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Reflection — An Honest Take 8 min

Honest Take — Before You Begin

Honest Take — Module 3: Strategy & Positioning — Who You're For, and Why They Should Care #

This is the module I expect you'll find the most surprisingly enjoyable, and I want to flag the reason before you start, because the enjoyment is misleading. Strategy and positioning are pleasurable for engineers in a way discovery isn't: it's a modeling exercise. You sit at your desk, build a mental model of the market, identify the gaps, write the document. The work is solitary, intellectual, and produces an artifact you can be proud of. That is the problem. The same affinity for clean abstractions that makes the work pleasurable is what makes most engineer-founders' positioning documents wrong — positioned to the author's satisfaction rather than to the customer's recognition. The document feels right, and no real customer would describe their problem in its terms or recognize themselves in its "ideal customer profile." The discipline of M3 is doing the modeling while staying tethered to the M1/M2 transcripts. If you write the positioning doc without the interview transcripts open in another window, you have stopped doing the curriculum.

April Dunford's Obviously Awesome is the book I most want you to take seriously, because positioning is the most leveraged single skill in this curriculum: a correctly-positioned product can survive a mediocre roadmap, weak metrics, and average distribution; a mispositioned product cannot be saved by excellent execution downstream. The book is short — six hours — and you should read it twice, because the second reading is when you start seeing its moves in everyone else's marketing copy.

Then run the worked example through it. ClearCal's default category — "AI workplace productivity tool" — is contested by dozens of funded competitors, and the tempting move is to position against one of them: "like Reclaim but for X." Dunford will tell you why that's dangerous — positioning against a competitor anchors the customer to the competitor's frame. The harder and better question is whether ClearCal is even in that category, or whether it's closer to "an executive assistant in software form, for people who can't justify hiring one." If that's the position, everything changes: the competitive set becomes non-consumption rather than Reclaim, the pricing logic changes (M9), the channels change (M10). That cascade is the work this module makes you do, and it's why the module is harder than it looks.

The Thiel-versus-Moore tension is real and I want to set it up honestly rather than pretend the curriculum resolves it. Thiel's monopoly frame — find a market small enough to dominate from day one — and Moore's chasm frame — enter an existing category through a beachhead and expand — are not competing answers; they are diagnostic frames for different markets. Thiel's works when you can name a niche with natural reasons not to attract larger competitors; Moore's works when incumbents already exist. Most engineer-founder products are closer to Moore's case, but the Thiel question — is there a sub-niche where I could own 50% rather than competing at 0.5%? — is worth asking of every product you run, and the answer is arithmetic about your actual goals, not allegiance to a framework. Separately: read Thiel's useful chapters even if you find the author objectionable. Taking what's useful from sources you disagree with about other things is a load-bearing PM skill, because most of the people you'll learn this craft from are people you'll disagree with about something.

Two quality checks on whatever you produce. First, if your strategy document reads like a wishlist — goals without a named diagnosis of what is actually true and constraining about your situation — that's the signal to go get Rumelt, whose diagnosis-policy-action structure forces the constraint-naming that most first strategy documents fail. Second, at some point you will write a positioning sentence with "AI-powered" in it as if it were an attribute. Cross it out. "AI-powered" is what the technology is, not what the product does for whom; customers don't buy the mechanism. The crossing-out is the discipline, and you'll do it more than once.

One scope note for the merged curriculum: an earlier draft of this module ended with a full portfolio-comparison checkpoint — ranking your products against each other in writing. That work now lives in M4, where it gets the forced kill decision it deserves, so don't do it here. What M3 must produce is the positioning document for your most alive product, because M4's triage, M6's PR/FAQ, M9's pricing, and M10's channel choices all consume it as input. If the positioning is wrong here, every later module computes on wrong inputs.

Conclusion #

M3 produces the artifact the rest of the curriculum is built on, and it is also the most pleasurable module to do — which is the warning sign, because the pleasure can mask the failure to stay tethered to the transcripts. Dunford twice, the category question honestly, the Thiel-or-Moore diagnosis by market rather than by temperament, and a positioning document a real customer would recognize themselves in. Keep the transcripts open while you write.

Predictions #

  • You will draft the positioning document in 90 minutes, find it satisfying, and revise it three times over the following week as Dunford sinks in. The final version will look very different from the first.
  • The category your product should claim will turn out narrower and more specific than the category you've been saying at parties. The narrower category will feel smaller and scarier; it is correct.
  • You will write "AI-powered" (or your stack's equivalent) as a positioning attribute at least once and have to cross it out.
  • Reading the monopoly chapter will produce ten minutes of considering whether your market has a dominable sub-niche, followed by premature dismissal. Test the dismissal: name the 1,000 most-likely customers and check whether a sub-segment exists where you could own half.
  • If your strategy document reads as goals-without-constraints, you'll discover it only when you try to act on it. Run the Rumelt test before then: does any sentence name what is true and limiting about your situation?
  • Some part of your M3 work will collide with what you wrote in the M0 position document. Note the collision in writing; the diff matters more than either version.