Having Difficult Conversations

Asking for a raise. Ending a relationship. Giving a critical performance review. Saying no to someone in need. Confronting disrespectful or hurtful behaviour. Disagreeing with the majority in a group. Apologising. Progress in life can often be measured by the number of uncomfortable conversations we're willing to have.

Having Difficult Conversations


Asking for a raise. Ending a relationship. Giving a critical performance review. Saying no to someone in need. Confronting disrespectful or hurtful behaviour. Disagreeing with the majority in a group. Apologising.

All of the above are conversations that people tend to regard as difficult, ones that we don’t generally look forward to having. Have you ever heard your car make a noise that didn’t sound right? Even as the noise grows louder, you put off getting it fixed. Then one day, your car breaks down. The realisation that you could have avoided the problem earlier hits you in the stomach.

It is the same with interactions we put off. At work, at home, and across the garden fence, difficult conversations are avoided every single day.

Not having those hard conversations is the silent business killer. It impacts everything and most of the time we don’t see the damage or impact. There is a tremendous unaccounted business impact of avoiding the difficult conversations.

By the end of this session you will understand the dynamics and reasons why these conversations are so difficult. You will feel more confident in addressing conversations that you have been putting off or are facing in the future and you will be more experienced already in the skills and strategies that are necessary to ensure these conversations go well.

Why These Conversations Are Difficult

Tim Ferriss says that:

A person's success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have.

That’s because not having those hard conversations is the silent business killer. And the silent relationship killer.  It impacts everything and most of the time we don’t see the damage or impact because we’re busy blaming the ‘difficult’ person, when actually an intervention by us much earlier could well have stopped a lot of the fallout. The impact of avoiding the difficult conversations in business is absolutely tremendous.

Of course, changing how you deal with difficult conversations takes work. Like changing your golf swing, adapting to drive on the other side of the road, or learning a new language, the change can feel awkward at first. And it can feel threatening: breaking out of your comfort zone is rarely easy and is never risk-free. It requires you to look hard at yourself, and sometimes to change and grow. But better the ache of muscles growing from an unaccustomed workout than the sting of wounds from an unnecessary fight or an unnecessary loss.

Difficult conversations are a part of life and too often we choose to avoid short-term pain at the expense of long-term reward. Unfortunately, this the same logic exercised by many business leaders when it comes to conversations with employees. Initiating a simple talk can be a real roadblock.

Whether it’s a performance issue or employees feuding, there comes a time when leaders must break the silence.

It’s easy for managers to brush the issue under the rug. They often don’t know how to handle the situation or emotional employees.

But avoiding these conversations can make the situation even worse. The longer you wait, the more it can affect the workplace environment and productivity.

It’s a shame because the potential rewards of addressing these situations earlier are rich. By the end of this video you will be able to alter your mindset to find these challenging conversations an opportunity to develop a relationship, to gain deeper understanding of someone, to remove an obstacle to greater performance or happiness, you will then feel less daunted by them. If you also follow the steps outlined today and put the learning into practice you will find difficult conversations becoming easier and causing you less anxiety. You will be more effective and happier with the results. And you will have less strife in your life, at work and at home.

So let’s get started.

When we say difficult conversations what type of conversations are we meaning? Pause the video a moment and write down a few that you can think of.

So, When we say difficult conversations what type of conversations are we meaning? Telling someone bad news; Asking for a raise at work; Giving someone negative feedback about their behaviour; Ending a relationship; Talking about tension points in a relationship; Asking for something you need; Confronting someone about a problem; Making decisions about finances; Raising issues with a supervisor or someone in a power position, saying ‘no’.

Difficult conversations are anything we find hard to talk about with another person. There are a number of reasons that make certain conversations difficult and an easy conversation can become a difficult conversation very quickly if we say something wrong, or get the timing wrong for instance.

The main reason that we find these conversations difficult is that they are emotional in some way and that the other person’s response may be unpredictable or predictable and unpleasant to deal with in some way, whether that’s through anger, through crying, or through the silent treatment perhaps. So what we do is we make a decision that weighs up whether it’s better to avoid the conversation or confront the situation and deal with it.

