expected of them during the onboarding period?
– Do new hires know what meetings and events they can expect to attend during onboarding?
– Have you clearly outlined the transition from onboarding to everyday job responsibilities?

📋 Feedback: Course Evaluations

Nothing is ever perfect the first time, and every time we onboard, we find ways to improve. For a truly employee-focused process, you need to build active opportunities to solicit feedback from recent hires. Data from formal surveys has many uses, but it may tell only part of the story. Anecdotal feedback, the kind you get while making small talk before a “real” meeting begins, is just as valuable—and sometimes even more telling. And remember: if you’re not going to act on feedback, why ask for it at all?

Ask yourself:

– What formal and informal opportunities are there for new hires to provide feedback about their experiences?
– How are you storing and analyzing quantitative and qualitative feedback?
– How can you expand the conversation by seeking onboarding feedback from managers and team members?

🚸 Stewardship: Parking Lot Duty

During drop-off and dismissal, a school parking lot is a frenetic place. It would be anarchy without someone acting as a traffic cop/cross-guard/rule enforcer/supervisor. Someone needs to be in charge, just as onboarding needs a clear owner. This doesn’t mean that one person should handle everything; but one person needs to maintain a big-picture view of the onboarding process, delegate tasks, make sure things are running smoothly, and design feedback loops. In the absence of a designated steward, things are bound to fall through the cracks.

Ask yourself:

– Does your onboarding have a clear owner?
– Have you created an intentional communication plan to share essential information with the employee prior to the start date and throughout onboarding?
– How can you partner across functions to improve the onboarding process or get greater buy-in from stakeholders?

🎉 Cultural Immersion: The Pep Rally

Who doesn’t love a good pep rally? Like lunchtime and school dances, pep rallies gave us a chance to catch up with our friends, make new ones, and relax from the tests, required reading, and high-stakes group projects. Incorporating breaks into the onboarding process leaves room for new hires to get to know their new colleagues as people, not just co-workers. We’ve experimented with a few different ways to encourage cultural immersion, from company-wide meet & greets to small-group cohort programs.

Ask yourself:

– What opportunities are you creating for new hires to get to know their colleagues and build relationships?
– Is leadership modeling connection-building?
– What aspect(s) of your company culture do you want your new hires to experience from day one? What are you doing to encourage that feeling?

👋 The Human Touch: Your Guidance Counselor

AI can do amazing things, but it can’t replace the warmth of human connection (yet). Centering the employee experience means preserving the human element. Especially when you’re processing a deluge of information, it can be a relief to know there is a living, breathing person who can parse your questions and find you the answers. It’s also important to have a contact besides the employee’s manager, which encourages new hires to be open and vulnerable about their questions without worrying about the power dynamic of a brand-new reporting relationship.

Ask yourself:

– Who is the ongoing “first-line” contact for new hires?
– How are you directing new employees to this primary contact?
– Are there both formal and informal opportunities to ask questions during onboarding?

The Final Bell

Designing a functional onboarding process is difficult. Designing an employee-centered process, doubly so. Evaluating your responses to the questions above can point you toward where your process might need work. Then, consider the assets you already have: stretch systems you already use and find team members who are passionate about welcoming new employees into the fold.

As students at the School of Onboarding, we’re sophomores: we’ve learned the ropes, and we know where all the classrooms are, but there’s still a while to go before graduation. In fact, graduation might not even be the goal.

Pliancy’s onboarding process isn’t perfect and probably never will be. That’s a feature, not a bug. Onboarding needs to change as companies change; companies need to change as the world changes. 

Every day is a first day. Are you up for the challenge?

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Building the Innovation Engine

Great ideas can come from anywhere. We’re building a process to harness that power and propel Pliancy forward.

Patricio Pace

VP of Business Operations

Imagine this: The year is 2028. Los Angeles has just hosted the Olympics. There are 14 Fast & Furious movies. All Sweetgreens are staffed entirely by robots. And Pliancy is seen as one of the top 10 most innovative companies in the United States.

It’s an ambitious goal, and it might feel a little outlandish to suggest, but we’d be foolish not to pursue it.

