Difficult Conversations in Change
The conversations we avoid are often the ones the organisation most needs to have.
What people are actually saying when they push back – and why we keep mishearing it.
There's a familiar moment in change programmes. The steering committee meets. The status report is presented. Milestones are reviewed, risks are discussed, and everyone agrees on the next steps.
The programme is still on track. Except several people in the room know it isn't.
The operational teams aren't ready. The proposed process hasn't been properly tested. Two senior leaders have entirely different expectations of what the change will deliver.
But nobody raises it. Not directly, anyway.
There are references to dependencies, suggestions for further engagement, and perhaps a request to revisit the timeline at the next meeting.
Everyone leaves knowing the conversation that needed to happen still hasn't happened.
And the programme continues.
What makes these conversations so difficult
We tend to think difficult conversations are difficult because of the subject matter. Disagreement, poor performance, unrealistic expectations, and conflicting priorities.
But in change management, the difficulty often has less to do with what needs to be said than with the consequences of saying it.
Telling a sponsor that their deadline is unrealistic means challenging a commitment they've already made. Questioning a proposed solution means confronting decisions that may have taken months to negotiate. Pointing out that employees are not ready means introducing uncertainty when everyone is looking for assurance.
The person raising the concern risks being labelled negative, obstructive or insufficiently committed to the change.
And so we learn to soften the message.
The organisation isn't ready becomes there are some readiness considerations.
The solution doesn't work becomes we've identified opportunities for further refinement.
The leadership team isn't aligned becomes we need to strengthen stakeholder engagement.
The language becomes more acceptable. The underlying problem remains.
The four conversations we keep avoiding
Having a difficult conversation doesn't require confrontation for its own sake. Nor does it mean challenging every decision simply because there's uncertainty.
It means recognising when the conversation we're having is not the conversation the situation requires.
Before moving to another action plan, communication campaign or readiness assessment, three questions are worth asking:
What do we know that we're not saying clearly? Is there an operational concern, an unresolved disagreement or a risk that has been softened until its significance is no longer apparent?
What decision are we avoiding? Are we asking people to compensate for something that requires an explicit leadership decision?
What happens if we continue without resolving it? Not in the language of a generic risk register, but in practical terms: who will be affected, what will stop working, and what will it cost to correct later?
The aim isn't to make the conversation more dramatic. It's to make the issue more difficult to misunderstand.
Sometimes that means saying, We cannot meet this date with the resources available.
Sometimes it means asking two executives to agree on an outcome rather than allowing their different expectations to remain hidden.
And sometimes it means acknowledging that the people affected by the change have identified a genuine problem with the proposed solution.
None of these responses guarantees agreement.
But each gives the organisation an opportunity to act on information it might otherwise ignore.
The shift this requires
Good change management isn't simply about helping people accept decisions that have already been made.
It's also about helping the organisation understand the human and operational consequences of those decisions while there's still an opportunity to do something about them.
And that requires a different kind of confidence from change professionals and their sponsors.
The confidence to distinguish support for a programme from unquestioning agreement with it. To recognise when reassurance is becoming avoidance. And to create room for information that challenges the preferred narrative.
Difficult conversations are not evidence that a change programme is failing.
Sometimes they're evidence that people are finally discussing what matters.
And the organisation that can have those conversations early is in a much stronger position than the one that waits until circumstances force them.
The difficult conversation doesn't disappear when we avoid it. It simply moves to a point where the cost of having it is much higher.
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Diane Gatto
Stories, insights and practical resources exploring the human side of working life — the assumptions, unwritten rules and difficult conversations that shape what happens.
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