Too often ‘avoid’ wins out, at the cost of future happiness and effectiveness. Because although avoid may sometimes be the right decision, most of the time, when these issues have come to light it's because it’s not the right decision to avoid it, not the right decision at all. We know in our heart whether we should be avoiding it or confronting it but we sometime choose to ignore it and just hope it’ll go away.

Pause for a moment and have a think about some of the advantages of deciding to try to avoid the situation and then some of the advantages of confronting the issue. Write them down.

Why is it so difficult to decide whether to avoid or to confront? Because we are weighing things up all the time. There are advantages to both but we have to decide between them. At some level , if we don’t confront then we may feel taken advantage of, our feelings may fester, we may wonder why we don’t stick up for ourselves, and we may rob the other person of the opportunity to improve things. But if we confront the problem, things might get even worse. We may be rejected or attacked ; we might hurt the other person in ways we didn’t intend; and the relationship might suffer. But then again, we might get it dealt with, we might set clear boundaries so it doesn’t carry on into the future, or so no one else in the team thinks it’s acceptable to behave like this, we might nip it in the bud or be able to provide help and support that is much needed.

In order to alter our mindset regarding these conversations we need to focus on the positives that can come out of having them if we handle them well. We also need to focus on our own resilience and the effect these conversations can have on us before, during and afterwards.

To do this we need to remember 3 things:

We are far more powerful than we think we are. We may not be able to control the other person’s reaction but we can massively influence it by controlling our own and preparing properly. The reason many of these conversations go wrong is that we haven’t put enough work into the best way to get the message across to ensure it’s heard properly and that the person reacts to it as helpful advice rather than as a personal attack. We just launch into it, from our own agenda, without giving a thought to how we want the person to feel when they emerge from the conversation and how we want it to move forwards afterwards. So, if it goes wrong, we’re much more to blame than we acknowledge.

We’ll cover how to deliver these messages clearly and get the best reaction in a separate video.

It’s also really important to go into these conversations in a positive frame of mind. And that’s two-fold. In the first instance I mean that you need to think of the meeting as a positive step, you are confronting a difficult situation which is a brave thing to do and you are going to get to the heart of the matter which means that you will be able to deal with it in whatever way is appropriate.

Secondly, It’s important to set a positive tone going into your meeting. If you have a negative approach, your employees are more likely to get defensive and argumentative. Pitch your conversation as a “quick chat” If you can. Don’t make it bigger than it needs to be. Avoid language that may suggest punishment or formality (unless it is formal). People will find the situation awful, they will be very uncomfortable. Don’t extend that any longer than it has to be, for their sake as well as your own.

We’ll talk about it more in the separate video remember so don’t worry too much about it now.

Always end the meeting on a positive note. Your employee should leave thinking they can do it, that you believe in them and want them to succeed. Then move the conversation on swiftly to something else that they have to engage with you about such as something trivial like getting a cup of tea, or another project that they’re doing really well on and that they’re excited about. This ensures that they don’t dwell on any negativity, in a way you’re a distracting them from what just happened but you are also making it harder for them to sink into any kind of sulk or negative spiral. Keep them engaged on that note as long as you need to be convinced that they’re over the possibility of the negative spiral.

The third thing we need to do is to conquer our fears. Let’s face it – no one likes conflict really. It doesn’t feel nice. You feel like this (anxious about speaking to them) because you care about the outcome and you don’t want to upset anyone, plus you’re a bit scared about how they’re going to react. It’s totally normal and it certainly isn’t a sign that the conversation shouldn’t happen. People who get good at having these conversations still don’t look forwards to them, or enjoy them, they just learn to ignore the fear and anxiety and get on with it, that’s all.

So, what I want you to do now that this lesson is coming to an end is to have a think about what your mindset is towards difficult conversations now. Have you well and truly acknowledged that it’s better to have them than avoid them? Have you clearly understood that you are more powerful in determining the outcome of these conversations than you thought previously? Do you believe that a fear of having the conversation is no reason not to have it?

Ask yourself these questions and be honest in your responses. You need to be convinced on these points.

How to Make Difficult Conversations Easy

In order to make difficult conversations easier you need to do some preparation. By this I mean both long term and short term preparation. By the end of this lesson you will have an understanding of the steps you need to take, both long and short term, in order to make the relationship as well as the conversation better, you will feel as though you are more influential in how these conversations go and you will be able to control the conversation to such an extent you can ensure its success.