Taking the Leap

I’m no stranger to taking chances—though not entirely on purpose. I started my career at a credit union. With no prior experience in retail banking, I prepared thoroughly, did my research, aced the panel interview, and was thrilled to get an offer for an entry-level position. On my first day on the job as I’m going through orientation, the executive vice president pulled me aside and said to me, “You know, Patricio, this is the first time in our 30-year history we’ve skipped over the teller role and hired someone directly as a member service rep without previous experience. We have very high expectations, so don’t let us down.”

It turns out the position wasn’t entry-level after all. I played it cool and just focused on getting up to speed quickly. No pressure!

I’m proud (and a little relieved) to say that I was able to live up to their expectations, eventually working my way up to branch manager before moving on. Now, what does this have to do with making Pliancy a leader in innovation?

Diving headfirst into this challenge taught me the value of ambition—even if it was blind ambition at the time. From the credit union to starting my own consulting business to leading Pliancy’s operations from a single-digit headcount to over 100, the challenges have often seemed insurmountable… until they weren’t.

Why Innovation Matters (for Pliancy)

When I say I want the Pliancy name to be synonymous with trailblazing innovation, it’s not merely for the sake of it. Instead, I’m focused on three primary benefits of an embedded culture of innovation:

– Improved unit economics and efficiency
– Game-changing breakthroughs in product, service delivery, process, and more
– Increased talent density

Unit Economics

Innovation means innovation at every level and at varying scales. Small tweaks to our processes can help us increase the value each item, or “unit,” generates for the business. We can do this by reducing costs, increasing production or delivery speed, or by improving the quality of our products. Regardless of how we improve our efficiency, becoming more efficient means we can devote more of our resources and energy to developing novel solutions.

Breakthroughs

Companies are more likely to achieve breakthroughs across their organizations by innovating rapidly and regularly. This can involve changing who they target (audience, business model), what they do (product, service delivery) or how they do it (process, tooling). Many companies have the potential to innovate; it’s only by doing so quickly and consistently that the results can snowball into changes that are greater than the sum of their parts. At this magnitude, breakthroughs can help companies beat out the competition to dominate, or even redefine, their industries.

Talent Density

Think about the companies that eventually transformed into the tech behemoths we know today. Before they ousted industry incumbents or created brand-new market categories, they were scrappy start-ups with far-fetched ideas, powered by ambitious, imaginative teams. These trail-blazing companies developed reputations for creating environments that embraced inventiveness and experimentation. Like attracts like: innovative companies attract high-performing, creative minds that topple boundaries and push one another to dream even bigger.

What We Talk About When We Talk About “Innovation”

What do you picture when you hear the word “innovation”? Most people think of huge product launches, revolutionary business models, or groundbreaking discoveries made in secretive R&D labs. Innovation on a grand scale is important, and those kinds of moonshot ideas propel us forward.

Iterative innovation, though some may consider it unglamorous, is equally vital. Small tweaks to a feature, a workflow, or a client communication can make tremendous cumulative impacts. What some see as “minor” updates help us move faster; improve quality (and therefore perceived value); automate workflows; and turn experiences from impersonal to inspiring for both our team members and our clients.

Innovation in Practice: Our Recruiting Process

I want to share an example from when I first joined Pliancy. Things were starting to take off and we were growing fast. Client referrals were coming in hot and it was starting to get challenging to find more talented folks to join our team because our networks were tapped. It was time to make the leap!

I created a quick and dirty recruiting process MVP (minimum viable product) so we could hit the ground running and learn along the way. I threw up a Craigslist ad, set up a mailbox for incoming applications, and created a spreadsheet to track the pipeline.

It was not glamorous but it allowed us to swiftly test ideas and iterate. Who needed to be informed about the process? What pain points did candidates experience? How long was everything taking? As we considered questions like these, we began evolving our recruiting stack to include an applicant tracking system, self-scheduling links, Slack alerts, interview templates, and workflow automations.

Incremental Innovation

Our secret to rapid iteration was a powerful feedback loop that we instituted early on. From the start, we did a post-onboarding interview with every new member of Pliancy to learn what worked and what didn’t, tapping into their wisdom and creativity to improve our system. We were crowdsourcing ideas from the very people experiencing the process.

