Two owners bring the same problem to their boards in the same week. The first types: “Should I raise my prices?” The second types: “I am raising prices 8% on January 1. Gross margin is 32%, I won 17 of my last 20 quotes, and nobody argued about the number. The risk I can't size is losing my two biggest accounts. Tell me where I'm wrong.” The second owner gets the better session every time, and it has nothing to do with how smart they are. They gave the board something to argue with.
About one question in twenty that reaches a session is some version of “what assumptions am I making that could be wrong?” Those sessions are consistently the best ones in the record. The owner leaves with a specific objection to a specific plan instead of a general talk about pricing. This post is about how to ask that way on purpose, and what to do with the answer once you have it.
Why “What Should I Do?” Gets a Generic Answer
An advisor can only attack what is on the table. Ask a sales advisor “should I raise prices?” and the honest answer is “I don't know yet; what is your close rate and what do prospects object to?” Marcus Reed will ask exactly that, and you have spent a turn of the session being asked a question you could have answered up front. Ask three advisors the open version and you get three parallel talks, each from its own discipline, none of them about your business in particular. They are not wrong. They are filling in the facts you left out with the facts that are usually true, and “usually true” is the definition of generic.
Give them a position and the session changes shape. Now David Chen is checking your 32% margin against your 8% raise and telling you the break-even is losing one account in five. Marcus Reed is asking which two accounts you are afraid of and whether you have called them. Tyler Brooks is asking what you would do in March if both of them left. Three advisors arguing with one plan, and with each other, is a different product from three advisors each proposing their own.
There is a second reason, and it is about you. A plan you wrote down before the session is a plan you own after it. “Build me a pricing strategy” produces a document the board owns and you will quietly ignore. “Here is my pricing decision; break it” produces a decision you made, with the holes patched. The owner's guide to working with your board puts this as rule two: show your thinking first. This is what that rule looks like in practice.
The Shape of a Question Worth Arguing With
Four parts, in order, one short paragraph each. You can write the whole thing in ten minutes, and the ten minutes is most of the value.
- The situation, with the numbers that matter. Not the history of the company. The two or three figures the decision turns on: revenue, margin, hours, close rate, customer count, whichever apply. If you do not have a number, say so. That is useful information too.
- What you have already tried or ruled out. This stops the board spending its first answer recommending the thing you did in June.
- Your position. The decision you intend to make, as a sentence with a verb and a date. “I am going to,” not “I am thinking about.”
- The specific thing you want attacked. The assumption you are least sure of, the risk you cannot price, or simply: “tell me the strongest case against this.”
The business is an illustrative composite: a two-crew residential cleaning company, the owner working on one crew three days a week, turning away about two jobs a week since spring. Every figure is part of the example.
Weak: “I'm turning away work. Should I hire another crew or raise prices?”
Strong: “I run two cleaning crews and work on one of them three days a week. We turn away about two jobs a week, roughly $9,000 a year in bookings. The average job is $180 and gross margin is 38%. I tried a waiting list; nobody waits. I am going to add a third crew in January rather than raise prices, because my customers compare quotes and I think a raise loses more than it gains. That is the assumption I'm least sure of. Tell me where I'm wrong.”
Same business, same decision. The second version takes ninety more seconds to type and hands the board five things to test: the $9,000 (bookings, not profit), the 38% margin, “nobody waits,” the belief that customers are price-sensitive, and the owner's own three days on a crew, which she mentioned as a fact rather than a problem and which any operations advisor will go straight for.
What the Argument Sounds Like
Here is the shape of the exchange on the strong version. These are illustrative responses in the advisors' own voices, not a client's session.
Dana Mitchell, Operations Advisor
You brought a count of the jobs you turn away and the thing you tried to fix it. Most owners bring me a feeling. Now look at what else you wrote: you run a crew yourself three days a week, and you put that down as a fact rather than a problem, which tells me you have never costed it. Before a third crew exists, walk me through the two days you are not on a truck. Who confirms tomorrow's jobs, who takes the callback when a customer is unhappy, who orders supplies? If the answer to all three is you, a third crew does not add capacity. It adds a third thing only you can run. Bring me the hours you spent last week on work that was not cleaning.
Tyler Brooks, Startup Strategy Advisor
You named the assumption you are least sure of, which is more than most founders will do. So let's go after it. Your whole plan rests on one sentence: “my customers compare quotes.” Some do. You have never tested whether the ones who turn into weekly accounts do, and those are the only customers a crew decision should be built around. You have also built no trigger. If the third crew still is not full by April, is that a slow start or a failed bet? Decide that now, before the van is leased. The part of this plan that worries me is not the hire. It is that nothing in it tells you when to stop.
