Recently, I have received an influx of coaching calls from individuals who are looking to make a career change, unsure whether to continue climbing the corporate ladder within their organization or to start on a new ladder. In one of my previous articles, Rethinking Career Advancement: Beyond the Corporate Ladder, I encouraged readers to view their career paths not as a ladder but as a roadmap with many available destinations.
Many people tell me that they love their company but do not see how that roadmap applies where they work. Some simply need help identifying the right areas to explore or the right people to connect with inside of their organization. Others may need to consider opportunities outside of their current organization, and this doesn’t mean that they need to leave their current organization. There are many volunteer opportunities out there that are great options for folks to gain experience without having to invest fully into a new adventure.
Lessons from My Own Career Change
When I faced this question myself, I learned several important lessons. Early in my career, I gained experience on strategic planning and organizational improvement. Over time, I began to specialize in operations, working closely with front-line employees to improve processes. I eventually reached a turning point in my career. One path would have led me toward branch management in the earth-moving industry; the other toward executive coaching. I chose the latter and, in 2009, shifted from doing improvement work to leading it. It was the best move of my career, though far from an easy one.
The transition required perseverance. For seven years, I worked as a consultant across Western Colorado while pursuing a business degree to strengthen my credentials. I have since facilitated hundreds of training classes, strategic problem-solving workshops, and spoken at innovation and performance conferences across various sectors, including hospitality, government, transportation, recreation, and healthcare. I followed a 15-year plan that I created using a simple visioning template, which focused on two areas:
- Outline where you want to be. This is not about a title or paycheck. It is about understanding your personal and professional identity—who you are, what you value, and what energizes you.
- Experience the role in person: A new step that I have added to my coaching sessions recently, and one that I had wished that I had done myself.
- Outline how you plan to get there. Identify your path forward at a high level so you can adjust as you go. Typically, that plan should include three areas of focus: education, experience, and professional relationships.
A Different Approach
Once you gain clarity on who you are and what inspires you, pause before moving onto the final step. I recommend taking an additional step that few people consider: experience the role in person.
Rather than immediately enrolling in courses, updating your résumé, or attending networking events, make sure that the role is truly the right fit. Many organizations, especially in the public sector, offer opportunities for site visits or job shadowing. There are also a bunch of volunteer opportunities out there. Identify one that aligns with your interests and connect with professionals in that field. I often encourage clients to partner with two or three individuals that they admire, shadow them, and learn about what their average day actually looks like.
For instance, many people who shadow me expect to see classroom facilitation, assuming that is where I spend most of my time. In reality, teaching occupies less than ten percent of my schedule. The majority of my work involves one-on-one conversations with leaders, helping them navigate challenges and documenting action plans. If someone pursued this career believing that it was primarily a teaching role, they might have been disappointed. Plus, having them shadow one of my classes may have confirmed that their career path was the right choice, but only to be further disappointed if this became a small portion of their full responsibilities. There are plenty of teaching opportunities out there, and I have shadowed a few professors, and even behind the scenes in their shoes is often different than what one might expect.
Job shadowing allows you to uncover the realities behind the perception. It reveals the work, the challenges, and the organizational culture in ways that job descriptions or interviews cannot.
Asking the Right Questions
When you reach out to professionals to shadow, be thoughtful about how you ask questions. Avoid general prompts such as “What does an average week look like?” Instead, ask:
- “What has been on your calendar for the past two weeks that you are excited about? What are you not as excited about”
- “What is coming up over the next two weeks?”
These questions provide a more accurate picture of the role and invite deeper discussion. If you notice major differences between past and upcoming weeks, ask why. Has something changed? Are there recurring priorities that often get postponed? These insights help you understand the organization’s rhythm, challenges, and culture.
On a sidenote, the above questions are also excellent ones to ask during a job interview. Another strong interview question is, “What reservations might you have about my credentials or ability to perform this role?” This allows you to address any misconceptions directly and leave a strong impression. Be genuine, especially when discussing organizational culture. If it is not the right fit, acknowledge it honestly.
The Bottom Line
Career transformation requires more than planning; it requires exploration. Just as I coach leaders to avoid analysis paralysis, which occurs when excessive planning and overthinking prevent action, it is important to take incremental steps, learn from experience, and adjust along the way. Engage directly with the work you aspire to do. Shadow professionals, ask thoughtful questions, and gain firsthand understanding before making your next move. Whether you are advancing, pivoting, or starting anew, clarity comes from experience and curiosity.
If you would like to learn more about the visioning template that I use or discuss your own career transition, I welcome the opportunity to connect. I do not charge for these conversations, although I must limit how many I am able to offer. Good luck on your journey.
