How to have difficult conversations

Life’s full of tricky conversations. In the workplace you might encounter someone who is often late because they have to take their child to school. You might disappoint staff by introducing a salary cap that will prevent them from getting bonuses.  Or, you might have to dash the hopes of a candidate who really wanted that job or promotion. 

AIM WA’s Chief Operating Officer Dr Shaun Ridley said these were the difficult exchanges that people replayed over and over in their minds before thinking, ‘Gee. I wish I’d said that’.

“They’re the types of conversations you think about in the car on the way home,” he said. “The conversations where you wish you expressed yourself better.

“So I wrote a book showing how people can better navigate tricky conversations and hopefully produce better outcomes for themselves and the person they’re talking to.”

Co-authored with professional speaker and master coach Paddy Spruce, the book – aptly titled I Wish I’d Said That – explores what to say and how to say it when you’re faced with difficulty in the workplace.

6 core principles you need to understand before jumping into any difficult conversation

As Dr Ridley explains, there are some key principles to work through:

1. Strong pre-existing relationships lead to better conversation outcomes, or rather, it’s harder to ask favours of people who don’t already like you

2. Always remember to focus on the issue, not the person

3. Treat others with respect no matter what they do

4. Assume tricky conversations may take a while

5. Assume the other party will prioritise their own best interests

6. Remember a sub-optimal outcome that can be implemented is better than a perfect outcome that can’t be implemented.

Dr Ridley said once professionals were ready to view discussions through this framework, it was time to diagnose the conversation that had been troubling you. 

“You have to think to yourself, what is my intent?

Be clear about that from the start,” he said. “You have to decide what content outcome you would like, which might be sharing information or enforcing a decision, and you also have to decide what relationship outcome you might like. 

“This part will probably require some self-reflection.

“You will think your intentions are honourable, but a lot of the time your main objective will be for you to win and the other person to lose.”

After some honest reflection, Dr Ridley said professionals should rethink their approach if their true motive was to embarrass someone, and should understand that a win/lose framework is only effective in a very small number of situations.

Instead, professionals should demonstrate how the other party will benefit from the exchange, which should strengthen the relationship and lead to positive reciprocation.

“After you have thought about what you want, you have to evaluate whether there is room for the other person to negotiate,” Dr Ridley said.

“If there’s not, make that clear, because people can tell when you’re disguising the truth but will respect you if you’re upfront.

“You also have to consider what level of commitment you need from the other person. If their active involvement is essential to the outcome you want, then you will need to frame the conversation in a way that suggests they own the outcome.

“You want them to be part of the actions required to shape the outcome.”

Once negotiation and commitment were considered, Dr Ridley said it was time to judge trust levels and relationship longevity to determine the conversation style, whether the person was reliable or may require an adapted approach, as well as whether you needed the relationship to last.

In the final stage of diagnosis, Dr Ridley said it was important to thoroughly assess the size of the issue at hand and the level of emotion that issue might inspire.

Describing this as strangely the most overlooked part of conversational strategy, Dr Ridley said people shouldn’t assume small issues wouldn’t have a high emotional response and he encouraged the Sundowner crowd to asses issues from someone else’s point of view.

“So, how about we diagnose these situations?” Dr Ridley said. “How might you diagnose a conversation with a parent who is regularly late because they need to take their child to school?

“What is your intent? What is their intent? Is there room for them to negotiate? Do you need them to commit to what you’re saying? Can you trust them? Do you want to maintain a relationship with them? What is the size of the issue for them and what is the size of the issue for you? Is there a high level of emotion here? Is it a big deal to them and a big deal to you?”

Though Western Australia’s professionals might feel ready to tackle the tricky and the awkward in the office after a workshop with Dr Ridley, the published author stressed his conversation tips were not a foolproof strategy.

He urged people to practice evaluating smaller issues before employing diagnostic tactics in important office situations and he reminded the crowd that strong feelings of discomfort around difficult conversations were unlikely to disappear.

“We’re uncomfortable because we care,” Dr Ridley said. “It’s a good thing. Sit with it. Erasing it isn’t the goal here.

“What this book aims to do is help you navigate the discomfort and hopefully produce better outcomes for you and the people you’re talking to."

Where to from here?

Struggling with how to have those difficult workplace conversations? End the struggle here. You'll be glad you attended our Having Difficult Conversations course - giving you the essential tools and skills to tackle these conversations and increase the likelihood of a successful outcome for everyone.