How to have a difficult conversation in the workplace (with examples) Difficult conversation? Here's how to do it.

Discover tools you can use that will help make that difficult conversation less stressful, with examples

Need to have a talk with a colleague about why they didn’t get promoted, speak to a coworker about their offensive behaviour, or explain to a client why you’ve missed a key deadline? You may be dreading the conversation. In this post we’ll show you tools you can use that help make that difficult conversation less stressful, with examples.
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Difficult, awkward, and uncomfortable conversations are part of the day job of being a manager. There are always going to be times at work where you need to have a talk with someone about a sensitive subject, which could go badly wrong.

Regardless of whether that’s telling a client (or your boss) that their request is unreasonable, holding a colleague accountable for a missed deadline, or confronting a team member about their poor work or disrespectful behaviour, these conversations feel stressful and uncomfortable because we're frightened of where they might go.

Most people find the challenge too hard and manage uncomfortable conversations by ignoring or avoiding them. Research shows that 70% of employees avoid difficult conversations with their boss, colleagues, or direct reports, and 95% of staff struggle to speak up about a concern

However, whilst having a difficult conversation with your boss or colleague may be extremely daunting, putting it off - perhaps in the hope that things will miraculously improve - can make matters a lot worse.

Not telling someone about a delay could cause bigger problems further down the line. Keeping quiet about concerns or not sharing a different view in a meeting can lead to projects failing. Challenging behaviours and rudeness can blow up if left unchecked, and small disagreements can turn into unhealthy conflict and have a big impact on your team’s performance and culture.

When avoiding a difficult conversation is a problem. A real life example

One of our clients recently took up a managerial post at a large organisation and discovered that the most senior person on their team had also applied for that post. They had been passed over for promotion and were now holding it against our client in all kinds of micro-aggressive ways. They said things like, “you are undoing all the work we have ever done here,” questioning every suggestion and proposal to the point of destruction, exhausting our client and everybody else on the team. 

Reluctant to have a tough conversation, our client tried being understanding and accommodating, and overlooked the behaviour. Unfortunately it didn’t work. The person concerned continued to sabotage everything, holding the team back and keeping everyone stuck in pointless conversations that went on for weeks.

What our client needed to do was to tell this person - in a clear and respectful way - that their behaviour was not okay and had to stop. They needed to say that it was affecting them, the work and everyone else too. 

Unfortunately they didn't - instead they effectively adopted a ‘do nothing’ strategy, something that is more common than you might think. Our fear of conflict will see us putting up with a great deal. In fact, Fierce Conversations found that the number one response to coping with toxic employees is to ignore them, with 44 percent of respondents noting this was their preferred approach. 

  1. Prickly Peers: Failure to confront rudeness, aggression, bullying, harsh language or resistance to feedback.
  2. Ticking Time Bombs: Failure to speak up when proposals and procedures are riddled with inaccuracies or faulty thinking. 
  3. Incompetent Colleagues: Failure to talk to peers and direct reports about poor work or lack of engagement.
  4. Abusive Bosses: Failure to openly discuss the damage done when people in power resort to control or rely on their position to push their own agenda.
  5. Management Chaos: Failure to get clarification when people feel uncertain around roles, responsibilities, and timelines.

The hidden cost of unspoken conversations

The study by Vitalsmarts also highlighted what happens as a result of avoiding a difficult conversation - the impact affects the work that people could be doing as well as the workplace atmosphere: 
  • 61% ruminated about the issue
  • 41% complained to colleagues
  • 32% did unnecessary work to avoid dealing with it
  • 24% talked around the topic

And their research into the financial cost of a delayed conversation:
  • 35% estimated the delay cost their employer between $100 and $1,000 for each conversation avoided, 
  • while 19% put that cost at up to $5,000.

The upshot is that however bad the news or sensitive the problem, the best strategy all round is to tackle it as early as possible and to have a conversation with the person concerned, however difficult.

In the example of our client, after discussing different ways to challenge their difficult colleague, they grasped the nettle and calmly explained to their colleague how the behaviour was making them feel and the impact it was having on them personally. The response was dramatic: shock, horror and guilt. There was an apology and a frank and open conversation about the colleague’s frustration. The behaviour did improve and ultimately the difficult person made the decision to find a new role, as their frustrations were with the organisation rather then our client. Our client was able to support them in securing a new role. 

It is often the case that embracing the conflict like this leads to good things. When you are avoiding conflict, rather than think about the worst that could happen, think instead about what is the best that could happen.

