There is a point in the future when a leader needs to depart. You can stay in the job until you stop breathing, as long as you feel like it, until the board throws you out or after regularly evaluating whether you are still up to the task and -- if you're not -- you can hire a replacement and get out before your company goes down the tubes.
The only responsible option is the last one. But John Doerr, the long-time leader of venerable Silicon Valley venture capital firm, Kleiner Perkins seems to staying as long as he wants. Indeed, as Fortune reported, Doerr has stayed in control of Kleiner at least a decade too long
Since then, Kleiner missed the best investment opportunities, got distracted by a money-losing investment thesis, hired and drove out many talented younger partners and continues to hang on despite it all.
Business is brutal and if you don't have what it takes to keep winning, free yourself of the illusion that you are indispensable.
And replace that with a process that I described in my new book, Scaling Your Startup. There I show why Ajeet Singh, the founder of ThoughtSpot, a business analytics firm, said he would leave his job as CEO when he was no longer the right person for what the company needed. In fact, every six months, he got anonymous feedback from employees, customers, and others on six questions.
In August 2018, Singh brought on a go-to-market expert, Sudheesh Nair, to take over as CEO.
Here are Singh's six questions -- how Doerr did not seem to be asking them -- and how they could help you choose whether to stay or go.
1. Do I feel bogged down or not?
A successful leader sets the pace rather than carrying heavy burdens. After reading the Fortune article, it struck me that Doerr does not seem to be happy -- and he's tried unsuccessfully to hire an outside superstar who can reclaim industry leadership for Kleiner.
Don't do that -- instead, develop high potential people into leaders by giving them increasing responsibility to prepare the company for when you'll step away and to keep yourself from feeling bogged down.
2. Am I having fun?
Leadership should be fun. Many leaders -- such as Carbonite founder and ex-CEO David Friend -- love turning an idea into a company that goes public. But these leaders don't enjoy the quarterly financial reporting process. So they bring in someone who does.
If you can't say you find enjoyment in your work, you should not hang on. If you do, you and the company will suffer.
3. Do people respect me or are they following orders?
If people are just following orders, you've lost the emotional connection with them. And they'll start to see you as the sole source of solutions for the company's problems.
If you continue to earn peoples' respect, they will tell you about problems and propose solutions. If you lose their respect, you are likely to become less effective as a leader and your people will stop thinking like entrepreneurs. This means they'll stop helping you identify and respond to threats and opportunities facing your company.
Doerr went through a hot streak at Kleiner from 1980 to the early 2000s -- investing in Netscape, Amazon, and Google. But since about 2004, he has dramatically missed Kleiner's goals of making money from investing in startups. That's because between 2004 and 2009, he spearheaded $630 million worth of investments in 43 "clean tech" companies which "flopped," according to Fortune.
Doerr seems to have lost Kleiner's respect with his "clean tech" detour but any challengers were powerless to stop him. The lesson: get out before you lose your organization's respect.
4. Are we hitting our goals?
If you can't set and achieve ambitious goals that your people meet consistently, you should find out the problems and fix them. If you don't want to do that or can't you should get out. Doerr has held on too long -- don't be like him.
5. Are good people staying and doing well?
A company's success depends on how well its leader attracts world-class talent and creates an environment that makes them feel that they are advancing their skills while making the company better off.
If you are losing your good people -- which Kleiner appears poised to do with the departure of Mary Meeker, its best performing investor (who is one of many of Kleiner's departed stars) -- your company is faltering. If your best people leave, the company will fall further behind. Your company's survival will depend on replacing yourself with a new CEO who can attract and retain the best people.
Nobody is indispensable -- so prepare for the day when a better successor will be in charge.