Before you take the job, read this
Elizabeth Freedman
C-Suite Performance | Executive Readiness & Onboarding | Leadership Team Impact | Succession Planning | Forbes Contributor | Keynote Speaker
What I hear too often from my executive clients:
“I wish I had known this before I took the job.”
When highly capable, well-prepared leaders keep saying this, it’s a warning sign. These are leaders at the top of their game. They’ve spent years building expertise, delivering results, and being groomed as key successors. Yet once they step into the big role, they discover critical gaps: It’s why you’ll hear comments like:
I wish I had known how much of a voice the board expects to have in my management decisions
I wish I had the full picture of how we were performing as a business before I took the job
I wish I had recognized how much resistance I'd face for my project or initiative
I wish I had recognized the dynamics on the team before becoming a member
I wish I had done more to understand how much time and access I would have to my CEO
I wish more people had been candid with me about my leadership style before I took the role
Good leaders know they’ll learn as they go. But stepping into a top role with too many surprises creates major risk for leaders and organizations.
Closing the Knowledge Gap: Start Here
Have a future-back perspective.
Ask yourself: A year from now, what will I wish I had known sooner? Then, go after those answers now. Ask for examples of how the board has influenced recent decisions. Talk to trusted colleagues about their interactions with the CEO. Assess your own team’s strengths and gaps before you’re in the seat. Look for specific examples, not just general impressions — they’re what reveal the “unknown unknowns.”
Provide the full picture. Too often, leaders aren’t given the full picture until after they start. One new leader put it this way: "I was told our business was in good shape, and I was naive enough to believe it. I get in the role, I look under the hood, and it's a mess."
A strong succession process builds in frank conversation — not just once, but as a regular practice. Organizations should check in with leaders a year into the role and ask what they wish they’d been told earlier. Then, bake those lessons into the process.