Challenging Conversations


As leaders we know that being able to have effective challenging conversations is important and often the more senior we get, the more important these conversations become. Issues with direct reports, peers and managers come up and need to be addressed but often we choose to delay these conversations or not have them at all.

But what stops us? We are capable and intelligent people and understand that unresolved issues have real costs in terms of performance, results and a wider impact on team members. Simply put, challenging conversations are hard and they are scary. As David Whyte, expert on conversational leadership, says “The courageous conversation is the one you don’t want to have”. In my experience in working with leaders across the globe, I often ask them “what stops you?” and the most common response I get is fear of the other persons’ reactions and fear of breaking the connection or altering the relationship we have with this person. This fear drives us to either avoid the conversation or have it in an ineffective way which creates what we fear the most and therefore reinforces our fears about challenging conversations.

But what if there was another way? The following are just a few tips to set yourself up to have the most successful conversation possible.

Prepare, prepare, prepare

Preparation is key when it comes to successful challenging conversations. Gathering relevant data, having specific examples, being clear on the impact of the issue, owning your part of the issue and showing that you want a positive way forward are some of the components to include in how you open this conversation. It is also important to consider your conversation environment ensuring privacy, eliminating distractions and scheduled at the right time of day. The tricky bit after all this preparation is to then let go and know that you are ready. What you don’t want to do is to over prepare and come across as a robotic recording. Make yourself some notes and trust yourself to open the conversation in the best way possible.

Be courageous and let go!

When you have prepared your opening to the conversation it is important to invite the other person to respond. It sounds obvious, but I have seen many leaders try to control the whole conversation because they fear the other person’s reaction, so they don’t let the other person respond. This in fact creates the exact reaction that managers fear most. Anger! It is disempowering and frustrating to be talked at. In order to create a successful conversation, you need to summon up your courage and open the conversation up so the other person can respond openly and honestly. At this point you have done everything you can to set up a successful conversation. If the other person choses to respond badly that is not on you but in the majority of cases, if the conversation is opened up thoughtfully, people will simply respond with their own thoughts on the situation.


Before you meet with the other person, take a few minutes with your feet on the ground and do some deep breathes. This works wonders for calming nerves and centring yourself, so you can open the conversation with confidence. It also helps to be mindful of your breathing during the conversation as well. We often hold our breath or run out of breath as we speak when we are nervous. Take a pause, breathe, and pace yourself. It is not a race.

As leaders grow in seniority, their ability to engage in challenging conversations becomes ever more important. In fact, leaders who cannot effectively deal with the uncomfortable people situations are leaders that in the end no one wants to work for. I would argue that the skill of holding challenging conversations in particular is a must for growing your own leadership career and driving performance and results. The above are just a few tips to ensure success. If you are curious in learning more about challenging conversations, you may be interested in our Challenging Conversation Leadership Workshop.


Leadership Workshops

Mannaz Leadership Workshops are drawn from our established and highly rated longer programmes and are specifically designed as practical stand-alone sessions.  They each include a selection of proven tools that you can use immediately to achieve real impact in your organisation.

Read more about the workshop “Challenging Conversations”

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