I have made grown men cry. I am not bragging about this. I am also not suggesting that grown men should not cry. Quite the opposite, I am happy to see a rejection of the toxic masculine norms that plague our society. A world where men feel ashamed and unable to express their emotions. I am not at all saying grown men shouldn’t cry. They should. But I reserve the right not to be the reason they cry, and often I have been…

No one wants to be the one who does the sacking, no one wants to be the person that lets the players know that they didn’t make the team this year, and no one wants to be the parent who does the grounding. But often, if we are the leader in the situation, the person responsible for the business, team or household, you have to make difficult decisions and deliver bad news like your The Grinch Who Steals Christmas. 

This blog is a bit meta because I feel like I am reluctantly delivering bad news to you. But I reckon when you became a business leader, you realised you must take the rough with the smooth… In this blog, I will be talking about difficult conversations, and it’s not going to be easy. Let’s try and take the bull by the horns. 

My name is Andrew SIllitoe, this is my blog, and we need to talk about how to have difficult conversations.

Tough calls and challenging conversations are the bread and butter of being a leader. They might even be most of the meal. They are difficult and uncomfortable, distressing and unwanted, but if you are looking for answers on avoiding tough conversations, you will not find them here. 

This blog contains no “get out of jail free” cards, nor hints and tips about surviving whilst burying your head in the sand. No great leader has achieved success without having tough conversations because those people don’t exist. There is no way of being a leader and avoiding the work it takes to be one.

If I have done my job right, this blog will be about the importance of difficult conversations and how best to have them. 

First, let’s discuss the classic avoidance techniques we all may have tried. Perhaps you have put off having a difficult conversation because “the time doesn’t seem right.” Anyone who has taken a trip down this particular wrong path will know that “the right time” to have a difficult conversation does not come. You might as well wait for the day when the hell freezes over or Michael Jordan stops being a basketball legend. It. Will. Not. Happen. 

 “If not me, who? If not now, when?”

There is never a good time to tell your colleague that they have not passed their probation period. There is never a time that makes confronting a teammate about bad behaviour less of a challenging conversation. 

Hell, there is not even a time when telling someone they have something in their teeth is not a bit cringe-worthy. The only thing that makes that conversation worse is leaving it until later. 

You must ask yourself, as Hillel The Elder asks, if not me, who? If not now, when? Obviously, that seems quite dramatic when you tell your partner they have spinach in their teeth at a party, but I hope you get my point. Delaying the difficult will help no one. Not even yourself. 

Brene Brown, the American researcher whose TED talk has had almost 17 million views worldwide, discusses the power of vulnerability. I think that’s an essential point when talking about difficult conversations. The idea that you find something difficult, that the challenge ahead of you makes you uncomfortable is not reason enough to not do it. 

Of course, having a difficult conversation is difficult. If it wasn’t, we’d just call it a conversation.

Avoidance is a classic technique from the same shop that sells chocolate teapots. Avoiding tough talks will not serve you. Brown states that “if you don’t talk to someone, you end up talking about them.” and I think this is absolutely true. Even on a personal level, if your partner is annoying you and you don’t tell them, but you do tell your friends, you are not setting yourself up for success and almost certainly booking yourself in for a short stay on the sofa. 

If you avoid tough conversations as a leader, you are being lazy. And I didn’t want to tell you that in case it is difficult to hear, but I am taking my own advice and telling you anyway.

It is also important to remember that a tough conversation comes because something is not right, especially in leadership. Something needs to change. If that is the case, you need to change it by having a tough conversation. From that difficult period, change comes.

When I was Head Coach of Team GB, I could see that momentum would build from these conversations. The tough conversations in the locker room act as a catalyst to improve performance. It is the same in business. I wonder if anyone reading this today is putting off a tough conversation?

It has taken me a while to get to this point, but I quite like having tough conversations. Mostly because I know they are essential and because I know they are what sparks real change and real improvement. 

It also helps me realise that I am wrong sometimes. I am not one of those leaders that goes into a challenging conversation swinging and leaving without a scratch. I have learned that I am human and not without mistakes. It has been during tricky conversations, the ones I’ve been dreading, that I find out I am wrong about things, that what I have previously thought is not actually what is happening. 

These conversations allow me to learn and improve as a person and leader. 

Once I realised and understood my values, I became better at these tough conversations. I became aware of what I was willing to compromise on and what I was not. Since learning this, I have become a better leader and person. I have noticed that these tough conversations are sometimes made bigger and scarier in my head than in reality, like the monster in your cupboard as a child that ends up being entirely made up.

I recently had a challenging conversation with a member of my team, which began by email. Anyone who has ever received a text message and taken it the wrong way will know what I am about to say. If someone types “I’M SOOOOOO SORRY” in capitals and you read it as them being sarcastic when they are just apologising, then you know that the written word can often be taken in many ways there letters in the dictionary. 

My colleague and I were emailing each other and getting quietly annoyed and confused. It was only when we bit the bullet and decided to have a call to talk it over that we realised there were more crossed wires than in an old box of Christmas tree lights. 

We learnt that we could have a difficult conversation and come out of it feeling better. Like a cold shower or a quick trip to the in-laws, it is often not as bad as you think it will be… and you are listening to a man who quit the same job twice in quick succession…

I once left a job at FTSE 100. Then I realised I’d made a huge mistake and asked for it back. I was offered my old position as long as I was committed to the role. A month later, I was offered my dream job at the management consultancy, so I had to tell my boss I wanted to leave again… I was not popular in the office that day. But I was the person who put my long term happiness over my short term distress.

And that’s what I hope you take away from my blog. There are tough conversations ahead for all of us, but they deserve to be had. So good luck. Keep it simple. And next time you have one, maybe you’ll think, “at least I’m not leaving the same job twice in a few months.” 

I’ve been Andrew “don’t sugar the pill” Sillitoe, and you’ve been very kindly reading my blog. See you next week.