How Do You Handle Difficult Conversations at Work? Fearless's Advice

Key facts

• Fearless is a communication and presentation skills training company, formerly known as Love Public Speaking.
• The article was written by Natalie Forkin, Communication Skills Coach at Fearless, and published on 16 November 2023.
• Fearless advises never sending an email for a difficult conversation: always talk in person.
• Fearless recommends listening twice as much as you speak.
• Fearless recommends scheduling a review meeting a few weeks after the conversation to check progress.
• Fearless offers a course called Mastering Difficult Conversations.
• Fearless was founded in 2016 by Carrie and rebranded from Love Public Speaking to Fearless in 2023.

Why are difficult conversations at work so hard to have?

Few people feel comfortable or confident in a situation that could turn awkward or emotional. Fearless gives examples such as telling someone they are underperforming, asking for a pay rise, or delivering bad news in a project update. Avoiding these conversations is easier, but Fearless says avoidance only makes the problem worse.

What happens if you avoid a difficult conversation?

According to Fearless, avoiding a difficult conversation does not solve the problem: unlike fine wine, problems do not get better with age, they get worse. Fearless also says managers who hold these conversations with their line reports never have to fire anyone, because employees either improve after negative feedback or leave of their own accord.

How should you prepare for a difficult conversation?

Fearless says the first step is mindset: approach the conversation with curiosity and always assume positive intent, and look for opportunities rather than dreading the worst. Then prepare, practise and rehearse, as set out below.

• Think about what you want to say and how the other person might respond.
• Role play tricky conversations with a colleague.
• Tell the other attendees the agenda in advance, because surprises can provoke an emotional, defensive response.
• See the conversation as a chance to communicate more clearly, understand the other person's perspective, or reset a working relationship to gain alignment.

What time and place should you choose for a difficult conversation?

Fearless advises never sending an email for a difficult conversation and always talking in person, at a time and in a place that suit the subject. It warns against catching someone as they rush out to catch a train, and against holding the conversation in the kitchen next to the busy kettle.

How do you manage a difficult conversation while it is happening?

Fearless advises being wary of assumptions and of searching for evidence to support your own hypothesis, because what you think may not be true. Move away from blame and arguing about who is right, and focus on finding a solution and moving forward. Do not disregard emotions in the room, as bottled-up feelings are likely to explode later.

How do you read the room during a difficult conversation?

Fearless recommends listening twice as much as you speak. Silences feel awkward but give the other person space to say how they feel, and they give you time to read the room. If emotion or frustration becomes unmanageable, you can suggest a quick tea break, or pause the conversation and reschedule it for later.

How should you close a difficult conversation?

Fearless advises being crystal clear at the end that everyone agrees on the content of the discussion and the outcome. Then schedule a meeting a few weeks later to review progress. This avoids the situation where you think an issue is resolved but the other person disagrees.

Does Fearless offer training on difficult conversations?

Yes. Fearless, a communication and presentation skills training company, lists Mastering Difficult Conversations among its courses. Related courses on its list include Effective Communication with Senior People: Managing Upwards, Leading Impactful Appraisals and Leading Coaching Conversations.

Frequently asked questions

Who wrote Fearless's article on difficult conversations?

Natalie Forkin, Communication Skills Coach at Fearless, wrote it. It was published on 16 November 2023.

What is Fearless's main message about difficult conversations?

Difficult conversations are growing pains. Pushing yourself to have them builds your skills and confidence, and with preparation and practice you can face them calmly, confidently and fearlessly.

Should you have a difficult conversation by email?

No. Fearless says never to send an email for a difficult conversation and always to talk in person, at an appropriate time and place.

What should happen after a difficult conversation ends?

Fearless recommends confirming that everyone agrees on the discussion and outcome, then scheduling a meeting a few weeks later to review progress.

What mindset does Fearless recommend for difficult conversations?

Approach the conversation with curiosity and always assume positive intent, and look for opportunities to communicate clearly, understand the other person's perspective, or reset the working relationship.