Do the job for a while before hiring someone to do it
A founder who has never run sales cannot judge a sales leader by the interview. The remedy is to borrow the job before filling it.
If you have never done the job, how do you know what to want?
The question comes from a post Ben Horowitz published in October, Hiring Executives: If You’ve Never Done the Job, How Do You Hire Somebody Good?, and it names a problem most technical founders meet around the time the company raises its first large round. The engineer who built the product now has to hire a head of sales, of marketing, of finance. Every candidate interviews well. None of them can be judged on the substance, because the founder has no picture of what excellent looks like in that seat.
What fills the gap is usually surface: confidence, a known company on the resume, the right vocabulary. Horowitz’s answer is to act in the role for a while before hiring. Run the team’s meetings, hold the one-on-ones, set its targets. A few weeks of that shows what the job actually demands, and the founder can then write down the strengths that matter and the weaknesses that can be tolerated, and interview against that list.
A plausible case: a founder who spends a month running the sales pipeline discovers that deals stall on security reviews, not on pitching. The right hire is then someone who has sold to cautious enterprise buyers, which is a different person from the charismatic closer who would have won the interview. The founder would also know what to ask references, having seen firsthand which problems the new hire must solve in the first ninety days.
The advice has limits. Some roles cannot be borrowed safely. A founder cannot act as general counsel or as the finance chief preparing an audit. There, the substitute is to interview a few people who have excelled in that job and learn from them what to look for. Acting in a role also costs time the company may not have, and a founder who enjoys it can delay the hire far too long.