Holding up the mirror: Six questions I ask before helping leaders navigate change

"You're swinging the dragon by the tail, Rita. It won't end well."

That was the response from a senior technology leader after I'd outlined my communication strategy for a multi-year offshoring program – a significant transformation facing our organisation.

There was a long runway ahead of us, which is exactly why I believed we needed to start the conversation early. The prevailing view was understandable though. The instinct was to keep the hatches closed until decisions had been made, then communicate with certainty once the path was clear.

Not everyone shared my enthusiasm, hence conversations about dragons.

Every experienced communicator knows the moment you're asking a leader to pause, reflect and look in the mirror long enough to see something they may be missing. Sometimes it can feel like a lonely place to stand.

The hard part of these situations is knowing when to hold up the mirror. Experience teaches you which issues deserve your energy and which don't. Over the years, I've found myself returning to six questions before deciding it's time to hold up the mirror.

1. Are we avoiding reality?

In our case, the world around us was already changing. Technology and globalisation were accelerating, and offshoring was no longer a theoretical discussion. Our people were already reading about it. If our people were going to hear about offshoring, I wanted them to hear it from us first. Leaders pretending it wasn't happening wasn't going to make it any less real.

2. Are we treating people like adults?

People don't always need certainty, but they do need enough honesty and context to make informed decisions about their own future. We chose to explain the bigger picture, including why the world of work was changing, why we were expanding our use of offshoring, and how it aligned with our broader strategy. We even gave everyone a copy of Thomas Friedman's The World Is Flat to help explain the forces reshaping our industry.

3. Will this give people more agency or less?

People often assume that talking openly about difficult change creates panic. In our case, it created choice. Some people began exploring new opportunities, while others took advantage of a retraining fund to pursue an entirely different career. We couldn't remove the uncertainty, but we could give people the time and context to make informed decisions about their own future.

4. What will people remember about how we handled this?

People rarely forget being blindsided. That's why I wanted our people to have time to process what was happening, ask questions and prepare before decisions began to affect their working lives. It didn't make the change easy, but I hope they could look back and feel they were treated with honesty and respect. To me, that's one of the truest measures of leadership.

5. Am I reacting, or exercising judgement?

Not every difficult conversation requires you to hold up a mirror. Good judgement means learning to sit with a situation or issue long enough to work out whether you're reacting to something that feels uncomfortable, or recognising something that's genuinely important. For me, this was one of those moments where saying nothing would have been a decision in itself.

6. What am I accepting if I walk past this?

Today we're living in a world where rapid change is constant, AI is accelerating the pace, and it feels like everything is on full throttle. My concern is that in the rush to move faster, the time leaders have to pause, reflect and really think is being squeezed. It makes this question more important than ever: what am I accepting if I walk past this?

Sometimes the answer is, "This isn't my battle" or"The organisation has made a considered decision." But sometimes it's, "If I stay silent, I'm accepting that people will experience this change in a way I don't believe they should." Those are the moments when I know it's time to hold up the mirror.

So, did swinging the dragon by the tail end badly, as my senior technology colleague predicted?

I don't think it did, because we gave people choice. It wasn't a perfect process and I don’t think any significant transformation ever is. but I still believe it was change managed with honesty, respect and empathy.

Experienced communication advisers add their greatest value long before anyone puts pen to paper. Our judgement comes with experience – getting some things right, getting some things wrong, and learning to recognise the critical moments that shape how people experience change.

Sometimes that can feel like swinging a dragon by the tail, but I think some dragons are worth waking.