Why You Struggle to Speak Up in Meetings (Even When You Have Something to Say)

I had an interesting conversation with a client recently who wanted to become more confident at work.

When I asked what confidence looked like to them, they described the kind of executive who can walk up to a group of people mid-conversation and just... join in.

You know the one.

Meanwhile, you’re awkwardly hovering three feet outside the circle, pretending to be deeply interested in your drink while trying to figure out the appropriate moment to share the relevant insight that you’ve already rehearsed six versions of.

In that time, that executive has already joined the conversation, contributed something, had a laugh, and moved on with their day.

What I find interesting about this comparison is that we tend to interpret their behavior as evidence of confidence. But I think there's something else happening that deserves our attention.

What looks like confidence might actually be a higher tolerance for risk.

Think about what's happening for the person hovering outside the circle. They're not necessarily lacking social skills. In fact, they might be incredibly socially perceptive.

They're already noticing who's speaking, who's listening, whether there's room for another person, whether they'd be interrupting, whether their presence would be welcomed.

And when they finally do join? They're simultaneously outside their own body holding a clipboard, conducting a live performance review.

Too much eye contact? Why did I say it like that? She made a face. Was that about me Oh god, I'm still talking.

LAND THE PLANE.

All that scrutiny makes something as ordinary as joining a conversation feel like a surprisingly high-stakes event.

Now consider the executive. They might not have any greater certainty that their entrance will be well received.

They may simply be more willing to find out. And that willingness makes an enormous difference.

The problem with wanting to feel confident first

For many high achievers, competence is what creates confidence.

We want evidence that we can do something well before we feel comfortable doing it.

Except when we're particularly risk-averse, we can end up waiting for competence before allowing ourselves to participate in the very experiences that would build it.

A rather inconvenient arrangement.

The executive who's comfortable entering conversations has likely accumulated hundreds, maybe thousands, of these little social interactions. Some went beautifully. Others were awkward. Most were probably unremarkable.

But each gave them an opportunity to practice navigating the interaction and discovering that even when things didn't go as expected, they could handle it.

Meanwhile, the person waiting outside the circle is still trying to determine whether it's safe to enter.

We want certainty before taking the risk. But competence comes from experience, and experience requires taking the risk before we have that certainty.

And for someone who grew up learning that saying the wrong thing, being misunderstood, or drawing unwanted attention came with consequences, that's a pretty tall order.

We're not all starting from the same place.

So how do we become more willing to take risks?

I don't think telling someone who's highly socially aware to stop overthinking is particularly useful.

Nor do I think the answer is to force yourself into uncomfortable situations until you magically stop caring.

I'd rather work with the person's existing tolerance for discomfort and gradually expand it.

Let's go back to that circle.

Maybe walking straight into a conversation with five unfamiliar executives feels like an eight out of ten on your personal discomfort scale.

Okay. That's a lot.

What would a three look like?

Maybe it's approaching a group where you already know someone and saying hello. You practice that until the anticipation isn't quite so consuming. Then perhaps you stay long enough to contribute one thought. Eventually you try entering a conversation where you don't know anyone.

You're still uncomfortable, but you've accumulated enough evidence from the smaller experiences that the discomfort doesn't carry quite the same threat.

And this is where we can actually influence how quickly confidence develops.

We can wait for life to hand us enough experiences that familiarity eventually does its job. Or we can deliberately create more opportunities to practice, starting with risks small enough that we're willing to take them.

Not overwhelming ourselves. Not expecting perfection. Just gradually expanding what we're comfortable attempting.

And whose version of confidence are we building, anyway?

There's one other thing I think is worth examining before we start practicing.

When we admire someone's confidence, we can accidentally assume we need to adopt their personality to achieve it.

We picture the charismatic, quick-witted executive who effortlessly works a room and decide that's what success should look like.

But maybe you're naturally quieter. Maybe you prefer listening before contributing. Maybe you need a moment to organize your thoughts because you care about expressing them accurately.

None of those things are inherently incompatible with confidence.

There's an important distinction between wanting to develop the skills to navigate social situations and believing we need to become a fundamentally different kind of person to do so.

The first gives us something useful to work toward.

The second can leave us perpetually measuring ourselves against someone we were never going to be.

So perhaps the goal isn't to become the executive who walks into every conversation without hesitation.

Perhaps it's to become someone who can feel that hesitation, recognize the risk, and trust themselves enough to participate anyway.

Even awkwardly. Especially while we're still learning. Because confidence isn't necessarily the absence of discomfort.

Sometimes it's simply having enough experience with discomfort that we no longer need to wait for it to disappear before we act.