How to Have a Difficult Conversation

Ohhhhh, don’t you just hate the feeling of knowing you’re going to have to have that awkward – or worse – conversation with someone?  I’m willing to bet that you know that feeling so well, you just got a bit of a sucker punching gut feeling when you read these words.

Maybe it’s a “we need to break-up,” an “I quit,” an “I made a mistake,” a “YOU made a mistake,” a “you just don’t get it,” or a “what the f*ck are we doing here” kind of conversation.  Whatever it is, chances are you’ve been avoiding it because of fear, vulnerability, and the perceived pain that might go along with it.

Trust me when I say that I am no stranger to the difficult conversation (on a couple of occasions, impossibly so), and that while it gets better over time, there are skills you can adopt to help you get better at handling them better too.

How do you have a difficult conversation?  Like this:

Prep Yourself  

Write out the details of your message clearly for yourself.  In reading and re-reading your thought process, you’ll get a decent handle on what you really want to say, versus what your ego thinks you want to say.  You’d be amazed at what this practice round of thought drafting does to streamline your own thoughts for you, and later for your audience, simply by getting out on paper what it is you actually want to accomplish.

Prep Your Partner  

Big news takes some mental prep for both parties, and purely out of respect for that process, I’m a big believer in giving some advance warning whenever possible. It’s worth scheduling some time to sit down (in person or over the phone) to chat.  Maybe that’s a text or email, a dropped into regular conversation mention, whatever works for you.  But a very simple “I’ve got some things on my mind that I’d like to discuss with you; how’s tomorrow at four?” gives both people some time to collect their bearings instead of being bombarded with a big shock.  And if your efforts to set up a more formal time to talk are met with “can’t you just tell me now?  What’s going on?” it is more than fair to honestly express that you are still gathering your thoughts and would feel more comfortable laying it all out at once.  Tomorrow.  That’s not being passive-aggressive, it’s exercising patience and rationale.

Be Clear With Your Intention  

This has been one of the greatest lessons I’ve learned.  “My intention for this conversation is to clear up some expectations surrounding boundaries / recent challenges in our relationship / communication issues we’ve been having / the misunderstanding regarding the Murphy file and I want to use this time to get us back on track.  I would appreciate the chance to speak first, and would then like to give you the chance to speak after that.”

Yes, this works.  Wonders.

It communicates that you are here to work together to solve a problem in a non-threatening and emotionally safe way, and that you’ve already put thought into what is about to be revealed.  Does it make the message easier to hear?  Maybe, maybe not, but it certainly does diffuse any accusatory tones or content.  If you put yourself in the shoes of the person at the other end of this conversation, I bet you can already relate to the calmness and clarity in the tone of the conversation.  This tender frankness feels like someone putting their hand on your shoulder comfortingly, while ripping off the band-aid.

Be Honest, and Be Kind 

Never forget that kindness and honesty go a long way.  We can deliver the same message in a number of ways, and by choosing to be kind about the delivery – rather than get caught up in ego and drama – will serve you well.  Trust me.  Similarly, if you choose to be honest about what is really on your mind – no matter how terrifying it might be to say aloud – if you choose to be clear-cut about your message, you will free up ambiguity, and make the overall conversation easier in general.  That honesty might even include “look, this is a really hard conversation for me, as I care about you / really value my employment here / have been your friend above all else, and still this is so important to me that it warrants this conversation.  Thank you for joining me.”

Part of being ever kind in the delivery of your message will include (what everyone who’s ever been to therapy will tell you) “I statements.”  Are you familiar?

Instead of:

“you make me so effing mad when you…” or

“ever since you did X, nothing has ever been the same…” or

“you did not pull your weight on the Murphy file and now we’re all f*cked…”

You can use alternates like:

“I feel incredibly hurt when…” or

“I have been feeling a huge shift since Thing X happened, and I am struggling to get my trust back…” or

“the client expectations were very clear surrounding the Murphy file and I feel that I did more than my share to make up for the deficit…”

When you switch up the focus from what the other person did or did not do, and shift it to focus on what you experienced, two things happen: (1) you are removing blame, making this a safe space without accusation, and (2) communicating your truth, and your truth alone, which cannot be refuted, or met with “yeah but…” and “but I never…”  It’s just the sharing of what you experienced to be true, and you skip the part where the blame gets passed back and forth a whole bunch, cutting right to the chase about what the real problem is.


Part of what removes some of the difficulty in this conversation is that you’ve already laid out a roadmap of what’s happening: I speak, then you speak.  As the “audience,” I already know that I get a chance to speak my own truth, after you’ve spoken yours.  If only we had a conch shell, right?  Same premise though: we’re both going to get the opportunity to say what needs to be said, which frees our brains up from panicking that we might not, making us better and more active listeners.

Knowing that, listen when it’s your damn turn to listen.  Respect that you’ve opened up a huge vein of vulnerability for both of you, and that the other party might need a minute to absorb what you’re saying before responding.  This is ok.  The waiting is part of the job of listening.

Work Together for Resolution 

Sometimes, depending on the nature of your convo, there might not be an easily findable solution; so perhaps the solution is then to touch base in two days to see where you’re both at.  Otherwise, work together to come up with a remedy that works for both of you, and stick to it.  Being this vulnerable is actually being very strong, and you’ll still need a tender approach to follow through.  Knowing the effort that you’ve taken to get to this point, be sure to continue to show up in that ongoing respectful way as you figure out what to do.


I am someone who needs to hear things seven times before they sink in (ask my best friend – she will confirm, at least seven times over that this is true), so at the end of a tough talk, I like to recap the highlights of what I heard in our exchange, then thank the other person for the chance to clear the air.  Maybe you are thanking their softness, their receptiveness, their openness and willingness to speak freely; it doesn’t matter.  The recap is a chance to confirm what you heard and what actions you’ll take next, and be openly thankful for the space to have done so.

These are guidelines will help you through virtually any tough conversation you need to have: with your partner, friend, kids, employer, co-worker, parent, great aunt twice removed.  They are human connection skills, and when you get comfortable in using them, while you may still get a few anxious butterflies leading up to “the talk,” you will know unequivocally that you have done hard things before, and that you continue to show up as a respectful, honest speaker and listener.  And yes, it will get easier, with you feeling better and more confident every single time.


Leisse Wilcox is a writer + mindset coach from a tiny beachfront town east of Toronto, who writes regularly at

A mom of three lovely girls, her passion is working with women to help them dig deep, get clear and confident with who they really are, help them find, express, and use their voice for good, in a lifestyle-friendly way.

When not happily engaged with clients or kids, Leisse can be found stargazing, dreaming about an A-frame cabin in the woods, or anywhere the tacos are.