What Investors Teach Us About Speaking Well

Follow This One Rule to Make Them Respect You More

Have you ever caught yourself softening your words?

Maybe you say, “I’m not sure, but…” or “This might be wrong, but…” That’s hedging—a habit where we add extra phrases to avoid sounding too bold. It’s common in job interviews, meetings, even casual chats.

The term “hedging” actually comes from finance, where investors protect against loss by diversifying—like betting on multiple outcomes to reduce risk. In speaking, it’s similar: we hedge to give ourselves wiggle room, a way to back off if things go wrong. But while it feels safe, it shrinks your influence.

In this article, we’ll dig into why we hedge, how it weakens us, and how to stop it to lead with strength.

What is Hedging?

Picture a job interview. A woman sits across from the interviewer. He asks, “What are your salary expectations?” She hesitates. She needs the job badly. She doesn’t want to ask too much and lose the chance, but she can’t ask too little either.

So, she says, “If I could get a 5% hike from my last salary, that would be great.” Her voice shakes. She doesn’t push. She’s hedging—leaving room to retreat if he disagrees. But this hands the interviewer power. He knows she’s unsure, maybe desperate. Her caution costs her.

Now imagine a meeting. Someone shares an idea: “I’m not very sure, but maybe we could try this. It’s just my first thought.” They’re scared of criticism, so they soften their words. It feels less risky—like a financial hedge against failure.

But it makes others doubt them. If they don’t sound confident, why should anyone else be? Hedging might shield you from judgment, but it keeps your impact small.

The Psychology Behind Hedging

Why do we hedge? It’s tied to our survival.

In finance, hedging spreads risk—like owning stocks and bonds so if one drops, the other might hold steady. In speaking, we do it to avoid responsibility. When we say, “I might be wrong,” we’re keeping an escape hatch open. It’s a way to deny our words later if they’re challenged. Taking a firm stand feels scary—like a threat to our safety. Uncertainty makes us want to dodge blame, so we soften everything to survive the moment.

This goes back to how our minds evolved. Long ago, disagreeing too loudly could get you cast out of the group. Staying likable was key. Today, that instinct lingers. In the job interview, the woman might’ve hoped her hesitation would win the interviewer’s sympathy—like he’d help her if she seemed weak. Instead, she lost ground. In meetings, saying “This may be wrong” is a plea for allies, not pushback. We hedge to feel safe, but safety doesn’t win respect.

Here’s a thought from Paul Graham: “Some say that qualifications weaken writing. For example, that you should never begin a sentence in an essay with ‘I think,’ because if you’re saying it, then of course you think it. And it’s true that ‘I think x’ is a weaker statement than simply ‘x.’ Which is exactly why you need ‘I think.’ You need it to express your degree of certainty.”

Graham’s onto something. Hedging shows how sure you are—or aren’t. But in real life, that softness often flops. “I think we should do this” hits weaker than “We should do this.” It’s honest, sure, but it risks making you look timid.

The Impact of Hedging

Hedging changes outcomes. In the job interview, the woman’s shaky 5% ask sounded like a plea, not a stance. The interviewer could offer less, knowing she’d likely take it. She gave up control.

In a meeting, hedging makes your ideas forgettable. Say “This is just an idea, but…” and people tune out. They think you haven’t thought it through—or worse, that you don’t believe it. Like a financial hedge, you’re covering your bases, but you’re not winning big.

It’s not about being cocky. It’s about trust. Hedging signals doubt—in your idea and yourself. Others notice. They’re less likely to back you. Over time, this keeps you from leading. If you want a raise, a project, or respect, you can’t keep watering down your words.

Strategies to Overcome Hedging

Stopping some negative habit starts with awareness.

Notice when you hedge. Do you say “maybe” or “I’m not sure” too much?
Are you leaving wiggle room with “This might not work”?

Once you spot it, you can fix it. It’s tough—hedging feels baked into us. But it’s not unbeatable.

Try silence. Instead of padding with “ums” or “maybes,” pause. Let your words breathe. “We should try this”—then stop—sounds stronger than “I think we should try this, but I’m not sure.” Silence feels awkward, but it adds weight. People don’t always push back; sometimes they just listen.

Next, commit. Pick your idea and own it. Don’t toss it out with “This might be dumb.” Say what you mean and stand by it. Hedging doesn’t fix a bad idea—it just dims a good one. Trust yourself, even if you’re not totally certain. No one’s perfect.

Last, build a failure budget. In finance, hedging avoids loss. In life, avoiding all risk keeps you stuck. Asking for a 10% raise might flop, but it might work. Pitching boldly in a meeting might draw flak, but it might shine. You have to risk stumbling to grow.

Rewind to the job interview. Imagine she says, “Based on my experience, I expect a 10% increase from my last salary.” No wobble, no “if that’s okay.” She sets the tone. The interviewer might haggle, but he’s working from her baseline. She’s driving now.

In the meeting, picture this: “We need to shift our strategy this way. Here’s why it works.” No “I’m not sure” or “Just a thought.” They state it, back it up, and hold firm. Criticism might come, but they’ve made a mark. Confidence sticks in people’s minds.

Conclusion

Hedging feels like armor, but it’s a trap. It’s the financial trick of playing safe—spreading bets so you don’t lose big. In speaking, it’s the same: we dodge responsibility, leaving room to backtrack. But it keeps you small. Paul Graham’s right—hedging shows your certainty. Too much, though, buries your strength.

Break it by watching yourself. Catch the “maybes,” swap them for silence or firm words, and stick to your guns. Accept failure might happen—it’s how you climb. Keep reflecting on this. Every time you see hedging fail you, your mind learns it’s useless. Push long enough, and you’ll hit an escape velocity—where dropping the habit feels automatic. Then, you’re free. Say what you mean. Own it. You’ll be amazed how far it takes you.