Each time we made a small tweak, it improved the experience by an incremental amount. We made the experience 5% better. Over time, those 5% improvements compounded upon one another. Our Associate Director of Talent, Jenny Kerdphoca, now leads this process and she continues to source ways to make the experience even better for our candidates and for our hiring managers.

I started us off with something very modest, but thanks to our belief in small-scale innovations (and a lot of hard work from our team members), today we have a world-class recruiting program that is strategic and data-driven. Even in just the past two years, under the People team’s leadership we have reduced time to fill (a key efficiency metric) by 6 business days, a 14% improvement. Iterative innovations like these set the bar ever higher, driving employee satisfaction and retention.

Why Ideas Fail

Great ideas are everywhere, but there’s a reason they say ideas are cheap and execution is everything: most fresh ideas die on the vine because people aren’t sure what to do next. This execution gap may be caused by a lack of information, motivation, resourcing, buy-in, or any of a thousand other constraints.

Think back to a time when you had an idea you wished would be implemented. You don’t have to think that far back, do you? Lightbulb moments, large or small, happen all the time.

Here’s one idea I had: about 20 years ago, I was trying to be healthier by cooking more frequently, but keeping the fridge well-stocked was a hassle. Vegetables and dairy went bad before I could use them; I would run out of eggs and not realize it until I was in the middle of a recipe. These frustrating situations made cooking and meal planning exponentially more difficult for me.

Then I was struck by a thunderbolt of inspiration. What if there was a smart fridge that would track its contents for you? When you brought groceries in, you could scan a barcode or RFID tag on the product and your fridge would then automatically know what items it held and how long they would be fresh for. No more running out of butter without an alert. Better make a salad with that tomato before it goes bad on Friday, you’d be reminded. Automagically, my cooking journey would be so much easier.

The Execution Gap

There were a few not-so-small problems with my idea. To start, I don’t have a background in industrial design, consumer appliance manufacturing, or setting up global supply chains. I also didn’t know how to develop a prototype nor did I have access to millions in capital to spend on R&D. Unfortunately my idea turned into an all-too-common “I wish someone would build that” scenario.

Today, smart refrigerators come with large touch displays and voice-controlled assistants. They’re Wi-Fi connected, and you can even view the contents inside remotely from your phone via embedded cameras. They may not be in every home yet, but both adoption and features are trending up and include things I couldn’t have even imagined when I first conceived the idea.

Sometimes I wonder what could have been. Twenty years ago, if I’d been able to connect my vision with the right skill sets and the right resources, would I be helming a smart fridge empire today?

Okay, maybe a smart fridge empire is a bit lofty, but the point stands. What if we closed the execution gap for folks who had exceptional ideas but didn’t know where to start? Didn’t know how to get traction? And what if we did that at scale?

From Idea to Reality

As Pliancy’s VP of Business Operations, I don’t expect my team to innovate in isolation. We’re inviting the whole company to participate in the innovation process and to contribute their ideas, their perspectives, and their expertise. My goal is to build a frictionless path that will help our colleagues move from ideation to implementation, unlocking the power of their creativity. By anticipating execution gaps and finding ways to bridge them, we will build a pathway to innovation that gets faster and smoother with time.

We’ve already identified some key ways to close the execution gap for our team members:

– Idea evaluation
– Implementation support
– Continuous feedback

Idea Evaluation

Evaluating an idea includes determining what success would look like, projecting the costs and benefits, aligning the idea to Pliancy’s strategic roadmap, and generating a proposal. But because most people don’t have training in these areas, they aren’t set up for success when seeking buy-in—no matter how good the idea is. We can help by creating proposal templates, conducting feasibility studies and analysis, building reporting metrics, or even modeling the performance and impact of an idea before it gets built.

Implementation Support

Making an idea into reality requires the right support at the right time, the same way a mechanic needs the right tools for any given job. Instead of sockets and wrenches, our tools are SMEs in project management, analysis, change management, communications, documentation, and more.

With a project management approach that values people over process, our team can develop project plans, define scope, identify contributors, manage timelines, and hold contributors accountable. Plus, no project exists in a vacuum. We must consider change management and clear documentation strategies, even if the shifts seem minor, to make sure the updates are adopted widely and operationalized for the long term.

