Questions to Ask During Hot Seat
Twenty questions for a hot seat session, where one person's proposal is opened up to hard questioning: testing evidence, assumptions, resourcing, risk, and stop rules, without turning the review into an attack on the presenter.
The questions
Open any question for the note
What evidence sits behind this, and who checked it?
Why ask it
Separates analysis from assertion at the start. The common failure is a chain that circles back on itself: a number from a deck, which came from an earlier deck, which came from the presenter's own estimate.
Which numbers in here are measured, and which are estimates you filled in?
Why ask it
A presenter who can immediately mark the difference has done the work. One who treats every figure as equally solid is usually carrying an assumption they have stopped seeing as an assumption.
What other options did you consider, and why did you rule them out?
Why ask it
People who genuinely compared options can name the one they nearly chose and what tipped it. When the alternatives sound like straw options, the conclusion probably came first and the comparison was assembled afterwards.
What assumption, if it turned out to be wrong, would change your recommendation entirely?
Why ask it
Forces a single point of failure into the open. If they name something trivial, press once more: the reluctance usually points at the assumption they are least sure of.
Who outside this room has seen it, and what did the people who would have to live with it say?
Why ask it
Reveals whether the plan has met contact with the people who would run it. Feedback only from peers and sponsors, and none from the operators, is the pattern behind most plans that fail in implementation.
What does success look like six months from now, and which number would show it?
Why ask it
A specific metric and a date make the plan falsifiable. Answers about momentum, alignment, or capability building signal that nobody has agreed what would count as it having worked.
What would this take in people, money, and time, and where would those come from?
Why ask it
The second half is the one that gets skipped. A plan that needs two engineers is a proposal to take two engineers off something else, and the presenter should be able to say what.
What is the smallest version of this we could run first, and how long would that take?
Why ask it
Tests whether the plan can be staged or is all-or-nothing by design. A presenter who resists any smaller version is often protecting the decision from evidence rather than protecting the design.
What have you already tried here that did not work?
Why ask it
Invites the history most presentations leave out. If nothing has been attempted, this is an untested idea rather than a refined one, which is fine as long as the room knows which it is looking at.
Has anyone else done this, and what happened to them?
Why ask it
Look for a named case with an outcome, including the failures. General appeals to what leading companies do tend to mean nobody has looked closely enough to find a comparable situation.
What would have to be true for this to fail, and how would we notice it happening?
Why ask it
Two questions in one, and the second matters more. Naming a specific signal, an owner, and a review point is the difference between a risk register and a monitoring plan.
What is the worst realistic outcome, and what would it cost to unwind?
Why ask it
Realistic rules out the theatrical worst case. What you want is the reversibility cost: contracts signed, data migrated, customers told, people hired. Cheap to reverse changes how much certainty you need up front.
If the first results are poor, what would make you keep going, and what would make you stop?
Why ask it
Agreeing a stop rule before the money is spent is the only time it can be agreed cleanly. If there is no answer to the second half, expect this to run until the budget ends rather than until the evidence does.
If we say yes to this, what gets less attention or stops entirely?
Why ask it
Everything looks affordable in isolation. A presenter willing to name what they would drop is treating capacity as finite; one who insists nothing suffers is quietly assuming spare capacity nobody has.
What would have to change elsewhere in the organization for this to work, and who owns that change?
Why ask it
Most plans have a dependency on another team's behavior. Naming the owner turns an assumption into a conversation someone has to actually have, usually before the plan can be approved.
Does the team have the skills to run this, and if not, how does that gap get closed?
Why ask it
Distinguishes a plan built for the team that exists from one built for a team that would have to be hired. Both can work, but hiring time is often left out of the timeline entirely.
Who will push back on this, and what is your answer to their strongest objection?
Why ask it
You are testing whether they have engaged with the best version of the opposing case or only the weakest. Presenters who can state an opponent's argument well are usually the ones who can get a plan through.
How would you explain this to the person who has to do the work on Monday morning?
Why ask it
Strips out the framing that only works in a boardroom. If the plan cannot be said plainly in two sentences, it will not survive being relayed down two levels of an organization.
What would you do differently with twice the budget, and what does that tell us about this version?
Why ask it
Reveals which constraints are actually shaping the recommendation. Sometimes the answer shows the plan is a compromise nobody believes in, and sometimes it confirms the constraint improved the design.
What question were you hoping we would not ask?
Why ask it
Works best at the end, after the pressure has come off. Asked with genuine goodwill it often produces the most useful minute of the session, and it signals the review was about the plan rather than the person.
Running a Hot Seat Well
Practical guidance for the conversation itself
How to Press Without Wrecking the Room
Question the plan, never the person
Ask what evidence supports this rather than why do you think that. The first invites a defense of the analysis; the second invites a defense of the self, and the room learns nothing from the second.
Set the terms before you start
Say plainly that the session is meant to find the weak points, that the presenter is not being evaluated, and roughly how long it will run. Without that framing, hard questions read as a verdict already reached.
Take one thread to the end
Three people asking one question each produces surface answers. One questioner following the funding assumption through four turns is where the actual problem usually surfaces.
Accept I do not know
Treat it as an acceptable answer and write it down as a follow-up. If not knowing is punished, the room will start getting confident guesses instead, which is far worse.
Close with the decision, not the critique
End by stating what happens next: approved, approved with a smaller first step, or come back with two specific things. A session that ends in general unease wastes the work everyone just did.
Question Sequences
Testing the evidence
- 1What evidence sits behind this, and who checked it?
- 2Which numbers are measured, and which are estimates?
- 3What other options did you consider, and why did you rule them out?
- 4What assumption, if wrong, would change your recommendation entirely?
Testing the downside
- 1What would have to be true for this to fail, and how would we notice?
- 2What is the worst realistic outcome, and what would it cost to unwind?
- 3If early results are poor, what would make you stop?
- 4What is the smallest version we could run first?
Testing whether it can actually be done here
- 1What would this take in people, money, and time, and where would those come from?
- 2If we say yes, what gets less attention or stops?
- 3What has to change elsewhere, and who owns that change?
- 4Does the team have the skills, and if not, how does that gap close?
Common Mistakes
- Asking a question you already have the answer to in order to demonstrate that you have it. The room notices, and the presenter stops answering openly.
- Piling on. Once one person has found the weak point, a second and third questioner on the same point turns a review into a public correction.
- Leading questions that smuggle in your preferred conclusion. You get agreement rather than information.
- Letting a confident tone substitute for an answer. Repeat the question once, plainly, before moving on.
- Ending without writing down what was unresolved, which means the same session happens again in three weeks.
- Running it on someone who was told it would be a routine update. The format only works when the presenter agreed to it in advance.
If You Are the One Presenting
- 1Mark your own estimates before anyone else does. Saying this figure is my assumption removes the most damaging discovery from the room.
- 2Bring the strongest objection yourself, with your answer to it, in the first few minutes.
- 3Have the smallest testable version ready as a fallback, so a hesitant room has something to approve.
- 4Say I do not know and note who will find out, rather than reasoning aloud toward an answer you do not have.
- 5Write down every unanswered question during the session, and send the list back within a day with owners against each one.