How to have difficult conversations at work
Most of us prefer to avoid awkward or tense discussions in the workplace, whether it's addressing performance issues, handling conflicts, or giving constructive feedback. However, avoiding these conversations can lead to bigger problems—misunderstandings, resentment, and a lack of progress. I have had only one workshop attendee in the last few years of running corporate training on this topic admit that he enjoys them!
So, how do you approach having difficult conversations with confidence?
Why difficult conversations at work are important
I believe that difficult conversations at work have become even more of an issue with increased hybrid working, it is easier for people not to have them as they rationalise they don’t have to see the person or people they have the frustration with as much and equally that it is difficult to have the conversation as they don’t see them and in person is often the best way to have a difficult conversation.
However, they are an essential part of working life. As humans, we all have different wants, values, beliefs and assumptions so differences are going to occur. In the professional environment, it is important these are discussed, both from the perspective of the best decisions being made and the best action taken, as well as to work effectively and positively together.
When I talk to clients about the need to speak up and have a difficult conversation, I argue that in many cases when it is related to core work and having a different opinion, it is what they are paid to do. Each of us is employed to bring our insights and perspectives regarding our area of expertise to our employer, for its benefit; it’s not just about getting things done.
Choosing when to have a difficult conversation
Many people avoid difficult conversations. However, often this is not a good decision. It can lead to resentment and frustration building up over time and a disproportionate overreaction to a seemingly small issue later on. I usually advise there are two main criteria – if either is the reality, then you need to have a difficult conversation:
If the issue is significant.
If the issue is likely to recur.
Difficult conversations usually involve something or someone that we care about. This could include a key decision/action on a project or client, a timeline change, an individual’s behaviour, individual remuneration or career development.
Whether or not we have difficult conversations is likely to relate to our default conflict mode. The Thomas Kilmann Instrument set out below looks at different conflict modes.
Many people’s default is Avoiding. However, this is only a good idea when there is a lot of emotion, and a conversation is best left to another time.
Competing – where someone is keen to engage with the situation, yet not to cooperate with others is the right mode when there is a crisis situation and a senior leader has to make a decision.
Accommodating – where someone is keen to raise a difficult conversation yet also yields more to others’ views is the best approach when you want to raise a challenging conversation but are aware the other person or people have greater knowledge on the topic than you.
Collaborating – where someone is keen to raise a difficult conversation and collaborate with others to get to an answer is the best approach when there is a similar level of knowledge among individuals.
Compromise can be a great solution in many situations but in some, there can be no compromise and a decision one way or the other has to be made!
It is helpful to consider what your default mode is and consider the scenarios above and, therefore, in what situations in your workplace it would be wise to shift your conflict mode, which is likely to mean raising a point in a potentially challenging environment or having a difficult conversation.
How to have difficult conversations
Deciding to have a difficult conversation is the first step but once you have committed to it, you need to plan it carefully. There is a lot to consider to maximise the chances of a positive outcome, both in terms of the outcome on the issue and maintaining or improving the relationship.
Yes, difficult conversations, when done in the right way, can improve professional relationships.
Here are some key points to consider:
When to have a difficult conversation.
Where to have it.
Whether to ‘warn’ the other person or people.
Think about what you will say.
Consider the other’s perspective.
The outcome you are looking for.
Key behaviours during the conversation to keep in mind.
If you or your team find it challenging to navigate difficult workplace conversations, contact Joanna to explore how she can support you.
"I highly recommend Joanna Gaudoin’s Difficult Conversations training course. Joanna’s expertise and engaging teaching style make complex topics accessible and practical. Her bespoke course provided our team with invaluable strategies for handling challenging discussions with confidence and empathy.
Joanna’s real-world examples and interactive exercises made the training both insightful and enjoyable. We have already seen a positive impact on our communication and conflict-resolution skills. Joanna’s guidance has empowered us to navigate difficult conversations more effectively, fostering an even greater collaborative and understanding work environment.
This training is a game-changer for anyone looking to improve their interpersonal communication skills."
- Gareth Burton, Managing Director, Assure UK & Progress Accountants