Continuous Feedback

Improvement is a never-ending process. Whether you’re launching a new product or a new workflow, considering any innovation “one-and-done” is a dangerous trap.

From the evolution of our recruitment pipeline, we know big things happen when we harness the power of feedback loops. Crowdsourcing suggestions allows us to consider a broad spectrum of experiences and opinions in order to improve processes one step at a time.

But feedback loops don’t happen on accident. Organic responses are great, though few may take the initiative to reach out unprompted. It’s critical to embed the feedback process into every project, providing structured opportunities to solicit users’ thoughts. Combined with objective quantitative data, comprehensive feedback loops ensure that we get the full picture of what’s working, what isn’t, and what could be.

What Comes Next

“Okay,” you might be thinking, “so what now?”

The honest answer is: we’re working on it. We know evaluation guidance, robust implementation support, and consistent, iterative improvement are key to closing the execution gap. With this knowledge in hand, we will find a way to make our idea (a self-propelling innovation engine) a reality and then use it to help others bring their concepts to life.

It won’t be an easy process or an overnight transformation, but we don’t expect it to be. More important than ease, and more important than speed, is the power of potential. Just like an internal combustion engine, we intend to harness the raw power of explosive ideas, converting that energy into motion and propelling Pliancy toward the future we dream of.

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Why Moving Past Fear is Essential for Asking Questions in the Workplace

There’s no telling where a simple question could take you. Here’s why and how you should take the leap.

Mark Wagner

Escalations Manager

This is the second installment of a 2-part series. Read Part I, “Ask Me Anything.”

What are you afraid of? In my last post, I described Pliancy’s open-access culture, the dangers of gatekeeping and information hoarding, and how openness can lead to skill-sharing and growth. That’s all well and good, but no matter how welcoming the environment, we can still be hamstrung by our own fears and uncertainties.

Fear (of asking questions, of embarrassment, of failure, or whatever else) can prevent us from asking important questions that need to be asked, which in turn prevents us from learning the information and skills we need to grow. If I can share one radical thought, it’s that we don’t need to conquer fear. We don’t need to beat it up and take its lunch money; we just need to move past it. Fear isn’t a brick wall. It’s a curtain.

So how do we push aside the Fear-Curtain™? I wish I could give you a definite, never-fail, money-back-guarantee answer… but we have different fears and different brains. What I can do is share what has helped me push my Fear-Curtain aside: letting myself be bad at things, reframing fear as opportunity, and accepting that embarrassment is only temporary.

Let Yourself Be Bad

Some of the best advice I’ve ever received was from a yellow stretch dog in a cartoon. “Dude,” he said, “sucking at something is the first step towards being sorta good at something.” I promise I don’t get all my sage wisdom from animated characters (just most of it), but this simple sentence has stuck with me. We’re going to try a lot of things in our short lives. We’ll probably be terrible at 80% of them, and there’s no shame in that.

We’re conditioned to believe that we fail more than others. In reality, that’s only because we witness every time we stumble. Behind closed doors, in other spaces, at all hours of the day, everyone experiences failure. Literally everyone. Even Beyonce. Let that really sink in.

The key is to let yourself be bad at the beginning. Keep at it, and you’ll get a little better. Ask questions to learn what you don’t know, and you’ll get better still. Before you know it, effort and knowledge quickly transform into skill.

Don’t forget about the 20% of new things you aren’t terrible at, either. Everyone has innate talents, including you, and natural ability and continued effort are a powerful match.

I’ve had a knack for technology my entire life, and I’m one of the lucky people who gets to make a living doing something I’m good at and something I like. But it doesn’t mean I took my aptitude and coasted on it. I’ve built upon it with each job, each certification, and each technological head-scratcher I encounter.

Trying (and trying again) is an important mindset whether you’re pursuing a professional passion or experimenting with a new hobby. No matter your baseline, the potential for growth is always there.

Reframing Fear as Opportunity

The next shift was changing my perspective to see opportunity where I once saw peril.

First, we should acknowledge that society has assigned a negative value to being unskilled at something. It can sometimes feel like failing at a new skill is a moral failure, e.g. “I am bad at juggling, therefore I myself am bad.”

