Your Former Direct Report Is Now Hiring You
This happens more often than people think. You recruited someone. You mentored them. You promoted them. You helped them navigate difficult situations. Perhaps you even told them they were ready for their first executive role.
Then, ten years later, you're looking for your next job. And you discover that they are now the CEO. Or the CHRO. Or the board member making the hiring decision.
And you're considering working for them. Suddenly, the career hierarchy has become rather interesting.
It can be uncomfortable
For the person who used to be the boss, the situation can trigger all sorts of emotions. “I trained them.” “I remember when they were a manager.” “They wouldn't be where they are without me.” “I can't possibly report to someone more junior than me.”
These thoughts may never be spoken aloud. But they can influence behavior. And that's where the problem begins. You may remember the person who worked for you. But they have spent years developing since then. They have faced challenges you haven't seen, made decisions that have failed and succeeded. They've worked for other leaders and built their own reputation. They've developed their own leadership style. They will now be an entirely different executive. You don't need to forget your history together. But you do need to respect who they've become.
One of the worst things you can do is remind them of your contribution. “You'll remember I gave you your first promotion.” “I always knew you'd make it.” “I was the person who hired you.” Perhaps all of those things are true.
But they don't help you get the job. There’s a high risk this person will regard your comments as condescending. And the focus won’t be on what you did for them ten years ago but rather, what can you do for their organization now?
There is an opportunity here and a risk
Having worked together previously can be a significant advantage. They already know something about you. They may know how you behave under pressure. They may know how consistently you deliver. They may know how you lead and inspire. They may know you’re supportive when things go wrong. That's considerably more information than an interviewer normally has.
But it also means you can't hide behind a polished interview performance. They may remember you too well and will have memories of the things they didn’t like about you all those years ago. Chances are high they won’t spend much time reflecting that you too might have changed, learnt and improved in recent years.
Put yourself in their position. Would you be comfortable hiring your former boss? Perhaps they are wondering: Will they respect my authority? Will they challenge every decision? Will they try to recreate the old hierarchy? Will they expect special treatment? Will they undermine me with other executives? Will they struggle when I make decisions they disagree with?
These are legitimate concerns. And as the candidate it’s up to you to address them through behavior. You don't need to behave submissively, as though you're suddenly junior to this person. Don’t make the interview about the past, but demonstrate that you recognize the relationship has changed. You might say: “I've watched your career develop since we worked together, and I'm impressed by what you've built. I'm interested in understanding what you need from this role now and whether my experience could help you achieve it.”
That's mature. It acknowledges the history without being trapped by it.
Don’t assume they owe you either. Perhaps you genuinely helped them, or gave them opportunities other people wouldn't have. But that doesn't mean they owe you a job. Their responsibility now is to their organization. Your responsibility is to determine whether you can contribute to it. That's the professional relationship.
What if you disagree?
This is probably the biggest test. If you are hired, you may disagree with your former direct report. That’s all part of being a senior executive. But disagreement needs to happen from the current relationship, not the historical one. Not: “when I was your boss, we would never have done this.” Instead: “I understand the direction you're considering. Can I challenge one assumption? I think there is a risk we should examine.” The second statement is a person acting like a senior executive. The first is a person still acting like the old boss.
Your reputation comes back around
Careers are rarely linear. The person you managed becomes your CEO. The person you reported to becomes your board chair. Someone you once interviewed becomes your peer. Someone who worked for you becomes your client. Someone junior to you becomes the person deciding whether to hire you. This is increasingly normal in senior careers. And the ability to navigate these changes without ego is a genuine leadership skill.
It’s another reason to treat people well throughout your career. The junior HR manager you dismissed might become a CEO. The executive assistant you barely noticed might become a board member. The candidate you rejected might eventually become a client. The person you mentored might one day be in a position to recommend you. I see this time and time again across the HR profession - you never know where colleagues will end up.
This isn't an argument for being nice because someone might become powerful. It is an argument for recognizing that professional relationships are long-term assets. Treat people well because that's who you want to be. Not because you might need them later.
And if they don't hire you?
Accept it professionally. You may be disappointed. You may even disagree with the decision. But don't allow the history between you to make the rejection personal.
They have a responsibility to make the best decision for their organization. You have a responsibility to continue managing your career.
You may work together again. You may recommend each other someday. The relationship doesn't have to end because one recruitment process didn't work out.
The final thought
There is something quite satisfying about seeing people you once managed become successful. If one of them eventually becomes the person interviewing you, that isn't an embarrassment. It's probably evidence that you did something right.
The challenge is to meet them not as the person that used to work for you, but as the leader they have become. And to allow them to meet you not as their former boss, but as the experienced executive you have become.
The best careers are rarely straight lines. Sometimes the person you once hired becomes the person who hires you. How you handle that reversal says a great deal about the leader you have become.
About the Author
Sally-Anne is appreciated across her leadership network for her constructive honesty and care. As a senior partner she brings many years of career experience supporting executives in their search for new career challenges, and in their search for high performing talent for their own teams.