How to have a Courageous Conversation

There will definitely be times when you need to hold a difficult or courageous conversation. This basically means that you have a situation that needs addressing. There are some things that just don’t go away or get worse the longer you leave them. It’s not just the natural consequences for leaving things, it’s also the pressure that builds up in you personally and that can lead to stress and be a real problem for leaders.

Many people put off having difficult conversations. There are lots of reasons. It may be that we just fear the outcome. We don’t want to hurt our relationship with the other person. Maybe we don’t want to feel uncomfortable, deal with the emotions of the other person or perhaps we are just not sure what will happen so we avoid it.

It may be that we are just feeling uncomfortable about something. Perhaps we’re angry at someone, we’re avoiding someone or something, we may be embarrassed or ashamed of something or just worried about the consequences of the conversation.

Benefits from holding a courageous conversation

There are so many benefits from having the difficult conversation such as:

  • The behaviour you’re addressing can cease from that moment

  • You can clear the air

  • You can get more commitment from your staff members

  • You feel less stressed

  • People will trust and respect you more

So, how do you start? Well identify what it is that you’re not 100% comfortable with – this is the dissatisfaction component of how we are feeling. We need to make sure what it is that’s making us uncomfortable and make that the focus. Now identify what it is that we want or need to express to the other party. Imagine the worst outcome that could happen as a result of having the conversation and accept that possibility. Let go of the thing that is holding you back and remember it’s okay to feel uncomfortable and focus on the fact that at least after the conversation you won’t have those feelings of trepidation any more – they’ll be gone because you will have addressed it.

When you address the person, you can explain to the person that you have some difficult feedback to share if you like. Brace them for what may be coming. You can even say that you feel uncomfortable about having to give the feedback. Avoid telling them that it’s someone else who has brought it to your attention. You could even say that the situation demands that you give the feedback. Get to the point quickly and link the change you expect to a positive business impact and agree on an action.

Suggested model to follow

For any difficult or courageous conversation, you may like to follow the simple DESCCO steps. These steps are another great way to give or discuss feedback and can be done in a one sided conversation way or by asking the other person to fill in each gap. It really does help to encourage self discovery.

Here are the steps:

Describe the behaviour

Express how you felt

Specify what you’d prefer

Consequences of the new action

Contract to act in the new way



Firstly, if you wanted to give direct feedback to someone say for complaining about everything you ask them to do, you might use it like this:

“Charles, when you complain about my direction, I feel like you don’t respect me as the leader of this team, I’d prefer it if you don’t agree with what I’ve asked that you wait until you have an opportunity when you can address me personally, tell me why you don’t like what you’ve heard and offer me an alternative. That way, you won’t be disrupting everybody else and potentially distracting them in their work flow and together we may find a better solution. So, can I expect you to do that next time you feel like complaining in the group? Okay.”

So, you’ll see in that short paragraph that we used all the steps of DESCCO in a simple flow:

Describe: “When you complain about my direction…”

Express: “I feel like you don’t respect me as the leader of this team.”

Specify: “I’d prefer it if you don’t agree with what I’ve asked that you wait until you have…”

Consequences: “That way, you won’t be disrupting everybody else and potentially distracting them in their work flow …”

Contract: “So, can I expect you to do that next time…”

Ok: “Okay.”

Each of the steps has an important element to play in helping people to alter their behaviour. Firstly, describing what they did helps the person know exactly what it is you’re talking about. It’s therefore much more useful if the feedback given is descriptive (i.e. factual). The expression component then personalises it and gives some meaning to the effect of their behaviour. Specifying another way of approaching it gives them an alternative and explaining the consequences (which could be good or bad) gives reasoning for the person to consider the new behaviour suggestion. The contract is a way of getting them to concur or show their understanding. The ending with ‘Okay’ is for them to agree.

In our example above, we have shown a direct ‘telling’ method of giving feedback. Of course, it can be even more powerful if you switch the ‘telling’ to ‘asking’ in each of the steps of the DESCCO process after the ‘Describe’ step. For example, “When you shouted across the office, what impact do you think that had on the rest of the team?” This way you will be able to uncover their understanding and thinking a lot sooner and potentially gain greater buy-in.

You may need to have a difficult conversation on the phone, or when someone calls in sick. Maybe someone is away and decides to text you or email you. You really need to pick up the phone and hold the conversation. A difficult conversation is just that – it’s a conversation. It’s not a series of emails or texts.

There are lots of techniques you can try. You can even use the phrase, “If you were me, what would you do?” It’s a great phrase to turn the tables and help the individual see things from your perspective.

One thing is for sure, the more you hold these conversations, the easier they become and you increase in confidence. When you have held the conversation, give yourself a reward task to do after dealing with the situation – you deserve it!