Speak now or forever hold your peace: 6 tips to help you have difficult conversations

How to have difficult conversations

Difficult conversations. I’ve had lots of them, as I’m sure you have.

There was a time when I’d avoid them like the plague. Particularly when it involved feeding back to someone who I didn’t really get on with, or who was higher up the food chain than me.

I didn’t plan for these kinds of conversations. As I say, I’d avoid them and then some random thing would set me off. I’d explode. Not be particularly constructive or precise. Make the other person angry and ultimately, make a bad situation worse.

Then, in 2004, I went on a development programme for facilitators. The feedback I received, along with the various models, have stood me in good stead since then. Since then, I’ve honed my approach to having difficult conversations and helped countless others do the same, through coaching and consulting.

There are six things I’ve found that can make the difference in a difficult conversation:

  1. Preparation: If you’re giving feedback to someone you know is likely to kick off, then you absolutely need to go in prepared. It can be helpful to jot down the key points you want to make, in priority order. That way, you have something to refer to if you get thrown off-track; and you’ll cover the big ticket items first, if you run out of time.
  2. Practice makes perfect: This has always made a difference for me and for managers I’ve coached. If you know you’re going in to a hornet’s nest, then having a dry-run with a trusted colleague can be really helpful. It can help to (a) reduce your fear (b) get feedback on your style and (c) hone your points so they are crystal clear.
  3. Specifics are important: A mistake that I’ve found many people make is not being specific in either what they’re saying or the feedback they’re giving. Going in without the specific example(s) you’re referring to will only undermine your credibility. As with tip number one, jot the example(s) down ahead of the meeting. This is particularly useful if you’re worried about getting tongue-tied through nerves.
  4. Space is important: Another one that links to preparation. Too little thought is given to the space you’re going to have the conversation. The type of space can have a real impact on how the conversation goes.  Would a private meeting room be best? Or stepping outside your office building and going to a local coffee shop? Or having a walk or talk? Or going to a local park (if the weather permits)? And always remember what Vincent Lombardi said, “Praise in public, criticize in private.”
  5. Ride the silence: This can be difficult for those of us who like to talk and see any silence as something to fill. This is, without a doubt, one of the most difficult but game-changing of the tips. When you’ve said your piece, allow the person time to reflect on it. Not everyone will come back straight away. Your job is to be comfortable with the silence whilst the other person gathers their thoughts in order to respond. I’ve found it really useful to have reminders to myself to ‘shut up’ – whether that’s putting my hand over my mouth (a physical reminder), or having a note to myself at the top of my pad. Silence is not your enemy. It is very much your friend.
  6. Put yourself in their shoes: This links to preparation and practice. Think about how you would feel if, say, someone more senior than you was about to tell you something that you really didn’t want to hear. How would you feel? What would make the difference – making a difficult situation a bit easier? Empathy is also needed in the conversation itself. Try and understand where the other person is coming from. As Stephen Covey once said, “Seek to understand, in order to be understood.”

BONUS TIP. Timing is everything: There are three aspects to this. First, make sure you have the conversation as close to the event or situation as possible. I’ve seen people leave it for months but by then the moment has passed. Second, just because the time is right for you, doesn’t necessarily mean it’s right for the other person. And third, never go in to a difficult conversation annoyed. In my experience, that never goes well.

These tips are by no means finite. They’re things that have worked for me, as well as colleagues and clients I’ve worked with. If you have things that you do, not included in the list, then why not share them in the comments section below?


Hayley Lewis is a chartered psychologist and a Fellow of the RSA. She founded HALO Psychology to help public sector leaders and organisations improve their effectiveness through the sharing and use of psychology. HALO offers a variety of services including coaching, facilitation and training. Contact us to see how we can support you with your own difficult conversations. 

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