5 top tips to have difficult conversations better

Would you like to have difficult conversations better? In this post I aim to share my experience of what works and what doesn’t.


Most of us avoid difficult conversations because deep down we hope that the need to have them will go away.  Occasionally, this happens and we are proved right for putting it off.


The person chooses to leave the organisation and we never see them again. A restructure and we’re given a different project. Or perhaps we move on ourselves and that deals with the issue.


In reality though, most of the time the problem does not go away and can even get worse if we don’t find a way to tackle things that are coming up.


Over the years of working as a mediator, I’ve learned some top tips  that make it more likely that we’ll get what we want when we have difficult conversations.  Here are my five top tips.




Have the conversation sooner rather than later


Many of us wait until things are really difficult before broaching the tricky subject. This makes the conversation more daunting than it needs to be.


This is true even in low-level situations where there isn’t really an overt ‘conflict’.


Imagine the following situation.


You are new to the organisation and your manager gives you a brief on a project that she wants you to work on. After reading it, there are several acronyms and terms that you don’t understand.


If you’re totally honest, you’re really not that clear on exactly what it is that you’re being asked to do either. You feel a bit frustrated and annoyed that she didn’t explain it in more detail.


However, thinking that you need to prove yourself because you’re new to the job, you get on and give it your best shot.


You set up some meetings to get started and at one of the meetings, someone asks for more background information about the project. You have no idea, so you blag your way through but the other person questions some of your answers. You feel mortified. You promise to go away and bring back some answers.


Now you know that you really need to have that difficult conversation with you manager and you feel embarrassed because it’s been three weeks and you know that you could have had the conversation three weeks ago.




Have the conversation in person, however hard it may seem

In the example above, the temptation might be to send an e-mail to your manager with a number of questions instead of facing her to ‘fess up’ that you need more clarity.



However, in my experience as a mediator, 99% of the time having difficult conversations over e-mail only leads to greater confusion and often worse. This is an extremely common trend because it sometimes feels easier.  Take a deep breath and ask for a meeting.




Prepare yourself for the conversation


Make some time in your diary to prepare for the conversation.  As you prepare, consider the following questions. What is your intention with this conversation? What do you need to get out of it? How do you want your approach to be with the other person?

Even taking 15 minutes to reflect on these questions will more likely lead to a better outcome.


Taking our example above, you decide that your intention is to admit that you’re not sure about the project and you need a bit more support getting to grips with it.


In terms of what you need to get out of it, you need some clarity on what the various terms mean and also on your role. You also need to know who is the best person to call on for future support and questions – your manager or someone else.


Finally you need to be heard and for your manager to understand that you need a bit more direction and support as someone totally new to the company.


You decide you want to be open, honest and to make an apology for not asking sooner.



Go in there with the intention to listen first rather than waiting to be heard


If you go in there with an intention to really listen, you’ll build rapport and be much more likely to get your concerns and needs heard.



A simple tip here is to reflect back some of the key things that the other person says. This is an extremely effective communication tool that has several purposes. It builds connection. It lets the other person know that you have heard them. You act like a mirror to their words and that means that they can correct anything that you may have misunderstood.  It creates much clearer communication. It’s about reflecting back the most important points.




In our example, let’s say that your manager tells you what the terms mean and a bit more about your role. You say to her, “so can I just check I’m getting this? You’re saying that IGP means the ideas generation project and that you want me to coordinate this project by focusing on building key partnerships and coming up with ideas for how to integrate these new technologies? So it’s an ideas generating role mainly?”.




However, you’re still left unclear about who to go to for support and reporting back. Your manager seems too senior but you’re not sure who else to go to.



Be clear, open and direct with your communication



It can take time to get clear. Don’t give up! If you still don’t understand what’s been said or think that they haven’t heard your perspective, you can state your point of view clearly, respectfully and directly. In this process, aim to communicate what your main need is.



“OK I think I’m much clearer on my role. I’m still not quite clear on who I report back to once I’ve done this initial scoping work on the IGP? Where does it go from there? I really need to know who to report to and also who I can go to if I still have questions.”


What would your top tip for having difficult conversations better be?



I’d love to hear!


A lesson in humility and empathy

This week I had a lesson in humility from my eight year old and four year old.