I’ll let you in on a secret: that’s not true. Having a skill is not positive or negative. Trying and failing to juggle doesn’t make you a bad person. Unfortunately, knowing how to juggle does not make you a good person, either. (I think you’re rad either way.)

What is a “Good” Question?
We shouldn’t assign value to specific types of questions, either. A simple question is no better or worse than an open-ended question. The right question, asked in the right context, could be more impactful than another—but change the environment, the audience, even the intonation, and it’s a whole new ball game.

Once I let go of the idea that failure is “bad,” I could focus on what I have to gain. Every time I start something new, I’m full of questions. “How do I…” “What’s the best way to…” “Is this right?” Every piece of knowledge I add to my collection helps me grow, and as a lifelong learner, it’s easy for my fear to become eclipsed by excitement.

I’ve Got No Strings to Hold Me Down
This mindset helped me get to Pliancy because the excitement of this role outweighed any anxiety I had that I might not be talented enough to be here. But here I am, a lean, mean, problem-solving machine, and I’m thriving. That same excitement-over-fear approach makes me perfectly suited for a job where I get to learn how to untangle new knots every day.

Trading the fear of embarrassment for the excitement of opportunity has enriched my personal life in unexpected ways, too. I’m a 36-year-old who plays on a kickball team and loves it, and if that doesn’t scream “I’m not embarrassed by what you think,” then I don’t know what does.

Failure at Pliancy

I don’t want to speak for my colleagues, but it seems like many of them have undergone a similar transformation. We’re an amalgamation of dreamers, creators, and problem-solvers. We swing big, and we’re too busy being excited by opportunity to be ruled by fear.

Failure is something to be celebrated. Sure, it would be nice if we were immediately successful at everything we did (that’s the dream, right?). But barring that, failure means we’ve pushed ourselves to try something new—and have likely learned a lot in the process.

Navigating the Obstacle Course

There’s no shortage of reasons you might hesitate to let yourself be vulnerable. Maybe your company culture doesn’t offer you a safety net for failure. Maybe you’ve seen others judged for asking what others considered to be the “wrong” question, or perhaps you yourself have been burned before. Mental health issues, including social anxiety, can ratchet the hurdles even higher, and as someone with anxiety and bipolar disorder, I relate.

When we stop ourselves from taking the leap, it’s commonly because we catastrophize. What if my coworkers think I’m asking a laughably simple question? What if there are follow-up questions and I don’t know how to respond? What if my team members judge me?

And to that, I say: Okay. What if?

This Too Shall Pass

More often than not, the worst-case scenario is feeling embarrassed. And once I realized—really, truly understood—that embarrassment was fleeting, my entire attitude transformed.

We all cringe at memories of things we’ve done in the past. Our brains like to show us our blooper reel while we’re trying to fall asleep. But the immediacy of embarrassment, that cover-your-eyes feeling, the hot flash of shame, dims eventually. The conversation will move on. Other questions will be asked. The conversation or meeting or day will end. Soon enough, I’ll forget too.

That’s a feature, not a bug. The purpose of embarrassment, in my worldview, is to course-correct behavior. It fades by design so you can dust yourself off and try again. Knowing that embarrassment is impermanent, who’s to say I can’t skip ahead to the chapter where I’m already over it?

Ways to Challenge Yourself

I’m not claiming I can make you immune to fear and embarrassment. I won’t be the star of a “Therapists hate him!” clickbait ad anytime soon.

Changing your relationship to fear is a personal journey, and it’s one that will be unique for each of us. I hope what you’re able to take away from my candor and experience is that it’s possible to build this kind of habit like you would any other.

If you’re interested in moving past a fear of asking questions, here are three suggestions for getting started:

Start with Yourself
Instead of focusing on what scares you, reflect on what you have to gain. Having questions can be scary, but it means you’re in a position to grow. Your question could lead you to a fun fact about armadillos (did you know they sleep for 16 hours a day?)—or it could lead you to the next great passion that changes your life’s trajectory. The possibilities are endless.

Walk Before You Run
Ask questions in safe spaces, then level up. Stack the deck in your favor by asking vulnerable questions in one-on-one conversations with trusted team members. (Is that already easy for you? Amazing. Keep going!) You can up the challenge depending on what intimidates you: group conversations, distant or senior coworkers, in-person meetings, or public venues, for example.

