The wall isn't random.
It has a shape.

Q1 · Buyer evolutionWhen you close your eyes and picture the exact buyer you want more of — the one who bought, loved it, renewed, and referred — is that buyer in your sales deck?

• Yes — the deck was built for them and still fits
• They're in there, but the deck talks to someone slightly different now
• My best customer and my "official" target customer aren't the same person anymore
• I just pictured a specific person — and I'm not sure anyone else on my team would have named the same one

Q2 · DifferentiationThe last time a prospect seriously asked "what makes you different from [competitor]?" — what actually happened?

• I gave a clear answer I'd given before and it landed
• I gave an answer, but I could feel myself reaching
• I pivoted to features, pricing, or the relationship
• I can't remember the last time someone made me answer that out loud

Q3 · Loss patternThink about the last deal you were sure you'd win and didn't. When the prospect finally told you why, the real reason was:

• A specific competitor advantage and I knew it going in
• What they told me and what I suspect are two different things
• "Timing" or "budget" — the polite version of "not quite right"
• I never got a straight answer and I stopped chasing it

Q4 · Pricing powerWhen you think about raising prices, the first feeling that shows up is:

• Confidence — I have the data and I know buyers will absorb it
• Hesitation — I know I should, but I don't have clean justification ready
• Fear — a chunk of the base would leave and we can't afford that right now
• I haven't seriously thought about pricing in a while

Q5 · Founder-led pipelineImagine you had to go three weeks completely offline starting Monday. What happens to the pipeline?

• Nothing — the team would run the motion and I'd come back to a normal week
• It would wobble, but the deals already in flight would close
• Deals would stall and I'd come back to a cleanup job
• The pipeline is me — this question is almost absurd

Q6 · RepeatabilityYour best salesperson — whether that's a rep or you — what's driving their close rate, really? The pitch or the person?

• Mostly the pitch — the motion travels to whoever's running it
• Half and half — the motion works, the right person amplifies it
• Mostly the person — it's hard to separate the two
• I've never actually tried to separate those

Q7 · Forecast accuracyWhen you close the quarter and compare it to the forecast you gave your board or team 90 days earlier:

• It's close — and when it isn't, I know why
• It's within range enough that nobody asks hard questions
• It's off often enough that I've quietly stopped pointing at the forecast
• We don't really forecast. We report what happened.

Q8 · Channel concentrationYour best-performing acquisition channel gets meaningfully worse overnight — an algorithm change, a policy shift, one partner goes quiet. How long before you feel it in revenue?

• Months — we're diversified enough
• A quarter — uncomfortable but survivable
• Weeks — it would genuinely hurt
• It already happened once and I still remember the year it cost us

Q9 · Shadow rolesWalk your org chart in your head. Find the functions where, if pressed, you'd admit you're still running the show. How many are there?

• None — every function has a real owner and I've actually let go
• One — and it happens to be the one I should still own
• A couple — I know which ones; I just haven't hired past them yet
• I'd rather not count

Q10 · Hire calibrationThink about your most recent senior hire — the one who was supposed to take something off your plate. Six months in:

• They took it and I haven't looked back
• They took it but I'm still checking in more than I expected
• They took it, and I've quietly taken parts of it back
• I haven't made one recently — I keep thinking I should

Q11 · Decision velocityHow many Slack threads or email chains are pinging you right now, waiting on your input to move forward?

• A few — my team makes most calls and flags only the real ones
• A normal amount — it's a weekday
• More than I can clear today, and that's been true for months
• I've started muting threads to cope

Q12 · The missing roleThere's a hire you've been circling but haven't made. What's the real reason it isn't hired yet?

• It genuinely isn't the right time and I have a specific reason
• I can't justify the cost against an unknown return
• I haven't found the right person and the search has drifted
• I think I'm afraid of what it means to hand that over

Q13 · Time allocationPick your last full workweek. Honestly: how much of it was work you'd want your replacement CEO to be doing, and how much was work you'd be embarrassed to hand them?

• Most of it was the replacement-CEO work
• Split — and I felt the tension the whole time
• Most of it was work someone else should be doing
• I don't like this question

Q14 · RecoveryWhen you took your last real break — phone off, laptop closed, brain actually off — what year was that?

• This one
• Last year
• The year before that
• I'd have to check photos

Q15 · Strategic timeThe last time you sat down to think about the company — not plan, not review, just think — what happened?

• It's on my calendar and I protect it
• I try, but the inbox eats it more often than not
• I think in twenty-minute gaps between meetings
• Thinking is something I used to do before I ran this company

Q16 · Unique contributionIf I asked you right now to name the one thing you can do that nobody else in the company can — and that actually matters for the next 12 months — how long would it take you to answer?

• Immediately, and I'm doing it
• Immediately, and I'm not doing enough of it
• It would take me a minute of real thought
• I've been avoiding this question longer than I'd admit