Ready for Your First C-Level Job? Ask Madeleine

February 11, 2023 Madeleine Homan Blanchard


Dear Madeleine,

I have had a long and varied experience in law. I started as a public prosecutor in corporate law and rose quickly to reporting to the General Counsel.

My current boss isn’t going anywhere for a long time, and I feel ready to go for a GC position myself. I put feelers out at the beginning of January. I believed taking that step would put a lot of things in motion—ready or not—based on my past experience. And that is exactly what has happened.

I have some really interesting interviews coming up for GC roles that present considerable gaps for me (regarding technical knowledge, not leadership). I am thinking about how to be transparent about strengths and weaknesses (i.e., opportunities to develop) without arguing against myself. I like being in a little bit over my head and figuring it out, but this would be the deepest water yet.

Any framing/grounding thoughts you can share as I expose myself for what might be next?

Ready to Take the Leap


Dear Ready to Take the Leap,

I am not a headhunter or a career expert, but I do have some thoughts based on working with clients who are always wrestling with getting hiring right. I think there might be some value to the perspective. I hope others with different expertise will add useful ideas in the comments, as well.

  • Make sure you are interested and engaged in the company and the industry, and well versed in the challenges they face, so at the very least it’s clear that you’ve done your homework. The last time our board interviewed people for the CFO position, I was a little taken aback by how many final candidates did not bother to achieve even baseline knowledge of our industry.
  • Study the CEO and ascertain what matters most to them. What is the vision, what are the values (if any), and how would you align with those in the job?
  • You can’t pinpoint all the technical gaps you may have, because you won’t know what you don’t know until you get in there and roll your sleeves up. But maybe you can speak to one or two of them and make it clear you intend to close the gaps, should it come up. I think preparation to address concerns is your best bet on that.
  • Clarify your top strengths for yourself. Based on your varied background, it sounds like you are a fast learner and have always depended on being able to figure things out. What else are you naturally gifted at, or what other skills have your developed along the way? Are you fast on your feet when decisions need to be made? Super calm in a crisis? A creative problem solver? Be prepared to share brief examples of how your strengths have been useful to your CEO or your team in the past.
  • If a comprehensive job description exists—and I find that even in mature, well-run organizations that is not always the case, especially for the C-Suite level—be ready to address each expectation with how you will rise to it.
  • Also be ready to emphasize any transferable experience and skills and how exactly you see them transferring to a different industry or company.

Finally, be prepared with questions that illustrate your curiosity about the business, the industry, and the culture. There is such a thing as a stupid question in this environment, so be sure not to ask something you could easily find answers to in the annual report. You might ask questions like:

  • What do you think of as your “secret sauce”—the thing that differentiates your organization from (name a competitor)?
  • Of all your strategic initiatives (extra points if you can name them), which is most critical right now?

Companies have two choices when hiring at the C level: either find someone who has already worked at that level (who usually demands a much higher salary) or take a risk with someone who is stepping up. There are advantages to each choice. The advantage of going with someone stepping up is more drive, hunger to prove themselves, willingness to try new things, and humility. You won’t be set in your ways, you will work hard to learn and find the best way. I would say given the kind of complexity any company is dealing with these days, that would be an asset. The more you can demonstrate those qualities—with, of course, the appropriate gravitas—the better off you will be.

Finally, preparation is your friend. Practice with a friend, mentor, or partner and give them some classic behavioral interviewing questions so you can respond with well thought through, succinct answers. Here are some behavioral interviewing questions you can use to get started:

  • Describe a situation in which there was a lot of disagreement and you needed to influence your leadership team to consider the option you were proposing more closely.
  • Discuss how you have dealt with a tight deadline that required you and your team to go above and beyond the usual.
  • What is the worst mistake you have made, and how did you deal with the consequences?

You can ask our friend Google for more examples. It will help you feel ready for anything. Good luck with your big leap. I have a feeling you will land in the right place.

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.


About the Author

Madeleine Homan Blanchard

Madeleine Homan Blanchard is a Master Certified Coach and cofounder of Blanchard Coaching Services. She is coauthor of Blanchard’s Coaching Essentials training program, and several books including Leverage Your Best, Ditch the Rest, Coaching in Organizations, and Coaching for Leadership.

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