CEO to CEO: What We Learned

CEOs at the morning workout. Photo credit: William Mackie.

On Friday, we had 23 CEOs from our portfolio gather to learn from experts and one another about things they could be doing better. Here were some of the highlights they shared as their favorite learnings:

  • There is no ‘aha’ moment of accomplishment when you’re CEO. You just keep forging on to the next challenge and providing the best guidance you can with imperfect data.
  • Define your Desired Future State. Three years out, what difference have you made in the world? What does the future look like in metrics/financials, people and strategy?
  • Small partners = small partnerships. If you’re going to invest the time, size matters for the value of the outcomes.
Andy Moss, CEO at Roadster, at small breakout group.
  • Partners care mainly about how your product will help them sell more of their product. So when developing a partner strategy, only do it when you have a repeatable process and your own sales team has had success that a partner can replicate.
  • 50% of your time should be spent recruiting when you have open spots. It seems like a lot but there is nothing you can do that scales you or your organization faster than surrounding yourself with a great team.
  • Think of your executive staff as a portfolio. Don’t just hire skills and abilities into a function — have execs augment other people on your staff and your own strengths and weaknesses. No one is every great at everything, so your job is to balance across your executive staff.
  • Be upfront about your weaknesses. When interviewing executives, own your own weaknesses as a way of having them reflect on their own — and also to make sure their weaknesses differ from your own.
Srihari Kumar, CEO at ZenIQ, and Steve Carpenter, CEO at Grovo
  • Do a shared “upfront” interview. Have everyone interviewing a candidate start the day together with a presentation from the candidate on the ‘standard’ stuff they would have gone through with each person — their prior jobs, background, anything significant worth calling out. Then, the interviews can focus on unique areas of contribution and what each person is trying to learn more about candidate.
  • Diversity is relative to the available talent pool. If it’s primarily caucasian in your geography, you can’t overachieve with the population you’re in. Try to find local data to calibrate your effort.
  • Sometimes you just have to make the candidate pipeline skew female. But having more women in leadership and across the org makes it easier to recruit women at every rank.
  • QBRs are important; do them often and do them well. When you discuss major strategic issues, ask each person to rate how strongly they feel about something on a scale from 1–5. Have the 1’s and 5’s share their opinions and debate. Then, revote. Usually, people will have moved more toward one direction and differing opinions will have been heard. Pick a key learning topic and dedicate a half day.
  • Invest in the company (your people), then customers, then the Board (investors). Most CEOs think of their relationships in this priority: Board/Investors, Customer, Company/Employees, when in fact it’s the opposite. With great employees and a healthy company culture, everything takes care of itself. This advice came from a CEO who used to believe the opposite earlier in his career and lived how inverting it yields far more powerful and scalable results.

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