from buddy to boss

If you’ve ever been promoted from within your flight department, chances are you’ve experienced moving from someone’s “buddy” to someone’s “boss.”

Suddenly being the leader of one or more of your peers can make for a very tricky and often sensitive situation. And, if it’s not handled properly, can lead to an uneasy work environment.

Having gone from being “one of the girls” to actually leading a team, I understand the ups and downs of this “phenomenon.” So I recently spoke to a couple of aviation directors who’ve been promoted into their roles.

In particular, I asked them to discuss any issues they faced, how they managed them and what tips they have for aspiring leaders.


Don’t be a ‘Boss,’ be a ‘Leader’ 

In the first case, an aviation director for a pharmaceutical company based in Chicago told me he had previously been in a managerial position but had no direct reports, and then was promoted to an aviation director with 20 reports, all of whom had been same-level friends and colleagues.

He told me: “When I was presented with the opportunity to lead this flight department, the first thing I did (after suffering a prolonged panic attack!) was to sit down with my leadership team to form what would ultimately become our guiding principle: to prioritize “people before process.”

“I don’t consider myself to be a very good example of a ‘boss,’ nor do I don’t strive to be one. Instead, I strive to be a ‘leader.’”

The director told me he took the advice of noted business psychology author Russell Ewing, who said:  “A boss creates fear, a leader confidence. A boss fixes blame, a leader corrects mistakes. A boss knows all, a leader asks questions. A boss makes work drudgery, a leader makes it interesting. A boss is interested in himself or herself, a leader is interested in the group.”

Sound advice, I think.

But just how does one handle difficult developments, or perhaps performance issues, as a leader and as a “friend”?

For certain, it will require a candid conversation, along with a professional willingness to accept accountability.

As the director told me, “It’s been my experience that when you are operating in an environment where people truly care about and respect one another, the business environment will take on those same conditions and characteristics and your relationships will be transparent, open and thriving in that environment as well.”

He went on to say that he realizes everyone is human and that things don’t often go perfectly. But, generally, he said, operating under the principle of prioritizing people before process has worked very well for him in his new role.

And he capped our discussion by offering yet another quote, this one from no less than President Theodore Roosevelt.

“People ask the difference between a leader and a boss. The leader leads, and the boss drives.”


Learning How to Have ‘Difficult Conversations’

My second interview was with a director of aviation for a financial institution based in Pittsburgh. His experience was when he previously had worked as a line captain and was eventually recommended for the role of chief pilot.

In his new job, he went from buddy to boss.

He told me he had 10 pilots that he had worked alongside at the time, a couple of whom were very close friends. In fact one of them was his best friend. And now he was expected to be their boss.

So how did he handle that transition?

“I had a long conversation with my then boss, who was the aviation director, and I asked if I could hold a meeting with the pilots, without him being present. I wanted to set the ground rules, discuss how I felt the role should be handled. And I wanted my team to know that I hoped to be a ‘pilot advocate,’ to help build this role, and only bring my manager into the picture when it was really needed.”

He told me that the meeting went well. He was able to establish a friendly—albeit newly defined—relationship with them, and, in turn, they were supportive of his taking the leadership position.

Later, he said he did find that working with friends as his direct reports presented some challenges.

“It was hard to have difficult conversations,” he explained. “I was fortunate to have 10 years of working in the Army National Guard, so I had experienced a lot of great mentors and leaders along the way… and some not so great ones. The good ones helped me work through the challenges and showed me how I wanted to lead.”

He told me that one thing he did was to set up a 360-degree evaluation, in which his team rated him on a number of leadership/performance measures. The one thing he saw consistently were comments about him not being inclined to have tough conversations.

“Initially I wasn’t good at it, but I was able to focus on that aspect of my performance and improve. The process was humbling but, at the same time, the evaluation was extremely accurate.”

Early on in his new role as “boss,” he says he didn’t want to embrace leading by fear, and he said he definitely didn’t want to get an “M.O.” for “doing as I say and not as I do.”

“This is a big lesson for a Chief Pilot,” he said, “to not just take the ‘cushy trips, the week day trips. You’ve got to be down in the trenches with the guys and gals.”

He made an interesting comparison to coaching your friends as you might coach your child in little league. When you’re the leader and your best friend is on the team, it’s easy to single out the person to be your favorite. And it’s also easy to hold them to higher expectations and treat them unfairly.

