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?

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Making Ironclad IT Security Simple for Finance

Many people view security and user experience as diametrically opposed. It doesn’t have to be that way.

Caleb Albers


The finance industry has a rap for moving slowly with respect to technology—and more specifically—IT security. However, because finance companies potentially have billions of dollars in assets under management, they’re highly targeted by bad actors.

It’s also important for security technology to be managed in such a way that it doesn’t have a large impact on user experience. You don’t want “security theater,” where the IT infrastructure seems very obvious and secure to the user, but isn’t really. Hackers can see right through security theater. And security through obscurity is akin to putting keys under your doormat.

When we first begin working with clients, we unfortunately see many poor implementations for modern systems like Single Sign-On or Multi-Factor Authentication. The other thing we often see is weak email security—one of the biggest threats for companies in general, and especially for financial firms.

These are problems we’ve taken particular interest in solving as a team of technologists, and doing so in a way that isn’t obtrusive to the user. In general, you could sum up our entire approach by saying we build guardrails that encourage best practices with respect to security, while also precluding bad behavior. We aim to make it easier to be secure than it is to not be.

Many people view security and user experience as diametrically opposed. It doesn’t have to be that way. You just have to think creatively in how you approach security implementation.


At Pliancy, we hit 100% Multi-Factor Authentication (MFA) compliance, which means that every single user employs MFA across all of our clients. In the finance field that’s incredibly rare, especially because we also take the extra steps to make it a good experience.

Typically we have clients come to us with 7-10 different systems that they log into on any given day. They have a username and password for each system, all of which they have to remember.

So we set them up with a Single Sign-On: each user signs once into our platform, which is verified with Multi-Factor Authentication. Once they’ve signed in using just one username and password, they can launch any of their applications with a single click.

It isn’t cumbersome. They don’t have to pull out some physical token on a keychain and read off digits, or anything like that. It’s just a push on their phone—click yes or no. That allows them access to all their systems for the day; they don’t have to worry about it again, and it’s far more secure.

We engineer each client platform to consolidate audit logs and perform anomaly detection. This will flag anything that seems odd by the parameters of each user. For instance, a user suddenly has 15 random login attempts from another country. We’ve designed the system to block those attempts automatically instead of having to look manually for those kinds of discrepancies after the fact.


We’re constantly looking for new ways to heighten security behind the scenes that are completely transparent to the user. We’ve done a lot of problem-solving to enhance email security. Email security is notoriously terrible, and notoriously intrusive to the user.

Sure, an overactive filter on your emails to catch phishing attempts or other threats probably does the job. And a lot of companies will try to solve email security with a purely technical approach like this. They install systems that filter email, scan for various things, etc.

But fundamentally, your best approach to solving that problem isn’t simply having that technical aspect in place: It’s layering that technical aspect with a user training process.

We’ve found there’s no technological substitute for informed users—those who are trained to identify emails that might be fishy. At the end of the day, the threat landing in your inbox isn’t going to compromise you. The breach happens when a user clicks on it. And that kind of stuff happens all the time.

So the approach we’ve taken is layering the technical implementation with a strong but unobtrusive educational component. We partner with a vendor that provides training materials, which we tailor to the client and review with them to teach them what looks suspicious, what looks legitimate, and how to tell them apart. We favor interactive training that employees can take at their own leisure.

We also send users test email campaigns that mimic common phishing tactics. Then we monitor the number of people who opened the email, the number of people who click on the links in the email, the number of people who filled data out on the fake page skinned to look like a Microsoft login page (for instance), and so on.

We track patterns and watch how they change over time with the introduction of security concepts through training. This allows us to tailor training to individual users who are struggling with specific security issues. Because nobody wants the mandatory three-hour training when they already understand the content, unless they need it for compliance regulation.

That’s just one example of how we can unobtrusively figure out where we need to focus our efforts to have the highest value. We know when clients are getting really good at identifying threats, because end users will start forwarding those test emails to our consultants and say, “Hey, this looks phishy. Did this not get caught by your system?”

That’s the goal.

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How Strategic Support Systems Supercharge Our Work

How much more could you achieve by focusing on the work that fuels you? We’re reimagining support systems as a necessity for progress.

David Aronica

VP, Strategy & Growth

Support systems are often overlooked as passive resources, there to assist and nothing else. But what if we reimagined support systems as tools of enablement; as a necessity for progress?

We all have tasks that we put off before we dive into our “real” work: writing that LinkedIn post, watching a webinar recording, or finally opening this spreadsheet containing who-knows-what. We always get there eventually, but there has to be another way.

At Pliancy, we believe the right support systems (with the right experts) can lighten burdens like these. And when you let your experts focus on the work that fuels them, you can help your teammates unlock their true potential.

The Big Impact of “Small” Things

Pliancy was built on the idea that partnering with clients to make strategic technological choices could fundamentally improve their business. That’s reflected in our company purpose: empowering tomorrow’s technology leaders to revolutionize how organizations value technology.

IT has historically been viewed as little more than a cost center: a necessary evil, a budget line item that unavoidably keeps rising as a company scales. Rarely do decision-makers truly consider the value that technology brings to their employees.

In modern office environments, where email, video conferencing, and digital collaboration are non-negotiable, any decision related to IT has a ripple effect on day-to-day employee performance and behavior.