Building your courage and your ability to have frank and difficult conversations is a useful skill for any manager. By increasing your awareness and experience of how to approach tough conversations you’ll learn how to manage situations with respect and honesty - and get better outcomes.

Here’s how to have difficult conversations

So how do you approach these kinds of conversations and find the right strategies to handle the interactions so that they go smoothly and better than you were hoping?

Having a framework for those hard conversations will help you get better at them and as you practise, your confidence will grow.

Here’s what to do:
  1. Face the situation head on
  2. Consider what is going on for the person
  3. Use an I-Statement
  4. Use the FONT tool
  5. Respond in a different way
We go into more detail about each of these steps with examples below:

1. In the first instance, face the situation head on and talk about it. 

Talking to your boss or employee about a sensitive subject can be an anxiety inducing prospect. You may worry that they are going to be defensive, or that they’ll be angry and aggressive. They might not listen. These are all certainly possible. 

But if you don't try to have the conversation, you can't make any progress at all. You'll just be stuck in a difficult situation. 

The truth is that when you have the conversation, it's usually not nearly as bad as you fear. 

2. Prepare for the conversation by reflecting on what might be going on for them

There could be many and various reasons why someone is behaving in a particular way. If they are delivering poor work, they may be struggling but feel unable to ask about it. If they are not engaged, they could have issues at home. If they are being rude they may be feeling aggrieved by unjust treatment.

Try putting yourself in their shoes before you start talking to them. 

In the example above of the person who was passed over for promotion and didn't get the job - their confidence or self esteem will definitely have taken a knock.

As a manager, your top aim should be to help this person to be a useful contributor again whilst making it clear that they can’t carry on behaving like that. 

3. Use an I Statement

An I-Statement - literally a statement you make that starts with the word “I” - tells another person how you are feeling in a clear, effective, and truthful manner.

I-Statements are a tool for holding a difficult conversation in a respectful, productive way. They are a powerful way to help you express your point to someone else without immediately causing them to feel defensive or aggressive, which allows them to respond rather than react.

The way to do it is to start with “I” and to structure what you say like this: 
“I feel X when you do Y, and [how their behaviour affects you].”

For example, “I feel upset and angry when you say things like that, and it is affecting how we work together.” 

If it’s appropriate you can add in - “I would prefer it if you didn't do that, and if you did Z instead.”

Be as truthful as you can because your true feelings are undeniable. And then it will be much more likely that you are able to have a real dialogue with them.

In contrast to an I Statement, if you start the conversation with the other person’s actions, or say “you make me really angry when you do X,” you’re sending the message that you’re blaming them and that they’re the problem.

An I-Statement is not blaming, it’s the opposite of making someone feel they are intrinsically bad or wrong (which is more likely to put them on the defensive), instead it’s about the consequences of their behaviour and makes space for the possibility that they could behave in a different way.

NB I-Statements can take a bit of practice as you can feel a little vulnerable when you use them, but they do work, so do persevere. Also be careful not to turn one into a ‘blaming you’ statement pretending to be an I-Statement. Eg “I feel that you are passive-aggressive,” is not an I-Statement.

4. The FONT tool

The FONT tool is a way to decode and focus the conversation so that you can discover what's really going on for people.

FONT is an acronym for: 
F - feelings 
O - observations 
N - needs
T - thoughts

The way to use it: whenever you're having a tough conversation with somebody, observe what you notice both about yourself and what you sense from them, within the four FONT categories, so that you can break the conversation down into something that makes sense and helps you handle it better.

For example, I might be observing your body language and notice that you’re looking away. I might think about what that might mean and realise that, “she's not listening to me.”

Or I might notice that you’ve become defensive. I might start thinking, “This is going to end really badly. We're going to start shouting and she may storm out.”

With that information, I could change my behaviour. I could stop trying to tell you something, and instead ask a question: “I noticed that you raised your voice when you said that. What's going on for you? How are you feeling?”

The ultimate aim of the FONT tool is to increase your awareness of what might be going on emotionally for the other person - their feelings and needs - and to bring those into the conversation. If you can do that, you are more likely to have a much more valuable conversation. 

If you just stick to actions, decisions, communication and results (ie the bit above the waterline in the iceberg model [see image below]), it’s more likely that you’ll get a defensive response. 

