High Growth Handbook: Scaling Startups from 10 to 10,000 People

The book runs nine chapters on scaling, each followed by an interview. Chapter 4, on building the executive team, is the one Management Craft draws from — Gil’s own text and the Rabois interview that follows it.

• The trigger for hiring executives is the founder noticing the company stop working. Gil’s account of the moment: “you will notice that lots of things start to break down” [1] — communication gums up, the sales pipeline depends on the founder, promotions of inexperienced people fail. The payoff on the other side is equally plain: “Once you hire your first seasoned exec who works out, you will be grateful for her presence” [2].
• The founder’s problem is not evaluating the candidate. It is not knowing the role. Gil’s fix is the research call: “if you are hiring a CFO, go and meet three or four great CFOs at companies a few years ahead of yours or larger public companies known for excellence like Google or Netflix” [3].
• He specifies what to ask them, and it is about the process rather than the person: “What interview questions, work projects, tests, reference-checking questions, or other approaches would they take to vet a candidate in this area?” [3]
• Rabois names the same problem from the operator’s side. “That’s a very significant challenge for people hiring outside disciplines that they’ve actually worked in” [4] — a great engineer can hire a VP of engineering and still have no idea what separates a good CFO from an excellent one.
• His answer is the technique he credits to Brian Chesky: “One technique I learned, actually from Brian Chesky at Airbnb, is to go find the five best people in Silicon Valley that do that role, and just have coffee with them” [4]. What it buys is a scale, not a shortlist — “in that dialogue, I think you form an ability to benchmark the differences between an A+ and a B+, so that when you meet new candidates, actual candidates, you can triangulate against the people you’ve met that are clearly stellar” [4]. On the back half of the hire, Rabois is categorical about references — “you should thoroughly do reference checks on executives, without fail” [5] — and gives a threshold for the decision itself: “you want to pull the trigger on an initiative or an executive hire when you’re about 70 percent confident that it’s the right decision” [6].

• You are hiring your first executive for a function you have never run. Without this book you interview candidates against a standard you do not have. Gil and Rabois independently prescribe the same prior step — talk to people who are excellent at the role first — which is what The Calibration Call is.
• You want a number for how many calls. The two accounts here disagree, usefully: Gil says three or four, Rabois says five. That spread is part of why the tool recommends a range rather than a rule.
• You are writing the role definition for The MOC. Gil’s question list is aimed squarely at that: what they would hire for, what traits, what interview questions, what tests.
• You are deciding whether you are confident enough to make the offer. Rabois’s 70 percent is the most usable line in the chapter, and its logic is about false negatives — hold out for 100 percent and you lose the candidate.