Notice that neither advisor answered “hire or raise prices?” Each went after one assumption the owner had stated, and they went after different ones. Dana's objection is operational: the owner is the bottleneck, and a third crew makes it worse. Tyler's is strategic: the plan has no failure condition. The owner now has two specific things to resolve and a disagreement to bring back. That is a session worth the hour. “Should I hire?” would have produced a hiring checklist.
Three Ways to Argue Back
The first answer is where most owners stop. The second and third turns are where the board earns its seat.
1. Correct the premise
“You read the $9,000 as profit. It's bookings, and at 38% that is about $3,400.” An advisor working from a wrong number will give you a confident wrong answer, and will revise it the moment you fix the number. The board is only ever as good as what you told it. If an answer seems off, look for the fact it is missing before you decide it is wrong.
2. Make two advisors fight
“Dana says I'm the bottleneck, so don't hire yet. Tyler says the real risk is that my customers aren't who I think. Which one decides it?” Your advisors answer independently and do not read each other's responses, so this is a question only you can ask, and it is the most valuable one in the session. The Board Sessions on this blog end exactly this way: a named disagreement in the record, and the owner's call.
3. Ask for the kill condition
“What result in sixty days would make you change this recommendation?” A recommendation with a failure condition attached is a plan. One without is an opinion. Write the condition in the record and ask about it when the date comes.
What Goes in the Record
When you argue well, the Boule Record from the session looks different. It does not say “discussed hiring.” It says what you came in intending to do, what the board objected to, and what changed. For the cleaning company it might read like this.
| Position on entry | Third crew in January; no price change. Owner's stated weak point: customers are price-sensitive. |
| Objections | Owner's three days on a crew uncosted; a third crew adds load to the one person who cannot be duplicated (Mitchell). No failure trigger defined for the hire; price sensitivity of repeat accounts assumed, not tested (Brooks). |
| Decisions | 1. Hire held, not cancelled. Reopens at the first session after the two items below are in. 2. New rates go on the next 20 new quotes as a test; existing accounts untouched. |
| Action items | Owner — log every hour of non-cleaning work for two weeks. Due: next session. Owner — report closes and objections, in the prospect's words, on the first 20 quotes at the new rate. Due: the session after next. |
| Open tension | Fix the owner's role before adding capacity (Mitchell) or test the price assumption first (Brooks). Owner's call once both reports are in. |
Evelyn Hart writes it that way because the next session opens with it. If the owner comes back in two weeks and asks about hiring again, the board does not start over. It asks what the quote test showed. That is the accountability loop, and it only works when there was a position to hold you to. An open question leaves nothing in the record but a topic. What a Boule Record contains shows a complete one, and what the board said about ChatGPT covers why the loop, not the advice, is the difference.
Before Your Next Session
Take the question you were going to ask and rewrite it until it contains three things: a number, a first-person sentence with a date in it, and the word “wrong.” If you cannot write the middle one, you do not have a decision yet. You have a topic, and the honest version is “I can't choose between A and B; here is what scares me about each.” That is still a position. The board can argue with a fear if you tell it what the fear is.
Then bring the argument back. The owner who returns with the quote test done and asks the board to update its recommendation gets a sharper second session than the first, every time. The ones who start fresh each week get a fresh set of generic answers each week, and the record shows it.
Frequently Asked Questions
Why does asking an advisory board “what should I do?” get a worse answer?
Because the board has to invent the facts you left out, and it fills them in with what is usually true, which is the definition of generic. A stated position with the numbers attached gives each advisor something specific to test, so you get three critiques of one plan instead of three unrelated lectures.
What should I include when I bring a decision to my board?
Four things, one short paragraph each: the two or three numbers the decision turns on, what you have already tried or ruled out, the decision you intend to make with a date on it, and the assumption you most want attacked. If you do not have a number, say so; that is useful information too.
What if I disagree with my board's answer?
Say so, with the fact the advisor was missing. Each Boule Board advisor answers independently in its own persona and discipline and does not see the others' responses, so an answer that seems off is usually missing a fact rather than wrong. Correct the premise, ask which of two disagreeing advisors should win and why, and ask what result would change the recommendation. The Boule Record keeps all three.
The Board Brief
Sign up and get the one-page Boule Record template: the decision on the table, what each advisor said, action items with owners and dates. Then, every two weeks, the Brief: one decision an owner faced, one number worth knowing, one question to bring to your board.
“I’m adding a third crew in January instead of raising prices, because my customers compare quotes. That’s the assumption I’m least sure of. Tell me where I’m wrong.”
Bring it to a weekly session. Advisors from finance, sales, operations and marketing argue it from their own corners, and you leave with a record of what was decided, who owns it, and by when. Next week, the board asks how it went.