Design Around Flaws

The reframe

Asked what weaknesses he must overcome to reach where he wants to be in a decade or two, Eric Glyman critiques the question itself. "If you're a one-person company, 'how can I change to get better' is exactly the right question. But if you're a 10-person or thousand-person company, you're on a team. You can change, or you can change how the team is constructed. That's the more interesting way to think about it."¹

At organizational scale, in Glyman's framing, a founder's flaw is a design parameter rather than a character defect to be fixed. It can be addressed by self-improvement or by constructing the surrounding team to be performant despite it, and he treats both as legitimate. "It's actually totally fine to have huge flaws, and you could decide to fix them, or you can say I'm going to design my life or the company to be performant in that context."

The worked example

Glyman offers a self-diagnosed flaw he calls "probably very surprising for Ramp scale." Faced with roughly a hundred important things to do, his mind starts on a blank sheet, writes down the top five to ten, and then forgets the rest and does not do them. That habit was fine when only one or two things mattered early on, but he describes it as company-killing at scale if ninety percent of issues are consistently ignored.

His compensation is not to fix the habit but to hire around it. "I surround myself with people who are operationally unbelievable, incredibly good at triaging, cascading, getting things done, making things move." The prioritization flaw is left unfixed and engineered around by the organization's design.

The boundary

Glyman marks a limit. The concept applies cleanly to capability and coverage gaps, less so to temperament. He contrasts his own case with Sam Parr's, whose flaw is emotional regulation and impulse control, captured in the rule not to make a decision "when hungry, pissed, or really happy," but instead to say "let me think about it." A personal-operating flaw of that kind cannot be fully outsourced to a team. The principle covers organizational-coverage gaps; the temperament side belongs to personal practice.

The idea is adjacent to but distinct from the argument that a leader cannot simply hand off tasks and walk away, sometimes called the delegation myth: that concerns handing off work, while designing around flaws concerns hiring to cover a permanent gap in oneself. It also depends on the people doing the covering being genuinely strong in exactly the dimension the founder lacks, which is the premise of the A-player framework. Glyman adds a hiring tell borrowed from Sam Parr's reference checks: ask a reference to rate a person one to ten, which is almost always an eight or nine, then ask what would earn the extra point. The answer surfaces the real weakness, and knowing it lets a manager decide whether the flaw is one they can design around.