Difficult conversations made a little easier

By Tim Farish

Most of us, if we’re honest, put having difficult conversations near the very bottom of our to-do list. If you’re like me it’s probably next to ‘lose weight’ or ‘get fitter’ and dealt with the same conviction: poorly and inconsistently.

Like most things we put off, there is a very good reason for it: we dread upsetting people or things not going the way we want. Sound familiar? Well, you’re in good company.

I have got better at having ‘difficult conversations’ over the last few years but still struggled until I came across a model that is being used in one organisation that has learnt the value of putting these conversations at the heart of its agenda. And, like most things in life, with a bit of structure and practice, I have actually started to enjoy those conversations that I used to find challenging.

A difficult conversation...

A difficult conversation…

So, why do we find conversations so challenging and difficult? Well, there seem to be several factors that contribute to this. For example: high stakes, strong emotions and opposing views. Most difficult conversations have somebody involved who is potentially sensitive to the subject being dealt with and it’s usually because they have something to lose. Strong emotion is also usually involved and often we believe that somebody could get upset or angry. And often very different opinions and perspectives are involved. Each or all of these factors can be present which make them so challenging.

So, what can we do to improve things and prepare ourselves?

The main thing is to do some planning in advance. By asking yourself the right questions you can ensure that important issues affecting both parties are considered while improving the chances of a successful outcome. Another by-product of planning is that it seems to deal with fear. Ok, it doesn’t get rid of it completely but, in my experience, it does get rid of the sense of dread and panic that often results in putting things off.

The following is a list of questions with examples to help guide you. If you are able to answer them in this order it will put you in good shape beforehand.

Question 1. – What is my intention (outcome)?

This is the most important question. It means that you can hold the bigger picture which is often lost when there is a potential conflict nearby. It also gives a sense of purpose to the conversation, which is always useful.

Let’s take the example of a boss who had to conduct a performance conversation with a member of their team who is struggling to meet expectations at the beginning of their career.

If you were planning the conversation from the boss’s perspective, your purpose could be to offer maximum support for your direct report while also stressing the importance of needing to meet performance criteria. By having a purpose which is ‘supportive’ you are more likely to sound so which will build trust with your direct report.

Question 2 – How differently do we see the problem?

Often both parties have very different views when it comes to a situation so it really is important to check this. If you can see the other person’s view then you are far more likely to get a successful outcome.

Building on the example above you could check in with your team member and clarify their understanding of what constitutes good and bad performance.

Then you can share your understanding and point out if there is any difference.

Question 3 – What is important to the other person?

When there are high stakes and strong emotions involved it is very easy to forget this.

Far too often we are consumed by our own interests and concerns and this can easily make a bad situation worse. If you are able to find their motives then it makes it easier to diffuse the situation. Finding out what matters to people can also help motivate them. And, maybe more importantly, you can then find areas of alignment too.

A good conversation….

A good conversation….

Question 4 – What is the actual ‘data’? And what judgments am I holding about this?

When we find people challenging we often put a load of judgments on them that are inaccurate. While this is a perfectly human thing to do, it only makes the situation more challenging for both of you. Maybe you think your employee is unmotivated or lazy. Well, what’s the data and is there another way of interpreting it? If you don’t check this out with them you can often antagonise without knowing it.

Question 5 – What’s my opening and close?

Openings are really important as they crucially set the emotional tone for the conversation. How do you want to begin? A good way is to acknowledge the person for something you’ve seen them do that you appreciated. You may have noticed the extra work that your direct report put into an urgent pitch. By noticing in this way, it makes people feel seen and builds trust. Closing is important too. What are you both agreeing to do now? What are the next steps? Some clarity on these points will ensure that a successful outcome is maintained.

Finally, don’t forget that while all this preparation is critical – it is still important to find the right time and the right place to have the conversation. Good luck!


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