How To Have A Difficult Conversation

For leaders, keeping your workforce engaged and happy in 2025 is more than just the pay packet, working conditions, and benefits.

The social contract between employers and employees has changed dramatically in recent years – especially since Covid. I speak daily with CEOs who share the challenges they are facing in this area.

However the core principles of employee engagement have remained constant over the past 20 years, but the context in which we work has shifted dramatically. Building relationships with colleagues, fostering open communication, and maintaining consistent engagement are now crucial to helping employees feel valued, empowered, and committed to their work.

At The Institute, we recently published research on employee engagement – ‘Engaging the Workforce of Tomorrow’. One of the most striking insights from the report is how recent uncertainty has affected employees, just as it has businesses and markets.

As a result, it is more important than ever for leaders to engage in authentic, honest, unscripted, and transparent conversations. An honest and transparent conversation will help employees navigate uncertainty and adapt to change.

However, things don’t always run smoothly. As leaders, we have to have difficult conversations with our teams or individuals.

Even for the best leaders, situations where there is hurt, anger or disappointment can be uncomfortable and awkward. Handling them successfully takes knowledge and experience in the school of hard knocks. However, there are few principles I’ve learnt from the CEOs I’ve worked with, and I like to share with others.

2. Don’t think you’re going to have a difficult conversation

The first principle is about your mind set. Don’t go in expecting to have a difficult conversation.

If we approach a meeting believing it will be hostile or simply awkward, this can often become a self-fulfilling prophecy.

Try thinking of it as an opportunity to communicate more clearly, address concerns, clarify misconceptions or simply build better understanding of each other’s perspectives or positions.

Believing the conversation may be challenging or combative will impact your approach and might make you more defensive or overly scripted.

This brings me onto my next principle.

2. A conversation is a dialogue, not a monologue

I always recommend going into every conversation prepared, but, in this instance not with a preconceived outcome in mind .

Remember it’s a two-way conversation and you are there to listen as much as talk. It’s a dialogue, not a monologue. Colleagues and employees might want to use the meeting as an opportunity to speak honestly and get something off their chest and you should give them the opportunity to do this.

Be prepared to hear their perspective, take as much time as is needed and signal to them that you are there to understand their position.

CEO of British retailer Sainsbury’s, Simon Roberts, talked to me about this on as part of my Head to Head series and podcast with CEOs and leaders. He admitted that leaders don’t always get everything right, but that means you’ve got to ‘do lots of listening’ to colleagues. At Sainsbury’s ‘every month we have an open call where any one of our team can dial in and ask me anything they want to talk about.’

This might mean you have to listen to some uncomfortable feedback or opinions. But that’s part of having an effective conversation that allows both to share their position.

Two businessmen sitting opposite at table in boardroom

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3. Don’t hide behind procedure

Today, most of us send hundreds of quick emails and texts every day. We are told that we are more connected than ever and communication has never been easier.

However, the speed and ease of communication has come at the expense of quality. We often default to what is easiest.

Difficult conversations can often be very emotive, so require a deeper level of care and attention to what we are used to giving.

It can feel easier to stick to a set script, however, in these instances, generic answers and rigid procedures can make matters worse, deepening frustration hurt or anger.

It’s about being heard and not just listened to. The phrase ‘I hear you’ is overused and often can feel empty.

Chris Pitt, CEO of British bank first direct, told me on my podcast that when he’s having difficult or boring conversations he thinks about how he can ‘talk in a human way and engage in a warm way’ and that ‘it’s not just about getting it over the line’.

So I recommend to leaders, don’t hide behind procedures. Be willing to go off script and do what you need to demonstrate you genuinely care. This will help build respect on both sides.

4. Be intentional

Finally, go into every conversation intentionally. Take some time in advance to mentally prepare and think about your approach. Be clear what you are trying to communicate and what you want to get out of it but also ask the other parties what they want from you.

This can be done simply by asking them. Do you want me to listen? Do you want me to provide advice? Do you want me to go away and action something?

Sometimes the answer might not be what you expect, so it’s always worth asking.

It’s easy for conversations to be vague and rushed, but this isn’t valuable for anyone in the long run.

Today our time and attention is constantly distracted by a stream of information and messages. Having real and authentic conversations is harder than ever. However, against this backdrop, building inclusive, supportive and motivating workplaces has never been more important. There is a clear link between engaged and happy employees and the bottom line.

Leaders must go above and beyond to connect with and support employees. Talking to them frankly and listening to their problems is crucial. This isn’t always easy.

These four principles should help you with some basic principles to stick to when approaching a tricky conversation, but it’s also important that your approach feels authentic to you as an individual, makes the other person feel respected and leads to the best outcome for all.