Geoff Smart: The 3 Hardest Questions About Your Career

I love helping people strategize about their career. A recently retired governor just contacted me to schedule a career strategy chat. I’m guessing he has a sense of what he wants to do next, but needs a sounding board in order to come up with a plan.

I hope that my approach (described below) will not only be useful for him, but also for you. It starts with answering these three hard questions:

  1. What is my skill-will bull’s-eye? Your skills (what you can do) and your will (what you want to do) line up in what Randy Street and I call the “skill-will bull’s-eye.” I recently helped a Fortune 500 VP find hers when she struggled to put her finger on her core talents and interests. Was it head hunting? “No.” What about coaching? “I don’t think so?” What about designing the process that businesses use to recruit? “YES! That is what I get to do only part of the time in my current job. That is what I want to do with more of my time.” Presto — a skill-will bull’s-eye!
  2. What are three career paths Force yourself outside the box by outlining three different career options. Following from the previous example, that VP had only previously focused on a corporate path. That was Path 1, so I asked what were two other paths she could consider. “Well, I guess Path 2 would be to try to join an existing consulting firm … and Path 3 could be that I hang out my own shingle and do that kind of work solo.” We discussed the pros and cons of each path, and she eventually chose Path 2.
  3. Who are 10 people who can help me get my dream job? Do you know “hundreds of people?” Great, but let’s prioritize the 10 most likely to get you your dream job. Start by listing past bosses who know your work and are well-connected. Now list clients or customers who respect you. Next, add a college friend or two with connections. Then a good recruiter, followed by any powerful family friends you may have. Once you have your 10, write out a half-page message summarizing the career path you’re looking for and the reasons you’d be a good fit for that path. End by asking for a few minutes of their time to pick their brain — minutes that will hopefully end in referrals to your dream job.

If you think these tactics are useful, please download our other free career strategy tools at

Dr. Geoff Smart is the No. 1 thought leader on the No. 1 topic in business: hiring and leading talented teams. Dr. Smart founded the leadership consulting firm ghSmart in 1995, a firm he still chairs today. He is also a nonprofit founder, government advisor, and Wall Street Journal best-selling author.