Call notes from a first conversation. Anonymised, shared with consent.
This call was with someone about eighteen months into consulting: internal audit and financial advisory work, some exposure to analytics and tooling, a few side projects and self-initiated product ideas. A packed résumé with visible effort behind every line.
On paper the profile looked solid. In practice it was trying to do too much at once.
The call was booked as résumé feedback. It became a reset on how Founder's Office roles actually get evaluated.
What he thought was wrong
He believed it was a readability and formatting issue. Is this readable enough? Am I featuring the right skills? Would this get shortlisted if you were hiring for Founder's Office?
Underneath sat the real concern, which he said almost as an aside: he'd done a lot, and he wasn't sure recruiters could see what he was capable of.
What I focused on instead
Not fonts. Not spacing. Intent.
What role are you actually applying for? Are you positioning yourself as an executor or as someone who thinks about the business? How does anything on this page help a company make or save money? If I had a hundred résumés in front of me, why would I stop on this one? And can I trust you to think without being told what to do every day?
That shift was deliberate. Founder's Office isn't a skills-matching role. It's a judgment role, and résumés built for skills-matching read as noise to the person hiring for judgment.
What those questions revealed
The résumé was dense and unfocused. Projects were described as features rather than business bets, so the reader had to do the translation work themselves. Achievements were in there, buried under volume. Technical skills were heavily over-indexed for a role that doesn't need execution depth.
Most of all, it described what was done without ever explaining why it mattered.
Which meant it never answered the one question the hiring founder is actually asking: can I trust this person to think like a founder when I'm not in the room?
The real issue
Not a résumé problem. A misunderstanding of the role.
Founder's Office isn't a junior generalist seat, it isn't a place to display every skill you've collected, and it definitely isn't a role where you wait for daily instructions. It's a role where you anticipate problems, connect dots across functions, and push outcomes forward without hand-holding.
If a founder has to tell you exactly what to do every day, you aren't reducing their load. You're adding to it.
What I told him to change
Write from a business lens instead of an activity list. Every line should answer one question: how did this help the business earn, save, or decide better?
Then cut aggressively. If something doesn't support the role you want, it goes. Effort and relevance are not the same thing, and a résumé that proves effort at the cost of clarity loses to a shorter one every time.
Stop hiding signal under volume. If you generated revenue, make it impossible to miss. If it was a team effort, say so plainly, because inflated claims get found out in the first interview anyway.
Projects need positioning, not just existence. Name them, frame them, explain what problem they solve and how they could become a business.
And side projects aren't a red flag, whatever the internet says. To the right founder they're proof you understand what building costs. To the wrong founder they look like a distraction, and you shouldn't want that job.
How it ended
The conversation left formatting behind entirely.
Not "how do I make this more readable," but "how do I show I can think like someone responsible for the business?"
That distinction is most of what separates a Founder's Office shortlist from a rejection.