How to master the art of difficult conversations

Difficult conversations handled badly can undermine your business. Here’s how you can make sure you handle such conversations the right way 

By Doug Aitken, associate, Remarkable Practice 

It’s easy to avoid difficult conversations, whether it’s challenging a key employee about falling results, chasing an outstanding invoice with a large and important customer or, indeed, a variety of other things.  

The risks of handling such conversations are high. If the conversation isn’t handled the right way, the key employee might walk. The large and important client might take their business elsewhere. In short, there is a lot at stake, which is why many people fail to have those same difficult conversations. 

Yet the risks are also high of not having those conversations. After all, what impact does you not addressing falling performance have on others within the team? What does it say about your credit control standards to your team if you continually bend them for that important client? 

A key facet of successful businesses is their ability to not only set high standards, but to stick to them. Many businesses will enthusiastically agree they have high standards. Yet when the chips are down, how many really adhere to those standards? And by bending the standards, you’re sending mixed messages to your team, to your clients and to the wider business community. 

Learning conversations dissolve difficulty 

What is the purpose of the conversation? If your purpose is unclear or not constructive, then no matter how you handle a difficult conversation, it’s going to go badly. 

When conversations go badly, sometimes it’s because we approach them as blame delivery exercises. What if, instead, we approached them with a genuine curiosity – as learning conversations instead of blame delivery? 

Think of your purpose as establishing three truths – your truth, their truth, but also a third truth, which moves you both towards resolving the issue or conflict. Think of this third truth not as mutual agreement, but a mutual or collective understanding. 

Remember, you’re talking about feelings  

Feelings are an unavoidable part of every difficult conversation. But in business – and in life – we can find it difficult to talk about feelings.  

If you fail to get your colleague to express their feelings, they will not hear you. People stop listening because they are thinking about how they are feeling. As a result, it’s unlikely they’ll want to, or be able to, understand you. 

Fail to express your feelings and your feelings could prevent you from listening and also from understanding. 

To reach mutual understanding, that ultimate third way, both parties must feel listened to and understood. All are important steps in clearing the decks for that final stage three – reaching a mutual understanding.   

Transformational skills that improve conversations 

Building the key skills to handle difficult conversations isn’t easy, but it can be done. When faced with a challenging situation in future, and once you’ve decided that it cannot be ignored, try this approach instead: 

1. Seek first to understand 

You need to learn their truth, so at the outset see your role as to ask questions. Set out to learn what happened from their perspective and how they feel about it. When they feel you understand them, they’ll be more open to understanding you. 

The three key skills to develop are: 

a) Ask great questions; 

b) Listen purposefully; and 

c) Demonstrate understanding. 

2. Share your truth 

Express as well as you can what is important for you to say. Share your views, your intentions and your issues. But avoid blame at this stage – it’s the equivalent of throwing petrol on a barbecue! So instead of venting your spleen, state your feelings carefully from your perspective. 

3. Solve the problem together 

Seek a third way.  

Now it’s time to work together towards a mutual understanding that you then turn into a new solution for both of you. 

Your ‘make it happen’ checklist 

Difficult conversations can be constructive or destructive. Make a leap towards making them more constructive by following these steps. 

Decide whether or not to have your difficult conversation   

• If handled well, will the conversation move your business forward?  
• If not, perhaps there is a case that it should be dropped. 

Have a clear purpose for your conversation 

• Make your purpose to seek understanding. Be curious. Make your conversations learning conversations. 

Accept that both parties contribute to the difficulty in some way  

• Joint responsibility shows you’re serious about reaching a satisfactory solution. 

Avoid the blame game 

• Accept responsibility for contributing to the difficulty. 

Be curious about their story 

• Their truth and their feelings. 

Share your story 

• Your truth and your feelings. 

Pursue a solution together 

“When conversations go badly, sometimes it’s because we approach them as blame delivery exercises.” 

AAT Comment offers news and opinion on the world of business and finance from the Association of Accounting Technicians.