What If…? Making Peace with Choices in Coaching through Supervision

Coaching is rarely linear.

It’s not a neat sequence of steps, nor a clearly marked trail from problem to solution. Instead, coaching is exploratory by nature—alive, dynamic, and often filled with ambiguity. And while this is part of its beauty, it can also be the source of a quiet, persistent tension for coaches:

• “Did I do the right thing?”
• “What if I’d asked that question instead?”
• “Should I have followed that other thread?”

These reflections—while natural—can slip into rumination. Coaches may find themselves replaying sessions, over-analysing their choices, and wondering if a different route would have been more impactful. The spectre of “what if?” hovers, whispering that perhaps they missed something vital.

It’s in this moment that supervision becomes not just useful, but essential.

There Is No Single Right Path

Unlike prescriptive models or diagnostic tools, coaching doesn’t offer a singular “correct” route through a conversation. A hundred choices could have been made. And in many cases, several of them would have worked. Others might have closed things down. Some might have opened unexpected doors.

The point is: we can’t know.

And yet, coaches are often left carrying the emotional residue of “if only.”

Supervision creates a space in which this uncertainty can be met with compassion. Not to dismiss it—but to help the coach make peace with it. Together, supervisor and coach can explore:

• What was chosen and why?
• What values, instincts, or hypotheses were guiding that choice?
• What else might have been possible—and how might it have changed the outcome?
• What is there to learn from this—not in regret, but in development?

This exploration turns “what if?” from a haunting question into an invitational one—a way to grow, not a reason to self-criticise.

Supervision as a Place of Integration

There’s a risk that, in seeking to “get it right,” coaches become hesitant, overly self-conscious, or trapped in performance. The richness of coaching lies in its responsiveness—but when doubt clouds the process, that responsiveness can falter.

Supervision helps coaches to:

• Acknowledge the choices they made and the conditions that shaped them.
• Reflect on the unconscious pulls or assumptions that influenced the direction.
• Develop greater awareness of alternative approaches—not to retroactively fix the past, but to expand future possibility.
• Trust the process, knowing that not every outcome is a measure of success or failure.

In short, supervision helps coaches move from regret to responsibility—owning their work with curiosity and care rather than shame or fear.

Letting Go of the Myth of Certainty

Much of the emotional weight behind “what if?” is driven by a myth—that somewhere out there is the perfect coaching move. The ideal intervention. The golden thread that would have unlocked everything.

But coaching isn’t chess. It’s not a game of best moves. It’s a human conversation in real time—with all the complexity, messiness, and unpredictability that entails.

Supervision offers a place to grieve that certainty—to let go of the fantasy that we could ever know what would have happened if we’d turned left instead of right.

And in that letting go, we gain something much more valuable: The freedom to be with our work as it is—alive, imperfect, human.

Conclusion: Choice, Not Certainty

The goal of supervision isn’t to rid coaches of uncertainty. It’s to help them live with it more gracefully.

It’s to support the development of a reflective mindset—one that embraces choicefulness over certainty, learning over perfection, and presence over performance.

Because coaching will never be about knowing what would have worked best.

But it can always be about growing our capacity to choose, to notice, to wonder—and to move forward with intention.