Not Sure Team Member Is “Very Happy”? Ask Madeleine

Dear Madeleine,

I have been offered a promotion and need to make a recommendation for the team member who will be promoted into my job.

I have one very likely candidate: my most promising employee. She is consistent with her deliverables and has led some projects for the team with great results. She gets along well with her peers and is well respected all around.

The interesting thing is that this person does not seem very ambitious. Whenever the topic of her career comes up, she claims to be “very happy” right where she is. I can’t tell if that is really the case, or if she just lacks confidence to aim higher.

I don’t want to apply too much pressure and end up demotivating her. What is the best way to approach this? I don’t want to be…

Too Pushy


Dear Too Pushy,

First, kudos to you for being sensitive enough to care about Very Happy (VH). The key here is get to the bottom of what her “very happy” means. It could mean “very happy for now” or “very happy for the foreseeable future/ you don’t have to worry about me wanting more and seeking an opportunity elsewhere,” or it might very well mean “very happy forever.”

It can be a mistake to assume anything, because your idea of what being ambitious looks like might not match someone else’s. VH may be the kind of person who doesn’t envision a possibility for herself until it is tangible. It might be that she is also worried about coming off as too pushy. You just won’t know until you investigate.

It is generally accepted that all managers need to develop a successor, so you might start by stating that as a fact and asking if she would like to be considered. You could also share that, in your opinion, she is the most likely candidate, but that you don’t want to pressure her. Let her know you are exploring and are open to the outcome.

There is a good chance that VH will ask exactly what the job would entail, so anything you can share about the job description and expectations around ramp-up time would be good to have at the ready. You may think she knows what the job is—but remember, she only sees what you do from where she is sitting.

It is possible, as you mentioned, that VH may not feel she is ready. If so, you will want to be prepared with observations about her strengths and how they would serve her in a more senior role. You might share the challenges you anticipate she would face, and how her experiences so far will have prepared her to rise to them.

If VH would continue to report to you, obviously you would be there to help her get settled in the role. If that is not the case, you might think about offering to mentor her through the transition.

It can be hard for people who have a strong drive to achieve and make no bones about it to understand those who are, by nature, more cautious and guarded with their aspirations. You already are receptive to how VH might play things close to the vest. Honor her nature and continue to be thoughtful, candid, and kind. You might just be able to draw her out enough so she will consider taking what, to her, might feel like a risk.

Love, Madeleine

About Madeleine

Madeleine Homan Blanchard is a master certified coach, author, speaker, and cofounder of Blanchard Coaching Services. Madeleine’s Advice for the Well Intentioned Manager is a regular Saturday feature for a very select group: well intentioned managers. Leadership is hard—and the more you care, the harder it gets. Join us here each week for insight, resources, and conversation.

Got a question for Madeleine? Email Madeleine and look for your response soon. Please be advised that although she will do her best, Madeleine cannot respond to each letter personally. Letters will be edited for clarity and length.

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