Having Challenging Conversations: Six Tips for Business Leaders


  Head of Creative Change at Impact International.

  WWS contributor info-icon.png


It is important that every business leader knows how to face up to difficult conversations.

Having Challenging Conversations: Six Tips for Business Leaders

Having a challenging, difficult conversation is something that on occasions is unavoidable. 

Whilst it’s not something that any business leader enjoys, it’s very important to consider how best to approach these conversations in a professional manner and how to generate a positive impact on your team member’s development.

A challenging conversation could be about dealing with issues such as underperformance or incorrect conduct, and it is important to review the predicament professionally. 

Here, we look at the challenges facing leaders in this situation and share the best hints and tips for dealing with difficult conversations:


1. Don’t Put the Conversation Off


Once you know there is a difficult conversation on the horizon, the natural temptation is to put it off. It is important not to let the need for the conversation drag on. Putting off the conversation can mean that by the time it happens, it is no longer relevant

Once there is a conversation to be had, the best course of action is to speak to the person as soon as possible. 


2. Prepare for the Conversation


Although it is necessary not to put off having the talk with the person in question, this is not a conversation you want to have in the spur of the moment. 

Make sure you are properly prepared and have all the facts needed for what you are going to be dealing with and know exactly how you are going to approach it. 

Different people will react to a confrontational situation in many ways, and it is of the utmost importance to understand the individual you are dealing with and how they are likely to react, respond and take the feedback. 


3. Find a Solution


The conversation needs to have a purpose and a goal, as well as a plan to work on afterwards. 

If you merely criticize and offer nothing constructive, then the conversation is not going to be a successful one. These discussions are not something anyone will enjoy, but remember they are worse for the person you are having the conversation with. 

It is important, if possible, to offer something to help the employee improve. At times these conversations will result in the termination of employment, but even in this outcome, it can still be possible to offer something constructive they can learn and benefit from in the future. 


4. Understand the Other Person – Allow Them to Speak


Leaders should ensure the person is understanding why the conversation is happening and what the purpose of it is. 

Allow them to ask questions if they feel necessary, and if you can see they are becoming upset or struggling with the situation, allow a moment for composure and for them to gather their thoughts. 

You want the meeting to be constructive and purposeful, so the individual concerned can take on board the conversation and then act upon your words. 


5. They Can Sometimes Be Avoided


This is not true for all occasions, but often as a leader or manager you can put steps in place so that a difficult conversation doesn’t have to be the result. 

You should strive to make feedback a regular part of day-to-day operations, as part of your team development. If you can see a member of the team is struggling with something, or is underperforming, this can be dealt with before a tricky conversation is needed with regular feedback. 

Obviously, this isn’t going to work on all occasions, and it is inevitable that at times the feedback will either not be taken on board or will not be acted upon, and the conversation will be necessary.


6. Development


It is important that everyone in the organization knows how to face up to a difficult conversation. 

As a leader, and as part of your team development, look to offer sessions ensuring people are trained for these scenarios. Make sure people know the key points; to prepare properly but don’t allow the conversation to be delayed too long, to allow the conversation to be two ways, find a solution and make sure you have onward steps. 

With everything in place for your team, as a leader you have done all you can to make difficult, challenging conversations in the workplace go as smoothly as possible. 

Dominic Fitch is Head of Creative Change at Impact International, a world-leading experiential learning company working to support global brands to prosper by delivering customized people solutions.