Before you coach the person, inspect the system


Hi Reader, Daria’s here.

Today I have a guest, Kyle O’Hagan, to dive into why coaching is not working for your organization.

A conversation recently started in a very familiar place: frustration with how people were working together.

There was friction. Responsibilities were starting to overlap. One person was challenging decisions, another was trying to protect ownership, and it would have been very easy to turn the entire discussion into a coaching conversation about behaviour. Who needs to communicate better? Who needs to be more collaborative? Who is being too difficult?

Those questions are not always wrong. Sometimes the problem really is behaviour. But the longer we spoke, the less satisfied I was with that explanation.

At one point I asked, in slightly cleaned-up wording:

“Are we solving for a bad attitude, or are we actually solving for a gap in how the work is designed?”

That question changed the direction of the conversation because we stopped talking about the people for a moment and looked at the work itself. Who actually owned the outcome? Who had the authority to make the decision? Where did one person’s responsibility stop and another person’s begin? When somebody disagreed, were they supposed to advise, challenge, escalate, or decide?

Once we started pulling those threads apart, the interpersonal problem looked different. The people involved were not necessarily behaving irrationally. They were responding to an environment where the boundaries were unclear and where multiple capable people had enough responsibility to feel accountable, but not enough clarity to know where that accountability ended.

That distinction matters to me because repeated friction is information. One disagreement can absolutely be a relationship problem. But when the same type of disagreement keeps appearing, especially around the same work, I think leaders have a responsibility to ask whether the system is manufacturing the conflict.

This reflection draws on real leadership coaching conversations. Identifying details have been removed, generalised or combined to protect privacy. The quoted question has been edited for clarity and anonymity.

Strong people can hide weak systems for a surprisingly long time. When ownership is unclear, they chase things. When a decision has not been made, they move it forward. When a process breaks, they create a workaround. When something falls between roles, they pick it up. The work gets done, so from a distance the operating model can look fine.

It is only later, when the same people start frustrating each other, that we notice the cost. By then it is tempting to label the tension as attitude or communication style, even though the behaviour may have been a rational response to ambiguity all along.

But fixing the system does not mean removing personal responsibility. Leadership requires judgement. If something does not make sense, I want people to say so. If a timeline looks unrealistic, challenge it. If the evidence is weak, ask for better evidence.

You can strongly disagree with a decision without needing to take the decision away from the person who owns it. The person making the decision has to tolerate challenge without treating it as disloyalty. The person challenging has to know when their role changes from influencing the decision to supporting the outcome.

For the person I was coaching, the takeaway was not to become less direct. I did not want to coach the challenge out of them. I wanted the challenge to become more deliberate. Push on the thinking, the evidence, the assumption or the risk. Then get very clear on where the decision lives.

The learning for me was more uncomfortable. I noticed how quickly even experienced leaders can personalise dysfunction. Somebody is frustrated, so we coach their attitude. Somebody is pushing too hard, so we coach their style. Somebody is resisting a decision, so we coach their collaboration. Those explanations are attractive because they give us a person to fix.

But what if the behaviour is partly a consequence of the environment we created?

A badly designed system is not permission to treat colleagues poorly. But it changes the order in which I want to diagnose the problem. Before I ask, “What does this person need to change?”, I want to ask, “What is the environment repeatedly asking this person to compensate for?”

Sometimes the right answer will still be a difficult coaching conversation. But I do not want coaching to become a way of making good people more tolerant of badly designed work.

Adapted from Before You Coach the Person, Inspect the System, originally published on Drift North.

About Kyle O’Hagan

​Kyle O’Hagan, CA(SA), is the founder of Drift North and leads EMEA Services and Global Emerging Solutions at Workiva. He qualified as a Chartered Accountant in South Africa, beginning his career at Deloitte in Cape Town before moving to Amsterdam, where he worked as a manager.

At Workiva, his career has spanned financial transformation, solution design, client and partner services, customer success and emerging solutions. He has led consultants, SaaS specialists and managers across European teams, with work spanning customer transformation and AI adoption.

His leadership philosophy begins with understanding the person and the situation. He sees leadership as a practice built through honest feedback, reflection and the willingness to admit mistakes and adjust.

Through Drift North and its newsletter, Between Versions, Kyle shares what he is learning from leading teams and coaching managers, including the conversations he has avoided, the decisions he has reconsidered and the habits he is still working on.

Talk to you next Tuesday

Daria

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