It was the end of the day and I’d been in on-line meetings all day and had also battled with some frustrating run-ins with technology. We’d just eaten dinner together as a family and that had gone remarkably well.

I knew I needed to get out and get some exercise.

As it had finally stopped raining I suggested to my eight year old son that we go out for a walk-run. We walk for a minute, run for a minute for ten to fifteen minutes. He likes it because he enjoys timing us and is much fitter than me. I always struggle to keep up with him for the running part which he finds funny.

At the last minute my four year old decided she wanted to come along too, instead of hanging out with her dad, and she grabbed her scooter. We headed out to the park and all was well. At first.

However, as we went through the park my daughter saw the skateboard ramp at the edge of the playground in the distance and wanted to go there to scoot. I said no. She protested. I continued to say no, that this was a short trip to the park for a walk-run, not a playground trip.

In truth, it was heading towards her bedtime and I was calculating how much I wanted to get them both to bed and have some time to myself.

I held my ground and we were in a full-on standoff. We made it home but we were both furious. As soon as we got in the door I shouted at her that I was really angry and I didn’t want to take her again next time if she’s going to yell and scream when we don’t do what she wants (oh, the irony!). She stormed off to her bedroom in tears of rage. I went and locked myself in the bathroom to calm down.

My son ran upstairs and I didn’t try to stop him.

Having taken some deep breaths, I felt calmer and when I came out of the bathroom, both of them were stood there waiting. She looked both bashful and cross and immediately blurted out, “Sorry mummy”. I thanked her for saying sorry.

I could tell she was still angry though as she wouldn’t look at me.

So, I gathered myself and asked, “Were you disappointed and frustrated when I said you couldn’t go to the playground?”. She nodded. “Did you really want to go?”. She nodded again and fresh tears came.

I said that I understood she really wanted to go and at the same time this was a short trip to the park just to do a walk- run. I explained that I felt frustrated when she didn’t accept that.

Next, I asked her, “how did you feel when I said I didn’t want to take you again?”. “Sad”, she said. “I didn’t mean it.”, I replied. “I was feeling cross myself and I said something I didn’t mean. I’m sorry. I would like us all to go to the park together again and maybe one time we can all go to the playground and another time we can just do a walk-run. What do you think?”

She looked me in the eyes and a big grin spread across her face.

“Shall we go and have pudding now?”, I asked. “Yeeeesss!” she yelled and raced back downstairs.

I said to my son, “You superstar! What did you do to calm her down?”. He looked very pleased with himself and told me, “I listened to her and got her to do rocket breath* and she did it funnily and we both laughed so she did it four times and she calmed down. Then I asked her if she wanted to say sorry to you and she said yes.”  I gave him a big hug, thanked him and we headed downstairs.

I was in awe of this boy who hates it when people get angry and shout.

He had the wisdom and kindness to see what his sister needed and to help her out. And he’d come to my help when I’d run out of emotional resources. I felt hugely grateful.

This morning I was still feeling guilty so when my daughter came in, I apologised to her again for the unkind thing I said and she replied, “It’s OK mummy I know you didn’t mean it, you’re still a child of God.”


*Rocket breath is a breathing technique we learned on a parenting course that helps young children to calm down.

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A revelation about working in teams

All of us have a preferred way of operating at work, our default mode, if you will. Mostly it is unconscious.

Often we make the mistake of thinking that everyone else sees things the same way that we do and this is where we can hit problems.

In my work training people to handle difficult situations, I use an excellent profiling tool that helps people to understand their natural communication and working style, especially when they experience a bit of tension.

Take the way a project is managed for example.

What is your starting point? One person will start out with building the relationships and gathering a strong network of people. Another might do a lot of background research on other similar projects, the history of the context or the latest research around the topic. A third person would start by getting down on paper the vision, strategy, goals, concrete outcomes and timescale. A fourth person might look at the core values and purpose and work on bringing together a team to work on building the project collaboratively.

You probably found yourself nodding at one of these examples and thinking, “well of course that’s the way to do it. Isn’t that obvious?!”. In reality, all of these approaches are valid and have different strengths to them.

The rub comes when two people with vastly different approaches are working together on a project, often for the first time. Add in different experiences, potentially different cultural backgrounds, workload pressures, diverse ways of communicating and handling disagreement and it’s no wonder that it can be a minefield.

