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The Leadership Chasm

Why transitioning to management is hard: The Leadership Chasm

When I coach founders and execs, I often encounter them in a point of transition. Reaching the point in your career where you transition from individual contributor to a people leader is often a story of struggle. Here’s why it’s so difficult to rise to the new challenge: The Leadership Chasm.

The leadership chasm represents the gap in skills, competencies and realities that now stand in the way for you to be successful.

The skills that got you here won’t get you there

For many first time managers, you achieve your promotion to people management by being stellar as an individual contributor. By executing well, you’ve shown that you understand what good output looks like. Naturally, the logic follows, if you’re elevated to a people leader you’ll be able to drive the same output through others.

Here’s the problem with this logic:

  • The skills and competencies to drive results through others isn’t the same as doing the work yourself. The work of the individual contributor is to actually do the work, while your work is actually to help your team achieve great outcomes. That means your core work are actually more around behaviors like motivation, feedback, and process/resource management.
  • The new work associated with your role isn’t as easy to measure, and may not be immediately obvious. It’s not as simple as helping your team deliver more of the work you’ve been delivering well to date. It’s about hiring, growing and retaining talent. It’s about unblocking team members and building better processes. It’s about inspiring them to deliver results. All of this is part of a leader’s job.
  • Accepting that not everyone works the way you do requires a mindset change. There are multiple ways to launch a campaign, ship a product, makes a sale, or otherwise execute great work. It’s not important that they do it in the way you’d do it, but it’s hard not to get hung up in details especially if you’re very familiar with them yourself.

This last piece is really important. A common mistake that new leaders make is they focus on delivering output through their team by intensely managing the execution process of others. How about you just teach everyone to do it the way you do it? Not everyone works the same way, and often this is the slippery path into micromanagement. Instead, your role is to help that person become their best self by providing them with resources, clear goals, and constructive feedback.

Facing your new reality

I remember telling my team, you’re the ones that are actually doing the work. Instead, I would be spending my days mired in budget planning, project reviews, team meetings and 1:1s, and recruiting. Outside of seeing bullet points on progress, I often felt distanced from the actual work of improving the company metrics. I deeply missed the execution work.

A friend helped me by asking, “What’s the most valuable thing you can do for the team that no one else can do?” It helped me see it in a new light. I was uniquely situated to helping the team procure resources (budgets), gather and disseminate information (reviews), give feedback (team meetings), and recruit teammates. And this was actually the most impactful activity for my time spent.

The sooner I came to accept that as my new reality, the sooner it enabled me to embrace these activities as productive and integral to my role. And by focusing on this, the sooner I came to realize that being great at these activities requires mastering a completely different set of skills and competencies.


This story about the leadership chasm isn’t about not focusing on the execution and deliverables that got you to where you are. I’m certainly not saying that, they do help. But I do think you need to develop a self-awareness about how different the skills and competencies are to operate as an effective leader. Recognizing where you have the most leverage to add value is important. And when you get too bogged down in managing execution over tactics, that’s when you’re stuck in the canyon.

Ada Chen Rekhi is co-founder & COO of Notejoy, a collaborative notes app for individuals and teams. She’s also an executive coach who works with founders and executives looking to scale themselves as they scale their teams. If you enjoyed this essay, follow her on @adachen and subscribe to her newsletter.