Designing Yourself Out of Your Weaknesses
Refuse to spend years becoming passably okay at something — negotiate the constraint at founding, in writing.
- Difficulty
- Moderate
- Time to result
- ~ongoing to results
- Steps
- 5
- Confidence
- 93%
Shah has had zero direct reports across 18 years and 7,000+ employees at HubSpot. The framework is a deliberate role-design process done at founding: name what you are genuinely bad at, refuse to invest years becoming mediocre at it, redirect those calories into your strengths, and — critically — extract an explicit, pre-emptive commitment from your co-founder that nobody will backslide when the inevitable emergency arrives. The payoff is capturing the upside of scale (big bets, long horizons) without its downside (management mechanics).
Origin
Dharmesh Shah's founding negotiation with Brian Halligan at HubSpot's founders meeting, sprung in the moment rather than pre-planned. Shah has published the list of questions he believes all co-founders should ask each other.
Core principles
- 01You could become passably okay at your weakness with training and coaching — the question is whether you want to spend years of your life doing that.
- 02You tend to be good at the things you enjoy and enjoy the things you are good at; the two are highly correlated.
- 03The upside of scale (big bets, long-horizon plans) and the downside of scale (management mechanics) can be decoupled — but only if you design for it.
- 04It is amazing what you can get away with in terms of shaping the universe to your liking. Founders wrongly assume things have to go a certain way.
- 05The exception proves the rule: some non-native skills cannot be delegated or avoided (Shah's keynotes) — those you must actually learn.
How to run it
- 1
Hold a real founders meeting with a real list
Sit down in the founding week with an explicit list of questions co-founders should settle: who is CEO, how decisions get made, what each person will and will not do.
- 2
Name the thing you are actually bad at
Be honest rather than diplomatic. Shah had been CEO twice and concluded he was bad at it — specifically at management as a craft, which is a core part of the CEO role.
Pro tip The role you have already tried and failed at is the most reliable evidence you have.
- 3
Refuse the 'passably okay' trade
Explicitly decline to spend years becoming mediocre at your weakness. Redirect those same calories into the things you are good at and enjoy — because those are highly correlated and compound faster.
Watch out This only works if the thing is genuinely delegable. Shah made an exception for public speaking precisely because he could not delegate or talk his way out of it.
- 4
Extract the no-backsliding commitment up front
Anticipate the emergency: 'our VP of engineering just quit, can you be interim and have the team report to you until we hire?' Get your co-founder to promise, in advance, that this will never happen. Shah explicitly went back to Halligan — 'no no, Brian, you don't understand' — to lock this in.
Pro tip This is the step everyone skips. Without it, the arrangement dissolves at the first crisis and never comes back.
- 5
Design the rest of the company around your actual constraints
Extend the same logic to everything else. Both founders were night people, so HubSpot had a hard 'no meetings before 11am' rule; later relaxed to 'you may meet before 11am, just don't invite a co-founder.'
Pro tip Test the assumption before accepting the default. Most conventions are negotiable if you simply try.
In the wild
At the founding meeting, Shah declined the CEO role (he had done it twice and knew he was bad at management as a craft), and then — spontaneously — asked never to have any direct reports at all. Halligan agreed casually; Shah pushed back to make him understand that this had to hold even during future emergencies, and they had a heart-to-heart to lock it in.
→ 7,000+ employees, exactly zero direct reports from time zero. Shah says he is having a better time at 7,000 people than he did at 70, capturing the upside of scale — big bets, long-horizon plans — with almost none of its downside, and calls it one of the best decisions he ever made, for both himself and HubSpot.
Both founders discovered after the fact that they were night people, not morning people. Rather than conform to convention, they simply banned all meetings before 11am company-wide for the early years, then relaxed it: meetings before 11am are fine, you just cannot invite a co-founder.
→ A trivially simple rule that preserved the founders' best working hours and demonstrated that most workplace conventions are negotiable.
Common mistakes
Investing years into becoming mediocre at a weakness
Coaching and training can make you passably okay at almost anything — but those same calories, spent on a strength you enjoy, compound much faster and keep you engaged.
Not securing the commitment against emergency backsliding
The VP quits, someone must be interim, and the founder who avoids management inherits a team 'temporarily'. Without an explicit pre-commitment, the arrangement never survives the first crisis.
Assuming things have to go a certain way
First-time founders in particular default to convention on role structure, meeting hours, and titles without ever testing whether the convention is actually required.
Is it for you?
Best for
Co-founders designing their roles at the founding meeting, especially a technical co-founder who does not want to manage people as the company scales.
Not ideal for
Solo founders and small teams with nobody to absorb the delegated work, or anyone whose weakness is in a skill that genuinely cannot be delegated or avoided.
From the transcript
“I don't want to spend any years of my life becoming passively okay at something I would rather take those same calories and take the…”
“there's going to be a time in the company it was like oh our vpf engineering just quit like just be interim something”
“I get all the upside of scale which is I can make big bets”
From the episode
Zigging vs. zagging: How HubSpot built a $30B company
Dharmesh Shah (co-founder/CTO)