If you’re in this exact situation and you’re thinking, “It’s me. There’s something wrong with me, I just can’t work with him/her,” I’m here to tell you that it’s not you. That bears repeating. It’s not you.

You probably just have vastly different styles to one or more of the others in your team, and you’ve probably never been taught the skills to handle those differences. Let’s face it, most of us haven’t.

It’s possible to work with people with very different styles to ours and to get on well. In fact, having diverse styles in a team setting is both a challenge and a huge potential goldmine. She will see things that you never would. He will stop you from wasting a lot of time (and therefore money) going down a rabbit hole. She will have the key connection that makes the programme fly. And so on.

For most of the people I’ve worked with, this is a complete revelation.

So what’s the difference between teams that manage to hold this diversity and make it work and those that crumble under the challenge? In my experience, there are three key pieces, self-awareness, skill and a commitment to work at differences. Where you have a team of highly self-aware and skilled people who are dedicated to sticking it out, style differences won’t lead to destructive conflict.

The good news is that all three elements can be learned.

People can grow in both self-awareness and their skill level with the right support, i.e. high quality training and ongoing coaching. Commitment to work through differences can be encouraged through developing an organisational culture that sees conflict as an opportunity for learning, growth and change.

How strong are these three pillars in your organisation? I’d love to hear!

Need help to build skills, self-awareness and confidence in handling differences?

Check out the Courses page of my website and look for Team Profiling here:



The power of a true apology – and why is it so hard to do?

The mediation session between Sarah* and Sandra* had gone well so far, but there hadn’t been quite the breakthrough that I’d hoped for. Sarah had admitted posting some things on social media about her work situation and had apologised to Sandra for this and for not talking to her directly. These were encouraging signs.

However, Sandra had not acknowledged the apology and I was starting to feel tired with the effort of encouraging them to hear one another more fully. I decided to call a coffee break and then check in with each of them individually. Privately, I asked them how they felt it was going, and reminded them of what they had said they wanted to get out of the joint session when we’d met previously.

Both agreed that they wanted to continue.

When I restarted the joint meeting, Sandra turned to Sarah and issued a whole-hearted and unqualified apology. Immediately, the tension began to dissolve and the conversation between them opened up.

They both shared openly what had happened and I was able to gradually guide them towards thinking about the future and how they wanted to move forwards. They reached a workable agreement and when I contacted them again a year later, they were happily working together.

In reflecting on this case, I was struck by the power of a true apology and also how rare it is. Courageously, Sarah had taken the first steps. Because it was genuine, it had the effect of transforming the situation once Sandra was able to hear it. So what makes a true apology?

These are some of the key elements. You can tell a genuine apology when it:

  • Comes from the heart, not from the head. This is hard to quantify but you know it when you see it and hear it.

  • Acknowledges the harm done to the other person or people.

  • Accepts and acknowledges your part in the situation – not necessarily taking full responsibility but admitting that you had a part to play.

  • Has no qualifications or justifications attached to it.

  • Comes with a willingness to hear the other person’s perspective. Again this is hard to quantify but it will emerge in the conversation whether or not this willingness is present.

  • Is offered voluntarily, never ‘required’.

The reverse is also true, you can recognise an apology that is not genuine when:

  • The body language betrays a lack of respect, such as arms folded, rolling eyes, tone of voice, tutting, despite the person ‘saying the right thing’.

  • There is no acknowledgement of harm.

  • The person does not accept the part they played in the situation.

  • They say things like, “I’m sorry if you felt that way…”, “I’m sorry it’s come to this but….” . These phrases are usually followed by an explanation, justification or qualification about why they behaved the way they did.

  • There is a lack of willingness to really hear the other’s perspective.

I also started to reflect on why saying sorry is so hard for most of us and I think there are a number of reasons for this.

We operate in a society that values expressions of strength and apologising is often seen as admitting failure.

As children, many of us were forced to apologise to our siblings or to friends before we were ready and before we were given a chance to tell our story. This was done with the best of intentions, usually to teach us social skills, and yet for many of us it felt deeply unfair because what we really needed was to be heard and acknowledged ourselves. The ‘sorry’ was probably needed, but later on when we’d had a chance to calm down and been listened to.

