How challenging conversations remove challenges

Performance-related issues, disputes between team members, behaviour concerns, feedback, difficult decisions and change… All of which would benefit from having an effective challenging conversation, but which are the issues most managers would prefer to not have to deal with.


“I really don’t want to have that conversation!”


I understand why people prefer to avoid dealing with tricky issues and having challenging conversations with colleagues or team members. They are awkward, uncertain, and often involve discussing a sensitive topic. Perhaps the conversation is also with someone who is known to react negatively or defensively.


Sometimes, challenging conversations are avoided in the hope that the issue will resolve itself. In my experience as a conflict resolution specialist, issues rarely ever get resolved simply through the passing of time alone.


In fact, more often than not, issues get worse when they are not productively and effectively tackled. Occasionally a bit of space can provide room for emotions to calm down, but it is worth remembering that time can also facilitate an embedding of potential assumptions, negative feelings and broken trust.



A manager may feel that is a more peaceful approach to not bring up a topic that is difficult to discuss or to avoid creating waves with someone, but that is a short-term measure – and what I would consider to be ‘peacekeeping’, rather than ‘peacemaking’.

If the issue revolves around someone’s work ethic or behaviour with colleagues or clients, then addressing it has the potential to create change.

Whereas, avoiding the topic means they are likely to continue on in the same way, or the delay leaves room for the problem to escalate. Which at the same time may be creating additional frustration amongst the team, or with clients. Your team will look to you to resolve issues that they have no control or influence over. So, the knock-on effect is the potential damage in trust with others in your team surrounding your competency to lead them - on top of the issue still not being resolved.


“How can I prevent the conversation from going badly?”


The first step is to get clear beforehand. Conversations like these tend to go awry because one or both people dump information on each other, to get the conversation out of the way.


Unfortunately, the latter approach often just leads to confusion and potentially more issues.


If you have thought through what you:

a) Want to achieve through the conversation;

b) Want them to take away from the conversation; and

c) Want to happen after the conversation


Then, you will be in a better mindset to approach it with clarity, to maintain focus during the conversation, and to phrase things in a way that is more likely to achieve those three aims.


“What if they always seem to take things badly?”


My second tip is to be aware of how much of what is being said by you in the conversation is a statement or opinion, in comparison to how much you are listening and asking ‘compassionately curious questions’. People underestimate just how much information, understanding and rapport-building they could be missing out on due to not giving space in the conversation to the other person.



Listening is not just about being quiet while someone talks, but also in how much you seek to understand where they are coming from. That is more effectively done if you allow room for them to talk openly, and you ask follow-up questions that come across as curious and compassionate, rather than prying and judgemental. Asking questions and listening also gives you the opportunity to clarify any information straight away, if there may have been a misunderstanding. Otherwise, they could leave the conversation with a completely different understanding to the one you were hoping for or believed they had.


In the ‘How to have challenging conversations course’ I deliver through Shades of You, I go into a lot more detail about how to give yourself the best possible chance of having a positive and productive conversation, but essentially the key aim of having a challenging conversation is to ensure you have addressed an issue clearly and that there is mutual understanding by the end of the conversation.


“What if the issue still isn’t resolved?”


If this is the case, my first question would be: Did you allow enough time for the conversation to take place? Yes, people’s time is precious but if the interaction was rushed due to outside factors, then it will inevitably impact the atmosphere of the conversation and the ability to address and resolve issues effectively.


My second question would be: Considering the topic of the conversation, would it be reasonable to expect the issue to be resolved after one conversation?

Sometimes a block to having a challenging conversation is the belief that it will not be able to achieve enough to make it worth having. To this belief, I would respond that unless the issue under discussion is truly insignificant or not relevant to them, most of the time an effective conversation has the potential to create incredible change.


However, sometimes the change may take time. The challenging conversation is often the catalyst, and the outcome is seen after further conversations or some reflection time.


“I just don’t have the time!”


Or, perhaps you would have more time and fewer issues if you had the conversation?

One of the criticisms individuals often have of managers is that they do not tackle issues well, if at all. In fact, when I have talked to individuals about what they most appreciated about their current or previous managers, the overwhelming majority of responses for positive traits most appreciated were that they were:

1. Caring

2. Proactive in tackling issues (whether they were organisational issues or people-related issues)


In the CIPD Report of January 2020 – ‘Managing conflict in the modern workplace' the results from their survey found that, in relation to workplace conflict:

‘Less than half of employees (44%) report that the conflict or difficult relationship has so far been fully or largely resolved, while over a third (36%) say it hasn’t been resolved.


These statistics are shocking but do not surprise me. I would love to see more managers, team leaders, business leaders and directors equipping themselves with essential communication and people skills, so that they feel confident to have effective and productive ‘challenging conversations’, to tackle issues, and to resolve conflict.


I will leave you with this…

Most challenges require action for them to be resolved. The most effective action comes from having clarity on the issues first. Clarity and understanding come from having challenging conversations.


So, if you would like to remove some of the challenges you are experiencing as a manager and leader, start by thinking about what conversations might need to be had. For more information on ‘How to have challenging conversations' complete our online course or book onto a webinar.



Emma Jenkings is a specialist in resolving conflict, and in helping organisations and individuals learn the skills to become better at managing and preventing conflict, so they can have more positive and peaceful relationships - at work and in their personal lives.



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