A CIO Told 300 Managers to Stop Pretending. It Was the Best Leadership Move I’ve Watched.

Years ago I sat in an auditorium at a bank I was coaching, watching a brand new CIO address close to three hundred middle managers from across technology. It was the kind of meeting where everyone shows up a little guarded. New executive, unknown expectations, and a room full of people who have learned that the safest posture in front of leadership is competence.

And he told them to stop pretending they know everything.

He said it plainly. He didn't value it. He'd rather they say "I don't know, let's figure it out," because it was more honest and because it would build better relationships with their teams. He told them that the days of scrambling before a big meeting with him or any other executive, trying to predict every question and prepare an answer for it, were over. Nobody can know everything anymore. He'd rather they be honest about that. Stop wasting your time on that, he said.

My jaw about dropped open. I think I had a tear of pride form in the corner of my eye, watching an executive say the thing I spend most of my working life trying to get executives to say. In my years as a Chief Technology Officer of multiple startups, I did and said similar things, but I was still learning myself. I tried to be relatable and empathetic, but it was many years later as I read and studied what it means to be an Enterprise Agile Coach that I learned the names and deliberate practices that refines this leadership posture. But this executive on stage made it perfectly clear. I couldn't have said it better myself, and I still re-tell the story, mostly because I wish more leaders in his position did the same thing.

What made it remarkable

Most leaders have absorbed the opposite instruction somewhere along the way. Command respect. Have the answer ready. Never be caught flat-footed in front of your peers. It isn't written down anywhere, but you can watch it operating in any large organization if you pay attention to what happens in the twenty minutes before a steering committee meeting.

But here's what I think that instruction gets backwards. If you want trust, you have to offer it first. Trust isn't something you can command into existence, and it isn't a reward that arrives after you've demonstrated enough competence for long enough. Somebody has to go first, and the person with the most positional power in the room is the only one who can really afford to.

That CIO went first, in front of three hundred people, in his first weeks on the job. And what he was actually doing, whether he'd have used the word or not, was being vulnerable on purpose.

Two people who have written about this better than I can

Brené Brown's research is where I'd start, because she takes vulnerability seriously as a leadership capability rather than a personality trait. Her framing is that vulnerability is the precondition for trust rather than a sign of weakness, and that the willingness to be uncertain in front of people who expect certainty from you is exactly the thing that makes trust possible. A leader who says "I don't know, what do you think?" to someone who came looking for an answer is making a deposit that no amount of directing can make. It signals that the other person's knowledge matters.

Edgar Schein takes the same idea and makes it operational at the level of a single conversation. In Humble Inquiry he argues that asking a question is itself an act of vulnerability. When you ask someone what they know, with real curiosity about the answer, you are admitting a dependency out loud. You are saying that their knowledge matters more than yours does in this particular moment. And that signal builds trust in a way that telling simply cannot, no matter how good the telling is.

There's a distinction of Schein's I keep coming back to. Most of us can manage general politeness and can agree in principle that humility is a virtue. Schein separates that from what he calls here-and-now humility, which is the specific and much more uncomfortable state of depending on someone in front of you, right now, for something you actually need. That's the hard one. It's easy to believe in humility as a value from a safe distance. It's a different thing to sit across from someone twenty years your junior and need what they know, in a room where other people are watching, when your own credibility feels like it's on the line.

That discomfort is the vulnerability. It's not a metaphor, and it doesn't get easier because you've read a book about it. It's the actual cost of the thing, and it's why so few leaders do it.

The exercise where leaders surprise themselves

Here's the part I find most useful, and the reason I keep running this with leadership teams.

Almost every leader I work with believes they ask questions. They'll tell you so directly, and they aren't lying. They see themselves as collaborative and curious and open to input, and that self-image is sincere. So I run an exercise adapted from David Verble's work on leader standard work, which I first learned from my friend and coaching partner Jeff Kosciejew.

It works like this. A leader records a real conversation with someone on their team. Nothing staged, just a normal working conversation. Then we transcribe everything the leader said, and we write it out one item per line. Every statement, every question, every aside, on its own line. Then we code each line as one of three things. T for a tell, where you delivered information or a decision. L for a leading question, where it had a question mark but you already had the answer. Q for a real question, where you didn't know what they were going to say. Then we count them.

The coding is what does the work, because you can't argue with it. It's your own words, in your own voice, sitting in a list in front of you.

What comes back is almost always a surprise, and the surprise is consistent. Most of what leaders count as asking turns out to be question-shaped telling. "Don't you think we should…?" "Have you considered…?" "Wouldn't it make more sense to…?" Every one of those is a tell wearing a question mark, and the person on the other side of the conversation knows it, which is why they answer the way you wanted them to.

Then we sit with a few questions together. Were your questions open-ended, closed, or leading? Were you exploring what the other person knows, or confirming what you already believed? Is there a pattern here you hadn't noticed before? And is there anything you'd want to change about how you communicate?

What follows is often the most candid conversation a leadership team has had in months. I've had leaders ask me to run the same exercise with the leaders in their own areas before we've even finished the debrief. The recognition it produces isn't about shame, and I'm careful to say so out loud before we start. It's about awareness, and you can't change a habit you've never actually seen.

I should also say clearly that none of this is an argument against ever directing. When the servers are down, direct guidance is appropriate leadership and has nothing to do with command-and-control. The exercise is about noticing when you're directing out of habit rather than because the moment calls for it.

The part that doesn't depend on your self-control

Here's my honest worry about everything I've written so far. Awareness is real, and the exercise produces it, but awareness fades. You'll walk out resolved to ask more and tell less, and four weeks later you'll be under pressure with a date moving and your instinct will reach for old habits, because that's the reflex that built your career in the first place.

