Dear Madeleine,
I am a senior leader in a highly specialized digital publishing organization and I have about 14 direct reports. Organizationally, I’m third in seniority. My plan is, by the end of 2025, to transition out of this role and into my own coaching and consulting business. I’d be working with some clients, but primarily in an adjacent field.
I am currently working on building up the coaching business on nights, weekends, and off hours. I’ve been able to grow what had been a side hustle into what looks to be a successful final chapter for me (I’m 60 years old) without it affecting my productivity in my current role. My boss is aware that I do this coaching and consulting work, but at this point he is not aware of my plan to transition into coaching full-time in early 2026.
My questions are: when is the appropriate time to tell my boss I’m planning to exit, and how do you recommend I share the news? I want to give him adequate lead time as I think this news will create some significant disruption, and I would like to be involved in handing off the baton to whomever is next to step into my role. But I don’t want to risk my boss overreacting and ending our relationship before I am ready to go.
Thanks for your wisdom. I just want to be—
Smart
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Dear Smart,
First, congratulations on creating a successful side hustle while working full-time. That takes a lot of focus and energy, and it is a huge accomplishment. And welcome to the coaching profession. I hope it brings you all the fulfillment it has given me.
I am struck by how thoughtful you are about your transition out, as you clearly have the success of your company at heart. Your question is interesting on many levels, and it is hard to give you a definitive answer without knowing your company’s culture and your boss. But just the fact that you are concerned about what to me sounds like an irrational overreaction is a clue that your boss values loyalty over proper planning. So, not to be annoying, but as a coach you will recognize the approach: Given what you know, what advice would you give a friend in your position?
I have such a high value for clarity, communication, and planning that it’s hard for me to get my head around a boss who wouldn’t appreciate the heads up, welcome your help in preparing your successor, and wish you Godspeed when you are ready to go. In fact, most leaders I work with would appreciate knowing what someone they depend on is thinking about the future. But you do have concerns, and they come from somewhere, so I encourage you to heed them.
It is the norm in most companies to encourage senior leaders to create a succession plan and actively develop their successors. It doesn’t sound like that is true in your company, but that doesn’t mean you can’t still do exactly that. I urge you to identify any likely candidates among your 14-ish direct reports. Once you’ve got your short list, you might delegate parts of your job or assign these folks tasks that will ensure they learn and develop. At least one or two of them will show evidence that they can take on your job.
The rule of thumb for senior executives is 60 days’ notice—ideally, 90 days for a super smooth transition. If you are really worried that your boss will fly off the handle and retaliate, I would suggest that you wait until you are ready to go and offer a range of transition time from two weeks (which is standard) to 60 days. That way you take care of yourself, you don’t run the risk of being ejected before you are ready, and you can flex as needed if you are asked to craft a sensible transition. Be ready with recommendations and your supporting reasoning for likely replacements. That would be the sane, responsible thing to do, and you’ll be able to hold your head high no matter what happens. You may or may not get to participate in the passing of the baton—that will be up to your boss.
I wish you continued stamina and lots of luck in this next chapter you are creating.
Love, Madeleine
About Madeleine
Madeleine Homan Blanchard is a master certified coach, author, speaker, and cofounder of Blanchard Coaching Services as well as a key facilitator of Blanchard’s Leadership Coach Certification course. 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.
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