Better Questions

Picture a board meeting, third item, a decision that's been coming for a quarter. Someone asks the opening question the way people on boards ask questions: fast, and in the form that gets a fast answer. Can we get this done by year end? Is she the right person? Forty minutes later there's an answer, and everyone leaves believing it was made in the 40 minutes. Much of it was made in the question. Whoever asked had already settled, without quite deciding, what he was afraid of and what he was hoping for, and the question carried both into the meeting looking like an open hand.

Our questions reveal our assumptions, expectations, fears, and hopes. That's the cheap part. The expensive part is that a question loaded with the wrong fear gets a confident answer, and the answer is wrong in a way that takes a year to surface, and by then it has a budget.

You ask, then you decide. That's the order everyone assumes, and it's often backwards. You're paid for answers, and you know it, so the question gets the least attention of anything on the agenda.

What the question decides

Edwin Friedman, rabbi and family therapist, put it in one sentence in A Failure of Nerve: "Questions are always more important than answers, because the way one frames the question predetermines the range of answers one can conceive in response."

Ask how fast we can close this and you get a schedule, with a date the team will now defend. Ask what has to be true for this to be right at this price and you get a list, with an item on it you didn't want to see. Same deal, same data. Whoever asked chose which meeting you were going to have.

Daniel Kahneman, in Thinking, Fast and Slow, found what the mind does with a hard question: "when faced with a difficult question, we often answer an easier one instead, usually without noticing the substitution." "Should we buy this company?" is hard. "Do I like this management team?" is easy, so it's the one that gets answered, and the answer gets filed under the hard question's heading. You did it on the way in.

Say the question on the agenda is whether to back the team through the next fund. Under it, unasked, sits whether you can stand to be the one who didn't. You decide on the second and answer the first at length, with slides. Everyone at the table can feel the second one and nobody names it, because naming it would be a question, and questions are for people who don't yet know.

They are preloaded. The table is set. The system is rigged.

The load is whatever you settled before you walked in, and it arrives in a shape that looks like curiosity. The people across the table can usually read it before you can. A good seller answers the question you asked. A great one answers the question under it, and the great ones are the reason the question under it is worth knowing before the meeting.

If one gives an answer before he hears, it is his folly and shame.

Loading the question is answering before you hear.

Where the answers come from

We want to believe someone has the answer. We love our answers and the experts who spew them. Questions are discounted.

An expert is someone who chose the question in advance and now sells you the answer. The sale works because you didn't notice that the choosing was the expensive part. The framework, the benchmark, the playbook from the last deal: each is an answer to a question somebody else asked about somebody else's company. The benchmark that says sales should be 12 percent of headcount answered a question a software company asked about itself in 2019, and you're a distributor in 2026. Coin in, answer out, and nobody asked what you wanted it for. There's an old Texas line for the expert at the end of his patience: I can explain it to you, but I can't understand it for you.

A framework used to check your own question is a tool. A framework used instead of one is a coin in the slot.

Buying an answer is a trade like any other. Charlie Munger had a question investors already know and mostly skip: every time you buy, someone is selling, so ask why you're on the right side of the trade. It's easy to ask and hard to hear answered, so it goes unasked in the meetings where it would have mattered.

Why it gets harder with seniority

The Munger question goes unasked most often by the people best placed to ask it, and Warren Berger, in A More Beautiful Question, found out why: "If fear is the first enemy of questioning, running a close second is knowledge. The more you know, the less you feel the need to ask."

In an industry, 20 years is 20 years of answers, mostly right, which is the problem. You stop noticing when you're guessing instead of knowing, because the two feel the same from inside. You walk into a new situation carrying a question that fit the last one. The question that fit the last acquisition, how fast can we integrate, walks into the next one and produces a plan, and the question that mattered there, whether the founder stays after the earnout, was never asked because the plan was already on the table. That's the answer that takes a year to surface.

To ask is to admit you don't know and that you care, and neither is comfortable when you're the senior person at the table. Your position taught you not to ask.

The yes-or-no question

In a complex world, we seem to crave binary answers all the more from leaders. The craving is yours as much as your team's.

One October I sat with a room of business leaders in Seoul and watched the hardest questions of the day get asked in the only form that could get a yes or a no. Go or not? Him or not? In or out by Friday? It wasn't a Korean habit. Watch what happens at your own table when the question is hard: somebody reshapes it to yield a yes or a no. The binary feels like decisiveness and is usually a poorly loaded question, because it was built to end the conversation, not to find anything out.

The alternative is a better-loaded question, asked once. What would have to be true? What are we assuming that we haven't checked? Who would we call if we wanted this to be wrong? Each gets you to a decision faster than yes or no, because each puts the assumptions on the table. When answers are multiplied, you have found a meaningful question.

The question asked to hide

There's a way to be wrong in the other direction, by asking too much. If a question can carry your fears into a meeting, the question you ask in order not to decide carries the biggest fear of all. Adam Grant, in Give and Take, calls asking questions a form of powerless communication. It works when you have no standing, which is why junior people are good at it and why it stops working the day you get the title. When you have all the standing at the table, a question is a fine place to hide. An hour of thoughtful questions, everyone nodding, nothing decided, and the one who asked the most leaves feeling like the wisest one there.

Those questions reveal something too, usually a fear of being the one who chose. A question asked to find something out has a cost: you might get an answer you have to act on. A question asked to hide has no cost, which is why it's so comfortable, and why it isn't a question at all. It's a decision not to decide, and it looks like curiosity.

The one discipline for both is loading the question once, before the meeting, knowing what it carries, and acting on what comes back.

The seat nobody wrote

If that much of the deciding gets done in the question, the scarce person in any company isn't the one with the answers. Answers you can hire or buy. The scarce person walks in with the better question, the one loaded with something other than fear, and there was no seat for him at that board meeting because nobody wrote the job that way. The head of sales is responsible for the revenue answer and the CFO for the cash answer, and nobody at the table is responsible for asking whether year end is the right question at all. The person who holds that seat spends the week before the board meeting on the agenda, not the deck, and the question he brings is the one the deck was built to avoid.

A back o' napkin approach to designing your executive team: 1. List your biggest/most vital questions. 2. Hire leaders who are responsible for those answers. 3. For advanced leaders, reserve a seat for someone who hunts for better questions.