Building Outsight: Great Leaders Don’t Go It Alone

Being a leader can be a lonely job. I remember talking to a senior leader many years ago and asking them what the biggest difference was in leading at new levels – they said: “Your lunch group gets smaller.”

It’s easy to rely on what we know and what has worked for us – not just in leadership, but in anything, really. And at some point, doing only what we’ve known to work will hold us back from learning and growing.

It’s a little like solo mountaineering or backpacking. Even with binoculars, you’re limited to only seeing so far on the path ahead. Will what you learned on the last hike or mountain work on this one? Maybe. But likely there will be many differences and new challenges that your current experience won’t cover.

In her book, “Act Like a Leader, Think Like a Leader“, Herminia Ibarra introduces the idea of “outsight”, gaining new perspective through new roles, networks, and experiments. She argues that greater insight doesn’t come from just introspection and reflection, but from taking action to use a wider lens. Look at the landscape around you, versus just looking in the mirror.

There are 3 levers that she mentions which help in gaining that external perspective:

• Redefine your job. Take on new projects, use your adjacent skills for different work, find ways to become more strategic.
• Expand your network. If your network is an echo chamber, you’re only going to hear your own voice, unfortunately. Think of your network like an arena, with diverse groups and different thinking.
• Play with your identity. This might feel scary, but think about “stealing like an artist”, made famous by Austin Kleon, where he talks about “casing the joint” – looking for ideas and behaviors that feel good for you to adopt or try out. Try on just 1 new leadership habit over the next 30 days, like asking more questions than providing answers. Could your identity shift a bit?

Getting an external perspective is amplified even more if you can take part in an outside trusted group. Sometimes the biggest breakthroughs in new learning come from peer support and the external vantage. We can’t see ourselves like others see us, and the biggest changes can come from someone else providing a different frame to look through. It’s possible to keep your lunch group wide and supportive!

This group perspective is so powerful, that’s why I’m partnering with Suzanne Weller in 2026 to deliver a 9-month group coaching program starting in January. If you’re interested, send me a note and I’ll provide more detail, or go here to get an overview.

That’s all for now, see you in 2 weeks!

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Here are a few resources that I’ve found interesting and have been sharing with clients:

1 // You were meant to be off-course – fighting the myth of the “next right step”. (3 min read)

2 // You don’t hate your job. You hate pretending to love it. (Wait for the end for some hopeful experiments to try.) (10 min read)

3 // Do you need to know what you’re going to do before you start doing it? Ideas arise through action. (5 min read)

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