During our recent Leadership Caffeine Jam Session (recording and session materials/#18), I shared the ten questions I ask myself (and answer) about my career at least twice yearly. The late, great management thinker Peter Drucker suggested five questions; the other five are my add-ons.

From Peter Drucker’s article, Managing Oneself at HBR (subscription or article fee)

1. What are my strengths?

2. How do I perform

3, What are my values?

4. Where do I belong?

5. What should I contribute?

Drucker’s Five Questions are Foundational to Us in Our Careers

We can only succeed if we leverage our strengths. #1 challenges us to gain input on our strengths or superpowers as I describe them. Key weaknesses should be strengthened, but we only succeed when we leverage our gifts.

#2 challenges us to ensure we know where and when we are at our best. It challenges us to tune in to our learning styles and recognize the situations where we can apply our strengths.

For me, #s, 3,4, and 5 are the money questions in Drucker’s five.

We all operate with a set of values, but we rarely take the time to think them through and run a process check on whether we are living them professionally. Are you with an organization where your values fit with their practices, culture, and behaviors? If not, consider changing.

The “Where do I belong” question is likely the one most considered in our post-pandemic world. What should I do next? Do I need a new environment, a gentle pivot, or a radical makeover? This question brings many to my Career Reinvent programs and coaching. (My Six-Hour Career Energize is designed to help people answer this issue.)

The “contribution” question ties to all of the above, particularly to your sense of purpose at this stage of your life and career. My purpose is to help individuals achieve things they never thought possible in their careers. If I’m doing something that doesn’t fit squarely into this purpose statement, I need to stop doing it.

What about you? What’s your sense of purpose at this stage? Are you bringing it to life through your work?

My Five Questions Build on Drucker’s and Support Continuous Growth

6. What’s my strategy for learning?

7. What evidence do I have that I am striving to think differently versus becoming a victim of my history and experiences?

8. Am I embracing or resisting change?

9. How am I affecting others?

10. How am I doing?

If you’re not deliberately learning, you’re moving backward at the speed of change. What’s your strategy for learning? Seriously?

If you’re not Thinking Differently in a shifting world of post-pandemic changes, the emergence of AI, and the many other profound issues in front of us, you’re rendering yourself obsolete. Are you open to new ideas? Are you willing to try new things? Do you actively challenge yourself to take the opposite position of what your experience tells you? Thinking Differently is a mind muscle that must be built.

How are you leveraging change? What have you changed in your life and career? Have you tried new assignments in your workplace? Are you extending your professional networks to new arenas? Are you actively reinventing your skills?

I love the “affecting others” question as a reminder that we all have an impact on those we encounter in our careers. Your actions today define someone’s backstories tomorrow.

And, what’s your measuring system for assessing how you are doing? Thinking about these questions is nice, working on them is critical, and measuring your progress is essential.

The Bottom Line for Now:

The group on the livestream jam session (#18) offered dozens of great ideas to bring these questions to life. I encourage you to soak up their ideas in the chat stream document and the many I provided via the video and mind map. Or, jot these ten questions down and create some time to ask and answer them and define your next steps for each.

Art's Signature