Last week I outlined the three key topics that leaders have highlighted as their primary people-related challenges right now:

  • How to lead remotely
  • How to have difficult conversations in the midst of Covid-19
  • How to maintain personal resilience and well-being

Our online session on ‘How to Lead Remotely’ was over-subscribed within just a few hours so an early heads-up that our session on ‘How to have Difficult Conversations’ will take place on Wednesday 24th June at 12 noon. Tomorrow, we’ll be sending you details about how to register.
In the meantime, however, I wanted to share some key points about how to have difficult conversations in the midst of the Covid-19 crisis. My high-level answer is ‘in the same way you have difficult conversations at any other time. With clarity, honesty and respect.’ But, I also know it feels like there is more at stake when people have had to deal with so much that is different and unpalatable over the last few months. Difficult conversations feel even more difficult.


To understand how to approach these, the first question is why is having difficult conversations different now compared to any other time in business? The two obvious answers are:

  • We can’t meet in the same physical location 
  • People are already having a tough time – it doesn’t feel fair to add insult to injury.

But neither of these is a valid reason to avoid a difficult conversation that needs to take place.

Difficult conversations can be held online via Zoom or equivalent, or even by telephone – the former is far preferable to the latter because you can see each other, so choose this whenever possible. And, if the conversation is needed, you are not doing anyone any favours by putting it off – in fact, it can do more harm as you will end up avoiding conversations at all or you will drop hints and give mixed messages. 
The next question is, what makes any conversation difficult anyway? Three main answers here:

  • The topic is sensitive – at the moment there are plenty of these – pay cuts; redundancy; being furloughed/being unfurloughed; unacceptable performance
  • The situation isn’t ideal – in normal times, this usually comes down to factors like ‘there isn’t anywhere private to have the conversation’ or ‘as soon as I ask to speak to the person, they’ll know something’s up’
  • You are concerned about your own, or the other person’s, reaction – and your ability to handle these well

These are all valid challenges at any time and I don’t think we should find it easy to have these kind of conversations. Impacting someone’s livelihood, telling someone they’re not doing an acceptable job, trying to arrange to speak to someone when the very fact of doing so will raise a red flag, concerns about emotional responses – it’s only human to feel challenged when faced with such factors.


So, if you find your stress levels rise in such circumstances, it shows you have empathy with others as a fellow human being and are feeling the feelings of any human being.


Good leadership is being able to have a difficult conversation with skill, even as we acknowledge all the challenges that surround it. It is not to build the ability to have the conversation and find it easy.


That brings us to the third question: how can a leader have a conversation that they find difficult in a skilful way? If you approach a difficult conversation with skill, it won’t matter whether the conversation is taking place in the same physical location or in a virtual setting. Equally, if you are not skilled in how you approach this type of conversation, being in the same physical location will not save the day. 


Here are my six top guidelines to help you have conversations that you find difficult with skill:

  • Unless the situation or topic is unavoidably out-of-the-blue, the conversation should never be a surprise. An out-of-the-blue example would be telling someone about the sudden death of a family member. Otherwise, the need for pretty much any conversation we’ll be having as leaders will have developed over a period of time. Underperformance doesn’t happen overnight, job cuts don’t happen overnight, even the likely need for furloughing people that has happened over the last few weeks was apparent before people were actually given the news. One of the main reasons that leaders find conversations difficult is that they ignore what is happening until it reaches crisis point. So, share information, give feedback, be transparent early on.
  • Before you sit down to have the conversation, prepare exactly what you will say to share your message. Keep it concise and clear. And then rehearse it so that you can speak with brevity and clarity when you are in the actual conversation. Never ‘wing it’ or hope you’ll find the words in the moment. This tactic will not work and instead you will waffle or be too blunt or even find you don’t say what you need to say at all.
  • When you are actually starting the conversation, avoid small talk. There is no way to make an easy change from chatting about the weather to giving a tough message. 
  • When you have shared your message, give the other person time to assimilate what you have told them. This part of the conversation is not about meeting your needs, it is about meeting their needs. This means that you stop speaking and respond to the other person. If they sit in silence, you stay silent (remember, there isn’t silence in their head. They are making sense of what you have said). If they ask questions, answer them with honesty and brevity. If they cry or shout or laugh, allow them the space to do so. 
  • When you have finished responding to their silence, questions or emotions,explain exactly what will happen next. Again, brevity, clarity and honesty on your part are essential.
  • Check if they have any questions, respond to these and end the conversation.

On Wednesday 24th June I’ll be running a 90-minute workshop to cover each of these in more detail, explain how to avoid the common pitfalls and answer your specific questions. 
For now, remember, it’s only human to find some conversations difficult. At the same time, they are an essential part of leadership and should not be avoided now any more than in ‘business as usual’ situations.
Stay safe, stay connected.

How to Have Difficult Conversations in the Midst of Covid-19