Early in my career, I often got nervous about speaking up or asking questions, especially in a larger group setting. Especially as a new leader, I frequently doubted myself and hesitated to speak up because I didn’t want to appear unintelligent or too critical of my peers or managers. If you know me now, that might be hard to believe, but it’s true.
I remember one meeting in Chicago thirty years ago where I was asked to attend a quarterly meeting that included many of the executive team. Although this group ultimately invited me, I felt like I wasn’t in a position to speak up and let my opinion be known because of my relative age and inexperience. So I sat there, taking it all in, not saying a word.
During a break, one of the leadership team noticed some topics were making me squirm, and he asked what I was thinking. I’d been sitting in the meeting silently disagreeing with a few things, becoming frustrated, which was apparently noticeable. He let me explain my point of view and encouraged me to speak up in the afternoon session. More on that later…
Why We Don’t Speak Up
If you have ever held back at work with a question or comment, know that you’re not the only one. Many people, especially those in roles with high expectations, get stuck in silence. They worry they’ll sound like they don’t know what they’re doing. Or that they’ll annoy someone higher up. Or that they’ll come across as a blocker instead of someone helping to move things forward.
The problem is that silence might feel safe in the moment, but it works against you over time. It creates distance, builds frustration, and wears people down.
“Silence might feel safe in the moment, but over time, it works against you.”
There are real reasons you might choose to stay silent. Perhaps you don’t want to look like you’re struggling or are concerned about getting on the wrong side of your manager or a peer. Or maybe you think you should already have the answers or have a distant memory of when speaking up didn’t go well for you. I’ve had coaching clients express all of these concerns.
An employee at one of my clients once told me, “It isn’t about the question or the comment. It’s the environment. Management only appreciates open ears and closed mouths.”
The peculiar thing is that no one in management had directly set these expectations. Yet, people had learned these rules because they had witnessed that it was safer to stay quiet than to speak up.
But what’s the actual cost of staying silent? Let’s look at that next.
What Happens When You Don’t Ask Questions
When you sit in silence, it is usually interpreted as consent. You might feel like the best approach to get through the conversation, but what it really means is:
You’re more likely not to completely understand a situation because you didn’t ask clarifying questions.
That others in the meeting are missing out on your expertise and your unique view of a situation.
However unfortunate it may be, it also means that you have entered the realm of slowly disconnecting from your work, your team, and your values.
Although not speaking up may seem the safest approach, it can be exhausting. You may find yourself in a position where you feel like your job is to make everyone else happy but yourself. That’s a difficult place to be in and isn’t sustainable if you want to enjoy what you do.
Asking Questions Is a Leadership Skill
It’s easy to forget that asking questions is a part of any job. A big part. Your unique experience and viewpoints are an essential part of why you were hired. All those questions during the interview weren’t simply to understand what you know; they were asked to learn how you think.
Understandably, you may not have answers to every question during the moment. But there’s no reason not to ask a question when you have one in order to gain more clarity for yourself and others. The best leaders I’ve worked with ask many questions and appreciate honest and direct answers. They do it to make things clearer for themselves and others. They want better outcomes. They want everyone moving in the same direction.
The best way to have your questions well-received is to ask them thoughtfully. A thoughtful question says that you’re paying attention, you want to make sure you (and others who may not like to ask questions) have a solid understanding, and you care about whether the situation being discussed is successfully navigated. A thoughtful question is direct, depersonalized, and kind is usually well received.
Also, questions move people more than directives. They open up the topic and pull people in. A good question at the right time can help people find understanding and alignment or prompt more discussion with those ends in mind. This is what good leadership looks like, and if you don’t see that at your company, I’d encourage you to be brave enough to fill the void.
But where’s the best place to start?
Start Small
You don’t have to flip a switch and change overnight. Start small. Before or during your next meeting, write down one thing you’re unsure of or curious about. Then, think through how to ask about it in a direct, depersonalized, and kind way.
For example, assume you have a question about a project’s timeline, and you’re hearing things that indicate the company hasn’t considered the impact of resource availability. You could ask:
“Hasn’t anyone thought about the fact that we all have things on our plates? This timeline seems ridiculous to me. Am I the only one?”
or,
“I’m curious if some of our key resource availability might put this timeline at risk. I’d like to see this be successful. What trade-offs are we prepared to make to achieve this timeline without adding additional resources or deprioritizing other efforts?”
Asking the question the first way will likely make you feel like you are, indeed, the only one.
Asking the second question shows you’ve paid attention to project risk and are interested in protecting the company’s probability of success. Plus, it opens things up for discussion.
Some other easy opening questions:
“Can you walk me through how you’re thinking about this?”
“What does success look like for this, from your point of view?”
“What’s the most important thing we should be focused on right now?”
So start small. Ask. Not to poke holes, to get clear. And realize that these questions aren’t interruptions. They’re signals that you care.
When You Don’t Feel That It Is Safe to Ask
It’s worth saying that not every place welcomes questions. Some teams are still stuck in a top-down, don’t rock-the-boat model. If you’re in that place, ask your questions one-on-one instead of in front of a group. Discuss the context and explain why your question matters and how it would help the team succeed.
Sometimes, it takes a bit of practice to feel comfortable. If you find yourself stuck, you’ll eventually weigh the trade-off of pushing yourself to gain the courage to ask your questions, or you’ll ask yourself, “Can I keep working like this?”
Back to Chicago…
During the afternoon session of that meeting three decades ago, I chose to speak up. I could have phrased the question better, and there were a few scoffs and eye rolls, and I immediately felt like I should have kept my mouth shut. But just as I wished I could take it back or find a place to hide, two others spoke up and echoed similar concerns.
The way others treated me after that meeting changed. I went from a quiet observer to someone who others knew would speak up, even if my questions met with the disdainful glare of others. Over time, I learned to phrase my questions better and enjoy the discussion that questions encourage.
What Question Are You Avoiding?
What’s one question you’ve been holding back? What would happen if you asked it? Consider how to ask it directly, in a non-personal manner, and in a kind way.
Then ask.
Things change when you stop seeing questions as a sign of weakness and start seeing them as a valuable skill. You’ll start being seen, heard, and driving the needed interaction.
You’ll grow faster and show up stronger.
Silence might keep things smooth. But it’s curiosity that makes things better.
Great post Kevin. I like the start small section as I think many people (not me of course lol) become paralyzed when the end point is the area of focus. I like to use a North Star approach to guide me generally…and short term wins to help me get out of inertia and into action!
Always love your writing. It makes me stop and THINK!
Important stuff, Kevin. Thank you.
I'd also suggest "Can you help me to understand ... ?" as a great way to initiate non-confrontational questions and answers. This was shared with me by a friend and colleague and feels easy and non-threatening.
The other thing your article reminded me of was the whole inquiry vs advocacy approach. Early in my own career, when I thought I was right, which was usually, I could be pretty rigid in presenting the "facts" as I understood them. This put people off, to say the least. I was choosing a single perspective and then defending or "advocating" for it. The problem is that all anyone else has to do is to find one flaw in your argument and exploit it, and you lose the argument. I hate to lose. ;)
Then I read about the inquiry approach, where you ask questions and invite other perspectives into the discussion. This is a much more inclusive, flexible, and fluid approach that encourages the contributions and honors the thinking of others. The whole team learns and gets better together. Pro Tip: Take note of and call out the positive contributions other team members make, especially to leadership. This is how the best ideas and the consensus to actually accomplish them are created.