Have you ever sat in a meeting, felt that knot in your stomach telling you the plan is about to go off the rails, and said… absolutely nothing?
Yeah, me too. More times than I care to admit early in my career.
We’ve all been there. The room is nodding along, the slides look pretty, everyone wants to be seen as a team player, and speaking up feels like throwing a grenade into the middle of all that harmony. So we swallow the unease, trust that someone else will say something, and hope for the best.
Here’s the brutal truth I learned the hard way: that single moment of silence can be the exact reason you never get the big role, the promotion, or the chance to actually run something important.
The Two Mistakes That Separate Real Leaders From Everyone Else
After twenty-plus years investing in companies and watching hundreds of executives either soar or stall, I’ve seen the pattern repeat itself so often it’s almost painful.
Great leaders do two things consistently that most people avoid like the plague:
- They trust their gut even when data says otherwise.
- They speak up first when they see trouble coming—even when it’s uncomfortable as hell.
Get those two right, and doors open. Get them wrong, and you’ll stay stuck in “high-potential” purgatory forever.
Mistake #1: Treating Your Intuition Like Background Noise
We love data. Spreadsheets, metrics, dashboards—give me all of it. But here’s something the spreadsheets will never tell you: sometimes your gut knows before your brain does.
I remember sitting in a board meeting years ago for a company we’d just backed. The numbers looked fantastic. Growth was accelerating, churn was dropping, the pitch deck was a work of art. Every investor in the room was ready to double down.
Except something felt… off. I couldn’t point to a single cell in the spreadsheet that was wrong. But the founder’s energy was frantic, the customer anecdotes felt curated, and the “hockey stick” projection smelled like wishful thinking dressed up as math.
I stayed quiet. So did everyone else. Eighteen months later the company imploded in a fairly spectacular fraud scandal. Turns out my gut had been screaming for a reason.
Your gut is the sum of every experience, pattern, and subtle cue you’ve ever absorbed—operating faster than conscious thought ever could.
That’s not woo-woo. That’s neuroscience. The best leaders I know treat that feeling like an early warning system, not random anxiety.
They ask themselves three quick questions when the knot appears:
- What exactly feels wrong?
- Have I seen this movie before?
- If I’m right, how bad could this get?
Nine times out of ten, the feeling dissolves under scrutiny. But that tenth time? That’s the one that saves careers, companies, and fortunes.
Mistake #2: Confusing “Nice” With “Helpful”
Being a team player is important. Being so afraid of conflict that you let bad decisions sail through unchallenged is career suicide.
I call it the team player trap. You want to be liked. You don’t want to be the jerk who rains on everyone’s parade. So you bite your tongue and tell yourself it’s not that big a deal.
Except it compounds. One small bad decision becomes the foundation for the next, and suddenly you’re knee-deep in a mess nobody wants to claim.
Real leadership isn’t about being the loudest voice in the room. Sometimes it’s about being the first voice when everyone else is pretending everything’s fine.
Someone has to be willing to stand up and say, “This doesn’t feel right.” If you want to lead, make sure that someone is you.
– A very expensive lesson I learned
Why Speaking Up Feels So Hard (And Why It’s Worth It)
Let’s be honest—calling out a bad idea in real time is uncomfortable. Your heart races. Your palms get sweaty. You worry you’ll look stupid if you’re wrong.
But here’s what I’ve noticed: the people who get comfortable being uncomfortable move faster than everyone else.
They build trust. They earn respect. And when things do go sideways (which they always do eventually), nobody is shocked when that person steps up to fix it—because they’ve been the one telling the truth all along.
Over time, that reputation becomes rocket fuel for your career.
How to Actually Get Better at This
Good news: these aren’t innate gifts. They’re muscles. And like any muscle, they get stronger with use.
Here’s the playbook I wish someone had handed me twenty years ago:
- Start small. Next time you feel even mild unease, voice it as a question instead of a statement. “Have we pressure-tested the worst-case scenario here?” feels a lot less confrontational than “This is going to fail.”
- Name the awkwardness upfront. Try: “I need to say something that might be uncomfortable…” It actually lowers defenses—people brace themselves and listen better.
- Separate the person from the idea. “I love where your head’s at, and I’m worried about X because…” keeps it from feeling personal.
- Follow the 24-hour rule. If something is still bugging you the next day, it probably matters. Speak up privately if the moment has passed.
- Track your batting average. Keep a private note of every time you spoke up. You’ll be shocked how often you were right—or how little fallout there was when you weren’t.
The first few times will feel terrible. By the tenth time, you’ll wonder why you ever stayed quiet.
The Compound Effect Nobody Talks About
Here’s the part that still blows my mind: once you build this habit, everything else gets easier.
People start coming to you before decisions are final because they know you’ll tell them the truth. You get pulled into bigger rooms. Your opinion carries more weight. Opportunities you didn’t even know existed start finding you.
It’s not because you’re smarter than everyone else. It’s because you’re one of the few willing to say what everyone else is thinking but too scared to voice.
In a world full of polished PowerPoints and forced optimism, that kind of clarity is rare. And rare things are valuable.
Your Move
Next time you feel that flicker of doubt, don’t push it down. Lean into it.
Ask the uncomfortable question. Send the direct message. Pull the person aside after the meeting.
It won’t always be popular. You won’t always be right.
But the people who change companies, industries, and sometimes the world? They’re the ones willing to be the first to speak when something doesn’t feel right.
The question is: when that moment comes—and it always does—will you be ready to be that person?
I hope so. Because the view from the other side is worth every second of discomfort.
