By Esther Boffey, Head of Learning and Development, Stanton House

Most leaders know when a difficult conversation needs to happen. The challenge is rarely recognising the issue, it’s finding the courage, clarity and right words to address it.

Perhaps someone’s performance has slipped, a colleague’s behaviour is affecting the wider team, a previously strong employee is struggling in their role, or an important commitment has repeatedly gone unmet.

We tell ourselves that we are waiting for a better moment, gathering more evidence or giving the person another opportunity. Sometimes that is appropriate. But sometimes we are simply avoiding a conversation that feels uncomfortable.

We recently brought our leadership team together for a workshop on handling difficult conversations, led by Lisa Quinn, MCC Executive Coach. The session focussed on situations we encounter within our own business, but the wider discussion felt highly relevant to leaders everywhere.

One of the ideas I found particularly powerful was that avoidance can sometimes masquerade as support. We step in, solve problems for people and absorb the consequences of missed expectations because we want to be caring leaders. Yet, in doing so, we may deny someone the clarity and accountability they need to improve.

Why do these conversations feel so personal?

Research from the Harvard Negotiation Project suggests that every difficult conversation contains three conversations: what happened, the feelings involved and what the situation says about our identity.

The first concerns the facts and where perceptions differ. The second covers the emotions sitting beneath the surface. The third, and often the hardest, concerns what the conversation appears to say about who we are.

For leaders who see themselves as supportive and empathetic, direct challenge can feel like a threat to that identity. We may privately wonder: “If I say this clearly, am I still a supportive leader?”

That question can cause us to soften the message until its meaning disappears, delay the conversation or avoid it altogether. Yet clear feedback and compassionate leadership are not opposites. Often, the more respectful choice is to tell someone what they need to hear while they still have an opportunity to act on it.

The Harvard Program on Negotiation also emphasises the importance of acknowledging the emotions involved. Preparation therefore needs to cover more than the points we want to make. We should consider what the conversation may bring up for both people and how we will remain constructive if emotions surface. If things become overly emotional, it may be best to end the session and continue the conversation at a later date.

Separate observation from interpretation

A practical framework can help when the stakes feel high. In our workshop, we used COIN:

·       Context: What is the specific issue or situation?

·       Observe: What factual behaviour have you noticed?

·       Impact: What effect is it having on the individual, team or business?

·       Next: What needs to happen from here?

For example, “You aren’t committed to business development” is a judgement. It invites disagreement about attitude or intent.

A clearer version would be: “I want to discuss your business development activity over the past month. I’ve noticed that you haven’t made any new business calls in three weeks. Without new instructions entering the pipeline, your future billings are at risk. I need you to protect time for business development each week. Let’s agree what that will look like.”

This reflects the principles behind the Center for Creative Leadership’s Situation–Behaviour–Impact feedback model. By focusing on observable behaviour rather than assumptions about someone’s character or motivation, leaders can reduce ambiguity and give the other person something concrete to respond to.

The “Next” stage matters just as much. A conversation may feel honest but still achieve very little if nobody leaves knowing what needs to change, by when and how progress will be reviewed.

When does support becomes enabling?

Another important part of the session explored the point at which continued support begins to enable an unresolved problem.

This can be particularly difficult when a leader has invested significant time in recruiting, training and supporting someone. Understanding the sunk-cost effect helped me see why we sometimes hold on too long.

The sunk-cost effect is a well-established behavioural pattern. Research by Hal Arkes and Catherine Blumer found that people become more inclined to continue with an endeavour after investing money, effort or time in it.

For leaders, this creates an uncomfortable possibility. We may continue with an arrangement because of what we have already put into it, rather than what the current evidence tells us about its future prospects.

The relevant question is not only, “Have I done enough to support this person?” We should also ask, “What is it costing the team to allow this situation to continue?”

High performers notice when standards are applied inconsistently. Colleagues absorb additional work. Managers spend more time compensating for the problem. Meanwhile, the individual may believe that everything is broadly acceptable because nobody has told them otherwise.

Support should include clear expectations, honest feedback, reasonable help and a genuine opportunity to improve. It should not mean protecting somebody indefinitely from the consequences of an issue they understand and have had the opportunity to address.

Turning intention into action

Knowing that a conversation is necessary does not guarantee that we will have it. Busy weeks have a habit of swallowing vague intentions.

Psychologist Peter Gollwitzer’s research into implementation intentions demonstrates the value of creating a specific “if–then” plan that links a situation with an action.

For example: “If I have not seen the agreed improvement by Friday, I will arrange the conversation for Tuesday morning.”

That small shift turns “I need to deal with this soon” into a defined commitment.

Five practical takeaways for leaders

1.      Examine what you are protecting. Are you safeguarding the relationship, or protecting yourself from discomfort?

2.      Address behaviour, not personality. Use specific examples that the other person can recognise and discuss.

3.      Explain the impact. Help them understand why the issue matters to their colleagues, customers or the business.

4.      Agree what happens next. Set clear expectations, support, timescales and a review point.

5.      Look forward rather than backwards. Base decisions on the evidence you have now, not only the time and belief you have already invested.

Difficult conversations will probably never feel completely comfortable. Nor should they. They involve people, relationships and consequences that matter.

The aim is not to remove the discomfort. It is to stop discomfort making the decision for us. Clear, timely conversations give people the best chance to respond, improve and succeed. That is not a departure from supportive leadership. It is one of its most important responsibilities.

About Outspoken:

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