“I’ve been guilty of both,” he told me. “Looking back, I definitely would have made different decisions on how to coach and mentor my friends.”


Tips for Aspiring Leaders

So, given their dual experiences, what are some tips they would offer prospective “buddies” who are about to become “bosses”?

Here’s a short list:

  • Clarify the roles—both yours and your direct reports.
  • Get involved—immediately in his new role as chief pilot, my second interviewee said he applied to be a member of the Chief Pilot’s Roundtable. “It was a tremendous asset to have that sounding board and be able to network and do industry benchmarking with my industry colleagues.”
  • Draw boundaries—where is the line between buddy and boss? What are the “gray areas” managers have to navigate?
  • Set clear expectations—Talk about what will change as well as what will not change. Then be consistent.
  • Explain your leadership style—If your direct reports know what they can expect from you, your chances of leadership success will improve greatly.
  • Lead by example/be a role model—What you do vs. what you say will influence your credibility.
  • Learn the difference between leading vs. managing—People don’t mind being led, but they will choose who they follow, and, inevitably, it’s someone who knows where they’re going.
  • Give your team members some ownership—Allow them to take calculated risks and push themselves to work beyond their full potential.
  • Don’t micromanage—Enough said.
  • Be open minded—Create an environment where people are free to share ideas, collaborate and thrive.
  • Find a mentor—Someone with whom you can discuss the challenges of new leadership.
  • Communicate often—Explain what’s going on in the department and at corporate. How do they fit into the big picture? Telling them what, how and why builds their confidence.

I think the most important consideration of all when you find yourself in a “buddy to boss” situation is to simply use your wits and a measure of good judgment.

Remember that people will respect you and your position if you let them understand you’re going to lead the team toward success—which is something anyone can relate to, and learn to love.


Have you Transitioned from Buddy to Boss?

What tips do you have for aspiring leaders in business aviation? If you’ve gone from “buddy to boss,” please share your experience(s) in the comments below.


  • When I went through the buddy to boss transition about 19 years ago, it was an eye opening, humbling experience. A couple of things i learned quickly and painfully. 1- Be careful of your words, as they are heard differently when you become the boss. An innocuous comment to a friend may be taken as a personal slight to a subordinate. 2- Make sure you don’t send the wrong message by doing one thing while asking others to something else, e.g. flying to a meeting at an out station while expecting crew members to drive. Even though there was justification, it sent the wrong message to the team, and taught me a great lesson in humility. In response, I actually had the opportunity to fly the team on our plane with their spouses to a company event on at the corporate headquarters, and I drove. It made a great impact on the team.

  • Unfortunately for me, I learned the hard way about the buddy to boss move. In my late 20’s, untrained as a manager of people (who just happened to fly aircraft), I had to manage my friends. Some took advantage of our relationship until I had to have the tough performance management conversation. The friendships died as a result. Since then I’ve “protected” myself from that situation by separating my work life from my family life.

    If you have friends at work and they report to you on some level, some will wonder if that influences your decisions about specific assignments or praise. Let’s say they do a good job and receive public credit. Some wonder whether they received the credit because they are your friend vs. having done the job well. Hard working people should not be robbed of true accolades because of insecure colleagues. I’ve not figured out a way to be an off-work-friend with a colleague (who reports to you), and not create that possibility which could stop them from truly shining for their business efforts.

    Taking a page from a management class, easy on people, tough on standards. I share that with my colleagues now so they know where I’m coming from. I agree with Mark Chaney’s response in regards to the words carry more weight today than they did yesterday and a casual comment can take on a life of its own. Being mindful of the business card you hold creates a burden as well as a reward. I also ensure that I live my business life at the same level that my colleagues do. Coach seats, standard hotels, etc…Took me years to earn trust and it can take me only seconds to lose it.

    I use a quote often now that I used when I coached kid’s sports. “We live and die on the field together”.

  • Mitch: Thank you very much for contributing your experiences and guidance on this matter. The conversation calls for many voices and much input. We truly appreciate your thoughtful reply!

  • Thank you for sharing these specific instances and experiences, Mark. The more we discuss the “hard lessons” we’ve learned, the more other people can potentially avoid them. I agree that a seemingly harmless comment or justifiable act and can be ill received in this complicated “buddy to boss” dynamic. I don’t know if the transition can truly ever be “mastered”, but the awareness you’re helping to create helps immensely!

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