Consider the Positive Impacts
When we fixate on asking questions, it’s easy to forget how fulfilling answering questions can be. Try seeing things from the other side: walk a teammate you trust through one of your work processes and encourage them to ask any question they can think of. You might be surprised at how fun it is to teach them about what you do. When you ask questions, you’re giving people that joy, too.

A Prediction for the Future

We’re human beings, not automatons. We don’t come equipped with all the knowledge we could ever need, we can’t be perfect immediately, and we certainly can’t be perfect every time. We will make mistakes; that just means we’re trying. We will have questions; that means we have something to learn.

No one needs permission to move past fear. But if you disagree, let me write the permission slip for you now: start today. Even if you move slowly, keep flexing that muscle and know that slow is smooth and smooth is fast. Someday soon—sooner than you expect—you’ll find yourself on the other side of fear, and you’ll wonder why it seemed so scary to get started. So I’ll repeat my opening question: what are you afraid of?

Keep Reading

Ask Me Anything: The Benefits of Asking Questions in the Workplace

There’s no telling where a simple question could take you. Here’s why and how you should take the leap.

Mark Wagner

Escalations Manager

This is the first installment of a 2-part series. Read Part II, “Moving Past Fear.”

Have you ever had a moment where you really took initiative, went for the brass ring, and felt on top of the world when you finally grabbed it? A few weeks ago, I did just that—only to look down at my hands afterward and realize they were covered in spray paint. That brass ring wasn’t brass after all.

After a flash of embarrassment, I shook it off. I was able to move on quickly because of two things: Pliancy’s remarkable openness and a learned ability to move past fear.

*Record Scratch* *Freeze Frame* Yep, that’s Me

First, I have to set the stage for my accidental transgression. As a remote-first company, Pliancy uses Slack to communicate. We have a ton of Slack channels to organize our discussions, including the AMA channel.

If you aren’t aware, “AMA” stands for “Ask Me Anything,” originating from the Reddit community of the same name. The original AMA subreddit offers anyone the chance to pepper people of note (celebrities, experts, individuals with unusual professions or life experiences) with questions about anything and everything.

Based on that description, Pliancy’s AMA channel seemed like a great place for me, a technical operations engineer who helps consultants tackle more complex problems, to kick off a “dumb questions only” thread. My intention was to offer a safe and friendly cocoon where people could open up about things they didn’t know but were too afraid to ask. Great concept, right? I thought so too… until, after I posted, I realized that the description of the channel specified that the “Me” in “Ask Me Anything” was meant for leadership team members only.

Whoops.

Open Source Information: Every Question is the Right Question

Luckily, I’m in a unique environment where I’m not made to feel less-than because of an honest mistake. My coworkers understood and embraced my intention, and I was able to answer a number of questions that they had never had an opportunity to ask.

Questions are always welcome at Pliancy because openness is an important element of our culture. (And I do mean all types of questions; dumb questions, good questions, important questions, and everything in between—though I don’t always agree with those labels.) This is a far cry from other IT companies and teams I’ve been part of in my 18-year career. To put it plainly, it’s an extremely punk rock way of doing things when you treat each question as the right question.

I have had the freedom to talk to anyone from day one: every consultant, developer, and manager, all the way up. I was never told, “Don’t ask X person about Y topic.” Instead, it was impressed upon me that if I had a question, I could and should go directly to the person I felt would answer it best.

The Advantage of Asking “But Why?”

A serial question-asker like me thrives in this environment. I revel in being the person with the most questions in the room. In my view, it means I have the most to learn from others and therefore the most to gain. It also means I have the power to create change. By asking “Why?” I can challenge the way things have always been done in a single syllable.

Asking questions—no matter how stupid we may feel they are—is the best thing you can do in almost every situation. They say that curiosity killed the cat; most people forget that satisfaction brought it back.

Look, I get it: this is easy for me to say. Asking questions is hard and potentially embarrassing. When I’m new, I bet some people assume I’m not the sharpest tool in the shed because I’m a constant loop of who, what, when, where, why, and how. Exposing the gaps in your knowledge is an inherently vulnerable act, yes, but that’s only half of the story. We also have to concede that, in many work environments, asking questions can be a gamble.

