Having difficult conversations with empathy in mind

Theo Kapodistrias
4 min readJul 22, 2022
Photo by Priscilla Du Preez on Unsplash

No one likes having difficult conversations.

These conversations are just that… difficult. We avoid them and we only have them when it’s absolutely necessary. But springing information on people in a surprising way is only going to cause more harm to the relationship than good.

Imagine if you were an employee and it was approaching the end of your probation period. You speak to your manager before your probationary meeting and ask ‘is there anything I should do in preparation? Is there anything I should be worried about?’ and your manager says ‘no way, it’s all good.’

For those first three months of employment, everything has seemed fine. You haven’t been warned about anything, it’s all kind of just been cruising along. Then it’s meeting time and you find out that your manager thinks you suck. The feedback has been provided in a rather brutal way, but they’ve attempted to make it sound constructive.

Have you ever heard of the ‘compliment sandwich?’ Here’s an example:

  • You get to the office on time, and that’s great.
  • Your work quality is poor and your colleagues have complained about your odour, not to mention how unresponsive and slow you are
  • But you’ve got a really great haircut.

It’s truly awful.

Whether it’s a performance conversation with a colleague, or you want to provide some feedback about something you’re not particularly happy about, it’s vital that you communicate that.

But a major question is — how can you do?

I’m going to introduce you to a structure that is used in the design thinking space.

The structure ‘I like, I wish, what if’ is a relatively popular design thinking activity used to gather feedback during the prototyping stage. This is where participants who were involved in a project come together and share feedback.

I want to look at it in the communication and conversation space because I think it can be neatly replicated. It kind of works as a more effective and far more useful ‘compliment sandwich’ as it provides more of a focus on emphasizing a means to improve rather than hiding issues amongst false commentary (but maybe your haircut is really good…).

I like

We start off with the ‘I like’ section.

This is a nice way to kick off a discussion with some positive vibes, focusing on the things that are good in the circumstances.

Let’s say you’re in a group project and you want to be able to let others know that you’re not happy with a particular colour chosen for the design of the poster. But you really like the font. You can start off with “I think it’d be important to have a discussion on how our project is going so far. I really like our font — it sets the scene and feels appropriate.”

And then after that, you could move on to the next section which we’ll discuss shortly. Opening with something positive allows receiving or hearing critical feedback easier.

I wish

This is where we’re able to frame how change or improvement can be implemented or should be implemented.

It’s used as the space to address concerns or issues which may arise. It should be constructive though. Not a place to simply throw someone under the bus, but a legitimate place for an actual discussion and a place where it can be provided considering the impact and means by which it’s delivered.

If we use the above example to continue on, we’d say “I wish though that we’d use a different colour for this. I’m not sure that the colour works well with everything else.”

There shouldn’t be any finger pointing or blame throwing — it’s just about raising the concerns or issues in a more constructive way.

What if

Finally, we look at our ‘what if’ section.

This is where you can bring up new suggestions or ways to address the matters and resolve them.

It opens up new things to explore in the future and leaves things in a more positive light. It looks and focuses on ways to improve things for the better.

If we look at our example above, we could suggest something like “what if we consider the season this will be released and see if the design matches what else may be around at that point?”

This approach means that you can open up possibilities without making anyone’s ideas feel worthless. It’s simply about exploring opportunities and new ways of thinking.

Can I help you?

  1. I coach people one-on-one to assist them with their communications and speaking needs with single sessions available and 3, 6 or 9 month packages.
  2. Want a speaker for your event or to have a training session in your workplace? Let’s discuss!
  3. Book a virtual coffee with me and we can chat further!
  4. You can download FREE resources here
  5. Listen to the Craft Messages That Matter Podcast available on Spotify, Apple Podcasts, and Google Podcasts

About the author:

Theo Kapodistrias is a multi-national award-winning lawyer and keynote speaker, trainer, and public speaking coach. He is passionate about community involvement and holds several voluntary positions, including as the Executive Director of TEDxHobart. His keynote speaking, training, and advising business is designed to help professionals and business owners to be seen, be heard, and make an impact through their voice and through their words www.theokap.com.au



Theo Kapodistrias

Award-winning Lawyer | Speaker, MC, Trainer, Coach — assisting individuals to speak up, show up, and make an impact — www.theokap.com.au