The most difficult conversation I’ve ever had

Wednesday 28 August 2019
Difficult conversations are a part of management – three senior leaders share their worst
Two people having a meeting out in the open

We spoke to three senior leaders in different industries with one question: What is the most difficult conversation you’ve ever had at work? Their conversations range from the practical to the unusual – let’s see what we can learn...


Sonia Aslam, Senior Manager - Transformation & Operational Excellence at Vodafone

I once had a performance-related issue with one of my team members. She was a recent graduate, starting on an internship programme that would lead to a place on a graduate scheme. She thought she knew it all. Despite being given coaching and mentoring for a few months, she was not improving. As far as she was concerned, we didn’t know what we were talking about.

I tried to help her by giving her some direct feedback with examples of how she could work better and develop herself, but she refused to listen to what I had to say. So I changed my approach. I asked her: “What’s motivating you?” I put the onus back on her – if she was there just because she thought she should be there, she should leave and do something she felt passionate about.

By doing that, it got her to think in a different way. She came back and said that she thought the role was right for her and that she wanted to progress. She started asking for help and guidance. I was able to give her the right support and put her onto tasks that I knew would help her grow in the role. By the end of the year she was offered an opportunity to join the graduate program at the company she did her internship in, but decided to pursue another opportunity which she discussed with me and was in line with her career aspirations.


Alex Bomberg, CEO of International Intelligence Ltd

One of my mantras is that every good security policy starts with a difficult conversation. With the clients that we work for, the majority of them have invested a lot of money into their security, but a lot of it is also in the wrong place. The issues are usually around the duty of care to their staff. For example, not having a policy in place for travel security. A lot of companies have that problem.

Managers don’t want to talk about the possibility of staff being affected by a terrorist incident or a victim of violent crime. People think it’s fine because nothing has happened to them personally, and they don’t want to scare people. They’re avoiding their own difficult conversations. But if something went wrong, people would ask them what steps they took to mitigate the risk. It’s a conversation that we have to keep revisiting over a long period of time. You have to keep making the point until they realise the gravity of the situation – that the worst case scenario is a corporate manslaughter charge.

However, the single most difficult conversation I ever had was with an ultra, ultra high net worth individual, one of the richest people in the UK. He had one computer in the house that he used to run his business – but we found out his son was also using it to download pornography. Trying to have that conversation with that person, that their son was putting their business at risk by doing...what he was doing, was very difficult. Particularly as it was a religiously sensitive household. In the end we put it in a report and let it sink in a bit before we actually discussed it.


Carl Reader, author of The Start-up Coach and founder and chairman of d&t advisory. 

In my career I've had to have many difficult conversations, ranging from staff members who have been through some of the worst tragedies that you can imagine, health issues, family bereavements, and other things that you couldn't wish on anyone. While these conversations are difficult, however, it’s never confrontational – you are solely looking to support your team member in the way that you'd hope that they would support you.

Instead, the most difficult conversations I've had are those that lead to letting a staff member go. While it is the right choice for the business – we have processes to go through to remove any personal bias that involves several key decision makers – as a human, it is very hard to let another person know that you are potentially reducing their ability to put food on the table. We naturally become close to our fellow team members, and this only makes these unfortunate conversations harder.

To make sure I’m effective in those situations, I constantly focus on the fact that I’m doing what the business needs. For example, if it’s a conduct issue, having this conversation will benefit the other team members. For performance matters, the benefit is that others will not have to unfairly carry a team member.

There are ways to make it easier on the person, but if you’re not careful it could result in you not actually having the conversation, making concessions such as extra notice periods, or ‘final, final warnings’. Sometimes, it’s easier for everyone if you just get on with it.

No matter the nature of the conversation, it’s always good to have a purpose for it; if you know what the resolution is, you can steer the conversation in that direction. Prepare yourself for the worst, hope for the best, and show up prepared. It’s important to tap into your emotional intelligence, and use your empathy to understand how this conversation would feel from the other side; this will help to keep the conversation mutually respectful.

For help on how to plot and navigate tricky subjects, watch our webinar on handling difficult conversations with David McLaughlin and Charlotte Bradshaw.

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