Finally, many of us have a deep rooted fear that in some way we are ‘wrong’, a failure, not good enough, an imposter and so on. At a subconscious level, we confuse admitting that we’ve made a mistake and done something we regret, with admitting that we’re fundamentally wrong as a person, something that deep-down many of us fear anyway. 

A true apology comes from a place of strength and it takes tremendous courage and discipline. Never doubt the power it can have to transform a relationship.


*Not their real names. Names and some other details have been changed to protect identity.


Why the small things matter in communication

In working with people as a mediator I’ve noticed a pattern about how differences turn into conflicts.

Usually, there is a single important event that happens between two people. It can be something said or done, or an e-mail or text message. I call this event a ‘precipitating moment’. From this moment one person starts to distrust the other just a little bit and from there it grows.

Let’s take a typical story. Sarah and Karen* worked for a medium sized charity based in different teams. On a new health project, their work crossed over and they needed to work together and liaise with the same external partners for the first time. Karen had been with the organisation for twelve years to Sarah’s seven months.

Karen prided herself on her attention to detail and good relationship with partners. Sarah was excited about the new role and keen to get stuck in. They had two partner meetings where Sarah suggested some ideas that Karen thought were not properly thought out. Karen said as much in the meetings and afterwards she’d got a number of ‘angry’ e-mails from Sarah.

Sarah, on the other hand, was getting frustrated. This was her first big project and she was keen to make an impact, but Karen was blocking her ideas. She e-mailed Karen to try and sort it out and they e-mailed back and forth but the messages became more and more heated.

Eventually, they just stopped communicating.

The ‘precipitating event’ in this story was the first partner meeting where Karen spoke of her concerns about Sarah’s ideas. This is where they started to distrust each other. The thinking goes, “I have been wronged, my perspective is right and they are at fault.” It becomes ‘me’ against ‘her’.

If I’m lucky as a mediator this goes on for a few months and then I’m brought in. More often though, this pattern goes on for a few years before it is dealt with and then I am contacted.

In this story, both women gained supporters for their point of view. Bringing others onboard creates an ‘us’ and ‘them’ scenario, which is another common pattern.  By this stage, often people stop using names and simply refer to ‘her’ or ‘they’.

In this case, the project limped on for a year until their senior manager found out what was going on. She tried to help by supporting Sarah’s side, which only made matters worse. The project was handed over to others and a mediator was brought in.

After an individual meeting with the mediator and one joint session together, they were able to sort out their differences and mend the relationship.

In fact, they booked a monthly lunch date to catch up since their manager had just won another contract that needed them to work together.

What went wrong?

Communication between Karen and Sarah was a big part of it. Although ideally they could have met before the very first partner meeting, they were both new to the work and feeling their way into it. However, after that first meeting, they could have recognised that there were some tensions they needed to talk about before the next partner meeting. It seemed quicker and easier to sort it out over e-mail so that is was they tried to do.

This seems like such a small thing but in my experience e-mail communication almost never works where there’s tension. Often it makes the situation worse, takes longer and creates more stress.

Meeting in person would have been much more effective, even if they had ended up arguing. 

However, like most of us, Sarah and Karen have never been taught how to ‘disagree well’ and were both feeling rather annoyed and frustrated. In truth, they were anxious about the idea of speaking face to face, so they avoided it.

Once they talked together with the mediator’s support they resolved the issues in one day. The conflict had gone on for a while so it took hard work and commitment, but they each apologised to one another and were able to understand each other’s perspectives much better. Together, they created a working agreement.

As well as these external events there were also a series of internal reactions and decisions made by Sarah and Karen. After that first meeting, each of them started to form thoughts and judgments in their minds about the other person, their behaviour, motives and even their core character.

This is a natural tendency when we find ourselves strongly disagreeing with someone else. It quickly becomes not just about us having different ideas, but about them being flawed as a person. These beliefs often come from a place of fear and anxiety about our own worth. It takes conscious effort, discipline and a choice to trust to move away from those beliefs and meet with ‘the other’. However, it is what can make the world of difference.

Changing the way we deal with disagreements starts with noticing them and making a conscious choice to do it differently this time.

Because conflicts always begin with the small things.

That is why they matter so much.



*not their real names. The story has had key details changed to protect anonymity.


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