How To Have Challenging Conversations

Typically, not calling it out and addressing the issue is the easiest option; letting the dust settle can seem the most harmonious solution.

In reality, the opposite is true. Ignoring the problem gives the offender and others the permission to repeat the offence again, so letting it slide can lead to a whole raft of issues lying dormant under the surface. Until, of course, the pressure gets turned up, or one of those undesirable behaviours raises its ugly head again and then the issue just might lead to someone blowing a fuse.

The difficulty with challenging conversations is that we can’t predict the reaction, or the outcome. They can be hard to facilitate, requiring courage and confidence on the part of the person who wants to bring up the issue, and, in order to be resolved, objectiveness, self-awareness and even humility from the offending individual or people.

The first step is to ask yourself why you want to have the conversation. If it's because there's a simple misunderstanding, then maybe you could just take it offline and talk it over with this person informally over a cup of tea, or when out for walk - but if not, then that means you need to use a more structured process.

That might be because the other person's behaviour has the potential to cause problems in the future. It may be that you fear they will react negatively; or because something needs to change in order for you or your team to move forward.

Depending on the severity of the issue, consider who needs to be informed before the conversation, or possibly even involved in the event – but don’t take the easy way out and always pull in a senior person. This can sometimes make the situation worse in the long term.

Follow these four steps to turn a potentially volatile conversation into the best chance of achieving your desired outcome

Timing is as important as any of the following steps. Although we recommend heading it off at the pass, be considerate of emotion, stress, workload and personal influences - catching someone in the wrong state of mind will set the conversation off on the wrong foot.

Delivering bad news, feedback or ‘suggestions to develop’ on a Friday afternoon is a no-go, just in case the conversation goes south, or you don’t get a suitable response. Leaving someone to stew over a weekend with no access to further information or support can be damaging... for them and anyone around them!

By definition, a challenging conversation is one that will either challenge you, or another person or team, so it’s likely that the event has already been clouded by many contributing factors and opinions.

To avoid your point getting lost, you'll need to gather clear evidence by documenting the observations, thoughts and feelings of anyone involved. This is an important part of the process as you may need to lean on the facts (which of course are also subjective and will require exploration) during the conversation.

Tip - use the sensory evidence feedback:

• This is what was seen
• This is when it was seen
• This is what was heard
• This is how people felt

Understanding your, and the other person's behavioural preference can help deliver the message more effectively. This knowledge will give you clues to how you can flex your style to get your message across for the most sustainable Impact.

Tip -

Use the Insights Discovery colour model of behaviours. Consider verbal and non-verbal styles of behaviour and adapt your delivery style and messaging accordingly.

Challenging conversations get emotional. People can become defensive or aggressive and might struggle to come to terms with the feedback being given. Managing our own emotions in the moment will in turn manage theirs - if you feel anxious, nervous or unsure, your energy will transfer.

Tip-

• Breath rhythmically before, during and after to regulate your heart rate
• Lean on your evidence - have a hard copy to hand to use as a prompt sheet
• Use the power of silence and don’t interrupt or dominate the conversation
• Allow time for reflection, questions and the opportunity to vent

Ask for a summary of reflections and actions from the other person. This will help you understand their perception, address any differences of opinion (you might need to go back to the evidence if they haven’t yet seen it). This will create more ownership and clarity around what needs to be done and also evidence for accountability.

Use SMART objective settings to deepen the actions and to make it real back in the workplace.


In summary, ignoring bad or inappropriate behaviour is giving permission for it to continue. By stepping in and engaging in a challenging conversation you stand a good chance of addressing the issue, gaining respect and developing your own skills.