Their Exit Strategy

Blaine Phelps
4 min readJun 10, 2024

For those professionals who want to grow and expand their careers, they need to be constantly learning — and growing — and moving up.

Let’s talk about the moving up.

Let’s talk about exit strategy.

Not yours. Let’s talk about the exit strategy of those above you.

When you are young, those above you are always moving up and on — with titles like “Lead”, “Asst. Manager”, “Supervisor”, or some kind of “level(s)”.

In other words, those above you are into their 2nd or 3rd year of starting their career and are moving up, leaving a vacuum for those below them (the newbie young professional) to move into and gain the experience they need for future advancement.

As I wrote about this before, I need to again remind you that this is a funnel. When you are young, there is a plethora of “moving up” opportunities. But as you age and move up, the opportunities continue to shrink (i.e. move down the funnel). There is only one CEO, maybe half-a-dozen VP’s, a dozen Directors, and two dozen managers for a company of 200 employee’s. The opportunity to move up shrinks the further you move up in a company.

Which leads to you jumping ship to take a “higher” spot at another company as you continue to advance your career — if there is no opportunity for you at your current place.

Now to a specific story I want to share with you.

Was mentoring a young lady who worked for a large city in Pennsylvania. She’s 35. She came to work for the city because they needed someone like her for a new position that they had just formed. She has been there for two years — kicked ass — and is now bored.

I asked her why she was now “bored”? People would die to have her job!

“I’ve done everything I can — and I love a challenge, and I love to learn.” (Someone right after my own heart!!!)

So I asked the question that not many people really ask (but they DO think about), “When is your boss leaving?”

Few people who are in the middle or bottom of the tunnel think about their bosses leaving. Even though they (you in this case), may have left a company to go work somewhere else and continue advancing down the funnel, why don’t we think that are bosses are doing the same?

With this young lady, it was an easy answer.

“When I was asked to come on board, the CFO, my boss, said that he was going to retire in a few years (he is now 79). I was led to believe that I would have a shot at the job. But I think that because of me, his job has been made a lot easier and he now see’s himself staying on a lot longer. I don’t want to leave — I want his job, but, I don’t want to wait much longer.”

How would you respond?

Here is how I approached this with her:

  1. “What is your boss’s (the CFO) exit strategy?”

That’s it.

She said she didn’t know.

I then said:

2. “Tell the CFO that you plan on leaving. You were promised/made aware of that you would be in the running for their position within a few short years (two years ago) and now it seems that that is no longer the case. If the CFO has no exit strategy, then it is time for you to move on.”

This would allow the young lady to know exactly what is happening in the future with her current and promised position.

If she truly did take a lot of pressure and responsibility off the CFO, he would not want that to come back on to him if she left.

If she was as successful as she says she is, the CFO will certainly not want her to leave — causing him to pick up all the stuff that she took over for him, then, if he left, he would leave the city in an unfortunate position (if they both left quickly in short succession).

In other words, by asking a boss what their exit strategy is, you can find out and plan your future accordingly. Not every boss is going to tell you that they are looking for another job though.

But some will.

Those that won’t talk about it, you can tell by their actions (i.e. they are checked out at work, not caring, etc.).

There were only two times where I was surprised when a boss of mine left. One was at my first job where I had only been there six months and the second was when my boss stood up in the middle of a meeting and said “I quit” (see #3 on this post).

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Blaine Phelps

Lucky enough to have traveled the world and gained experiences that I like to share - and I do it now, through life coaching, mentoring, and teaching.