Because a difficult conversation is, well… difficult, here is another perspective on how to master them. Using an insightful question to open up a better experience for both parties.

Guest blogger William Buist joins our gathering on this topic, with his tips from experience as a leader. William is a mentor to business owners & leaders, as well as a professional speaker. He’s also the Ethics Officer for the Professional Speaking Association, so brings that perspective too.

You may recall that William has shared with us before on leadership topics including asking beautiful questions, extra-ordinary leadership & collaboration. In this post, he shares his tactics for having an effective ‘difficult conversation‘…

All sorts of difficult conversations

Over the years, I have had to hold many difficult conversations

Sometimes, these have related to career development for people in my team, who are underperforming. Perhaps they are challenges with other parts of the business, who are unable to deliver what they promised. Sometimes I’ve had to address complaints from clients and customers of the business, or concerns from others who interface with it.

Most often, because of the roles that I’ve held over the years, those conversations have been referred to me when others have failed to address the challenge of the issue or the complaint. 

The time you have can trip you up

Now, the reality is that you have time to consider the upcoming conversation. You have time to play it out in your mind, ahead of the actual conversation. We make assumptions about how we will address the issue, and how the responses will arrive. Then you have the conversation.

None of your planning or little of it actually plays out in reality. So many difficult conversations fail to reach a satisfactory conclusion. I think this is partly because we plan rather than develop an approach. In some cases, that approach can make matters worse; when those conversations fail to reach a mutually acceptable conclusion. 

Techniques that can help you reach resolution

I’ve learned a number of techniques that help create the environment in which a successful resolution of any difficult conversation is likely. (Resolution means that you have successfully concluded the conversation with a mutual understanding, not necessarily agreement.)

This has been about treating the conversation as a collaboration, rather than as a contest. That means that all the parties involved are working collectively to achieve a common goal

The dreaded redundancies challenge

Imagine for a moment that you have to make redundancies. Firstly, in this conversation, there are some things which are not up for negotiation. Yet that doesn’t mean that the conversation is simply one of communicating the fact of the redundancy.

By viewing it as a collaboration we need to consider the outcome, beyond the fact of redundancy. There are usually options for any business to take a variety of actions in the process of separating and terminating the contract of employment. Options that can support and help the individual as they move on to another part of their lives.

In my experience, those options are often determined before the conversation takes place. Too often this is an attempt to deflect a difficult conversation with an attempt to find a solution that will be well received. The point of considering this as collaboration is so that on those areas where the outcomes are not fixed, you can focus on finding a mutually acceptable way forward. 

What helps with a difficult conversation? 

(1) Clarity on the purpose of the conversation

I think there are two parts to the answer to that question. The first element is being really clear and transparent about the purpose of the conversation you’re about to have. Why are you having a conversation in the first place

Suppose, for example, you need to have a difficult conversation with a customer who has been upset by the service they’ve received from another part of the business. An issue which has been escalated to you. That conversation is best started, in my opinion, by agreeing that the purpose of the conversation itself.

That is so you, as the business representative, get a real sense of clarity about the issue. You also probably want to understand the feelings and concerns that the customer has. You want them to be heard. 

It is vital for people to feel that they have been heard. They need more than just an acknowledgement of their words. They need their feelings and their intentions explored through incisive questioning. For them to know with certainty that you have understood the issue. Those incisive questions are often the most powerful way that we can demonstrate our ability to listen and understand. 

(2) Clarity on the outcome you both seek

The second part of the conversation that I think is equally important is to agree to the outcome that you’re both seeking. And again, questioning the other person to ensure that you have real clarity on what they are expecting is important here

We’re reminded regularly, by watching the news of people standing outside courts having won major damages, that often all they really wanted was an apology. Why did it not happen? 

I would suggest because nobody from the business asked what they wanted, nor really listened to the answers. The difficult conversation with a difficult customer can so often be resolved, simply by really hearing what it is that they expect to happen next. That needs a series of insightful questions based on the information they have provided. 

Do you see the power of questions?

When we are given the space to explain our concerns, in any difficult conversation. When we are asked insightful questions that explore the detail. When those asking validate their comprehension of the replies. Then, we know for sure that we have been heard.

When those questions explore: what can be done and detailed explanations of what is, and is not possible, in the spirit of finding common ground – the chances of finding it dramatically increase. 

I believe that ability, to openly ask the insightful questions that are needed to explore the topic and be willing to adapt to the answers that are provided, is the difference between an ordinary business and a great one. In the final analysis, difficult conversations are the place where the courageous use insightful questioning to build genuine transformation.

Thanks to William for that advice & for highlighting the importance of such questioning to understand.

Do you have any ‘go-to‘ questions or approaches that have helped you have more collaborative ‘difficult conversations‘? If you have tips to share with other leaders on this topic, please use the comment box below.