Moving On When Your Boss is Your Mentor
This is my site Written by Alora on December 17, 2008 – 1:15 pm

I recently got a phone call from a dear friend who found herself very conflicted about an unexpected career opportunity that hit her from out of the blue. After a few minutes of talking, I was a little confused why she seemed to be so conflicted, because — with one or two minor exceptions — it actually sounded like a potentially great move, and one with far more opportunity than her current role.

And then she said it: what she was really angsting about was telling her mentor, who also happened to be her boss. And she was seeking my input specifically because he also used to be mine.

The entire conversation got me thinking: twice in my career I have had amazing mentors who also happened to be my boss. In both cases that was a great combo because it meant lots of access, tons of opportunity to learn in practical settings, lots of hands-on collaboration and great platform on which to build a really strong relationship. However, in my case, there was also one very serious downside in both cases — and it wasn’t as much about them as it was about me, and it’s one that I see in my friend now, and in other people over the years (including at least one person for whom I was the boss/mentor): when your boss is your mentor, it’s easy to stay at a job for too long out of fear of letting your mentor down.

In hindsight it is very clear to me that both times my boss was my main mentor, I stayed at a company long after I should have left — which caused a series of secondary problems I didn’t foresee. But hindsight also makes the “why” very clear: I didn’t want to let down my mentor, who was in the habit of counting on me, just as much as I was in the habit of counting on him.

In speaking to my friend, I outlined an approach to what is ultimately a difficult conversation to begin. (Dr. Lois Frankel has written about this issue as well, particularly for women who have a very father/daughter type of relationship dynamic with their mentors.)

1.) Be first and be direct.
Don’t let your mentor hear the news from someone else. In order for a mentor to be a mentor, he needs to know what is important to you, what your goals are and what you’re thinking. A mentor who doesn’t know that your long-term goal is to be CIO or that you’re hoping to move across the country is not in a position to be a good mentor to you; and if you don’t share that information with him, then any decision to make to achieve any of your big picture goals is always going to come as a surprise.

And definitely do not let your mentor hear the news from someone else — this is a particular danger if your new role is within the same company. A new boss is almost always going to talk to your current boss (most companies require it as part of an interdepartmental interview process), and if your mentor gets ambushed with the information from someone else, it’s going to make things very awkward for you to talk to him later. It’s also a disrespectful thing to do to someone whose opinion and respect you supposedly value.

2.) Be rational about your reasons.
This one can sometimes seem harder than it really is, especially if your reasons do not appear rational on the surface. For instance, if you suddenly find that half your department is being outsourced, but you are safe, then it can appear that electing to leave yourself is strictly emotional and unnecessary. But that’s not necessarily true at all. In a world of constant IT outsourcing, being one of the handful of remaining professionals in the ghost town of what was formerly a large technology organization is a rough gig. Watching your friends and colleagues leave, riding out what is a difficult transition period, witnessing the evaporation of the organizational culture and still getting your work done in and among all of that chaos is extremely difficult to do. The argument that, “At least you still have a job!” is not invalid, but it’s also not the whole story. If part of your reason for leaving is that the existing situation is so impactful to morale (including your own) that you are finding productivity to be increasingly impossible, then that is a rational argument for leaving.

Other good reasons for leaving include one of the biggest ones of all: opportunity for growth. Your mentor should be very clear about your long term goals (at least as clear as you are). And any mentor worth their salt (and your loyalty) should be helping you meet the goals necessary to achieve those ends. A good mentor should also recognize when he can’t provide you with as much opportunity as you can find somewhere else. But when you speak to him, be prepared to outline the reasons you feel the new opportunity offers you more than your current role does. A good mentor may question, clarify or offer suggestions you haven’t considered, but he should never, ever dismiss your opportunities for growth or progress as unimportant.

3.) Be prepared for an emotional response, just in case.
People are people, and as much as you may be dreading telling your mentor, your mentor could have a hard time hearing that you are leaving (especially if he didn’t see it coming). This is often especially difficult news when he has come to depend on you to handle something particularly big/nasty/difficult so well that he doesn’t have to worry about it and can focus on other things.

If you know your mentor well enough, you will probably have a good idea what an emotional reaction is likely to look like: Angry? Disappointed? A guilt trip? A counter-offer? Whatever tact is most likely, have a counter-card ready to play in case it is necessary.

If your mentor is likely to get passive-aggressive and toss a bit of a guilt trip at you when he is upset/surprised, then you have two choices: find a guilt trip you can toss back out at him in the moment if necessary; or be prepared to point out that he is getting emotional and attempting to guilt you (most people don’t necessarily realize they are doing it in the moment, so you can often put a quick stop to it this way if the person does truly care about you).

With some people it’s best to match them quid pro quo rather than to potentially embarrass them by pointing out that they are being petulant and unfair. It’s a little manipulative, but it saves face, which can sometimes go a long way towards maintaining a strong relationship after you’ve departed. So being prepared to toss some guilt back his way if he tries to guilt you into staying is often a way of getting him to back down without overtly taking a pie in the face. Guilt can also work well if his inclination is to get angry; handled correctly, you can diffuse him a bit by making him realize he’s being a bit of a bully.

4.) Be grateful.
If your boss is your mentor it’s because he has made investments in you — financial as well as emotional. And the reason you feel conflicted about leaving is because you are grateful for everything that he has done and do not want to disappoint him. But, as is the case with most daily relationships, we rarely tell the people who matter most in our lives how we feel. So take this opportunity to thank him for everything he’s done and everything you’ve learned; point out to him that the lessons he’s taught you have been valuable and that this new opportunity offers you the chance to apply those in a new setting and further develop your skill set. The “I am only in a position to take on this new challenge because of what I’ve learned from you” argument serves the dual purpose of being both effective and true, so take advantage of it.

Of course, the fact is that people are human and if your boss is your mentor then he should care about you and want what is best for you. One of the things you may have to brace yourself for is that your boss could be consumed enough with his own problems that he has some trouble being gracious about you needing to do what you need to do for yourself, especially when it has the unintentional and unfortunate side effect of making his life more difficult in the short term. But, once again, if your boss really is a mentor, then once he has some time to process through your news (and your reasons), he’s likely to come around. You may just need to be prepared to give him some time before you can expect a lot of sincere congratulations on your new job.