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.


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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