Clear & Kind: The Power of Difficult Conversations at Work

A Q&A with Elaine Dutton & Olivia Bilocca

In today’s dynamic workplaces, difficult conversations are a core leadership skill. So, why do so many leaders still avoid them, delay them, or mishandle them? What gets in the way? And how can we get better at having these conversations that shape culture, performance, and trust?

Elaine Dutton, Founder of The Change Agent, and Olivia Bilocca, Founder of Ethical Living, sat down to explore what makes tough conversations both necessary and transformative.

1. Why are difficult conversations such an important (but often overlooked) part of leadership today?

Elaine: The expectations from leaders have changed drastically over the last 50 years. Authenticity and integrity are now essential, especially in today’s knowledge economy. Leaders aren’t just managing processes… They're expected to motivate, address human dynamics, and resolve tensions. Trust often develops in the moments we’re willing to lean into discomfort. Avoiding hard conversations doesn’t solve problems, it just buries them, where they quietly erode morale and team cohesion.

Olivia: Difficult conversations are where real leadership shows up. They’re not just about managing conflict, they're about building trust, clarity, and accountability. But because they often involve discomfort, many leaders avoid them or rush through them. In today’s fast-moving, people-driven workplaces, that avoidance comes at a cost: unresolved tension, misalignment, and disengagement. When we learn to approach these conversations with presence and care, they become one of the most powerful tools we have for fostering growth: both personal and organisational.

2. What holds leaders or teams back from addressing tough issues? Is it fear, lack of skills, culture, or something else?

Elaine: I think 'all of the above'. Leaders are human. From what I see around me, many genuinely worry about damaging relationships, saying the wrong thing, or making things worse. Culturally, many of us grew up in environments where speaking was penalised or where silence is mistaken for harmony. Others have simply never been taught how to have productive hard conversations.

One manager once asked me - 'where do I even begin?!' So they delay, soften the message or dilute it to a point where the other party doesn't even realise there is an issue, or some avoid it altogether. There is also a genuine worry that if the conversation turns sour, the person might leave the organisation, with re-hiring nightmares pushing leaders to postpone or soften a hard conversation - they would almost prefer not dealing with the issue completely than risk embarking on a never ending recruitment drive.

Olivia: As Elaine mentioned, fear is huge. But a major issue is also lack of practical skills. Many leaders simply haven’t been shown how to hold a constructive, compassionate tough conversation. On top of that, if the broader culture rewards harmony over honesty, or avoids vulnerability, it makes it even harder. That’s why our work focuses not just on individuals, but on shifting the systems and expectations around them.

3. How can organisations build a culture where honest conversations are expected?

Elaine: Start at the top. There’s a Maltese phrase - “Il-ħuta minn rasha tinten” - meaning the fish rots from the head. Leaders must be open to feedback, willing to sit with discomfort, and able to hold space for disagreement without defensiveness. Systems matter too: clear values, psychological safety, training, and follow-through all make a difference. Culture is shaped by what gets talked about, and what gets tolerated.

Olivia: Yes, it starts with modelling. Leaders need to show that honesty can coexist with care: that speaking up is a form of respect. It also means creating systems that support this behaviour: regular feedback practices, space for reflection, clear norms around conflict, and real consequences (or rewards) tied to how people show up in tough moments. Culture isn’t built by policy alone (barely ever, actually), it’s in the daily micro-behaviours. When leaders and teams see that tough conversations lead to better outcomes, the culture starts to shift organically.

4. What myths exist around “difficult conversations”?

Elaine: I think some people might think that difficult conversations have to be confrontational. They don’t. They have to be clear, honest, and intentional. As Brene Brown says "Clear is Kind". It still leaves room for you to be empathetic and forward-looking. Clarity and compassion can co-exist!! Another myth is that if the other person gets upset, the conversation has failed. That’s not true. Discomfort is part of growth. The goal isn’t to avoid emotion, it’s to handle it constructively.