The most important thing you can do in terms of making these conversations easier is to prepare for them. In the long term that means accepting that creating a trusting relationship with those in your team is of fundamental importance. Watch the Creating a Culture of Trust lessons for how to do this. You need to actively, consciously and consistently behave in a way that maximises trust between you and your team so that when you have to say something that’s difficult for you to say and difficult for them to hear that you both know that the content of what you’re saying can be trusted to be in their best interests. So make sure you watch the Culture of Trust lessons and behave in a way that maximises trust at all times.

In the short term you need to fully prepare for the conversation rather than just winging it, which most people do most of the time. Fully preparing for the conversation means thinking about how you want the person to feel at the end of the conversation and then working out ways to say what needs to be said with this in mind. It also means, of course, that it’s important for you to find out the facts and any relevant context before you begin the conversation.

The more you prepare, the better the meeting should go.

Remember that as a business leader, you’re also a coach. It’s up to you to provide everything your employees need to succeed. It’s important that you’re as committed to your company’s overall goals as your employees are. And that means not speaking to people in a way that leaves them deflated and unmotivated, believing that they can’t do the job, or that you have a problem with them, or that they can’t do anything right. You and your preparation for this meeting can make the difference between someone leaving the conversation feeling motivated and inspired, worthwhile and valued, or deflated, unmotivated, incapable and worthless. Make sure you do your job properly before you criticise others for not doing theirs.

There are 4 important factors to consider when having a difficult conversation. These are as follows:

Number 1 - Be fair

Hold all your employees accountable to the same performance expectations.

Have the same dialogue with anyone who is slipping. You don’t want to make it seem like you’re alienating or picking on a certain group or individual. Or that you never pick up on certain people even when their performance or behaviour requires it. This is part of your long term leadership behaviours and will establish trust in you and the team. Make sure everyone knows and believes and witnesses you being utterly fair all of the time. This doesn’t mean that you pick up on everything all the time, sometimes you might turn a blind eye, but it means that you consistently and fairly turn a blind eye to everyone, not just those you lunch with or know socially. Nothing undermines your position more than the existence of favourites or a clique.

Being fair also refers to the fact that we shouldn’t base our opinions on just one side of the story, or on opinion, even if it’s our own. We should base our opinions on the facts and only the facts. This means finding out the facts, either beforehand, if it’s to do with metrics, or as a combination of others’ testimony if it’s to do with a situation that has developed between individuals and the testimony of the person with whom you are having the conversation. Don’t decide before you hear all the facts and review all the facts, or you could be blamed for getting it wrong.

Use any’ complaints, first-hand accounts from any witnesses and the facts to determine what actually occurred. Take a step back and understand there’s more than one side to every story. So be fair. Have the same standards for everyone, including yourself, and don’t pre-judge.

Number 2 is Talk adult - adult.

Eric Berne has a theory of Transactional Analysis that acknowledges the different ego states within us all. There are 3 ego states according to his theory. We are all, at varying times, either parent, child or adult, these states are regardless of whether you are actually a parent or not. What it means is that we inhabit a role of parent, for example, if we are telling someone off, using language like, “I’m very disappointed in you” and imposing rules that must be obeyed. If someone else does that to us then we necessarily inhabit the role of child. Neither of these is a great leadership model. We must work hard to be in adult state as much as possible and to ensure that we do not do things or say things that result in the other person being demoted to child state. Staying in adult state requires no overly emotional language, sticking to the facts, and talking to someone like they are an intelligent, competent grown up, with a job to do, not a naughty child who has disappointed you.

Number 3 is Keep it confidential

You want to be as confidential as possible when addressing difficult situations. Any employees who aren’t involved shouldn’t be aware of the situation. Anyone who doesn’t need to know, shouldn’t know. If employees come to you “confidentially,” make sure they understand you cannot guarantee 100 percent confidentiality. Depending on what they disclose, you may have a responsibility to take action or speak to others. When I’m coaching I always make this clear to people at the outset of our coaching relationship.

