Career Transitions

Every great manager has had a challenging career transition. Every great manager has taken a chance in moving into a new role that they were not fully prepared for. And every great manager came out of the experience the better for it!

Challenging transitions take a number of forms. Some are individual contributors to managers. Others are public to the private sector. And others are taking on a very different role or working in a new location. These transitions may or may not have been by choice.

What made these transitions challenging was the need for new skills, different management styles, or new ways to operate. And some involved very different locations and/or cultures. Because of this, they all required a steep learning curve to be successful.

This gap in experience and expertise typically created a good deal of stress and anxiety. But the great managers worked through them, learning a tremendous amount along the way, and preparing themselves to take on even larger challenges in the future. 

Enough from me, let’s hear it directly from them. This is followed by a structured summary that should help you as you pursue a challenging career transition of your own.

Cultural Differences

One challenge that you might face is the result of different cultures. This can be country or company culture.

International assignment. When I took the job, I was surprised by a boss change. I had to figure out everything on my own. Surprisingly, I learned a lot and came out stronger after the experience.

Bob Worrall

It would have to be starting a company in India and kind of deciding to move to the U.S. The reason for that was there are a lot of cultural differences in both these countries, especially in India.  You were always taught not to be very bold, the culture is that it is kind of masked as humility, but it’s usually that we don’t think too bold. In the U.S. it is exactly the opposite. People are always thinking boldly.

Anup Gosavi

Public to Private Sector

A transition that might be more difficult than any other is moving from the public to the private sector or vice versa. The two quotes below come from great managers who moved from the military to the corporate world. Others might be for-profit to a non-profit, university to a corporation, or government to commercial.

Military to a civilian career. No-one tells you where to be, what to do. You have to figure it out yourself.

Josh Lory

Military to the corporate world. In terms of differences, the biggest most striking difference that I’ve seen in the corporate world coming from 15 years as a fighter pilot in the military is that there is a sense of urgency to accomplish a mission in the military, particularly on Elite teams that just don’t exist in the corporate world.

Joel “Thor” Neeb

New Role / Skills

The most common reason career transitions are challenging is that you are taking on a new role that requires different skills.

Leadership for a huge challenging program with lots of visibility. Outside of my area of expertise/experience. Hard decisions, learned so much, propelled my career.

Laura Ortman

When I moved from customer support to product manager. I took the opportunity as it seemed to be a good step in learning. But I realized that my heart was in customer support.

Rupinder Saini

Company transformation. I was not bought in early, I did not perform well, it was very hard to take.

Robin Matlock

Individual Contributor to Manager

A very frequent answer that I get to my question about the most difficult transition, and to some degree a subset of the earlier area on new roles/skills, is the transition from individual contributor to manager.

The transition from an individual contributor into a hopefully half-decent leader.

John Dolan

Individual contributor to manager. So you go from an individual contributor to a leader. It requires that you change your approach and you don’t just continue leading from the front and tell people what they need to do. You need to earn their buy-in, get their fingerprints on the plan, it’s a different skill set and different muscles.

Joel “Thor” Neeb

When I became the new manager of the team that I was a part of. Learning what to do, what to delegate (fishing vs teaching someone to fish).

Anil Virmani

Increased Scale / Scope

A typical career transition is to take on a new role with more scale or scope. This often requires new skills or an evolution of existing skills.

I think probably the biggest transition I had (and you and I did it together) is when I was running a relatively small team of about 20 people and then all of a sudden because of organizational change, I was running a team with a hundred people and then six months later it was a 300 team of people. And going from a world where you’re managing people where you know everybody’s name to where you can’t get everybody in a room together to do an organization meeting because you are spread out across the globe and there’s no way you can know everybody. You need a new set of tools and techniques for managing. You have to learn how to scale with that and you have to think differently about the kind of leaders you have on your team and the trust you put in them.

John Gilmartin

Technologist to GM. God that was stressful. I was really a fish out of water. I didn’t know what I should be doing. I think the hardest challenge, honestly Dale, is that I didn’t know how to ask for help either. That’s something if I look back, I have got to get better about asking for help if I feel like I’m just overwhelmed and don’t know what to do.

Kit Colbert

The first time managing a large team across locations.

Anil Virmani


All transitions have been hard and I would say even painful because you are on a learning trajectory that starts from the bottom all over again, but because it’s a conscious decision I stick to it.

Simran Singh

There is so much to be learned from challenging new roles and career transitions. But change is a bit scary, and working through the challenges can be daunting. There are three things that you need to keep in mind along the way.  

Be Patient

It will take time for you to come up to speed. You intuitively know this, but as a strong performer, you will want to show others that you can do a good job. Be patient. You will be given the time. Don’t waste the opportunity!

Have Confidence

You bring skills and experience. You are good at what you do. You know that you can learn. Keep in mind that, while you are learning new things, you bring value!

Listen and Learn

Ask a lot of questions. Probe deeply. Look for differing opinions. Seek to understand. Begin to build a network. Avoid making suggestions – there will be time for that later.

Do It!

You are now in the domain that you know. You have spent the time to come up to speed. You understand the role or job. You know who to listen to and trust. You have ideas. You now need to execute.

If you follow these, you will not only be successful, you will be amazing!

See Also

Categories: Leadership


Leave a Reply

Avatar placeholder

Your email address will not be published. Required fields are marked *