Olivia: Exactly. One big myth is that it has to be confrontational or emotionally charged. A difficult conversation isn’t necessarily dramatic - it’s just one that requires courage and care. Another misconception is that being “nice” means avoiding tension. In truth, avoiding hard topics can be more damaging in the long run. The most compassionate leaders are often the ones who are willing to say the hard thing, with empathy, clarity, and respect.

5. Can you share a moment when a tough conversation led to a breakthrough?

Elaine: A company that I was once advising had an employee who was sadly undergoing treatment for a health condition. In spite of this, he wanted to continue contributing to the company and keep his position, which was quite a high-ranking one, to keep him motivated. But in reality, this person’s performance was understandably suffering and there were certain decisions that couldn’t wait too long to be made. While the company wanted to support this employee, they needed to find a way to make things work better - be it through restructuring or taking on additional support. Sometimes, the more we avoid having these conversations, the worse we make them out to be in our heads. Once we sat down to talk, the response was not one of defensiveness, but one of relief - this employee was extremely eager to discuss having additional support, but he didn’t know how to approach the topic. In the end, it was a win-win for both parties!

Olivia: There was a situation where a leadership team had been skirting around an issue of underperformance for months. It created a ripple of resentment and confusion throughout the organisation. When we finally created space for an honest, structured conversation - naming the issue openly, exploring its impact, and aligning on expectations -  it was like a weight lifted. Not only did the individual shift their behaviour, but the team’s trust and cohesion grew stronger. It wasn’t easy, but it was a turning point.

6. What advice would you give to leaders who want to get better at tough conversations?

Elaine: For me, the cardinal rule before engaging in any planned conversation, is to ask myself - "what do I really want to achieve from this conversation?". In the best case scenario, how do I want the other person to feel, think, and act? What results will I expect to see if this conversation turns out to be fruitful? 

These questions steer me to be intentional and clear. I avoid falling into the trap of starting from a really far away point, or getting lost with examples or issues that are irrelevant. 

I would also say that it is important to be clear about your emotional state - don't enter a complex conversation when you are angry - the likelihood is that those emotions will cloud your judgement and your words. You can, however, be honest about how something has made you feel in a way that is assertive but not judgemental e.g. "I would like to discuss issue XYZ that happened yesterday. It made me feel rather disappointed because ..." 

Finally, create space for the other person to respond. End with a question like, “How do you see it?” or “What’s your take?”

Olivia: I would say start with yourself. Reflect on your own responses to conflict, what triggers you, what you avoid, and why. Then, begin building your toolkit: practice active listening, get curious before you get defensive, and learn to pause rather than react. And remember, you don’t have to be perfect, just intentional. Investing in training or guided support (like this workshop) can be a powerful first step. The more you practise, the more these conversations become less about fear, and more about possibility.

7. Finally, what motivates you to do this work?

Elaine: I’ve seen how powerful these conversations can be. They unlock stuck dynamics, rebuild trust, and shift performance. I’ve also experienced hard conversations where the outcomes were not always positive - like someone leaving - but the clarity still helps everyone move forward. I believe the quality of our conversations reflects the quality of our leadership. And when we help people show up more bravely and more humanely, even in those hard moments, we create more effective and higher performing teams, and more sustainable organisations. That’s work worth doing.

Olivia: At its core, this work is about connection. I believe that when we’re willing to face the hard stuff, with honesty and humanity, we unlock not just better outcomes, but deeper relationships. I’ve seen how transformative it can be when people feel seen, heard, and respected, even in disagreement. That’s what drives me: helping leaders and teams find their way through complexity, and come out the other side with more clarity, strength, and trust.

Want to empower your team to have better conversations?Join our upcoming workshop* on Navigating Tough Conversations to develop the skills you need to face these discussions head-on. Email us at info@thechangeagent.eu or visit our Workshops page to learn more.

*Our upcoming workshop is now fully booked! Please get in touch to register your interest to be the first to know about our future workshop dates.