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Newsletter Issue 38

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 Sahil Lavingia

Sahil Lavingia is the CEO and Founder of Gumroad, an ecommerce platform for creators. He was also formerly employee number two at Pinterest. Most recently, he made headlines with his wonderfully written piece, titled, “Reflecting on My Failure to Build a Billion-Dollar Company”. I couldn’t wait to have him on The Heartbeat to share his story, in person. In this episode, we chat about the importance of context in both success and failure, giving yourself optionality, and the degree to which presumption of success matters.

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

What I’ve been writing lately

Managing managers: How’s it different?
“Domain expertise and domain leadership are not the same thing. Knowledge, of course, is formative for decision-making and credibility, but it’s not the driving force behind helping a group of people work together, get aligned around common objectives, and make progress.”

Am I micromanaging my team?
“Wouldn’t your team want to know your opinion? They might. But when you assert your opinion before they ask for it, you can obligate a team member to do something your way.”

What I’ve been reading lately

Managers Can’t Be Great Coaches All by Themselves
Highly recommend reading this piece. “The second surprise: Those hypervigilant Always-on Managers are doing more harm than good. ‘We thought that category would perform the best, so this really surprised us,’ Roca says. In fact, employees coached by Always-on Managers performed worse than those coached by the other types—and were the only category whose performance diminished as a result of coaching.” Published in Harvard Business Review

Three keys to faster, better decisions
“Fewer than half of the survey respondents say that decisions are timely, and 61 percent say that at least half the time spent making them is ineffective. The opportunity costs of this are staggering: about 530,000 days of managers’ time potentially squandered each year for a typical Fortune 500 company, equivalent to some $250 million in wages annually” Written by Aaron De Smet, Gregor Jost, and Leigh Weiss, McKinsey Quarterly

How to Get Others to Adopt Your Recommendation
“There are four audiences to whom people in the workplace bring recommendations: those who approve a recommendation (a manager or top executive) and those who execute a recommendation (peers or a broader audience). It’s important to understand the different ways to speak to each group.” Written by Nancy Duarte, MIT Sloan Management Review

What A CEO Does
A short piece from 2010, but nevertheless resonant: “A CEO does only three things. Sets the overall vision and strategy of the company and communicates it to all stakeholders. Recruits, hires, and retains the very best talent for the company. Makes sure there is always enough cash in the bank.” Written by Fred Wilson, AVC

Three ways to demystify disappointments at work
“Seek to understand, not judge. When someone acts in a way we don’t expect or want, we can make some pretty quick — and often negative — assumptions. But the truth is that the stories and logical forces that lead to those actions aren’t inherently good or bad. By staying neutral in your attitude, you won’t waste energy blaming others for undesired outcomes, taking ill-fated action based on your assumptions, or lamenting a past you can’t fix.” Written by Jesse Sostrin, strategy + business

How to Deliver Constructive Feedback in Difficult Situations
“Indian philosopher Jiddu Krishnamurti noted, ‘The ability to observe without evaluating is the highest form of intelligence.’ An observation is something you actually saw or heard in the past. You can think of it as raw information.” Written by Dave Bailey

A handy leadership tip

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

How do you deal with diverging point-of-views between you and your boss (or another senior leader)?

  • Ask “why?” Start with the assumption that people are reasonable people making rational decisions.
  • Align your core values with theirs. Explain what is motivating you – and how lined up it is with what they ultimately want, as well.
  • Earn their trust by showing, not just telling. Is there anything that you can work on, that directly contributes to the company primary goals, that shows your point?
  • What is the one thing you can fix right now? Avoid the desire to solve everything at once and focus on just one thing that can be a visible quick win.
  • Ask, “Do we really disagree on core-beliefs?” If you disagree with someone else on core-beliefs, then the change will be an uphill battle (and you may want to seriously consider if it’s worth the trouble and if you should look for a new job).
  • Look for an outside advisor/mentor. A third party can bring objectivity to a disagreement, and protect the company’s privacy. When doing this, it’s important to phrase things carefully to not turn the situation into office politics or gossip.
  • Recommended reading: “How to Win Friends & Influence People” by Dale Carnegie.

Just for fun

The elegance of nothing
Lovely crystallization by Seth Godin on brands that seem like “nothing.”

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.