Number 4 is to Find the right setting

By identifying the right setting, you’re helping set the tone of the meeting. Depending on the situation, your office is usually an acceptable location for the conversation. But it might be more appropriate to have the conversation off-site, in a coffee shop, out for a walk. Taking it off-site can mean that the person can open up more to you, and not be inhibited by the potential of anyone else walking in or looking in or having to go back out of the room in a ruffled state. It’s also helpful for them if you can completely remove the potential for being overheard. If it’s serious, though a cup of coffee may not be appropriate. In any case, choose a safe environment that makes everyone feel comfortable. Think about this from their point of view as well as your own.

What if it all goes wrong?

It’s rare for conversations like these to get out of hand. But if employees act rude, begin swearing or displaying aggressive behaviours or even crying excessively, then it’s time to end the meeting calmly and exit the situation. Behaviours like this can be used to attempt to control what you are saying. They are effectively an adult tantrum. By ending the meeting you are not pandering to their emotional outburst, not rewarding it.

If your employees’ are upset and likely disrupt the rest of the office, consider asking them to go home for the day. This will allow everyone’s emotions to settle down.

Then reflect on what happened in the meeting that led to the escalation so that you can correct it in future interactions with these employees. Could you have prevented the outburst? Was it something in particular you said, a specific phrase? Learn from the situation so that it doesn’t happen again. If you can’t pinpoint what it was that caused the conversation to break down it might be an idea, if appropriate, to ask the person themselves.

You might say something like this: when we last spoke it didn’t go as I had planned, or perhaps as either of us wanted. To be honest I’m not entirely sure how it all went wrong, was there something in particular that I said or did that upset you? Then stay quiet. For a reasonable amount of time. If the other person is quiet it’s probably because they are working out what to say or how to say it, if they were going to say there wasn’t a problem and it was just the final straw that day they probably would have said it straight away. Silence is often a marker of a mind working. Don’t interrupt it and make it necessary for them to say something while they are thinking hard.

Finally, don’t let difficult conversations wreck your efforts to retain and attract great employees or stop you from addressing issues that need addressing. If you don’t have the difficult conversations then your good employees will get frustrated that issues within the team or with others aren’t addressed and people ‘get away with stuff’. The last thing you want is your great people getting frustrated and leaving.

Also, don’t let a bad experience put you off having difficult conversations. We all get it wrong sometimes. Learn from it, move forwards and have another go the next time it’s appropriate. If it’s appropriate for you to apologise because a conversation went wrong, then apologise, have another go and move on. But next time you have another go make sure you have prepared for what can go wrong too, that way you’ll minimise the chances of it actually going wrong.

So, let’s move on to the Preparation & Practice stage - this is where we can prevent most of the reasons a conversation is likely to go wrong from happening in the first place. There are 5 steps. The first step is to weigh up the pros and cons of having the conversation - honestly, not to find a reason to get out of it but just to make sure it’s definitely the best thing to do. We don’t need to pick up on everything, sometimes if we change our own behaviours and find a different way to encourage the person to not do a certain thing any more we can avoid having a difficult conversation altogether. So it’s important to see if there’s something you can do that will get the same result. So, what are the pros and cons of having a difficult conversation, pause the video and write some down in your notebook.

What pros and cons did you come up with? Let’s see if we can add a few to your list.

So, the pros of not confronting the issue are: it might resolve on its own, you don’t have to do it, you might not make it worse, someone else might do it.

The cons of not confronting however are: it might just carry on, it might get worse, others may resent you for letting them get away with it, so it therefore undermines your authority, and your team, it might reduce team cohesion, or performance, or make it unpleasant for others to be at work. It might stop new ideas being brought forward, it might place you in a difficult situation legally if you don’t confront unacceptable behaviour or practices, it might affect your sleep, you mental health - and that of the team, it might reduce your chances of promotion, it might stop the person developing, or prevent them knowing that people find that behaviour unacceptable. There are so many cons to not having the difficult conversation that it’s very hard to justify not having it. But even so, you need to weigh it up as sometimes changing some behaviour of your own can have the effect you are looking to achieve.