Our experience suggests that most people don't bring feelings and needs into the professional domain and yet they're so important. If you try to address an awkward relationship with all its difficult context without talking about emotions and needs, you'll have very limited leverage to affect change.
We may pretend that everything happens above the waterline - what's going on below the waterline is equally if not more important.
The first time you try using FONT, you may find you’re really good at the thoughts and observations parts, but perhaps not so good at recognizing feelings or needs.

The more you practise, the more you're able to do it on the fly.

Five core emotions
To help you identify what people’s feelings are, this is a helpful shortcut to use with the FONT tool - the five core emotions:
MAD (Angry)

Arguably all emotions are a variation on these five. 

If you can find a way for the person to tell you how they’re feeling, for example they might say, “I don’t feel safe. I'm feeling a mix of anxiety (scared) and anger.”

Then you might be able to understand what their needs might be, you can empathise with them and try to find a solution. 

If their needs are for esteem, acknowledgement and feeling valued, then you can find things that you can praise in this person to help them feel more valued, and look for opportunities to acknowledge them. That might be a way to decode the tension in the relationship.

There are two ways to work with FONT: 

i. In the moment 
Use it to steer a conversation into what's really going on. This often leads to an amazingly releasing conversation. It requires a certain level of skill, and there is some risk. Even if it doesn't succeed the first time, the attempt won't necessarily end in disaster. 

ii. Reflecting after the fact 
Review the conversation and re-run it using FONT to help you understand what was going on. What did you see? What were you thinking about? What might they have been thinking?  What might they have been feeling? What needs could be driving them? 

Even if the situation crashes and burns at the time, spending a bit of time afterwards thinking about what you could have done differently will help for next time, when you’ll be better able to recognise what is happening and try something new because you've done the prep work. 

In either case you might not get it 100% right, but at least it gives you a working hypothesis that you can try out to see if it makes a difference. 

Being able to say to someone, “I can see you might be getting upset. How are you feeling?” can go a long way to resolving the situation. If they can be honest about what they’re feeling, then you can say, “Okay, let's just talk about what you need.” 
Examples of needs
The Center for Nonviolent Communication has examples of needs to help give you some clues about things that people might need.

5. Respond to a difficult conversation with the opposite  

This is an approach that’s helpful if someone is either very emotional or very factual:
  • If somebody hits you with facts and figures, you respond with feelings and emotions.
  • If someone is very emotional, you respond with facts and figures. 
Imagine an awkward conversation with a colleague who’s delivered some poor work, they start listing all of the facts and figures about how such and such is wrong and it's not their fault. While they're stuck on the facts and figures, they’ll be building a metaphorical wall around them and you won’t be able to move the conversation forward. If you introduce feelings and emotions, you can change the dynamic of conversation and shift it into a space where you might be able to have a transformative chat. 

Or perhaps the opposite happens and the conversation goes the way you were frightened it could: they become very emotional. What happens if they start crying and say, “Oh my god, I'm useless…” or alternatively they become really angry? A way to respond is to, firstly, acknowledge and bring empathy to all that feeling. Then bring in some facts and figures to try and get back into a conversation. 

This can be quite a useful tool if you find yourself stuck because it’s easy to remember:
  • If it gets really messy, stick to facts and figures and try to build the communication back up from there. 
  • If it's too ‘facts and figures’, bring emotions in and start a dialogue around those things. 

Three examples of situations that are likely to involve difficult conversations and how to deal with them 

These are examples of scenarios where difficult conversations might become dysfunctional, and where people can easily become defensive:
  • There’s a restructure and your job is at risk
  • “You're not doing your job”
  • Offensive behaviour

i. There’s a restructure. People are at risk of redundancy
If you have to restructure your team, some people's jobs are likely to be at risk. They might need to change jobs, or maybe there will be a cut in the number of posts. People often come into restructuring conversations with a lot of anxiety. The minute you say, “This is happening, and everyone's going to have a one-to-one meeting with me about their role,” people's stress levels shoot up. They will start to quietly panic and worry about their mortgages. 

Sometimes this is unwarranted, they may be at less risk than they think. But because they're terrified, they might become really belligerent, and for example might threaten to bring their union rep in. 

Using the FONT tool, you can reflect on what is going on for them - likely you've put them into absolute turmoil, so what do they fundamentally need? 

You might observe that they're agitated, their voice is raised and they're being quite aggressive. You might also be thinking, “this is terrifying,” and you might become defensive yourself. If the conversation starts spiralling out of control, the advice is to stop, identify what you're observing, and try to inquire what their feelings are. 

