Senior executives can spend years thinking rigorously about strategy, talent, capital allocation, and organizational performance while giving surprisingly little strategic thought to their own careers. That gap sits at the center of this Partnering Leadership conversation with Kelly O. Kay, Managing Partner of the Global Software Practice at Heidrick & Struggles and co-author, with Jeffrey Sanders, of Show Up to Win: How to Land the Leadership Role You Want. Drawing on decades of executive search experience, Kelly offers an unusually candid look at how senior leadership opportunities actually develop, how executives are evaluated, and why an impressive track record alone does not guarantee continued career momentum.
Kelly challenges the transactional way many executives approach career decisions. A call from an executive recruiter does not have to mean deciding whether you want a particular job. It can be an opportunity to understand how the market sees you, build relationships with influential executives, directors, and investors, learn about another industry, or develop the fluency required to operate at a higher level. Those conversations can create options years before an executive actually needs them.
The conversation also gets inside the mechanics of senior-level hiring. Kelly explains why previous accomplishments must be translated into the specific challenges facing a new organization rather than simply presented as proof of future success. He shares how executive interviews have evolved from question-and-answer sessions into substantive executive dialogues, why self-awareness can make a candidate more compelling rather than less, and how reputations formed years earlier can quietly influence opportunities an executive may never know existed.
Mahan and Kelly also explore what happens after an executive lands the role. Kelly explains why a new CEO needs people willing to tell them what others may be reluctant to say, and why understanding the organization you are joining matters as much as convincing it to hire you. The discussion reinforces an important theme throughout Show Up to Win: career management is not something executives should suddenly begin when they are ready to leave. The relationships, reputation, judgment, and market understanding that create future optionality are built over time.
The episode closes with a practical discussion about AI and executive career management. Rather than using AI simply to research a company or generate polished answers, Kelly explains how senior executives can use it as an interview coach to role-play likely questions, sharpen their thinking, and prepare for the priorities of a particular interviewer, company, and role. It is a timely example of how technology can strengthen preparation while leaving the most consequential part of the process distinctly human.
Actionable Takeaways
- You’ll learn why career management should begin long before you are considering a move and how that creates greater optionality over time.
- Hear how to rethink the executive recruiter’s call and why a conversation can be valuable even when you have no interest in the job.
- You’ll learn why past performance is necessary but insufficient and how to connect your experience to what a new organization actually needs.
- Hear why executive interviews should feel less like selling and more like an executive dialogue that reveals how you think and what you would contribute.
- You’ll learn why acknowledging a capability gap can strengthen your candidacy rather than make you appear less qualified.
- Hear how reputations quietly shape opportunities before you even know your name is being considered.
- You’ll learn why aspiring CEOs need to develop the ability to think and communicate at a different altitude.
- Hear why every new CEO needs a truth teller willing to surface realities others may be reluctant to share.
- You’ll learn how to use AI as an interview coach to pressure-test your thinking and prepare for the people and priorities in the room.
- Hear why you should never simply put your leadership story on “play” and tell it the same way to every audience.
Connect with Kelly O. Kay
Kelly O. Kay at Heidrick & Struggles
Kelly O. Kay LinkedIn
Show Up to Win: How to Land the Leadership Role You Want
Connect with Mahan Tavakoli:
Mahan Tavakoli Website
Mahan Tavakoli on LinkedIn
Partnering Leadership Website