Okay so the second step is to think about the practical sides of the meeting and prepare for those. It’s important to take the time to think about this now. You don’t have to think about it in such detail every time but if you do your thinking now it will all come easier every other time. So, there are many things to prepare. Pause the video take a moment and have a think about what you should be thinking about before the conversation even starts…pause the video and do it now

So it’s really important to emphasise preparation. What did you come up with on your list? We came up with the following: Where to have the meeting/conversation - meeting room, which meeting room, off-site - where is an important factor to think about, then when - as in what day of the week, time of day, whether it’s before someone goes on holiday or after, before an important life event or should it wait until afterwards - how urgent is it, then what to say, obviously, as well as how to say it, what to avoid saying, how do I make sure the message gets across but avoid hurting someone or demotivating them, also duration - how long should it be - is it the kind of conversation that needs to be over with as quickly as possible for their sake, or do I need to make sure we’re both undisturbed for a decent chunk of time, who should be involved? Do I need to make it official and bring in a 3rd party, company policy, legal issues, HR issues - do make sure you’re not doing anything that’s going to get you or your company in trouble. So these are pretty big categories but you might also want to think about smaller issues such as, do I need to make sure I have tissues in the room. If you have thought of this and the need arises you will be so relieved you prepared for it. If you haven’t thought of it and the need arises it will be incredibly awkward for both of you.

People who don’t take the time to prepare can mess up, no matter how experienced they are. The more practised you are the less time it will take you to quickly run through the checklist but at first you should really take the time to go through it properly.

Step three is you really need to focus on what you are going to say. If you have decided to initiate the difficult conversation it is very important to be clear on the purpose or intention of the conversation. What is it that you are hoping to achieve or change by having this conversation? This should be the first question you ask yourself when you sit down to do your preparation in terms of what to say. Your purpose or intention will guide what you need to say. They will provide you with the ‘end goal’ that you need to work towards. So if your purpose is to convey the message that someone’s work is not up to scratch and motivate them to be more hardworking or less careless then you need to make sure that everything you say motivates them to do better, and doesn’t demotivate them, or make them feel as though they’re not good enough.

If your purpose is to let them know that a particular type of behaviour is unacceptable then your end goal is to have them understand why that’s the case and buy in to not doing it anymore. This is quite different from telling them they just can’t do something anymore and leaving it at that.

This kind of process is called beginning with the end in mind. It’s what most people don’t take the time to do, so they end up saying and doing things that mean that the final effect of the difficult conversation ends up being what they didn’t want, an upset colleague, who thinks less of you now, or someone who feels useless and as though they’re not good enough, or someone who has been defensive throughout and now just feels as though you are a bully, or just an unpleasant person.

It’s so important to know what you want the outcome to be and to make sure everything that you plan on doing or saying, and everything that you think about doing or saying during the actual conversation itself is run through this filter before you act on it.

Step four is to write out and refine the content of your opening statement. This is where many difficult conversations begin to fail. It is very hard to recover from a poorly crafted or poorly delivered opening statement. Your opening statement can be viewed as an honest invitation or it can be perceived as a threat that actually shuts down, or creates defensiveness in the other person.

This is why it is critical to write down and rehearse your opening statement until you are satisfied that it communicates exactly what you want to say. Your opening statement has the greatest chance to influence a positive result. It can also be the most stressful part of the conversation.

In your opening statement it is important to do the following four things:

Opening statement can be broken into 4 parts: the first one is the

Invitation to Engage: so examples of this might be:


Part 2 is the Message, what exactly do you want to communicate?

  1. Part two Expresses Your Purpose & gives Reassurance to the other that you are going to listen to them, so it might be something like this:

In part 3. You need to Describe the Gap between what’s expected and what’s actually happening. So it might be something like, your team are responsible for creating and communicating the marketing strategy and reporting back on performance. At the moment that doesn’t seem to be happening.

Then you move onto part 4, which is. The Question

End your opening statement with a question that invites the other person to present how they see the problem. For example, “Do I have this right or am I missing something?” or “Are you aware of that?”


Step 5 in our Difficult Conversations process is to end the meeting with a way forward that’s acceptable to both or all parties. So it might be that you agree to meet back in a week’s time, during which clarity will have been gained on the points in discussion, and a specific path forward planned. Or, with a conversation that’s pertaining to personal issues, body odour, or dress code, for example, that might be more embarrassing for the individual, your ‘way forward’ might be that you never speak of it again and carry on as if the conversation hadn’t happened, as long as the issue is dealt with, thus saving the face of the person in question. There are so many different topics that people regard as ‘difficult’ that it’s very difficult to cover them all but this 5 step process should be able to guide you through pretty much all of them. If you think about the opening statement it could be used for personal situations too, not just work.

