Interrogation Kit

Five Questions Before You Call It a Strategy

A pre-flight checklist for the new PM about to send a strategy doc into a room full of people who will agree with it politely and ignore it entirely.

There is a very specific kind of disaster that happens around month four of being a new PM: you volunteer to "pull together the strategy" for something. You write an eight-page document. It gets reviewed on a Friday. Everyone says nice things. Nothing changes.

The problem was not the writing. The problem was that the document answered the easy questions (what will we build, what metrics will we chase) and skipped the ones that actually force a decision.

The five questions below are a pressure test. Before you circulate anything with the word strategy on the front page, run the draft through each of them. If you can't answer one cleanly, you haven't finished writing yet. You've just written a prettier wish list.

Question 01

What does winning actually look like — in a sentence, with a date?

Not a mission. Not a vibe. A state of the world you can point to and say "that's the thing."

Failure mode: "To be the leader in our category." Leader how? Measured by what? Over whom? By when? "Leader" is what you write when you have not decided.

The test is simple: if two smart people read your winning condition and come away with different mental pictures of the year being over, your winning condition is a Rorschach test, not a target. Replace it with something that can be photographed.

Question 02

Which users, and which of their alternatives, are we actually fighting?

Your real competitor is not the company with a similar logo. Your real competitor is whatever your user does on Wednesday afternoon when they don't open your product.

Failure mode: "Everyone who needs better [category] tools." There is no such person. Every buyer has a specific workaround — a spreadsheet, a meeting, a Slack thread, a prayer. Name it.

A new PM will often describe their user as a segment ("mid-market operations leaders"). That is a demographic, not a decision. Push one layer deeper: what are those people doing right now instead of using your product? The honest answer is usually more specific and more humiliating than the deck allows. Write that down anyway.

Question 03

Why us, and why not a team of four smart people with a weekend?

This is the part of the strategy where you describe your unfair advantage. Most strategy docs skip it, which is how you end up with businesses that are theoretically good and practically cloneable.

Failure mode: "Our team is passionate and experienced." Good news — so is everyone else's. "We ship fast" is not a moat. Neither is "we care about our customers."

Real answers sound like this: we have a distribution channel nobody else can reach; we have five years of proprietary data; we have a structural cost advantage that our competitors' business models can't copy without cannibalising themselves; the incumbents can't match this without undermining their revenue. If you cannot say something in that register, you do not have an advantage. You have ambition, which is different.

Question 04

What are we not doing — and who is going to be unhappy about it?

A strategy is, structurally, a list of refusals. If your doc has no refusals, it is not a strategy. It is a yearbook.

Failure mode: A section titled "non-goals" that contains three bland lines nobody would have done anyway. ("We will not pivot to hardware." Congratulations.)

Real non-goals cost you political capital when you publish them. They kill somebody's favourite project. They close a market you quietly wanted to keep as an option. The fact that writing them down feels slightly dangerous is the proof that they're real. A strategy is a commitment; a wish list is a hedge. You can tell which one you've written by the number of people who wince when they read it.

Question 05

What has to be true for this to work — and what would make us change course?

Every strategy is resting on assumptions. Name them, and name what data would invalidate them. Otherwise you'll be defending this document in April with arguments that were already wrong in February.

Failure mode: A strategy with no falsifiable claims. Everything can be re-described as "we're still on track" if nothing was ever defined as "off track" in advance.

The most useful thing you can put at the end of a strategy doc is a short section called "What would change my mind." Two or three signals that, if you saw them by a specific date, would force a revisit. Nobody does this. It is the single highest-value paragraph in a strategy document, and it costs nothing to write except honesty.

How to actually run the five questions

You do not run this on your own. You run it on a draft, with one other person, in a 45-minute working session. Their job is to play the role of a thoughtful cynic. Their one rule: they are not allowed to say "that's fine." They must either challenge the answer or suggest a sharper version.

Run each question for eight minutes. You will get through all five. You will have a list of four or five weak spots. You will now have a second draft that is meaningfully better than almost any strategy doc circulating in your org, and you built it in under an hour.

A word on the rooms where this lives

As a new PM, you will not be the person presenting The Strategy. What you can be is the person who walks into the room with a printed copy and, in the Q&A, asks a version of question four. "What are we explicitly not doing this year that we could have?" If the answer is vague, everyone in the room now knows what you know — which is that the strategy is a hope wearing a blazer.

You do not need authority to ask the question. You need the question.

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