Thinking Alone?

Earlier in my career, I was kind of sort of sure that I was doing leadership “right.” I’d worked for some great folks, and although I didn’t think they made it look easy, exactly, I also didn’t think it would be that hard.

Sometimes I was right. I felt like I was in the right gig, learning a lot, and making some good things happen.

Other times, “Be careful what you wished for, Gary” ruled the day (and the night). I had dreams about my office chair swallowing me up. I had Sunday Scaries on Mondays and Tuesdays too.

Given to drama, I’d wax Shakespearian in these moments, saying things like “uneasy lies the head that wears the crown” (and then halfheartedly laugh at myself). 

I assumed that feeling inundated, unsure what to do, and self-doubt were just part of the gig.

You might ask me why I didn’t have ample support. I did have lots of support. More than I expected before I took the job.

• I had a supportive and smart board (and knew how lucky I was).

• I had a strong senior team.

• I worked with a coach (to help me improve how I worked with my board and senior team).

Still, in these challenging moments, it didn’t seem that any of those good folks should be burdened with this hard-to-name feeling (or that I wanted them to see me as confused as I felt).  So, I turned to Chunky Monkey, an extra morning at the gym (in a vain attempt to make up for the Chunky Monkey) and one more rewrite of that delicate email – hoping the feeling would subside.

It did sometimes. And it didn’t other times.

Years later, I hear versions of this story all the time – mostly from leaders early in their tenures, like I was. They might be coaching clients who don’t want to use me as a therapist (I send a heartfelt thank you) or over lunch with a dear colleague who is feeling the heaviness of the crown in that moment.

Like me, on paper, there are supports in place. And yet, when the conversation turns to how they’re dealing with culture, staying connected to what’s happening in their world, or thinking about the big picture, there’s often a pause and a sigh.

• They know to be careful about what they say to their board – to wait until their thinking is ready for prime time.

• They’re mindful of what they share with their team, knowing they could be sending emotional signals or panic that will echo for weeks to come.

• Coaching helps, but it’s really about being stronger and more effective in the leadership role. 

This feels different.  What’s missing isn’t support. It’s the type of support.

What I was missing in those moments – and what these good folks are missing too – is lateral perspective. Lateral perspective is the clarity that comes from being connected to other leaders – people who do your job, experience the same joys and anxieties, and have nowhere else to turn (except to you!).

Teams, boards and coaches can’t replicate the experience of hearing how other leaders in comparable roles wrestle with similar questions.

Boards sit above. Teams sit below. Coaches sit alongside, but one-on-one. So much of what you are accountable for runs up and down the org chart and then back up again. And some very important work of leadership – sense-making and developing a broader perspective – doesn’t happen well vertically.

You need a healthy dose of lateral perspective to balance all that vertical perspective.

But what sort of lateral connection do we need? We’re adding yet another dance partner or two to an already-full dance card. 

Let’s dig in there a bit. 

Leaders tend to find lateral perspective in two ways:

• Informal Networks – trusted relationships with colleagues outside the organization that we rely on for immediate perspective, emotional processing, and sense-checking in the moment.

• Formal Cohorts – intentionally designed peer groups that bring together leaders with comparable responsibility to think alongside one another over time.

As you think about which might help you, it helps to be clear about the distinct function each serves.

Both can offer a place to bring unfinished thinking, test what you are seeing on the horizon, and be reminded that you are not the only one navigating uncertainty with limited information. But the format matters.

Most leaders rely on informal networks, whether they think of them that way or not.

These are the people you call after a hard board meeting, when your Spidey Sense is activated after a meeting with a local elected official, or when you see changes in your community that might have broader implications.

These may be former colleagues with whom you’ve built trust over the years, who know your patterns, and don’t mind a little straight talk. Or they are the peers who hold comparable responsibility, ask better questions than they give advice, and notice when your thinking sounds maybe too reactive or – maybe worse – overly certain.

Informal networks are valuable because they are flexible. You might chat once or twice a year or once or twice a week, depending on what’s happening in the world and what perspective they bring. They help you feel less isolated.

They are fragile in that they depend on your peers to be available when you need them, having built up enough goodwill to occasionally cash in on, and remembering to pick up the phone in the moment (rather than wallow in your anxiety du jour).

For some, this network might also be people who generally agree with you. That may feel reassuring, but it is unlikely to sharpen your leadership.

Informal networks work well when we activate them at specific moments. They are less effective when we need a strong structure, continuity, agreed-upon expectations, and follow-through. That is a load that goodwill among colleagues was never designed to hold.

That is a gap that formal cohorts can fill.

A strong cohort creates a consistent, psychologically safe space where leaders bring unfinished thinking, are questioned rather than advised, and leave with expanded perspective and clearer judgment rather than pat answers.

Cohorts are often structured around specific topics or case studies, but the focus is less on advice-giving or problem-solving in the moment (though that may occur) and more on challenging assumptions and strengthening how leaders think over time. A cohort may include peers from your own field or leaders from entirely different sectors, both of which can deepen perspective in different ways.

Outside facilitation often plays a critical role, helping the group stay focused, surface patterns, and maintain norms of challenge, reflection, and accountability.

Informal networks and formal cohorts are not competing solutions. They are different ways of meeting the same underlying need for lateral perspective.

Informal networks provide immediacy and connection to trusted colleagues, usually in your field. Formal cohorts provide depth and thinking beyond your business and often outside your field.

None of this replaces the important roles played by boards, senior teams, or coaches. You need to turn to them regularly for the perspective they bring.

Lateral support expands that ecosystem by filling a gap – one that I found was hard to name and impossible to fill until I did.

If leadership is a thinking role, then where and with whom you think matters. As you think about your own leadership today, ask yourself:

• Who helps you examine assumptions before they turn into conclusions?

• Where do you take ideas that are not ready for your board or your team?

• What happens when the people you usually rely on are unavailable?

Having a network ready to activate – and being that network for others – when the path is unclear reduces the time you spend in uncertainty and whatever negative feelings happen for you in those moments.

Leadership rarely suffers from a lack of smarts or effort. It suffers from lack of perspective.

And perspective is almost always built in relationship.

Expanding your network of support and making the time to draw on its energy can make the crown a little less heavy.

If you want to explore what kind of lateral support would best serve you at this stage, I am always happy to have that conversation. You can reach me at gary@garybagley.com or via LinkedIn.