Which is why the third person I'd point you to is the one who matters most in practice.

David Marquet took command of the USS Santa Fe on short notice, having trained for an entirely different submarine. Early on he gave an order that was impossible to carry out, and his crew started to carry it out anyway, because he was the captain and that's what you do. That was the moment he stopped giving orders.

What he built instead was a language pattern. Rather than asking permission, he asked his crew to say "I intend to…" They stated what they were going to do, and his job was to say "very well" and mean it. The decision moved to the person who already had the information, and his authority was acknowledged rather than exercised.

The reason this matters for everything above is that it's structural rather than behavioral. If the decision genuinely belongs to the person doing the work, your leading question stops being much of a problem, because it's just an opinion they're free to decline. Your weight has nothing to land on. You don't have to be perfectly disciplined about how you phrase things, which is a relief, because nobody is.

Marquet told the Santa Fe story in Turn the Ship Around!, and that's the one most people know. But the book closer to what I'm describing here is Leadership Is Language, which is entirely about the distance between what a leader meant and how it landed.

What makes "I don't know" safe to say

The objection I hear most often, usually from someone senior who has been quiet for most of the conversation, is that a leader who says "I don't know" looks weak. And I understand the worry. But I think it comes from hearing only half the sentence.

"I don't know" on its own is a shrug. It hands the problem back without a plan and it leaves the room less certain than it started. That's not what the CIO said in that auditorium, and it isn't what Brown or Schein are describing either.

The whole sentence is "I don't know, so let's figure it out, and let's go find data to back up the decision." That's a method. It replaces one person's guess with a process the whole group can run, and it gives everyone in the room a job. Nobody looks weak proposing that. What it actually does is move the standard for a decision away from who has the most confidence and toward what the evidence supports, which is a much better standard and one that survives the leader turning out to be wrong.

That distinction, in my experience, is what lets a skeptical executive accept the whole argument. They aren't being asked to be uncertain in public. They're being asked to be honest about what's known and specific about how the gap gets closed.

Where this shows up in the decisions that matter

I want to connect this to the work leaders actually spend their time on, because it isn't confined to one-on-one conversations.

Think about how the big decisions get made by senior leaders. Designing team structures. Planning budgets. Prioritizing which initiatives get funded and which get deferred another year. In most organizations these happen in rooms where the prevailing posture is advocacy, because everyone believes, usually correctly, that they're in a competition for scarce resources and the most confident case wins.

So what do you get? You get leaders arguing strongly for things they only half-believe, using information they know is half-assed, because the format rewards conviction over accuracy. I've watched this in funding conversations more times than I can count. Nobody in the room is being dishonest exactly. They're responding to what the room is asking of them, which is certainty they do not have.

And that's expensive, because those decisions are the ones that are hardest to reverse. A structure you designed on the strength of the best-argued case rather than the best-evidenced one will keep producing the problems you designed it to solve. A budget allocated the same way locks in that error for a year.

And notice what's actually wrong with those rooms, in Marquet's terms. The decision is sitting where the authority is rather than where the information is. The people who know most about whether a structure will hold, or whether an initiative is worth another year of funding, are usually not the people in the room arguing about it. They're a level or two down, and nobody asked them, and the advocacy format means nobody in the room has much incentive to go find out.

The alternative isn't a better meeting format with the same leaders. It's a leader willing to say, in that room, that they don't know yet and here's what they'd need to find out. Somebody has to go first, again. And the same reason it works in a one-on-one is the reason it works here: the moment one person stops performing certainty, it becomes possible for everyone else to stop too, and the conversation can finally be about what's actually true.

Where to start

So what can you do right away? Doing the full leadership role playing exercise I would normally recommend isn't realistic, so just be more mindful in your interactions this week. Are you always providing solutions, or do you ask questions that help your people grow? Do you pretend to know answers, or do you show a little vulnerability and offer to explore the answer together? How much curiosity can you sit with before you reach for the fix? And where in your week is there an opportunity to ask instead of tell?

And if you want one sentence to carry into your next meeting, take this one. "Is that a decision, or are you just thinking out loud?" Anyone can ask it, at any level, including the newest person on the team, because it reads as wanting to get it right rather than pushing back. It costs nothing, and it can save a team three sprints of work nobody actually chose.

You don't need permission to go first. You just need to notice the moment where you could.

Leadership and culture is one of five layers in the operating model behind the book Assembled. Aligned. Adaptive. It's the one I'd argue is least optional, because the questions leaders ask, or fail to ask, decide how clearly anyone can see the other four. Chapter 15 is where the trust chain and the coding exercise live, and you can find it here.

Hi, I'm Brian Link, an Enterprise Agile Coach at Huntington National Bank and Adjunct Professor at Columbus State Community College who loves his job helping people. I call myself a "Practical Agilist" because I pride myself on helping others distill the complexity of the agile universe into easy-to-understand, common-sense terms.

I'm the author of Assembled. Aligned. Adaptive., written for leaders who keep getting told to "build the environment where teams can succeed" without anyone saying what that environment actually is. It synthesizes fifty of the best thinkers on strategy, product, flow, organizational design, and leadership into one integrated operating model: five layers, one question each, and the leader behaviors that make each of them real. Evan Leybourn, co-founder of the Business Agility Institute, wrote the foreword.

Start with the free summary, order a signed copy, or find it on Amazon in paperback and (soon) Kindle.

My earlier book, the Practical Agilist Guidebook, covers the same mindset at the team level. It's a reference for practitioners, with Scrum Master and leadership tips, AI prompts, and recommended reading in each of its 24 topics.