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How Are You Leading?

“A leader is best when people barely know he exists, when his work is done, his aim fulfilled, they will say: we did it ourselves.” – Lao Tzu

Today’s Operators Manual mini-sode talks about what it means to step back and let other folks lead. It’s a tricky topic on a human level involving more than delegation and trust. It circles around fear of letting go and other fears that come with not being “at the top” as a leader. 

We talked a bit about this in a longer form podcast conversation a few years ago on servant leadership. It was accompanied by a hearty blog post that had a handful of good nuggets on Top-down and Upside-down pyramids as leadership models, a “Leader’s Manifesto,” and some good nuggets, including this question: 

Are you leading to serve on behalf of something larger than yourself and all the folks who are working on behalf of that, or do you have a bunch of people who work for you?

(If you haven’t read that post in a while, it might be worth revisiting. See also: A Third, Much Greater Thing.) 

Stepping back and letting other folks lead brings up a lot of things for those in the lead role in an organization. Specifically, it can bring up lots of feelings around trust, decision-making, and fear of letting go.

I’ve seen many teams be undermined by a controlling CEO/founder who merely has ‘a bunch of people working for them.’ At the end of the day, the ol’ right-side-up pyramid doesn’t scale because leadership doesn’t scale when there’s one person at the top who makes all the decisions, all the time, and is in all of the meetings, and is perhaps stuck in quite a few patches of weeds. 

(What’s the team’s experience of this, you might wonder? It’s often full of face-palm moments, frustrations, and a host of other unpleasant feelings caused by working under leaders who won’t let their leaders … lead. In short, it’s not uncommon to end up working on finding clarity about transitioning out of the company. So, if you’re working on building a culture people will want to stay at, or if you’re battling retention, it’s worth looking at this issue either directly or squinty-eyed to make sure you’re covering all your bases.) 

In 360 Reviews, we’ll hear feedback on the CEO that sounds like: 

  • “… in the weeds.” 
  • “… we need them to work on vision and strategy.”
  • “… needs to delegate more.” 
  • “… micromanaging.”
  • “… jumps in and makes rash decisions which we all then need to clean up.”
  • “… it doesn’t work when they’re leading product and sales, and trying to be CEO.”
  • “… doesn’t listen to the executive team.”
  • “… it’s their way or the highway.”
  • “… they’re burned out because they don’t stop working.” 

In a debrief on a 360 Review with these themes noted as areas of growth, we’ll often ask some good questions to start exploring what’s behind some of these behaviors. As conversation starters, they might sound like: 

  • In what ways, in what areas, are you afraid to let go? 
  • If you were to let go, in your mind’s eye, what would happen? 
  • What would need to be in place, what would you need to see or experience in order to let go? 
  • In what ways are you holding yourself back as a leader by doing these things? 
  • In what ways are you holding the company back? 
  • What does the team need most from you? 
  • What skills or hires or commitments do you need to make to step back and take your seat as the leader on the up-side-down pyramid model?

As you feel into your own leadership style, consider: what stops you from stepping back and letting others lead? How do you help your leaders own the problems they need to solve and hold them accountable? When do you step in and use the right-side-up pyramid model?


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