We need to talk in a good way card

How to have difficult conversations

Business wISDOM
By Team Holly & Co


Knowing how to have difficult conversations can change your life. It empowers you to speak your mind honestly, remove blockers and helps you build better relationships with others. Discover the secret to tackling awkward topics head on…

Sit in the uncomfortable chair

Why is it so hard to have difficult conversations?

As small businesses, we are surrounded by an f-word: ‘Feedback’. If it’s not feedback, it’s the other one: ’Fear’. But do those two factors really need to ‘facilitate’ each other? We had an enriching conversation with our resident expert coach and business psychologist, Kate Downey-Evans, and the good news is she shed some light on it for us. So, take a deep breath; because the answer is… No.

You know that situation, we all do — when something ‘off’ has occurred and you know in your gut and your heart what needs to be said but it just seems too hard. Or unkind. Or awkward. You don’t want to fall out with the person or diminish their confidence in any way, and you certainly don’t want them to confront you, so you try to let it go… But it’s then left unresolved isn’t it? And they do it again. Of course they do because they don’t know not to.

It’s not just about instigating difficult conversations, but how we receive them, too

Similarly, it’s often just as tricky when people need to tell us something tricky. If we get a negative review or are discussing pricing, for example, and it’s not been sensitively handled, it can affect us tremendously. So how do we learn to have those difficult conversations well? How can we move things forward in a proactive manner and iron out differences of opinion in a better way, and encourage others to do the same? Well the good news is, it’s actually quite straightforward.

Giving honest feedback while tackling difficult conversations

There’s a great phrase that says, ‘Don’t seek praise, seek criticism’. Why? Because you learn more from it. When Levi Roots was on our Conversations of Inspiration podcast, he told our founder Holly Tucker that he’s rebranded failure as feedback. Feedback is so important, and it’s good to remember that…

  • It doesn’t always need to be positive (just honest and helpful)
  • It almost always helps us to develop in some way
  • It gives us clear direction so we know what’s expected of us, and sets a benchmark
  • If done well, it usually helps improve engagement and relationships
As small businesses, we are surrounded by an f-word: ‘Feedback’. If it’s not feedback, it’s the other one: ’Fear’. But do those two factors really need to ‘facilitate’ each other?

How to have a difficult conversation when you don’t like conflict?

Well the good news is that in many ways, you’ve actually already done the hardest bit; you’ve founded your own business. You’ve created great products or services, sorted out the numbers and worked the long hours. Now that takes bravery. Compared to that, this is probably quite easy. Few people actually enjoy conflict, but conflict doesn’t need to be aggressive. It’s a disagreement and these are usually resolved by listening to each other.

In fact, the Harvard Business Review found that the more you listen, the better employees think you are at giving feedback¹. Having difficult conversations well just takes practice. So here are some techniques to help…

When confronting someone, make your intention clear, avoid apologies and do it quickly

It can feel uncomfortable to broach a subject we don’t really want to, but it doesn’t need to come with a side order of apology. It is perfectly reasonable to set out expectations with your team or let your distributors know that inflation isn’t just on the news, it’s effecting you too. So as soon as you’ve opened your laptop, picked up the phone, or taken a seat, kick off immediately with the headlines: outline your intention. It softens the sting for the recipient whilst giving them the space to process and prepare themselves for what’s to follow. Plus then you’ve got the hardest part out the way.

With difficult conversations, take the emotion out

Difficult conversations can so often feel like they’re loaded with emotion but as soon as we remove that from our narrative, it becomes easier. Besides, it’s rarely as bad as you think. If your customer has received the wrong order, are they really blaming you, the founder, or do they just want to vent? Remember, it’s unlikely to be personal. They just need a problem solved. You’ve created something wonderful enough to attract them to shop with you in the first place, but somewhere along the line a mistake has been made. Reframe it. Rather than it being a difficult conversation, could it actually be an opportunity to show how terrific you are at fixing a problem whilst solidifying loyalty? It’s how you deal with the conversation that will matter.

How do I stop being scared of hard conversations?

A cold chill runs down the spine and our fears are realised — we’re not good enough, we’re rejected and no one likes our product or brand, or the way we do things. It can be hugely triggering and that feedback will follow us to the bathroom, to the breakfast table, whilst we’re waiting for the car to be MOTed — it is all we can think about. Take. A. Breath. Remember that feedback is just an opinion, it isn’t fact. Our temptation when we feel vulnerable is to catastrophize or exaggerate. Put it in its rightful place and deal with it that way. It’s much easier and will use up a lot less energy.

Awesome Less Awesome Wooden Sign
How can we move things forward in a proactive manner and iron out differences of opinion in a better way, and encourage others to do the same? Well the good news is, it’s actually quite straightforward.
A toolkit for modern life book by Emma Hepburn

How to receive feedback? Take time out to consider it

If the difficult conversation is aimed at you, try and assess what the person is looking for and what their intention is. As soon as you ask yourself what they need from this conversation, you are free to engage. The same can be said if we are the one giving the feedback. Providing examples can really help someone understand the purpose of the conversation and suspend blame. Having time and space to think about the issue can really help put it in perspective too, so where possible, factor this in.

What is +EBI or ‘even better if’?

Our resident expert business psychologist and coach, Kate Downey-Evans, suggests that the easiest way for us to hear and connect with others is to use the +EBI technique (Plus, Even Better If).

  • If you want to bring up a difficult subject, the words you use to convey it will be critical.
  • Try highlighting their ‘plus’ points and then following with, ‘It would be even better if…’.
  • The accusation has been eliminated and it provides something tangible to connect to.
  • Plus people are more likely to want to help you, or you’re more likely to arrive at an agreeable solution, if neither of you feel attacked in any way.

Of course, the really tricky part of having difficult conversations can be instigating them in the first place. It is all too easy to succumb to avoidance and ignore your gut feeling, but this rarely helps. It is a recurring theme in our community that listening to your gut should always win. So remember these techniques, take a deep breath and go for it! The quicker you take action, the quicker the situation can be resolved.

How to have difficult conversations: key takeaways…

There are three main things to remember here.

1. Honest feedback is important:

It helps us develop and sets expectations so having difficult conversations is the kind thing to do.

2. Plan your approach to the conversation:

Make your intention clear, avoid apologies, take the emotion out, try the +EBI technique and do it quickly.

3. Take time out after the conversation to digest it:

Avoid catastrophizing, let it sink in and decide what positive action you can take off the back of it.

Images: 'Sit In The Uncomfortable Chair' — by Team Holly & Co, 'Do What You Love, Love What You Do' Book — by Holly Tucker MBE.

Sources: 1. The Harvard Business Review on giving tough feedback

Related content