To take one “small” example: if an external business partner emails an attachment, it could be flagged (and quarantined) as potentially malicious. If each message needs to be manually released by an IT admin, that wait could delay your employees’ work by hours or days.

What more could your team accomplish if they had that time back? And if a troublesome quarantine policy is known to cause issues, how many of them are committing the security sin of using something other than their corporate email address to speed things up, data risks be damned?

Investing in Next-Level Support Resources

Changing minds starts with changing the conversation. Instead of focusing on cost, the question should be, “What productivity is technology driving for my business?” And to put even more of a people-first spin on it: “How can technology make life easier for my employees?”

We think about our operational resources in the same way, and this question was core to our strategic planning process. As Pliancy’s VP of Strategy & Growth, I am acutely aware of how implementing the right tools and processes can make our team members’ lives easier. This means freeing them up to flex their core competencies, solve the problems that matter, and supercharge what’s possible for Pliancy.

To that end, we thoughtfully invest in next-level support resources that set our consultants, engineers, and other technologists up for success:

-A PMO with strategic management skills to plan and manage projects efficiently, so technical SMEs spend less time chasing updates and more time doing the work that fulfills them

-A data team to integrate data science and analytics into our strategic planning and decision-making processes

-An in-house creative agency to deliver best-in-class visual branding and communications on organizational and individual levels

-A learning and development program designed for the whole person, emphasizing technical upskilling and complementary soft skills in equal measure

-A business operations function to execute strategic management tactics, allowing us to analyze and resolve high-level organizational challenges

Professional Development: A Tale of Two Pliancies

For much of Pliancy’s early history, we were a small shop. Consultants (and for a long time, every employee was a consultant) wore many hats. Projects were managed through Slack messages and spreadsheets. Branding was established by an outside agency, but day-to-day client communications and internal communications were most often written by whoever needed them. Learning opportunities were tech-focused and peer-led. Some data was available, but there was little time to dig deeper or leverage it to its full potential.

And here’s the remarkable thing: it worked. Thanks to the grit of our team members, the power of automation, and the clarity of our technical vision, Pliancy flourished. We built our own tooling to optimize our resources, and our backyard acted as a testing ground for developing, iterating, and perfecting the tech-enabled services we offer to clients. Our efficiencies facilitated exponential growth, and we bootstrapped our way to seven offices across the US.

If Pliancy could achieve this degree of growth through a scrappy, “all hands on deck” mentality, imagine what more we will accomplish with expert support resources in place.

Today, technologists can partner with a project manager for collaborative initiatives large and small. With a PM working to lock project scope, establish timelines, and track deliverables, consultants are freer to do deep work instead of herding cats. Technologists can also lean on Pliancy’s creative team to produce on-brand presentations and decks, client messaging, case studies, employee engagement, and even personal LinkedIn branding.

Personal and professional development opportunities are carefully designed and consistently scheduled by an L&D specialist. Our growing data team provides metrics that enable us to track how we’re serving clients and monitor our own performance as we iterate and improve.

With these strategic investments, we’re not depending on momentum alone to keep us going. We’re deploying resources to accelerate everything we do.

Bringing Best Practices Home

As I hope is abundantly clear, we aren’t interested in being just another MSP. We don’t want to be an MSP within the narrow confines of that definition at all. We want Pliancy to be something else greater altogether.

That’s why we don’t limit ourselves to industry best practices. We’re on the lookout for best practices, period. That means integrating proven tools and methodologies from agile startups, socially conscious nonprofits, ambitious entrepreneurs, respected Fortune 500s, and everything in between. A good idea is a good idea; it’s up to us to figure out if and how we can make it work for Pliancy.

Letting Experts Be Experts

Implementing new concepts and ideas is not an easy process, and we go through growing pains like everyone else. Though we don’t always succeed on the first try, we match those learning experiences with a willingness to evolve and an openness to new perspectives.

Especially at the leadership level, it’s critical that we don’t let ourselves be guided by ego. We don’t need to be the heroes that save the day. If I struggle to execute on an idea, that doesn’t automatically mean it’s a bad one. I don’t throw my hands up, forget it, and move on; I bring in an expert who knows how to do it right—and then I get out of their way.

Just as we look across industries for best practices, we look across industries when hiring SMEs to power our support systems. While we emphasize shared values in our staffing process, that doesn’t mean we aim to surround ourselves with carbon copies. Diverse perspectives are the driving force behind forward-thinking innovation, and it is mission critical that we enrich our organization with individuals from a broad spectrum of professional backgrounds, life experiences, and identities.

Long-Term Investments Over Short-Term Gains

As a business, we’ve proven that our concept—a tech-enabled, professional services approach to IT—works. Our next task is to establish methodologies and systems that will not just support us, but propel us forward as we continue to grow.

Committing strategic planning efforts and the staffing resources to the construction of these support systems is a big swing. It’s expensive, it’s hard to do right, and their impacts are often difficult to quantify. But we’ve never been afraid to do the hard thing. We’re lucky to have the stability to make investments in our systems and our people even though they don’t boost our bottom line immediately.

Persisting with patience is in Pliancy’s DNA, because we acknowledge that deep, pervasive change is made gradually and intentionally. We’re in it for the long haul. Are you?

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