Why smart people sound unsure

When people doubt you, the natural move is to explain more.

But this usually backfires, even if it’s not immediately apparent to you.

A senior leader I once coached (*a composite of several investment executives) was a true expert in his field. Within a multibillion dollar fund, he headed the team for a specific investment class and had developed his expertise from over 20 years of making calculated bets, many of which achieved outstanding returns.

Every few months, he was expected to introduce and defend his positions to the company’s board, comprised of executives from other industries – many of whom didn’t have prior experience with investing, let alone in his specialty area.

Of course, my client understood the value of boards and investment committees being made up of people with a diverse set of backgrounds to avoid groupthink and to invite new perspectives from outside the narrow categories of each business area in the company.

So it didn’t surprise him, that at most every board meeting, several members would ask questions that were seen as basic by him and his team members.

Knowing that finance and investing weren’t their “first language” he would go out of his way to explain the fundamental terms of his products and how they related to the market. He also would answer each question about his decisions by laying out both sides of the issue so no one could say he had missed anything.

He chose this approach to hopefully never be caught not knowing the answer to a question, and remove any doubt in their minds about his analysis.

While he thought this style was working well, his CEO told him that the board was having difficulty trusting his judgment. This caught my client by surprise. And it admittedly frustrated him.

He confided to me in our sessions, “I don’t get it. They barely know what we do and don’t take the time to learn about investing themselves, so I walk them through everything. Sometimes over and over again. I give them all the information, from both sides, so they know I analyzed everything beforehand.

“It shouldn’t be my fault that they don’t keep up on their own. Sometimes I wonder, are they even listening to me explain how things work, or do they just enjoy having things to question because it makes them look smart?

He may have been onto something.

Several members did feel exposed by their lack of expertise relative to my client. And as board members, they were being asked to approve decisions in an area they didn’t know well. So for them, their questions, no matter how basic or repetitive they seemed, were how they showed they were still doing their jobs.

The irony of it all, I observed, was that both sides – the board and him – were trying to make sure they looked smart in the eyes of others. But being seen as smart was the wrong objective.

When my client’s answers came back long and balanced, the board couldn’t tell what he personally thought. So they asked more questions, often resulting in another both-sides take.

What they were secretly hoping was that he would lead them somewhere, not just teach them the “basics.” So, what he saw as them asking elementary questions because they didn’t understand the business, was an inaccurate read, but hard for him to see when he was so focused on assuring them.

The board was asking these questions in the absence of him starting with a point of view. They were actually less concerned with knowing “how the sausage was made” as he thought, but because they weren’t hearing him assert his view and bottom lining it with conciseness and confidence, they were slowly losing trust in his decisions, which led to them asking more questions.

This was a classic case of a leader trying to show he was smart but forgetting that his audience already knew he was. They didn’t need to be reminded he was smart; they needed to know whether he was someone they could follow.

Why this happens to most of us

When we feel doubted, we give more: more caveats, more sides, more detail.

Each additional detail feels safer to the person offering it, because it feels like they’re being generous and giving more “icing on the cake.”

But to the listener it sounds undecided and too safe, as if they are throwing everything at the wall to see what sticks, rather than being sure and convicted in what they want to say.

And a listener who can’t tell where the other one stands will keep asking until they find out, or worse: zone out, maybe talk about the speaker behind their back and avoid future interactions when they require deep engagement and trust toward shared goals.

This week’s method: The Headline Rule
How to keep a smart answer from sounding unsure.

Going forward, my client adjusted his approach and changed the order of what he said.

That’s right: it’s not earth-shattering advice yet sometimes the simplest tweaks create the most needed outcomes.

It’s a way to change how an audience perceives you, called the Headline Rule:

1. Say your position in the first sentence.
Write it the way you would write a headline. “I recommend we delay the launch by one quarter.” Then give your reasons.

2. Say what would change your mind.
“If the pilot numbers come in above target, I’d move forward.” This tells people you have a view and that you are open to being wrong.

Adam Grant’s 2021 book Think Again provides a strong basis for the idea that people trust you more when you are open to being wrong. There is a “confident humility” that comes across which boosts credibility and followership.

3. Ask for a response to your position.
“Which part of that do you see differently?”

Ask one person at a time rather than the whole table. Each person gets something concrete to react to, so there is room for more individualized feedback and specific aspects of your message to parse out and agree/disagree with.

When my client tried these steps out, he noticed the board’s questions changed from “what do you think?” (setting the stage for more proving of his knowledge) to “what would it take?” (setting the stage for followership and a path toward execution based on the premise that everyone already knew he was smart and capable).

Your turn

Think about the moments in your work and life where you are being asked to lead and may struggle with how much to “show your work” vs. asserting your point of view about the work.

Indeed, getting this right is a dance and different settings, audiences and decisions all determine which side requires more emphasis. About your audience, ask yourself: are they beginners in your expertise area and/or particularly sensitive to not being experts?

Or conversely, do they see themselves as experts and expect you to demonstrate a certain level of knowledge or something else before taking your lead?

Either way, the Headline Rule is an effective one for testing what works for the audience you are seeking to influence.

Try it in one place where you usually over-explain. It could be a meeting, a hard talk with someone you manage, or a decision with a friend or family member. Basically, start with your answer, say what would change it, and ask them what they would see differently based on your view.

By the way, you don’t have to have absolute certainty around your view to do this.

After all, it’s not good practice to be so convicted about something that you create self-inflicted blind spots.

You only have to be clear about where you stand today and deliver that view with confidence as well as a willingness to be pointed out wrong. It’s your point of view in clear, concise terms that people are asking for when they keep asking questions, and once you give it to them, most of the pressure will ease.

P.S. Are you, or someone you know, moving into a bigger role?

I’ve written a free guide about the five changes executives scaling up often don’t anticipate.

Free download: What Changes When The Role Gets Bigger

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Nihar Chhaya is a trusted coach to CEOs and senior executives at over 40 of the world’s top companies including American Airlines, Coca-Cola, Cox Enterprises, Lockheed Martin, DraftKings and others.

A Master Certified Coach (MCC) recognized by the International Coach Federation, Nihar helps leaders navigate transitions, lead more strategically, strengthen their influence, and build trust across their teams.