Bringing Compelling Stories to Life

How to manage challenging conversations


One of the most challenging things a leader faces is creating alignment amongst a team. This is also critical in the work I do and can be extremely challenging, particularly if I don’t have a prior relationship with a client or leadership team.


I am reminded of an engagement I did with a company where we were turning their strategy into a story and animation. The process had gone extremely well, so well in fact, that they engaged me to work with their most senior leaders to personalize the story. As we were about to start that session, the Managing Director asked if I had a copy of the final animation that I could share with the team. They had seen earlier versions and loved it but were excited to see the finished product.


It seemed like a good way to start the session so I played the video and when it was finished I asked “What do you think?” There was a brief pause before one leader spoke up:


Jim: “I guess I’ll go first. I don’t like it and I don’t think it works.”


Mark: “What makes you say that?”


Jim: “I don’t like the metaphor. I think a bike race makes me think of doping and we don’t want to be associated with that. I think it sends the wrong message to our people and I’m not comfortable having that as a symbol of our strategy. Sorry I don’t mean to be negative.”


This was a leader who had just returned from leave and had not been part of the process, and yet his feedback threatened to derail the engagement. Worse still, I was about to begin a four hour session with this team.


In order to navigate this challenging conversation, there were 6 critical techniques I relied on that any leader can use:


  1. Test the assumption

The first step is to establish if an opinion is shared by the group. To do this you need to test the assumption. A great question to ask is “Does anybody else feel that way?” If they don’t, then the issue is with that individual. If others feel the same way, then you know it is something that you need to address.



  1. Empathise, don’t accept

Once you have identified if there is a shared issue or not, the next thing is to demonstrate that you understand the persons point of view. Here it is critical to validate their view but also show that there can also be alternative points of view.



  1. Make them own it

When someone describes a problem they have, it can easily create more work for you and end up with you owning their problem. A way to avoid this is to get the person to do something. You can ask them “What could you do to help fix that?” In this way, you force them to own the problem.



  1. Be Defenceless

When someone is being critical and directing their criticism at you, it is natural to become defensive and feel the need to justify yourself. A powerful technique is to not engage and remain defenceless. Instead you can call out their behavior, for example “You sound really passionate about that.” This will typically lead to the other person justifying themselves.


  1. Lose the judgement

In most cases, people respond in a negative way if they feel they are being judged. In fact, judgement can lead to confrontation and a break down in trust. The antidote to this is to assume good intent and not take anything personally. This will stop the other person from feeling judged and can be a great way to build trust.


  1. Ask a better question

The most effective technique in managing a challenging conversation is to simply ask a better question. For example “What makes you say that?”. “What would it take?” “How would you know?” These questions force the person to reflect on what they are saying, and are an effective way to get clarity on what they need.


By using these techniques, I was not only able to defuse a challenging situation, but I was also able to build trust with Jim and align him with the team. In fact, they were so effective that Jim asked if I could work with him 1-1 and we began a coaching relationship soon after.


These six techniques are ones that you can also use to manage challenging conversations. They will not only help to improve your communication, but they may just enable you to turn detractors into believers.