The 3 Hardest Questions about Your Career

I love helping people strategize about their career.

A recently-retired governor recently contacted me to have a career strategy chat. I’m guessing he will tell me he has a vague sense of what he wants to do next, and that he would love a sounding board to come up with a plan. I’m honored that he reached out and a little nervous because I don’t know him that well yet. I hope that my approach (described below) will not only be useful for him, but also for you.

My colleagues and I love to help people in this way, because success at work is a big factor in feeling successful or unsuccessful in life. And most people are pretty bad at managing their careers.

We have a huge database of 17,000+ leaders’ careers and have counseled thousands of leaders about their career success. My colleagues Elena Botelho and Kim Powell have an awesome book on career paths to CEO, due out in 2018. And the book I want to write after that is about “career success for everybody” (not just leaders who want to become CEO).

We have advised all sorts of interesting leaders on their careers— billionaire entrepreneurs who want to brainstorm about the next stage of their impressive careers; bestselling authors; 8^th graders from charter schools in low-income neighborhoods; newly-minted Harvard MBAs and Ph.D.s who want to rule the world; pop stars who want to branch out into business; private equity titans whose identities are rooted in “deal-making” but who want to do something else next; homeless men and women at a “jobs roundtable;” you name it.

My consistent observation over two decades of doing this work is: no matter your background, you are likely to struggle with managing your career.

I want to make it easier for you to manage your career by helping you answer the 3 hardest questions.

1. SKILL-WILL BULLSEYE: What is my skill-will bullseye?
   

   In our book Who, Randy Street and I talking about hiring people whose “skills” (what they can do) and their “will” (what they want to do) match the scorecard for a role. This is their “Skill-Will Bullseye.”
   

   We’ve found that the same logic applies from the opposite direction.
   

   A VP at a Fortune 500 company recently contacted me for a career chat. She expressed an interest in transitioning from HR into consulting. I asked her what things she wanted to consult on. She struggled to put her finger on exactly what she viewed as her core talent and interests. I asked her, “Head hunting? Do you love the thrill of the chase?” “No,” she said. “Coaching? Are you great at becoming a leader’s most trusted advisor?” “I don’t know about that one,” she said. “How about designing recruiting processes and helping clients manage their processes effectively.” “YES! That’s what I think people would say I’m best at. 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.”
   

2. THREE PATHS: What are 3 career paths?
   

   For the person in the previous example, she had only focused on a corporate path previously. “Yes, you could design your role at your current employer to match your skill-will bullseye,” I acknowledged. “What are two other paths you could consider?” I encouraged. She said, “Well I guess path 2 would be to try to join an existing consulting firm that specializes in talent management process design and execution. Or…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. She chose path 2, to try to join an existing consulting firm.
   

3. LIST OF 10: Who are 10 people who can help me get my dream job?
   

   People always struggle with this one. They tell me “I know hundreds of people.” I say, “Yes, you may know hundreds of people. That’s good. So let’s prioritize the list into the top 10 who are most likely to be able to help you get your dream job.” Don’t send out blast emails or posts to social media. The key here is to prioritize the list and invest real time in exploring your career plan in some depth with the people on the list.
   

   Start by listing past bosses who really know your great work, and who are well-connected. Clients or customers who respect you should go on the list. And it’s a good idea to add a well-connected friend from college or graduate school, a recruiter or two, and powerful family friends if you have some.
   

   The number is 10. Once you write out the 10 people who can help you, create a half-page message that summarizes the career path you are looking for, why you are a great match for that, and ask for a few minutes of their time to pick their brain about how you might find your dream job. Those conversations will turn into referrals, which will turn into getting your dream job.
   

Maybe one day, career management will be entirely automated. Big data and algorithms will come to you with amazing opportunities. But in the meantime, to get your dream job, you have to do the work. Start by answering the 3 hardest questions about your career.

If you think these tactics are useful, please download our other free career strategy tools at SMARTtools for Leaders™.