Dear Madeleine,

I am a VP of sales for a global software organization. I love my job, which is good because I work constantly and have for the past 25 years. It has been rewarding and I have saved enough to be able to think now about maybe slowing down. I have been discussing retirement with my wife and she is excited to have me around more and to travel, visit our kids and grandkids, etc.

My boss recently shared with me that he wants to groom me to take over his job. I was absolutely surprised by this as I never imagined I would be even as successful as I am, let alone considered for the senior leadership team.

This has sent me into a tailspin. I am just a sales guy. I never completed my degree because I did so well at my first sales job, which I had taken only to pay for college. At that point I was married with a kid on the way; you know how that goes. The next thing you know, 25 years has flown by.

All the people on the senior leadership team have MBAs from fancy schools, drive fancy cars, and go to fancy places. That just isn’t me. I don’t see myself being able to relate to these people—and I know my wife would not be comfortable with these folks. I haven’t even told her about this possibility because I know she will be disappointed at the prospect of the shift in our plans. It would mean, I am sure, ten more years of my working like a dog. Also, I don’t see myself as particularly strategic; I don’t know how I would add value to that team.

On the other hand, what an opportunity! I am trying to think this through logically but am barely able to think straight. Help?

In a Tailspin

Dear In a Tailspin,

Wow. As problems go, this is such a wonderful one! And I know how overwhelming this must be, so I don’t want to minimize that. I can offer you a plan for tackling this decision that will hopefully set you up to be at choice. This is a coaching term we use to express the process of looking at the whole picture, understanding what you can control and what is most important to you, and then choosing what actions you will take to achieve what you most want.

1. The first order of business is to establish what you want. Right now it is about what your boss wants (a successor) and what your wife wants (more time with you). Just because you never dreamed something would happen doesn’t mean it isn’t possible—and this magical thing is happening for you now. The question is: do you want it? Right now you can’t even access your own voice because it is getting lost in the noise of your fear. So let’s address that.
2. Face your fear: You say you are “just a sales guy.” Sales is arguably the most valuable competency in any organization—after all, there is no business without customers. People who are good at sales are astonishingly good at relating to other people. And successful sales leaders are excellent at directing and supporting others to do the same. Of course you are strategic—you don’t get to be VP in a global software company if you aren’t strategic! Because you are unclear about your strengths, you might want to ask your boss what it is about you that makes him think you should be promoted. That would help you understand what he values in you and get you past the notion that you are simply a regular guy who is lucky.
3. Stop focusing on the past: Let’s talk about this story you are telling yourself that everyone on the leadership team is too fancy for you. Cut it out. This is just complete hogwash. Maybe a couple of them have some made some fancy lifestyle choices, but that doesn’t make them different from you. I have worked with enough executives to know that almost to a person they are not only grateful for the opportunity they had to be educated but also still pinching themselves at their luck. Most of them know they aren’t better or much smarter than anyone else and many suffer from imposter syndrome. Almost everyone who achieves a position in senior leadership feels as if they don’t quite measure up for some reason and don’t quite belong. So you didn’t finish college. So what? Your boss doesn’t care. Maybe some other people will; but you can’t control that. Trust that you will be able to leverage your people skills to find something you have in common with each and every one of them, and trust that your wife will be able to do the same if she knows it is important to you. People are just people. You know that. So stop putting them on a pedestal.

To cut through the noise here, take yourself out for a long walk and ponder these questions:

• What is interesting or exciting to you about this opportunity?
• Are you signed up for the learning curve it would entail?
• Which of your strengths would you be able to leverage?
• What kind of an impact would you be able to make on the organization?
• What would you be able to accomplish?
• What would you have to give up to avail yourself of the opportunity?
• Are you willing to do that?

Once you have some clarity about your answers and decide you want to go for it, you can have a serious sit-down with your wife. If she is as eager to spend time with you as you say, she probably still actually likes you, is your best friend, and has your back—so I suspect she will be willing to support your quest.

Finally, I want to challenge your assertion that accepting this job would mean you can’t travel and visit your kids and grandchildren. Possibly the real opportunity here is for you to get creative—find a way to achieve undreamed-of success at work and have more space and time for your family. This is the ultimate senior leadership challenge, and you seem to have enough going for you that you are probably up to it.

Breathe deep, my friend—and congratulations!

Love, Madeleine

About the author

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.

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