Startup hiring is hard. Hiring senior leaders, 10X harder. Hacks & tricks rarely work. But over the years, I found a magical question that never failed me Hiring Senior Leaders is one of the most important & riskiest things an entrepreneur does. Make a bad hire & it can cause havoc. I made this mistake & it set the organisation back by 12-18 months & it shot my confidence for a long time. But if you make a good one, it can transform your trajectory. After the initial mistake, I made a big change in our hiring process → started doing Simulations It helped us to hire 6 senior leaders over 24 months. They all turned out to be rockstars & 1 of them even took over from me as CEO. I have written about both of these episodes & my learning from them before. (links in comments) But even as I became confident in our process, when the final decision time came, I would still feel a bit uncertainty & nervousness. Then I discovered a question that became my go to tool for demystifying tough hiring decisions. I would think of the person we were evaluating and ask: ”If our roles were reversed, would I want to work for this person?” If my answer was a strong yes, we would roll out the offer immediately. If my answer wasn’t a strong yes, then it was a signal to myself to proceed with caution. I would dive deep into my psyche to understand the hesitation & unless I could 100% convince myself & the core hiring team, we would say No. Counter-factuals are not possible in hiring & so we can’t prove if we were right in every Yes & No we gave. I can just point to the fact that after the 1st disastrous senior hire, we went on to make a series of great senior hires & never made any major mistake again. And for me, the final clarity & confidence, often came from this 1 simple question. Is there a question or principle that you use when you are wrestling with a difficult hiring decision? ————————————————
My post on when I made the mistake of hiring the wrong Sr. Leader & what I learnt from this:
My biggest mistake as a CEO taught me to prefer cats over casinos