Obstacles to Openness

In my experience, there are two separate but related workplace behaviors that discourage openness: gatekeeping and information hoarding.

Gatekeeping: I’m the Captain Now

Gatekeeping has become incredibly normalized, especially in larger and more traditional workplaces where it can be spun as due diligence and adherence to process. Gatekeepers often have bureaucratic mindsets. They leave you hanging for hours on end over a task that takes five minutes because they believe they know what’s best. To them, “what’s best” means wielding power through arbitrary waiting periods and hoops to jump through.

Working with a gatekeeper means being beholden to their schedule, their mood, and their attitude. You have to stay on their “good side” by whatever means necessary, lest the gatekeeper cut you off from the resources you need or the opportunities you want.

Information Hoarding: No Follow-Up Questions Allowed

Information hoarders limit access in a different way. Instead of obstructing access to a process or conversation, information hoarders protect their own knowledge. They’re dragons sitting atop knowledge for no reason other than to have it, and no, you cannot take a quick peek.

“Make yourself indispensable” is common career advice. Many (misguidedly) interpret it to mean that a monopoly on specific knowledge will make a person’s job more secure. If you’re the only one who understands how a process works or the only one with a certain skill, how could the company function without you? I hate to break it to you lifers out there, but graveyards are full of supposedly indispensable people—and still the world keeps turning.

Both gatekeeping and hoarding information reek with the stench of “the way we’ve always done things.” They are a means of preserving the status quo and discourage equity in the workplace. How can we fight against behaviors like this? I’m glad you asked.

“Automating” Solutions By Sharing Skills

Like many technologically inclined people, I love automation. There’s something remarkable about being able to program a machine to detect an issue and solve it on its own.

When we openly share skills with others, a similar magic takes place. I spend most of my day fixing problems, and they can fall into two categories: common or weird. As you might guess, the weird ones take a lot longer to fix. So what’s the easiest way to free up time to tackle the weird stuff? Teaching others how to quickly identify and resolve common issues.

When a consultant files a ticket, often I will make sure to connect directly with them over a Zoom call and explain what I’m doing and why I’m doing it. This creates a situation where a consultant can likely resolve the issue themselves the next time or at least know exactly what to ask for. I may not be programming my colleagues like I’d program a machine, but I am giving them the instructions they need to fix a problem themselves. You could say that teaching is the human version of automation.

Because I don’t need to use access or information as currency at Pliancy, there’s no benefit to preserving the mystery of my solution. I offer it up freely, and the result is a win-win-win. The consultant can move on to other issues, the client gets billed for less time, and I bounce right back to solving those weird problems. The more power I can pass on to others provides me more time to deal with new (often more interesting) problem sets.

Paying It Forward

I’m lucky to have had managers who have shared knowledge liberally, taught generously, and given me space to ask anything I needed. It wouldn’t be fair for me to not do the same for others. Some days I marvel at how lucky I am to have landed at an organization filled with people who feel the same way.

I’m aware that my experience is the exception, not the rule. Even if you’re swimming against the tide at your place of work, there are still ways to encourage openness in yourself and the colleagues around you. Challenge yourself to reflect on these questions:

Who can you be open with at your workplace, and why? How can you add more people to this circle?
How transparent are you about your work and projects? Can you open up your process to your team or other team members?
– If you are a supervisor, how can you foster an environment of transparency with your direct reports? Do you provide opportunities for them to ask questions? Do you model openness and vulnerability, publicly and privately
How can you challenge your leaders to be open and honest?

Your Mission, Should You Choose to Accept It

If you don’t agree with me, try it. Try being open, genuine, and transparent with your coworkers, supervisors, and leaders, and press them to do the same. Open your locked doors, take down the walls of privileged access to others, and let people ask questions: simple questions, open-ended questions, challenging questions, you name it. Prove me wrong. Show me that efficiency, happiness, and retention don’t increase.

What I’ve found is that I exist and mesh here at Pliancy in ways I’ve never been able to do at other companies. I’ve flourished because I can be open with my co-workers. There are no hidden rooms, no one is out of reach, and you won’t get your hand slapped for asking questions. If that’s not the most punk rock thing you can do, I don’t know what is.

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