Chapter 7

Leadership team

A conductor carrying a thick, well-worn score walks to the podium in front of a waiting orchestra

Even the best get it wrong

“The Michael Jordan of exec recruiting only gets it right 2 out of 3 times.”

Tony XuDoordash

First principles of executive hiring

  1. The CEO should lead the hiring process. No one knows the company better than you do and no one will sell the company better.
  2. Conduct no more than 2 exec searches at a time. Exec searches take 3–4 months and are incredibly time-consuming. You can’t do a good job if you take on more searches.
  3. Hire for the next 12–18 months. Avoid hiring a great exec at the wrong stage. Look at the current team and 12–18 months ahead, then identify critical gaps.
  4. Org structure and exec hiring go hand in hand. You might need to adjust the structure to set execs up to solve key problems.

Hire for the right stage

Make damn sure you hire executives for the right stage.

$1M$10M$40M$100MEVANGELISTMR. MAKE ITREPEATABLEMS. GO BIGMR. DASHBOARDS

The executive hiring process

StageTime
Speak to subject matter experts1–2 weeks
Choose the hiring teamNo set time
Draft the job scorecard1–2 weeks
Source candidates2 weeks
Build the relationship1 month
Evaluate candidates1 month
Close them1 month

See also Brian Armstrong’s guide to hiring executives.

Reading time
1 min
Updated
1 Nov 2026
Chapter
7 of 10