I remember being at the bank with my mom when I was young, watching the teller type on her computer and calculator. That looked exciting. I also remember longing to scan groceries and type in the codes on the cash register at the grocery store. Those jobs looked important and fun.

Then I decided I wanted to be a lawyer. A steady diet of Law & Order, Matlock, and Ally McBeal will do that to you.

In high school I loved art. When I entered university, I thought I was going to be an artist. Then I took my first psychology class and was completely hooked on human behavior. That interest turned out to be both fascinating and incredibly broad.

It has taken years, decades if we are being honest, to figure out what I wanted to do. Even now, as a business owner and someone who develops people leaders for a living, I am certain there will be pivots and shifts ahead.

This is not a story about indecision. It is a story about how careers actually work.

Many young leaders, new managers, and even very seasoned professionals struggle with the same question. What do I want to do? And even when you land in a role you truly love, things change. Your boss changes. The economy changes. Clients change. Organizations restructure. The ability to adapt matters more than picking the perfect job title.

Research backs this up. Longitudinal career studies consistently show that most professionals will make multiple career pivots over their working life, not because they failed, but because their context evolved.

So instead of asking “What job should I choose?” a more useful approach is to ask better questions. Here are three that matter.

Question One: What Problems Do I Actually Enjoy Solving?

Research from Harvard Business Review has shown that long term engagement is less about role titles and more about the type of problems people work on daily. When work aligns with problems you find meaningful, motivation and performance increase.

This matters for managers in particular. Many people are promoted because they are strong individual contributors, not because they enjoy solving people problems. Suddenly the work shifts from doing to guiding, coaching, resolving conflict, and making decisions with incomplete information.

This is one reason structured manager training matters. New managers often need support not just with skills, but with how they think about their role, growth, and long term direction.

In coaching, this question often reveals a mismatch. Someone may say they want to lead, but what they really love is deep technical problem solving. Neither is better, but confusing the two leads to burnout.

Managers who understand the kinds of problems they enjoy are more likely to seek roles that fit them, delegate effectively, and stay engaged through change.

Question Two: What Strengths Do Others Consistently See in Me?

Decades of research from Gallup shows that strengths based development leads to higher engagement, better performance, and lower turnover. People grow faster when they build on what they already do well.

Yet many professionals answer career questions by listing gaps. I need more confidence. I need better executive presence. I need to fix what is not working.

New managers often focus on what they think they should be rather than who they already are at their best.

Coaching shifts this conversation. When leaders understand their natural strengths, they make better career decisions, communicate more clearly, and lead with more confidence. Strength awareness also creates flexibility. When circumstances change, leaders who know their strengths adapt faster because they are not anchored to a single role identity.

Question Three: What Am I Willing to Keep Learning as Things Change?

The World Economic Forum continues to emphasize adaptability, learning agility, and emotional intelligence as critical skills for the future of work. Careers are no longer ladders. They are evolving systems.

This is where many people get stuck. They search for certainty in a world that does not offer it.

Managers who succeed long term tend to share one trait. They are willing to keep learning. Not just new skills, but new ways of thinking about leadership, feedback, and themselves.

Coaching supports this by helping leaders reflect, adjust, and make intentional choices rather than reactive ones. Instead of asking “Is this the right job forever?” the question becomes “What is this role teaching me right now?”

That shift alone reduces anxiety and increases resilience.

Why This Matters for Organizations

When organizations invest in manager training and coaching, they are not just building skills. They are helping leaders ask better questions about their careers, impact, and growth. Managers who understand what they enjoy, where they add the most value, and how they continue to learn are more effective. They navigate change better, support their teams through uncertainty, and stay engaged as roles evolve.

Careers are rarely straight lines. They are shaped by curiosity, context, and courage. The goal is not to eliminate pivots, but to navigate them with intention. These three questions offer a grounded approach to career development that works across every stage of leadership.

This is where coaching and manager training make a meaningful difference. At Plum Leadership Group, we support leaders through uncertainty, new responsibilities, and career shifts. Through coaching and our Manager Essentials program, leaders build clarity, confidence, and practical people leadership skills. Registration is now open for the Spring Manager Essentials cohort for new and emerging managers ready to lead well as their careers continue to evolve.