A reflection on coaching, career development, and why asking better questions is often more valuable than providing answers.
Early in my management career, I thought one of my primary responsibilities was solving problems. When someone came to me with a challenge, I tried to help. When someone wanted career advice, I offered guidance. When a team member was uncertain about what to do next, I worked to provide an answer.
The instinct came from a good place. I wanted people to feel supported, and I had experience that could help them move forward. Most new managers are promoted, at least in part, because they have demonstrated an ability to solve problems. It is natural to carry that strength into leadership and assume the team benefits most when the manager continues doing what made the manager successful.
Over time, I began to see the limitation in that approach. The moments that created the greatest growth were not always the moments when I gave someone the answer. More often, they were the moments when someone reached an answer with greater clarity and confidence because I had helped that person think through the problem.
I could solve the problem in front of us, or I could help someone build the ability to solve the next one.
Good Intentions Can Create Dependency
When a manager knows the work well, providing the answer is often the fastest option. It resolves the immediate issue, reduces uncertainty, and allows everyone to move on. In a busy environment, that efficiency can feel responsible.
The tradeoff is easy to miss. If the manager always supplies the answer, people may become more dependent on the manager rather than more capable themselves. The team gets through today’s problem, but the manager remains the first stop when a similar question appears tomorrow.
I am not suggesting that leaders should withhold information or turn every urgent question into a coaching exercise. Sometimes people need a direct answer, a clear decision, or immediate support. The leadership judgment is knowing when the situation requires an answer and when it creates an opportunity for another person to develop.
What More Than 50 Career Journeys Taught Me
Over more than 20 years as a manager and leader, I have had the privilege of helping more than 50 people explore new roles, technical specialties, leadership positions, and career paths. Some achieved exactly what they originally set out to do. Others discovered that the role they thought they wanted was not the right fit.
Across those experiences, one lesson appeared repeatedly: the most valuable career conversations were not always about helping someone reach a destination. They were often about helping someone decide whether the destination was right in the first place.
One person became strongly interested in a technical specialty within cybersecurity. He connected with people already working in the field and began learning what the path would require. Then the momentum faded. Communication with a potential mentor lapsed, and the follow-through did not match the level of interest he had initially expressed. The issue was not capability. He was not ready to commit to the technical learning and sustained effort required to become successful in the specialty.
Another person was interested in moving into sales. Rather than treating the desired role as the answer, we explored what the work actually involved. He spoke with people closer to the role and developed a more realistic understanding of the expectations, pressure, and effort behind the opportunity. He discovered that the reality of the job was more demanding and different from what he had imagined.
Neither story ended with the career move originally being considered. I do not view that as a failure. Both people gained something valuable before investing significant time in a path that may not have been right for them: clarity.
Interest and Commitment Are Not the Same Thing
Those experiences changed the questions I ask when someone expresses interest in a new role, specialty, or career direction. Interest matters, but interest and commitment are not the same thing. People can be attracted to the title, visibility, compensation, challenge, or idea of a role without yet understanding the work required to succeed in it.
A manager can respond by immediately creating a plan to help the person get there. A coach takes a step back and helps the person determine whether “there” is actually where the person wants to go.
That means exploring what is appealing about the opportunity, what the person expects to change, how the role aligns with strengths and interests, what development will be required, and what the person is genuinely willing to invest. Sometimes those questions strengthen the commitment. Other times they help someone make a different decision. Both outcomes are useful because the objective is not to push every ambition forward. It is to help people make informed choices about their future.
The Shift From Advice to Discovery
As my coaching approach evolved, I began using structured exercises that required people to put pen to paper. I know that may sound old-school in a world filled with digital tools, dashboards, and increasingly instant AI answers, but I have learned that clarity often emerges when thoughts leave our heads and land on a page.
A career goal can sound compelling when it is spoken. It becomes harder to hide weak assumptions once someone writes down why the role is appealing, what success actually requires, what the person is willing to invest, and what the person hopes will be different after getting there.
We also explored strengths, development opportunities, interests, motivations, and the reasons behind a stated goal. One exercise I used regularly started as what I called the Four-Whats, but over time it evolved into the Six-Whats.
People would put pen to paper and answer six deceptively simple questions:
- What am I good at?
- What could I be better at?
- What do I like doing?
- What do I not like doing?
- What am I willing to do?
- What am I not willing to do?
At first glance, the exercise looks simple.
In practice, it often reveals important contradictions.
Someone may be good at something they dislike doing. Someone may genuinely enjoy an activity they have never considered pursuing professionally. Someone may be interested in a role but unwilling to make the sacrifices required to succeed in it. And sometimes that’s where the most important insight emerges.
Because career success isn’t determined solely by what we’re good at or what interests us. It’s also influenced by what we’re willing to commit to.
Combined with Five-Why exercises and guided reflection, the goal was to move beyond the first answer, which is often the easiest answer rather than the clearest one.
Writing does not just document thinking. It sharpens it.
The exercises were not tests, and there was no preferred conclusion. Their purpose was to slow the conversation down enough for the person to distinguish curiosity from aspiration and aspiration from commitment. They gave us something concrete to examine together rather than relying on a broad statement such as, “I think I want to do this.”
My role shifted from mapping the path for someone to helping that person evaluate the destination. Instead of beginning with, “How do I help this person get there?” I began asking, “How do I help this person determine whether this is truly where the person wants to go?”
New managers often believe leadership is about providing better answers. Experience taught me that leadership is often about asking better questions.
Coaching Builds Capability
Advice, experience, and direction all have value. I still provide them. But advice primarily transfers what the leader knows. Coaching helps another person develop a clearer way of thinking, make a decision that belongs to that person, and build confidence in navigating future decisions.
That distinction matters beyond career conversations. When leaders ask people to assess a situation, consider options, explain their reasoning, and recommend a direction, they are not avoiding responsibility. They are helping people build judgment. Leaders can still challenge assumptions, identify risk, provide context, and make the final decision when appropriate. The difference is that another person participates in the thinking rather than simply receiving the answer.
This is another form of enablement. The goal is not to make people solve everything alone. The goal is to make sure leadership support creates greater capability rather than permanent dependency.
Final Thought
Looking back, one of the most important shifts in my leadership philosophy occurred when I stopped measuring helpfulness by how many problems I personally solved. A leader can become the answer to every question and still limit the growth of the team.
Most people do not need someone to map their entire future or solve every problem in front of them. They need someone who will listen carefully, provide context, challenge assumptions, and help them reach greater clarity about what they believe and what they are prepared to do.
Sometimes the right response is a direct answer. Sometimes it is a decision. Sometimes it is immediate intervention. But sometimes the most helpful thing a leader can say is:
“Let’s explore that together.”
Because the best leadership outcome is not always solving the problem faster. Sometimes it is helping someone become more capable of solving the next one.
Photo courtesy of Anastasia Petrova