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Newsletter Issue 37

Every few weeks, I ask one question to a founder, CEO, manager, or business owner I respect…

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The Heartbeat Podcast: A chat with Bryce Roberts

Bryce Roberts is a long-time, well-respected investor having co-founded O’Reilly AlphaTech Ventures – and more recently, started an investment firm that supports profit-focused companies, called Indie.vc. In our conversation, we chatted about the importance of accepting your mediocrity when you first start out as a leader, and not relying on having a mentor to save you, and being open and honest with yourself in order to evolve in a leadership role. Enjoy!

Listen to the podcast and read the transcript of the interview here.

What I’ve been writing lately

The hardest leadership advice to follow: “Work on the business and not in the business”
“Yes, conventional wisdom says to “sleep on it”, to step away from the work to get a fresh perspective on it. And yes, I’ve vigorously nodded my headed in agreement whenever someone espouses something along those lines. But, if I’m being honest with myself, how often do I personally act on that recommendation?”

I’m writing a Guide on Managing Remote Teams – would love your input!
If you haven’t shared already, I’d love to know: What are your biggest challenges or questions around managing remote teams? You can take the survey here – and for the first 1,000 people who fill out survey, I’ll send you a free copy of the guide once it’s done!

What I’ve been reading lately

How leading CEOs manage their middle tenures
“The first theme: keep raising the level of ambition. One thing that we heard in almost all of the interviews was, of course, as a CEO, you start out with a high ambition. Almost everybody does some form of resetting the baseline, resetting the ambition, in the first year. What differentiated these high performers was not how high the ambition was at the beginning but whether they raised the ambition as they went.” Podcast transcript with McKinsey partners Sean Brown, Rodney Zemmal, and Matt Cuddihy, McKinsey Quarterly

The confidence premium
“This year’s CEO Survey reveals a dramatic drop in CEO confidence. We observed a 12 percent decline in the net balance of CEO confidence from last year. This foreshadows even more subdued global GDP growth than some leading economic forecasts suggest.” Written by Bob Moritz, strategy + business

The Value of Taking a Sabbatical
“Absence is a great measure of leadership effectiveness. When a great leader is absent, the team steps in to fill the gaps without any real disruption. Maybe that’s why I was nervous to take time off for eight years — I was afraid to face all of the ways in which I’ve failed as a leader and failed to set my teammates up for success. But in hindsight, it’s exactly what I needed to understand my leadership strengths and weaknesses.” Written by Nick Francis, CEO of Help Scout

The five types of communication problems that destroy company morale
“There’s a saying in software that all bugs are eventually user interface bugs, because someone has to see them to report them. In organizations, it often seems like all problems are eventually communication problems, because communication is the way we interface with each other—and the way most problems surface.” Written by Cate Huston, Engineering Manager at Automattic, Quartz

Why Setting Ambitious Goals Backfires
“Our most ambitious goals have driven our most counter-productive behaviors, like focusing solely on short-term gains at the expense of the long-term. Conversely, our sweet spot of productivity, creativity, and ambition has come when we’ve intentionally set modest, straightforward, and unambitious goals.” Written by Brendan Schwartz, Founder and CTO at Wistia

A handy leadership tip

From our online leadership community of 1,000+ managers in The Watercooler in Know Your Team

How do you structure your all-company meetings?

What to talk about:

  • The “why” behind the actions in each department and how they relate to larger company goals
  • Challenges each department is facing
  • Top projects of each department
  • Company-wide retrospective on what’s been working, what’s not
  • Mission, vision, and values and give examples of how a specific value impacts an every-day decision (sometimes this is a discussion, sometimes it’s a presentation)
  • Financial update
  • High-level business development and project updates
  • Travel things happening in near future
  • Open it up for questions

What to NOT talk about:

  • A laundry list of progress being made

When to hold them + how often:

  • With 10-person remote company: Three times a year, done more as a “retreat” that lasts 7 days
  • With 20 people: Once a month, called “coffee hours”
  • With 40 people: Weekly, every Monday
  • With 130 people: Once a quarter

Other considerations:

  • Have 1 (sometimes 2 people) different person present each section so the meeting doesn’t feel like a drag
  • Videotape them in case someone’s not able to be there
  • Ask if people find the all-company meetings valuable
  • Make them optional

Just for fun

Michelin restaurants and fabulous wines: Inside the secret team dinners that have built the Spurs’ dynasty
Loved reading absolutely every bit of this piece.

Written by Claire Lew

CEO of Canopy. My mission in life is to help people become happier at work. Say hi to me on Twitter at @clairejlew.