Most of us will find ourselves in a situation where we will be faced with the prospect of having a difficult conversation with someone at work.  Whether it’s because there’s been a difference of opinion, a performance issue, a missed deadline, or some other conflict that’s arisen, difficult conversations can’t be avoided in the workplace.

What Makes a Difficult Conversation Difficult?

Given that we’ve called it a “difficult” conversation, we’ve already tarnished a normal conversation into something that we now believe to be difficult.  So one of the first things I recommend is to stop calling it a difficult conversation.  I’d rather have you think about it as just a conversation that may feel uncomfortable for a moment during the conversation.

How to Have a “Difficult” Conversation

Now, if you Google “difficult conversation”, you will get thousands of opinions on how to manage one.  I’m now going to add my advice to the list!

No conversation is difficult until you decide it will be difficult. 

We have conversations all the time that are uncomfortable in parts, or we find ourselves saying something that creates a less-than-ideal atmosphere between us and the person we are talking to.  We talk to people about their behaviour all the time.  We give them feedback.  We tell them something they might not want to hear.  And we continue to live another day.

We can often reflect on what we could have said to have that conversation go differently.  This is especially the case when we have upset the other person.

Planning Your Conversation

Here’s some things you might want to think about the next time you are faced with an uncomfortable conversation:

  1. Consider what you want to achieve by having the conversation. Is it important enough to warrant the effort? Your recollection of whatever happened will be different to theirs.  Be clear that it’s going to be worth the discomfort to address it.
  1. Be clear on the facts of the situation versus your interpretation of what happened. You will always look at any situation through your lens, your perspective. Your perspective isn’t the truth.  Consider how the police investigate any crime – they seek the facts of what happened, the timeline, the events, the behaviour.  They are less concerned with opinion and interpretation.  Get clear on the facts, the mechanics of what happened rather than your opinion or interpretation of it.
  1. Plan the conversation you want to have. Share the facts, share the effect it had on you, share what you would have preferred.  Ensure you allow the other person to share from their perspective.  Everyone does things for a reason that makes sense to them.  Very rarely do we deliberately mess up.  Get curious on what happened in their world that had them behave in a particular way.
  1. Agree expectations for the future. Are you both clear on what should happen the next time a similar situation happens?  Have you put appropriate support in place to prevent a reoccurrence?  Have you set up a plan to minimise the chance of it happening again?
  1. Welfare check. Have you both said what’s needed to be said? Are you back to feeling a level of comfort?  Are you able to let it go and move on?

If you choose to have the conversation, you must own your version of events as being just your version of events.  Understand that how you see it is different to how anyone else may see it.  Not until you have the conversation can you begin to be clearer on what happened on the other side of the fence.  Use the conversation to build the full picture and then to move forward.

Last Thoughts

Most people don’t want their behaviour to negatively affect others.  Be a contribution to the other person so that they can learn and grow from their experiences.  Allow them to contribute to you.

Conversations are moments in time.  Some are more significant than others.  Some can change the world.  All conversations can feel easier when you go into them with the best intentions and a willingness to communicate openly and honestly, without trying to be better, look better, or know better.

Get My Blogs Straight to Your Inbox

Subscribe To My Email List Here

* indicates required



Please select all the ways you would like to hear from Career Coach Jenny:


You can unsubscribe at any time by clicking the link in the footer of our emails. For information about our privacy practices, please visit our website.

We use Mailchimp as our marketing platform. By clicking below to subscribe, you acknowledge that your information will be transferred to Mailchimp for processing. Learn more about Mailchimp’s privacy practices here.