If they're feeling angry because they feel threatened and don't feel safe, you can calm their feelings by talking about what the options are for them. 

This could be, for example, “the first option is that we redeploy you and there are a number of roles that you should definitely consider applying for because you'd be really good at them… these are the opportunities…”

Then communicate what the scale of the risk to them is:
“Even if there are not quite enough posts left after the restructure, there are some people on the team who want to leave and who are going to be quite happy about that. 

“So actually, you're a lot less at risk than you realise. Maybe this is an opportunity, because in the new posts there are more opportunities for development. You could expect to get a pay rise quite quickly.”

If their original reaction to the news was: “This is outrageous, I am so angry because of the way this was communicated.” Their need is acknowledgement that the process was a dog's dinner, and perhaps an apology and a recognition of the harm that's been done. By addressing that need, you can move the conversation to a different place.

ii. “You're not doing your job”
Someone you are managing is not doing their job and is performing badly. You need to have conversations with them to try to improve. 

You might have a ‘you need to improve’ conversation with a simultaneous thought at the back of your mind that, “this is going to end in a formal performance management process, which is going to be horrible,” which can lead to the conversation being a clumsy one.

The formal process happens when you've told someone that their work is not up to scratch and they haven't improved it. You've talked about it on three occasions, and you've given them three months to change, but they haven't and in this formal process if you don't see improvement their job will be at risk.

It's a challenging and uncomfortable process for the person concerned and usually you destroy the relationship in the process. They end up leaving anyway which may be what you really wanted, but they're miserable and you're miserable. 

Often it's avoidable - if you can intervene early enough.

If you’re able to talk to them early, use The Three Key Questions [link to TSH post] to help them understand what you need and how they’re measuring up:
• Does this person know what's expected of them?
• Do they know how they're doing? and 
• Do they know where they're heading? 

In that conversation you be really clear about what is expected of them. Then you can monitor how they are doing, and you can identify what help they might need to do it. They’ll (hopefully) improve and you’re more likely to avoid the whole performance management process. Win.

iii. Offensive behaviour
Here’s a scenario. John has made a complaint about Sharon. He's quite upset about something that happened last week. You've only heard John’s side of the story and you'd quite like to know what happened from Sharon’s point of view.

That might be a difficult conversation where you're trying to find out the facts about a disagreement.

In this case, use the FONT tool to help you decode what actually happened and find choices about how to interact.

Sharon says: “We were in the kitchen. John came out having left his used lunch bowl and dirty coffee mug on the side. I just lost it. I swore and shouted at him and I might have called him a nasty name, because I always do the washing up and no one ever says thank you and no one does it.”

Manager: “Oh, I notice you're raising your voice even when you’re talking about it now. It seems like you’re getting quite angry and upset. Can we just cool it down? How’re you feeling?”
Sharon:  “Yeah, sorry. It just made me feel really angry.”
Manager: “What do you need?”
Sharon: “I just need not to be the only one that cares about this stuff.”

Manager: “Did you know that actually John had gone in to put stuff in the dishwasher and it was full and badly stacked and so he had to reorganise it. And there were some bits that didn't fit in. So he put them to one side and put the dishwasher on, fully intending to come back later and load the dishwasher.”

Sharon: “Oh… I didn't know that. I’ll go and apologise to him and try not to react without checking in future.”

Manager: “Yes, that sounds good. Thank you.”


Hopefully having read this you have a better understanding about the cost of avoiding difficult conversations and have some tools that’ll help you face them, have better dialogues that'll lead to better outcomes.

The more experience you have of difficult conversations, the better you’ll get at them, and then they might not feel so difficult.

360 degree reviews can help

A 360 degree feedback review can also be a useful tool here, because it creates a neutral and a safe space for people to articulate what they might not be able to say in person about what their experiences are, without exposing themselves in a dangerous way, for example, when there are power dynamics at work. 

In addition, 360s’ are designed to invite constructive feedback through the way the questions are written and to be balanced: they’re an opportunity to talk about strengths as well as weaknesses and to feel valued and appreciated. Knowing that you are valued makes it easier to hear about things you could improve.

If you’re looking for good 360 review software that supports the growth of your employees and your organisation, and removes the complicated admin that can accompany 360’s, use a tool like AdviceSheet, it is really that simple.
AdviceSheet has:
  • Transparent pricing
  • Automates the process
  • Anonymous participants
  • Confidential reports
  • Free from meaningless metrics
  • Questions that stimulate insightful answers