I Interviewed Five Ex-Leaders and This Is Why They Left Leadership!

What’s a standard leadership career path look like?


Calvin Bushor

2 years ago | 7 min read

Leadership is the obvious career path for most people as they start their careers, or so people think! People begin their careers looking upward at the ladder and just start climbing.

During their ascent, a new ladder appears, one of leadership, management, and responsibility of people and a team. It’s clearly the next right ladder to climb because that’s what we think a career should look like. We think we should eventually grow into a leadership role and continue to climb.

Many career “mountaineers” have made this journey upwards to then give it all up and climb back down the leadership mountain. Why? Why do some leaders choose to leave leadership?

What’s a standard leadership career path look like?

The standard leadership career path looks something like this. Graduate from a university with a degree somewhere in the ballpark of your first job.

Get an internship to earn some credibility and hopefully open some doors. Start your first job as an entry-level title! Work a lot. Learn a lot. Get promoted from an entry role to a regular title. Continue working a lot. Learn even more. Start to mentor entry-level people. Get promoted to a senior title!

You guessed it, get back to work! Lead a project or two. Mentor more people. Present some important stuff to some important people during some important meetings. Get recognized for a job well done. Interview for a leadership opportunity. Get the job and start your leadership journey! Congratulations!

Not all careers are linear like this, but you get the point. We are taught that becoming a leader is the natural progression of our careers. Then why do so many leaders stop and leave leadership?

I interviewed five ex-leaders and this is why they left leadership!

Here’s why five leaders who’ve made the standard leadership climb decided to change course.

1. They missed executing

This person was a software engineer before they entered into leadership. They were your typical go-to person for all things related to engineering and problem-solving.

They were skilled in mentoring others and often found themselves in the high-pressure communication seat where they led important discussions and presentations. As a leader, they did a good job. Their team delivered. Their team was growing, and their team was happy.

When I asked this leader why they left leadership, they said that they missed writing code and solving problems. They felt they were good at being a leader and their results supported this opinion, but they got more joy out of programming and acting as a tech-lead.

People don’t realize that often, leadership roles take you out of the day-to-day problem solving and instead, you focus your energy on solving different, non-technical problems, like team design and team health. Missing execution is a common feeling people have when they transition into leadership, and this is why this person went back to software engineering and writing code.

2. They felt their skills slipping away

Interviewing someone who was a Product Manager turned Team Leader, I learned that they felt as if they were losing the skills that they’ve developed over the past decade. They began to develop some insecurity and had imposter syndrome when entering the ring with Product Managers who focused on being expert Product Managers every day.

They felt as if they couldn’t keep up anymore and they didn’t want to lose what they’ve learned all these years. They moved out of leadership and back into a Product role. Since making this decision, they are doing a wonderful job at leading their product and have helped other Product Managers excel through their mentoring.

Feeling as if your skills are slipping away is true with all roles, not just Product Managers when people move out of executing and into leadership. Your time shifts from learning new skills and tools to solve your role’s problems to spending most of your time on other things, like meetings, your team, and helping them thrive.

How do you succeed as a leader if you are not THE expert anymore? This is the question many people struggle with losing their expertise in a given skill or craft. Leadership is a craft in and of itself. To succeed as a leader means learning to let go of your past-self and evolve into someone new. This person decided that leadership wasn’t for them right now and chose to focus on being a great Product Manager.

3. They strongly dislike meetings and politics

With leadership, sometimes you spend more time and energy going to meetings. Meetings with the business. Meetings with partner teams. Meetings to prepare for other meetings.

Leadership often means an increase in a communication role which can translate to more meetings. This person knew this going into their leadership opportunity and tried to overcome this increase in meetings, but they struggled.

What pushed this person out of leadership though, were the politics they experienced. This person’s definition of politics was, “Having to kiss babies to get anything done.” This person is a very direct person and the combination of more meetings and a need to “kiss babies” to get stuff done, made this person frustrated and leave leadership.

Here’s my take on both of these points. Yes, as a leader, you will experience more meetings. Part of our job is to share information. We help the business know what we are doing, why we are doing it, and how well it’s going. We also learn from meetings what’s happening around us and we communicate it with our teams.

Learning how to adapt to this norm as a new leader takes time. Learning how to control your own calendar and to say no to things is another skill leaders need to develop so that meetings do not take over your life.

Now, regarding the point on experiencing politics, I’ll interpret what I think they were saying. When they said that they had to kiss some babies to get stuff done, I interpret this as needing to develop relationships with peers and partners across your business to influence and persuade.

Developing this skill is hard but also part of the job. It’s not necessarily politics, it’s taking the time to learn how to communicate what you need from people and how you can help them. Learning how to influence and persuade is a hard skill to master.

Sometimes people run into real political issues and when that happens, it’s a major bummer. Usually, the root of the problem is learning how to communicate and how to develop relationships with people so that you can communicate more effectively. Maybe this person experienced real political issues and if they did, I feel for them.

4. They weren’t set up for success

This person really was not set up for success. They were previously in IT, Information Technology. They were the main help-desk person who took technology tickets and helped resolve issues with computers, telephones, etc.

There was an opening for a management role at their company and they were persuaded to take the job. This person was handed an entire department to manage which turned out to be a complete cluster. There were no processes in place.

The technology was outdated and had some massive opportunities for improvement. To make matters worse, this person was given no leadership training to help them succeed. Three months later, after trying their best to make it work, they not only stepped away from leadership, they left the company!

I feel bad for this person because they did not get to experience healthy leadership. They entered into a mess and they did not get any help. Now, this person is not jaded when it comes to leadership and recognizes that it’s not always like what they experienced. They are open to becoming a leader again someday but learned a valuable lesson. Next time, they need to do more homework about the position, as well as fully understand the support system around them so that they ensure they are set up for success.

5. They didn’t like it

Plain and simple. This person entered leadership thinking it was their next step in their career and learned that leadership wasn’t for them. It was a mix of all the answers above.

They missed executing. They didn’t like spending the majority of their time communicating in meetings. They felt as if they were losing their skills and falling behind. They also said that they didn’t get joy out of helping the team grow and succeed which, is pretty important if you want to be a leader of a team.

This person struggled to admit they made the wrong decision but ultimately came to the conclusion that they needed to make a change.

Their pride delayed the time it took for them to pivot back to what they were doing prior but learned that staying in the role was hurting everyone more than it was helping, including their own career. Now, they are a lead designer at their company.

Leadership isn’t for everyone… right now

These leaders highlight an important lesson, that climbing the ladder isn’t always the best career path. People enter and exit leadership for many reasons.

One thing that stands out to me from interviewing these ex-leaders is, choosing a non-leadership path is perfectly fine. Each of them is excelling in their careers since they’ve exited leadership. Some of them consider trying leadership again in the future and look forward to applying what they’ve learned from their first-round at it.

Maybe leadership isn’t the right path for you, and that’s okay. Maybe it’s not right for you, right now, and that’s okay, too. Learn what makes you tick, what brings you joy, and understand what energizes you so that you can make the right career decisions for you. Choosing to pass on leadership or to take a break from it is not a forever decision, you can always try leadership at a later time.


Created by

Calvin Bushor

Technologist, leader, writer, and I created to help new tech leaders be better leaders and build awesome dev teams! #LeadershipLife







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