Not Sure You Want to Be Groomed as an Executive? Ask Madeleine

Dear Madeleine,

I have a great job that I love, with a terrific company. I kind of stumbled into it and felt really lucky to find a job that suits me, with people I respect and like.

I recently had a performance review and my boss made it clear to me that the sky is the limit for me in the company, including a shot at executive leadership in the long term. The thing is, I’ve never given any thought to moving up. I’ve just had my head down trying to do a good job without really considering what might be next. I’ve never seen myself as someone who might even manage people, let alone whole sections of the business.

This apparent lack of ambition might have something to do with the fact that I am an athlete and spend all of my free time training for ultra-marathons and triathlons. I don’t know if I can really do both—rise through the ranks at work and continue to compete as an athlete.

I have made a list of pros and cons (which my Dad recommended) and scoured the internet for help, but I am none the wiser. I’m not at all sure about what I want.

What are your thoughts on this?



Dear Uncertain,

How delightful to field a good problem! Because it is good; I am sure you know that. But that doesn’t mean it is easy or simple. This sudden vision of possibility will trigger some research and some deep introspection. The great news is that you have time on your side.

The traditional pros and cons list is useful to gain clarity on binary decisions—go/no go, do this or do that—where you have a lot of information. But this decision is not binary, it is extremely complex; and you don’t have nearly enough information. You need to learn not only about what is possible for you but also about who you are and what is important to you.

First: Gather information about what is possible for you.

How to do that? Start by collecting intel about what it might look and feel like to be a senior executive. The most expedient way to do this would be to identify senior people in your organization and ask for an informational meeting. It doesn’t have to take long. Most leaders are happy to be tapped for advice, and most people love to talk about themselves.

To help you shape an idea about what a day in the life is like for a senior executive in your company, try asking questions such as:

  • What are your values? Over the years, what has been most important to you?
  • Have you been able to stay aligned with your own values as you have risen through the ranks?
  • What are your most and least favorite parts of your job?
  • What has been most surprising to you about moving into executive leadership?
  • How do you spend the bulk of your time?
  • What does life/work balance look like to you?
  • Have you been able to enjoy other things in your life outside of work?
  • Where do you feel you have had to compromise?
  • Do you have any regrets?
  • What advice do you have for me?

Of course you are not the people you will be interviewing. That’s why it is so important to understand each person’s values. The more people you interview, the broader a picture you will be able to paint for yourself.

Second: Gather information about who you really are and what matters most to you.

It sounds like you are on the younger side, and God knows we are all a work in progress no matter what stage we are in. So whatever you identify right now will only be a start—but it will help you build and refine the answers over time.

I found a great model in one of my all-time favorite go-to books, aptly named The Decision Book: 50 Models for Strategic Thinking by Krogerus and Tschappeler. I cannot recommend it highly enough because it is simply an overview of a bunch of terrific models to shape our thinking around:

  • How to understand yourself better
  • How to improve yourself
  • How to understand others better
  • How to improve others

It contains almost all of the models I use with clients again and again.

Your first stop, I believe, will be the Crossroads Model, which comes from a consulting firm called The Grove. Here are the questions it proposes you answer:

  • Where have you come from?
    • How have you become who you are?
    • What have been: main decisions, events, obstacles in your life; who are your influences?
    • Think about: your education, your home, where you grew up.
    • What are key words that strike you as important?
  • What is really important to you?
    • Write down the first 3 things that come into your head.
    • What are your values?
    • What do you believe in?
    • Which principles are important to you?
    • When everything else fails, what remains?
  • Which people are important to you?
    • Whose opinions do you value?
    • Who has influenced your decisions, who has affected your decisions?
    • Who do you like, who do you fear?
  • What is hindering you?
    • What in your life prevents you from thinking about the important things?
    • Which deadlines are in your head and what prevents you from making them?
    • What do you have to do, and when?
  • What are you afraid of?
    • List the things, circumstances, or people that cause you to worry and rob you of your strength.
    • What things, circumstances, or people make you worry?

Now look at your notes. What is on your list and what is missing? What is your story?

Study the roads that lie ahead of you. There are 6 examples. Imagine each one.

  1. The road that beckons: what have you always wanted to try?
  2. The road you imagine in your wildest dreams, regardless of whether it is achievable or not: what do you dream of?
  3. The road that seems most sensible to you—the one that people whose opinion you value would suggest to you.
  4. The road not traveled: the one you have never considered before.
  5. The road you have already been down.
  6. The road back, to a place you once felt safe.

You have your work cut for you, Uncertain. I am absolutely convinced that if you get a start on these two ideas, you will have a lot more certainty—not soon, but soon enough. You don’t need to rush. Make your plan, get going on it, take your time, and stay relaxed. Don’t listen to anyone who claims to know what your path should be. Do your due diligence and listen to your own inner voice, and you will know enough to at least take the next step.

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.

One thought on “Not Sure You Want to Be Groomed as an Executive? Ask Madeleine

  1. Wow, Madeleine gave some excellent next steps and resources to get you started. I would also like to point out that you were recognized for this opportunity while you being authentically yourself. Don’t ever lose that authenticity, even as you move through your career and learn more about how other people handle their roles. Stay true to yourself. You rock!

Leave a Reply