Courageous Conversations – A How To Guide


In this article we offer some useful tips and guidance on courageous conversations, including knowing when to have one, how to raise it, and how to get the most out of it.

The alternative to having a courageous conversation is to tread the path of least resistance, which involves ignoring or avoiding the subject altogether. Do not do this!

The chances are that if you’re reading this, you’ve already followed this route on a couple of occasions and you’re now ready to find out how to have a difficult and courageous conversation.

What are courageous conversations?

Courageous conversations are the difficult to broach subjects with those close to you – at home with your spouse, at work with your colleagues, boss or HR representative, or even with a client.

They are the sort of conversations that can stir vivid emotions on either side meaning, that to handle them effectively, you’ll need to tread carefully, mindfully, and observe how the conversation develops throughout the discussion.

In order to mitigate risk, it’s worth considering the risks you’re taking simply by having the courageous conversation. You should consider the motivations of the other parties involved, and what may trigger certain reactions (although this is impossible to entirely predict…) and how the conversation could, and should ideally, end.

This allows you to attempt to steer the conversation towards an ideal conclusion without traversing pain points or emotional triggers in someone else.

Given that the conversation isn’t going to be straightforward, it’s just as (if not more) important that you can keep your own emotions under wraps too.

One way to do this is to stick to the facts, because facts cannot be ignored or refuted. If your information is accurate, then by being prepared with accurate data, you can demonstrate that there IS a problem, without using unnecessary personal opinion or repetition.

Another great idea is to practice what you’re going to say beforehand, so it doesn’t come out in a blurry mix of awkward words, clouding the discussion from the very beginning.

Example courageous conversations

Try placing something in the blanks here:

When you ____ I feel ____ because _____. In the future I would like ______.

An example might be :
When you talk over me in meetings I don’t feel valued because I can’t say what I want to say to add value to the conversation. In the future I would like you to please refrain from talking over me, or if you feel it’s urgent, to ask me if I’m done so I can allow you to talk over me by choice.

Another example might be:
When you say derogatory things about minorities I feel awkward and embarrassed because I am friends with some people in those groups, and I would hate for them to know that I was with someone who spoke about them in that way. In the future I would like it if you could speak about people to me, as if my friend is stood next to me, so you can imagine how your words affect others.

You could use this format to ask your spouse to clean up after cooking, keep the garage tidy, come home from work earlier.

Who coined the term courageous conversations?

While it’s not clear who actually coined the term, it seems as though it’s become a popular way to dress up a ‘difficult conversation’. By having a courageous conversation rather than a difficult one, you’re more likely to validate your own motivations to raise a difficult subject.

In the most liberal age humanity has ever seen, we are in need of more gusto in combating the personalities that weigh us down. Whether it is a boss who always talks over you before you’re done with your point, a parent who expresses racist or homophobic views, or a workplace discussion on gender equality – these conversations are becoming more prevalent and important, and the courage to raise them is more readily available.

When should I have courageous conversations?

If the subject needs to be raised, and you can see a viable outcome.

Courageous conversations at work and in the workplace

If you are at work and you feel as though there are any of the following issues occurring – it might be worth raising the conversation about them today.

  • A failure to coach, educate or train staff.
  • A failure to set clear business and personal goals.
  • A failure to effectively delegate from management, or to allow delegation by any other members of staff.
  • A failure to celebrate company successes or team achievements.
  • An inflexible leadership style which seems incumbent.

Courageous conversations pdf

Here is a link to an informative 8 page high quality pdf which will help you to prepare for and carry through a courageous conversation.

Courageous conversations training

Contact us at We-Q where we’re focused on helping leaders and teams have the conversations they need. If you’re part of a team looking for some tangible and practical support, take a look at We-Q’s team diagnostic tool which has everything you need for a safe, progressive conversation within your team.