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3 Questions to Find Your Ideal Career Path

Most people struggle to manage their careers, but you don't need to.

Key points

  • To find your ideal career path, you must match your skills (what you can do) to your will (what you want to do).
  • In brainstorming about your next move at work, it’s useful to imagine three possible career paths branching out from your current position.
  • Ask yourself, "Who are ten people who can help me get my dream job?"
Sergey Nivens/Shutterstock
Source: Sergey Nivens/Shutterstock

We all know that success at work is an important factor in feeling successful or unsuccessful in life. And the truth is that most people struggle to manage their careers. I want to make it easier for you to manage yours by helping you answer three difficult questions:

1. Skill-Will Bullseye: What Is My Skill-Will Bullseye?

In our book on hiring best-practices, Who: The A Method for Hiring, my colleague Randy Street and I talk about hiring people whose “skills” (what they can do) match their “will” (what they want to do). This is their “skill-will bullseye.”

We’ve found that the same logic applies from the opposite direction to people seeking roles that fit both their “skills” and their “will.” Here’s what that can look like in practice.

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, “Headhunting? 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.”

The VP had discovered her “skill-will” bullseye, the sweet spot where what she could do overlapped with what she wanted to do.

2. Three Paths: What Are Three Career Paths?

In brainstorming about your next move at work, it’s useful to imagine three possible career paths branching out from your current position.

Take our VP again: she had previously pursued only a corporate career path.

“Yes, you could design your role at your current employer to match your skill-will bullseye,” I acknowledged. “But what are two other paths you could consider?”

She reflected, “Well, I guess path two would be to try to join an existing consulting firm that specializes in talent management process design and execution. Or, path three could be that I hang out my shingle and do that kind of work solo.”

We discussed the pros and cons of each path. She chose path two to try to join an existing consulting firm.

3. List of Ten:

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 ten 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 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 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 good family friends if you have some.

The number is ten. Once you write out the ten 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 three hardest questions about your career.