A few months ago, I was running a presentation workshop when a young team member asked me a question.
”What do you do when you don’t know how to answer a difficult question from a senior leader?”
I answered as best I could. We moved on.
But the question stayed with me long after the workshop had finished. Not because I wasn’t sure what words to use, but because I had a feeling she wasn’t really asking about presentations.
She was asking what that moment would mean about her.
I understood that question. I spent years asking it myself.
The definition I quietly invented
Early in my career, I was invited to a brainstorming session. We split into groups, gathered around flipcharts and started throwing out ideas.
Everyone seemed so fast.
Ideas bounced around the room before I had even decided whether I agreed with them.
I’ve always been someone who thinks first and speaks second. But sitting there quietly felt unbearable.
So I said something.
I can’t remember what the brainstorm was about anymore. I can’t even remember what I said. I only remember that, halfway through explaining my own idea, I realised I didn’t really understand what I meant.
I hadn’t spoken because I’d finished thinking.
I’d spoken because silence felt more dangerous than a half-formed idea.
No one had ever told me that competent people answered quickly. I had simply looked around the room and decided that they did.
They remembered numbers.
They had opinions ready.
So I quietly built a definition. Competent people always had something to say. Competent people always knew.
Looking back now, I don’t think I was trying to contribute. I was trying to prove that I deserved to be there.
Success changed the stakes
As the years passed, something unexpected happened. People started relying on me.
Campaign performance.
Consumer insight.
Commercial results.
The numbers gradually became part of my job. Eventually, they became part of my reputation.
At first, I enjoyed that. Then I noticed something I hadn’t expected.
The more often I knew the answer…
the more frightening it became not to.
Before important meetings, I rehearsed every possible number. Every likely question. Every challenge I could imagine. Not because anyone demanded perfection, but because I’d quietly convinced myself that competence had to be demonstrated over and over again, one answer at a time.
The meeting I had rehearsed for
Eventually, exactly what I had spent years preparing for happened.
My VP asked me a question.
I didn’t know the number.
I searched my notes.
Nothing.
For a few seconds I felt the familiar instinct to keep talking while I thought. To fill the silence. To rescue the moment somehow.
Instead I simply said,
“I don’t have that number with me. Can I come back to you?”
She nodded.
”Of course.”
Then we carried on discussing the actual decision we were trying to make.
That moment stayed with me. Not because it taught me that saying “I don’t know” is easy - it still isn’t. And not because every room responds like that.
Some meetings genuinely reward confidence. Some leaders value speed. Sometimes hesitation costs you. That is part of professional life.
But this meeting forced me to ask a different question.
Had I misunderstood what people were actually judging?
I had been admiring the wrong thing
After that, I started watching senior leaders differently. Not for how quickly they answered. For how they thought.
I noticed one Director wasn’t afraid to let silence sit for a few seconds before responding to a difficult question.
I watched another openly say she didn’t know exactly how the market would evolve, only that we’d work it out together.
I watched someone else have her assumptions challenged in front of a room full of people. She didn’t become defensive. She thanked the person who had challenged her thinking and said she’d strengthen it.
None of those moments made me trust them less. Quite the opposite.
There was something deeply reassuring about people who didn’t need to perform certainty. They seemed secure enough to examine their own thinking instead.
Then I changed sides of the table
The biggest shift didn’t happen when I became more experienced. It happened when I became responsible for other people’s work.
I started reviewing presentations. Listening to recommendations. Watching junior team members present to senior leaders.
And I realised something that caught me completely off guard.
I wasn’t judging them the way I had spent years judging myself.
When someone on my team presents a recommendation, I don’t expect them to remember every number in the appendix. I want to know they’ve understood the problem. That they’ve done the work. That they’ve challenged their own assumptions. That if I ask a difficult question, they won’t panic - they’ll think.
Somewhere along the way, I realised I had been holding myself to a standard I wasn’t holding anyone else to.
I had imagined competence was built one answer at a time. From the other side of the table, it looked much more cumulative than that.
The trap isn’t mine alone
The longer I’ve worked, the more I’ve realised I wasn’t unusual. I’ve watched people answer before they’ve finished thinking. I’ve watched conversations move so quickly that admitting confusion seemed harder than asking another question. I’ve also watched thoughtful people delay decisions while waiting for certainty that never arrived.
They look like opposite behaviours. One rushes towards an answer. The other postpones one. But I wonder if they’re driven by the same fear: that uncertainty will make us look less capable.
I sometimes wonder how much energy we all spend protecting ourselves from that feeling. Energy that could have gone into asking better questions. Learning something new. Or solving the problem sitting in front of us.
Strategy changed the question
A few years ago, I was asked to recommend a new Disney Cruise proposition designed specifically for the UK market. We’d never done it before. We could analyse the audience, the commercial opportunity and everything we’d learnt from other markets.
But one question remained.
Would UK families actually want this?
There wasn’t a report that could answer it. There couldn’t be.
We eventually recommended launching it anyway. Thankfully, it worked. But that’s not the part I think about most often. What stayed with me was something much simpler.
The analysis stopped.
The decision didn’t.
For a long time, I’d treated unanswered questions as a reflection of my own competence. Strategy slowly taught me that many unanswered questions don’t belong to me at all. They belong to the decision. My job isn’t to eliminate them. It’s to understand them well enough to recommend a direction anyway.
The balance I’m looking for
I used to think becoming more senior meant knowing more. In some ways, it does. Experience gives you patterns. It teaches you which questions deserve another week of analysis, and which are unlikely to become clearer no matter how long you wait.
But it also brings you closer to questions that simply don’t have complete answers.
How will customers respond?
Is this the right strategic bet?
When have we learnt enough to move?
These days, I’m less interested in trying to remove uncertainty than I am in understanding it. I’m trying to make recommendations without pretending certainty exists. To stay open to changing my mind without becoming paralysed by indecision.
And now that I lead others, another question has appeared. How honest can I be about uncertainty without making everyone else feel uncertain too?
I suspect that balance never disappears. Perhaps it simply becomes the work.
I think back to that workshop question quite often now.
”What do you do when you don’t know how to answer a difficult question from a senior leader?”
If someone asked me again today, I’d still tell them what to say. But I’d probably ask them something first.
What do you think that moment is testing?
For years, I believed every difficult question was judging whether I deserved to be in the room. Today, when I ask someone a difficult question, I’m rarely interested in whether they happen to know one particular answer.
I’m watching what they do next.
Do they bluff?
Do they become defensive?
Do they become curious?
Can they separate what they know from what they’re assuming?
Can they keep thinking?
Perhaps that’s what people had been noticing in me all along.
Not whether I always had the answer.
But whether I could stay thoughtful after I’d run out of them.
···
Still asking.