Critical Questions to Help You Level Up in Your Career

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Every year I read Peter Drucker's classic article, "Managing Oneself" as part of my personal-professional career navigation process. His powerful questions and frank commentary on what we need to do in our careers help me reorient and reset on my priorities and activities. 

It forms a key foundation for my Pragmatic Learning Network course, Level Up Power Skills: Influence, Lead and Develop Yourself Differently. 

If you’re a subscriber to HBR's online library, read the article. If not, do yourself a big favor that will pay dividends throughout your career and buy a copy. The article is arguably more relevant in today's chaotic world than when it was written in 2005—a testament to Drucker's long-range view on people, management and society.

Here are some of the highlights that I always find myself going back to:

Drucker's 5 Key Questions in "Managing Oneself"

1. What are my strengths?
Most people think they know what they are good at. They’re wrong.

2. How do I perform? (How do I learn?)
Amazingly, few people know how they get things done. Too many people work in ways that are not their ways, and that almost guarantees nonperformance.

3. What are my values?
The mirror test—what kind of person do I want to see in the morning?

4. Where do I belong?
Successful careers are not planned. They develop when people are prepared for opportunities because they know their strengths, their method of work, and their values.

5. What can I contribute?
What does the situation require?


How's Your Career Going? Are You In Alignment?
If things aren't working right for you in your position or career, chances are you’re out of alignment with the real answers to one or more of Drucker's questions.

I regularly see people working in areas and in roles that fail to draw upon their unique skills—their superpowers. They struggle.

Others fail to tune-in to and live their values. When your behaviors are dissonant with your values, you struggle. 

And sadly, many others fail to find ways to contribute that reflect themselves at their best.

You cannot be successful in any phase of your life unless you understand yourself.

Choose to ignore what drives you and where and how you thrive, and this state of dissonance will breed dissatisfaction and less-than-optimal performance.

You cannot fight "you" and win in the long-term.


Six Add-on Questions to Create Focus in Your Career
With a nod to Drucker and the wisdom in his article, I want to add a second set of questions. My questions are a subset of his, and merit consideration given the context of our current and emerging world:

  • What am I doing to learn?
  • How hard am I working at rethinking and reframing?
  • How am I doing to embrace and adapt to change?
  • How am I impacting others?
  • Am I maximizing my impact?
  • How am I doing?

Let’s break down these questions and look at them in more depth to see how they can help you level up in your career. 


What am I doing to learn?
Whether you recognize it or not, you’re involved in the real-world equivalent of what video game designers describe as “leveling up.” When you think you’ve mastered a situation, something changes in the external environment that challenges what you know and how you’ve done things. Accordingly, you must start over, learning and developing new behaviors, while finding new ways to defeat these unfamiliar adversaries. 

Rinse and repeat. 

Oh, and the situation grows more complicated. 

All of us in our careers face two simultaneous level up challenges. First, we must continue cultivating new skills and cast away old approaches in the face of change and complexity. And second, we must strive to help our firms do the same. The former is challenging, the latter is exponentially more complicated. 

What are you doing to keep learning? Are you exposing yourself to new ideas and new approaches? Are you challenging yesterday’s processes and ways of doing things?

If you’re not learning, you’re moving backward at the speed of change. 


How hard am I working at rethinking and reframing?
Yesterday’s assumptions are the seeds of tomorrow’s obsolescence. Most of us operate with hard-wired views of the world, even if we think we’re open-minded. That’s a prescription for disaster, particularly in the world of product management. 

What are you doing to continually refresh the framing of your firm, your markets, and how you are approaching your career opportunities? What are you doing to challenge your assumptions? Are you inviting others to challenge assumptions? And what are you doing to change the view? Remember, if you always look out the same window to your customers, markets, and opportunities, the view never changes. 

If reframing isn't a regular part of your personal strategic planning, you are in danger of growing obsolete. Here's a simple mantra to bring to your work and professional development: "Rethink Everything!"


How am I doing to embrace and adapt to change?
We've all been fed a line of baloney about our dislike of change. If we didn't like change, how did we as a race spread out across the globe and into space? Humans thrive and adapt to change, yet in our workplaces, we seem resistant to upsetting the status quo. That's laziness talking. 

Learning to embrace change as an opportunity is a superpower in today's world. So is finding ways to create positive change around you. While you can’t control the larger forces driving change, you can learn to see them emerging, and you can plot your way forward by choosing where to contribute and how to perform. 


How am I impacting others?
Your decisions surrounding people open up new timelines and ultimately become the backstories for those you touch during your journey. Effective professionals are acutely aware of how they impact others in their daily encounters. 


Am I maximizing my impact?
The great product professionals I've worked with strive to cultivate influence and gently but deliberately impact what gets done and who gets involved. And when they're successful, they create heroes out of their team members. 

What's your influence strategy? Are you building "clean power?" And, how are you doing creating heroes as you strive to help your firm and teams level-up? 


How am I doing?
This question is my favorite. You need help answering it. Effectively, you're solving for seeing yourself as others do. Gaining honest, unfiltered input is never easy, but it's worth the effort if you listen and act. 

Start asking today, and start working on the information. What begins as an awkward exercise with less than complete feedback will become comfortable and transparent over time.


The Bottom Line (for now)
You own your own career. You also play a disproportionate role in the success of your organization. Take this work of developing yourself seriously and enjoy your remarkable adventure. 

Art Petty

Art Petty

Art Pettyis an executive and emerging-leader coach and leadership/communication workshop developer and leader. He also writes the Management Excellence blog and Leadership Caffeine articles and books. Connect with him on LinkedIn or follow him on Twitter.

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