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Newsletter Issue 45

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 Will Larson

Will Larson is the Head of Foundation Engineering at Stripe, and author of An Elegant Puzzle. I thoroughly enjoyed reading Will’s book – both deeply insightful and enormously practical – and couldn’t wait to talk to him about it. In our conversation, Will shared his perspective that not all decisions are final, the salience of self-awareness, and modeling your behavior for your organization. Catch our full chat below…

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

Have you been enjoying these Heartbeat episodes, lately? If so, it’d mean the world to me if you wrote us a review in iTunes. The more reviews we have, the more we’re able to share all our lessons from leaders. Thank you! <3

What I’ve been writing lately

How to collaborate effectively in a remote team
“I’d noticed how it wasn’t necessarily the tools themselves that made remote teams effective: It was how a team chose to use those tools. The processes and systems instilled to collaborate in a remote team – that’s what contributes to success.”

Managing up
“Possibly the most constructive way to manage up is to make sure you’re clear on what your manager expects of you. Without clear expectations, naturally, it’s easy to step on each other’s toes, misinterpret a comment, or be offended by a request.”

How to run a successful team retreat
“The 4 essential elements to include in your team retreat – and the exact 3-day team retreat agenda we held for Know Your Team.”

What I’ve been reading lately

If You Want Engaged Employees, Offer Them Stability
“Most organizations struggle to find the right balance between stability and change, which in turn affects individual contributors. But in the race for innovation and digital transformation, the idea of stability has been somewhat lost in the mix, and there are strong indications that we should revisit its merits. If you want to develop an environment where contributors thrive, your workforce must be able to count on some basic things — such as role clarity, timely feedback, adequate resource allocation, and attention to how our work is structured.” Written by Marla Gottschalk, Harvard Business Review

Getting personal about change
“[…] we found that executives at exactly zero companies that disregarded an analysis of employee mind-sets during a change program rated the transformation as “extremely successful.” Conversely, executives at companies that took the time and trouble to address mind-sets were four times more likely than those that didn’t to rate their change programs as at least “successful.”” Written by Scott Keller and Bill Schaninger, McKinsey Quarterly

4 Steps to Becoming a More Self-Aware Leader
“It is also good to keep in mind that just because you learn something actionable about yourself doesn’t mean you necessarily have to act on that knowledge. “It’s more about listening and deciding, ‘OK, given what I’m trying to do for the organization, and for myself, is it worth it to make the change or not?’ Effective leaders read the situation, figure out what’s required of them, and choose to respond in a way that’s appropriate, authentic, and valuable to their team,” Booth says.” Published in the Kellogg School of Mangement Insights

Clearbit’s approach to management
“Great management training consists of many things, from training videos to handbooks to 1:1 coaching. We are developing a system at Clearbit to do all of this, and our plan is to publish as much of it as we can so people can apply it to their own organizations. Our internal wiki contains a Manager’s Handbook — a living, breathing, compendium of all our best practices.” Written by Alex MacCaw, CEO and co-founder of Clearbit

A handy leadership tip

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

Facing failure – how do you identify it, and talk about it as a leader?

How to identify failures:

  • Have a go-to trusted person. Whether it is your manager, a coach, or a team member you trust, establish a trusted person who will help you call out failures. This has been my best source of identifying failures. This is hard to find, and super valuable once you do.
  • Establish success + failure criteria with your direct report(s). What are the objective alarms, or guardrails? This helps make it clear to identify the failure – and prevent it from happening in the first place. Also decide when is a good time to evaluate and circle back on this criteria.
  • Create a forum. Sometimes, simply asking “what’s not working” and seeking out negative feedback can help you identify failures as you go. However, keep in mind that when someone calls out a failure, how you react as a leader is critical. This can make or break the usefulness of the forum. Also, one Watercooler member noted how retrospectives are a good way to do this as a team – but only useful for identifying failures in things where you have a specific delivery schedule and are prompted to set a retro up in the first place.

How to address failure with your team:

  • Closure only comes with 100% honesty. Everyone knows the elephant in the room. If a project failed, or you messed up, or someone else messed up – everyone likely already knows it. It does no one any good to skirt the issue. Downplaying a failure can be worse than ignoring it.
  • Eat the elephant one bite at a time. The more difficult a conversation and the more complex the issue, the more conversations must exist to uncover the whole topic and to uncover the whole situation.
  • Leverage one-on-ones. The fact that you (hopefully) have a conversation scheduled to talk about what’s on people’s mind gives you the perfect opportunity to talk about the failure, why it happened, and what can be improved. Use this time not as a status update, but to have you sharing thoughts, ideas, fears, failures.
  • Look to foster a “no guilt” culture. If you want people to honestly talk about why, how and when they failed, it is necessary to have a safe environment for people to assume their mistakes. Reveal your own mistakes. Don’t be accusatory. Offer a way forward by focusing the discussion on what to do next.

Just for fun

Skip the small talk (part one)
Love these questions that Lama Al Rajih shares.

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.