So, just to recap, the 5 stages are:

What I want you to do now that this lesson is coming to an end is to have a think about a difficult conversation you have had in the past, or one that you should be having soon and go through all those steps.

We have made great progress in improving the health of the nation - helping people to live longer lives. However, many people are spending too many years in poor health, with these gains in health not felt equally across society. But this is not inevitable; much of ill health could be prevented. Prevention is crucial to improving the health of the whole population, and helping secure the health and social care services we all value and rely on. It will also boost the health of our economy. You might wonder why, all of a sudden, I’m talking about health, but it’s because we can apply the prevention message to leadership too. Similar to health of a population, many of our difficult conversations could have been prevented yet we allow ourselves only to focus on the treatment rather than the prevention.

If you Do a quick google search on difficult conversations, you’ll find that 99.9% focus solely on how to conduct the conversation. It’s far better to explore how we can prevent as many “difficult” conversations as possible. We can do this by having what we call the Expectations Conversation with everyone in your team, or with whom you have a relationship, either at work or at home, in order to very clearly spell out your expectations of each other. We go through the expectations conversation in a separate video so please watch that and have those conversations with everyone. It’s the best thing you can do to reduce the amount of difficult conversations you will have to have. When you do have them, it also makes them easier as you started on the same page of understanding so will find it easier to regain that. As well as that you can use it in your opening statement, so ‘you know when we had that conversation about what you would want me to do if you weren’t quite performing as hoped, well this is that conversation - then straight into part two of the opening statement.

Being able to carry out these conversations makes you a better leader and a better person. As with any skill, Practise means that you will get better, so whether that’s practising on a trustworthy person before you start the conversation or whether it’s making sure you no longer avoid the difficult conversations, being able to carry out these conversations is vital to your success and the success of your team. Most people don’t want to have these conversations but they need to, in order to be their best selves, and it’s the same for you too.

As always, if you need any specific help then do get in touch with us on info@quarterdeck.co.uk and we’ll talk with you about how you can move forwards in the best way.

The Reasons People Fail

Many managers believe wrongly that inadequate workers choose to perform badly. They surmise that employees could do better if they wished. In reality, the two greatest reasons for nonperformance are that employees do not know what they are supposed to do or do not know how to do it.

According to research, most cases of nonperformance is related to one of four reasons:

  1. Not knowing what it is you want them to do. Whether that’s their core role, dressing standards, sales targets, or arriving on time.
  2. Not knowing why you want them to do it. Knowing why they do what they do and how it relates to the big picture makes people more motivated because they can see their value in the workplace. Feeling valued and worthwhile is hugely important to people. It makes people go the extra mile when needed and can help them maintain the quality of their work.
  3. Not knowing how to do what you want them to do it. Many people are just dropped into their role with barely any training. They’re expected to know what to do. The amount of people who have said to me, “I’m paying them enough, they should know” is incredible. If you don’t explain how you would like things doing, whether that’s the cleaning or the sales process then you can’t blame them when they don’t do it the way you want it done, when they just do their best, or what they think is their best, when they do it their own way. Which brings me to the fourth reason people fail and that’s because
  4. People think they have a better way. Now they might have a better way, and that would be fantastic, but they also might rationalise so they don’t have to do things they don’t like to do. So for example they might say that cold calls don’t work, it’s better to send emails, because they don’t like calling people and being rejected, or being overheard in the office.

Many leaders expect their people to be able to read their minds. They can’t. And they shouldn’t be punished for not being able to. They shouldn't be made to feel stupid, or worthless because of a failing in their leader, a failure to ensure absolute clarity in terms of their role and the expectations that go along with it.

The Expectations Conversation is the best way to prevent all of these reasons. Dealing with the all the aspects of a person’s role before they even start is the absolute best, but if you already have your team in place then doing it as soon as you can is the next best way to prevent any of these being an issue. Clarity and absolute honesty are the way forward and getting this on the table as early as possible is the way to go.

If you haven’t already then watch the video entitled the expectations conversation and get cracking with it with your team as soon as you can.

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