The most underrated quality of exceptional leaders

Fernando Carrillo
londonsleadershippodcast
7 min readJun 29, 2020

How to have brilliant, difficult conversations is the lost art of leadership

I still get scared to have the conversation I know I need to have and have needed to have for a while. I feel as though if I have this conversation my relationship with this person may topple like a pile of Jenga!

It has to do with a lot of things. I HATE hurting peoples feeling, I WANT to be loved…by everyone, and I just find it awkward. Oh, and sometimes, I don’t think I am the right person to have the conversation with them.

I have tried all the excuses in my head. And in practice, to no avail.

When I don’t have the conversation, the problem only gets worse.

I have learnt through trial and error and error and error… and error that the most underrated quality of exceptional leaders is the ability to have brilliant, difficult conversations.

Yes, its hard work

Yes, I could ignore the horrible attitude that is plaguing the team and slowly destroying everything we are building (a bit too far?)

Yes, I could ‘empower’ others to have the conversation…..I KNOW YOU HAVE DONE IT!

I realised that every way I tried to get out of these conversations, there was no escape. It was up to me to have the conversation, and I should say, part of the reason why I was so scared, was that I had messed this up so many times. I had gone in with the best of intentions and come out wounded by my inability to communicate the issue accurately and my genuine desire for good in the person’s life.

Kim Scott who wrote the book, Radical candour (my favourite as of yet on this topic) says:

“There are two dimensions to good conversations: care personally and challenge directly.” “It’s not enough to care only about people’s ability to perform a job. To have a good relationship, you have to be your whole self and care about each of the people who work for you as a human being.”

Here are some tips that I found helpful in having brilliant, difficult conversations and they all start with P… I got you:

1. Be prepared

For me, this was a significant step when I was learning how to have difficult conversations. Initially, I would get so emotional and flustered in the conversation because I didn’t know how to say what I wanted to say that I would end up making the issue seem worse than I had intended it to be.

Or even worse, the person would leave the conversation, not knowing why I had spoken to them as I was not clear in my language, and I did not give any actionable steps. To make it worse, they probably worried about me, due to the level of anxiety I was showing and the array of words I was using.

After failing at this multiple time’s, I realised that I needed some sort of framework to handle the conversation as that way, I could rely on the framework and trust the process. So, if you are a framework person, or need guidance as to what to say and when … here it is:

· What I like (Mention a positive aspect of the behaviour at hand — try hard to find one haha)

· What I don’t like (Mention the negative aspect of the behaviour at hand — Don’t mention so many, just the one that most affects you)

· What I want (Give a practical step for the person to improve in that area)

· If you do (Show them the positive effects of the change on them and the people around them)

· If you don’t (Remind them of the dangers the attitude is having on them and the people around them, paint them a picture of what the future may hold if the attitude remains)

This framework has helped me prepare for conversations and guide me in the heat of the moment! Try it!

It is the perfect balance of caring personally and challenging directly. If you, like me, tend to lean towards the care personally side a bit too much and you tend to be light on the challenge, it may be useful to ask “What did you hear me say today?” at the end of the conversation. If the person has not been able to work out what you didn’t like and what they could do, you may need to go through it again until they understand it.

Something to add and a critical point to consider is that the higher the relationship level you have with someone, the more direct and less prepared you can be. The lower the relationship level, the more prepared and balanced you need to be.

Lastly, in some situations, you may not have time to prepare. So, try to have the framework memorised so you can tick off the points in your head. However, when something happens, the sooner you have a conversation with someone, the better.

Ken Blanchard calls it “One-minute redirects”.

It is best just to call someone and speak to them of the incident that occurred moments before. This way, it will be evident in both your minds and you can move past the awkwardness of calling a meeting and not knowing what to name the subject in the email!

Once again, if you have time to prepare, prepare. If you have the opportunity to have the conversation close to the time the event took place that is even better.

Generally, the closer to the time of the event the conversation happens the more significant the impact of the feedback will be.

2. Be precise

What can happen when we are in the conversation is that we can overdo what we want to say with the number of words we use. For this reason, the framework is hugely beneficial.

Nevertheless, it is still important to consider when and how to pause.

Remember, we have been thinking about the situation and the conversation for what feels like a lot of time. The person in front of us is coming to terms with what we are saying for the first time.

We want to get everything that’s in our head out on the table as we have finally found the courage to have the meeting.

What can happen is that we just dump all our thoughts straight away and leave the person with months’ worth of thinking to digest in a few moments.

To prevent this, say what you need to say in as few words as possible and then pause.

Wait

Wait

Let them process and think of something to say. You have thought through how the conversation is going to go. You have the framework that you know you need to get through. LET THEM THINK.

When they respond, do not ignore what they have said in your desire to follow the framework.

Listen, respond to their thoughts, and when the time is right, move on to the next stage of the framework.

You mustn’t interrupt. Wait until they have finished their thought.

Give the person time to process and reflect.

Then be precise again with your words, say what you need to say and nothing more.

Trust the framework, some sentences will sound harsher than others, but that is ok.

Be precise! No more words!

3. Be patient

If you are anything like me, you want the person to take what you have said, apply it and one second later be a better person because of it.

Unfortunately, that is not going to happen.

It takes time and for some longer than others

Here is an excellent way of understanding how a person responds to a difficult conversation. It is also known as the grief curve, but for this purpose, it will be called the brilliant, difficult conversation curve.

Now please ignore my terrible handwriting but please do applaud my brilliant use of colour.

As you can see from the curve, time is required for a person to move through the normal emotions of dealing with a newly presented issue.

It is crucial as a leader to be aware of these stages and to be able to assess where a person is on the curve as that will be indicative as to the language and attitude to have. For example; the tone and approach used when a person is in denial would be different to when they are in the self-blame segment of the process.

Understanding this curve has transformed the way I have conversations, and more than anything has allowed me to manage my emotions when dealing with the responses I get from the people I lead. I am more aware of their thought process and therefore, can tailor my approach. As a result, I have seen better results in the conversations I have had.

To close, I hope this helps you! This is my first post on Medium, and I will be writing every fortnight with practical tips on my learning experience in my journey of leadership. I still have a long way to go, but I just want to share what I am learning along the way!

Remember, to have difficult conversations, be prepared, be precise and be patient!

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