The Best Career Advice I’ve Received Were Questions

abstract background with letters and question markHere are four powerful questions and lessons learned that helped shape me and my career:

1. Would you be interested in being mentored?

While I was in college, someone older and wiser asked me if I’d like to be mentored. The thought of seeking out a mentoring relationship had never occurred to me. I said “yes” and am extremely grateful. He offered genuine concern, ongoing guidance, challenging feedback and encouragement through a pivotal season of life. This experience helped shape and grow me and helped give direction to my life and career. As a result, I try to pay it forward.

Lesson learned: Getting ongoing individualized help from an expert who is truly looking out for you and your success is extremely valuable. Many of us don’t know to ask for this; it often takes a friend, boss, mentor or coach to invite us into that relationship.

2. Can you do your job effectively without promoting yourself?

The answer was “no” – according to my supervisor in my first job after college as he gave me a performance review. I struggled with his advice; I strongly valued being humble and letting my work speak for itself. Several years later, my naiveté, pride and lack of skill in navigating organizational politics came back to bite me. I was passed over for a promotion and was not as effective as I would have liked in persuading others to adapt my team’s proposals.

Lesson learned: There is an appropriate and skillful way to promote yourself, your team and your ideas in order to be as effective as possible. You can do this while keeping your integrity and not being over-political.

3. If you could do anything you wanted to do that they’d pay you to do, what would it be?

As I was getting ready to leave a job I didn’t like, it was this question that helped me envision the perfect next role within my current company – even though it hadn’t existed before.

Lesson learned: Don’t limit yourself only to pursuing jobs that currently exist or jobs where you’re currently qualified. Write your ideal job description and pitch it to someone who may find value in what you’d bring. And as an organizational leader, why not ask those you lead what they’d really like to do in the organization if they could do anything?

4. How’s work?

Since leaving a steady corporate job with a predictable paycheck, I’ve been tempted to answer the “How’s work?” question based solely on how much money I’m making that month. Instead, now I try to remind myself to consider the following:

  • Am I enjoying work most of the time?
  • Are my key stakeholders happy (boss, clients, team, colleagues, etc.) with the service and value I’m providing?
  • Am I having a positive impact in line with my vocational calling?
  • Is my work ‘working’ with other life priorities?
  • Am I seeing financial success?

Lesson learned: Beware of falling into the trap of overemphasizing money and title; be clear on your own definition of life and career success.

I’m thankful for the people around me who have been willing to ask me tough questions. Often they have been exactly what I needed to hear. 

Joe Baker is a Partner and Executive Coach with PeopleResults. In his work as a leadership consultant and executive coach, he helps leaders define their career success, surround themselves with great mentors and advisors and move forward towards effectiveness, impact and fulfillment. You can reach him at or on Twitter @JoeBakerJr.