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Handling Difficult Conversations with Customers, Clients and Colleagues

12th September 2019, 15:09
Sales and marketing
Difficult Conversations

This post was written by Elaine Warwicker, Director of Canny Conversations, who specialise in internal communications, marketing strategy and culture change. As part of our Gloucestershire Expertise series, we are giving local leaders the opportunity to share their knowledge and experience, to help other ambitious enterprises grow. If you would like to contribute to the series, please email

Elaine gives us her guide to having better quality conversations, and tackling those you may be avoiding, to help grow your business...

Most challenges can be overcome with better quality communication. And – in my experience - that’s true whether at work, or at home.

The reality is that no-one operates on their own. Even if you’re a one (wo)man band – we all have customers or suppliers of some sort - who you will need to communicate with, and who will need to communicate with you.

Even if you’re really good at presenting or negotiating – the chances are you might not be as good at listening, comforting or praising. We’ve all got something to learn when it comes to improving our communication skills.

And the hardest bit for us all to handle is the ‘difficult conversation’.


What is a difficult conversation?

Difficult conversations can be about a major issue or a relatively trivial situation. They can be anything from addressing a team member’s punctuality, or telling a customer that their prices are going up, to admitting to your fellow Board members that a large error has been made within your function. 

No-one likes to have difficult conversations. But some people are better at them than others – and, we can all learn how to improve.

More often than not, the conversations we categorise as difficult are to do with emotions and feelings.

We find it easy to talk about projects, timelines or systems; so why does it get so hard as soon as we suspect that someone might get angry or upset? Why do conversations become much more difficult when emotions are at play?

There are two main reasons for this – which are worth understanding:

  • A disagreement of any kind – at home or at work - can feel like a threat. And your body reacts to threats by triggering your sympathetic nervous system to get ready for a fight. So, while your mind is reacting to your project getting bumped off the priority list, or your wife forgetting to put the bins out again; your body is preparing to run away from a sabre-toothed tiger! Your heart beats faster, your breathing speeds up, your blood moves away from your organs into your limbs, your muscles tighten – and you generally start to physically feel uncomfortable.
  • Reactions are often unpredictable. We all have two types of brains, two minds and two different types of intelligence – rational and emotional. The emotional mind is far quicker than the rational mind, which is why we sometimes say something rash in the heat of the moment, before our rational mind has had chance to catch up.

And, in the middle of a challenging interaction, we’re not just aware of our own physical discomfort, and the likelihood of our own irrational reaction - we know that the person or people we’re dealing with are probably in the same place!


How do you know if you need to have a difficult conversation?

The last thing you want to do is have unnecessary confrontation.

So, before you start to tear a strip off that supplier about the delayed deliveries this week – just pause for a moment, and ask yourself four questions:

  1. Is there a positive reason for me to raise this issue? (will it change things in the future? Was it a one-off? Does everyone already know that things need to be better?)
  2. Do I have all of the information I need to have this conversation? (do I know why things were late? Do I know it wasn’t down to someone in my team? Or an unavoidable personal issue?)
  3. Is now the right time? (will I delay things further to stop everyone right now? Are emotions already heightened, and might tomorrow be better?)
  4. Am I the right person to have this conversation? (should the account manager have it? Is it a team-leader level issue?)


OK, I know I need to do it – what should I avoid?

Once you’ve given it due consideration, and you know that you need to have that tricky conversation – there are two things to avoid.

  • Putting it off – ‘I’m sure they won’t do it like that again, I’m really busy today, I’ll leave it and see if it happens again’…
  • Getting someone else to do it – ‘you get on really well with Doris, she trusts you, it will sound much better if you tell her.’ Or, even worse - telling everyone else in the office, in the hope that someone else will mention it to them first.

You need to get on and have the chat sooner rather than later. And the following steps will help.


Ten steps to a better quality conversation

  1. Plan for it
  • What do you want the outcome to be? What do you need them to know? What do you need them to do next?
  • If you don’t have all of the information – what questions do you need to ask?
  • Who else needs to be involved? What do the next steps look like?
  1. Put yourself in their shoes
  • Try to assess all possible outcomes or reactions in advance so that you’re ready to respond. And remember that there are many different versions of the truth.
  • What will worry them? What may cause anger? How can you deal with that? What questions might they ask you?
  1. Think about location and your surroundings
  • If you’re in a meeting, do you really want to do this with an audience? Can you go somewhere more private?
  • Is a face-to-face meeting possible – or will it have to be on the phone? 
  1. Be clear about what you’re saying
  • Try to avoid ambiguity - softening your language so you don’t hurt someone’s feelings can sometimes lead to the message missing its mark!
  • Can you sense-check what you’re planning to say with a trusted colleague beforehand?
  • And, while you’re in the conversation, do check in for their levels of understanding as you go.
  1. Try to find the ‘AND’ stance
  • In a disagreement, there’s rarely only two options – can you find out more about the motivations behind their preference? Can you find any other options?
  • “Rather than going with your idea OR my idea – can we find a way of achieving what we both want?”
  1. Be mindful of their emotional reactions
  • Watch for the emotional reaction - if they’re getting angry or upset, offer to get a glass of water, or just give them a 2 minute breather.
  1. Be aware of your own emotional reactions
  • Try to stay calm - can you try to control your emotional reactions?
  • If you can feel yourself getting angry, or upset - take a breath, and pause.
  1. Listen really carefully
  • Don’t just focus on what you need to say – it’s as important to listen to what’s being said to you.
  • And, be aware that their first response may be the emotional one. Ask questions to give them time.
  1. Plan for a pause
  • If the conversation is not productive, if emotions are running too high, or it’s just too hard for one or both of you to process all of the information – be prepared to reconvene at a later time.
  1. Agree the next steps
  • Ensure you reach an agreement of next steps – even if it’s to chat again tomorrow.
  • What happens next? Who needs to do what?


Practice makes perfect!

As with anything, the more you do it, the better at it you get.

Even though you still may dread those tricky conversations – the better you get at it, the easier it becomes.

And, you’ll quickly find that when you address small niggles earlier on, they don’t turn into bigger issues.

Having lots of minor tricky conversations on a day-to-day basis is much better than waiting for those major sabre-toothed-tiger-shaped problems to bite us on the bum further down the line.

Good luck!


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