Difficult conversations at work are part and parcel of being a leader. But surprisingly, managers often turn a blind eye and wait out discomfort for different reasons.

However, shying away from tough conversations won’t do you any favours and can lead to growing resentment between you and your team members.

At Bolt, we promote a culture of continuous feedback. In addition to yearly performance reviews, managers and employees have informal chats every few weeks. It enables constant development as employees get more insights into their current performance and have more feedback points to work on.

When there’s a need for a more serious one-on-one conversation, Bolt’s People Partners offer managers a helping hand to ensure the hard conversation goes smoothly and productively.

We talked to Hedda Lindwall, Regional People Partner at Bolt, who shared insights on initiating and managing difficult conversations at work. So if you’ve been postponing such conversations, check out these tips.

Create a difficult conversation framework

When preparing for a tough conversation, ask yourself two questions: why am I having this conversation, and what am I trying to achieve?

Five tips for good preparation:

Use keywords: you can’t script a hard conversation as you can never predict how the other person will react to your message. Instead, write down a few keywords to keep the conversation on track;
Collect examples: if you want to discuss someone’s behaviour, collect as many concrete examples as possible — with the date, subject, and any people who were present. That way, there can be no doubt about the accuracy of your statements;
Collect solid and irrefutable arguments to support your message;
Collect documents to back up your statements: contracts, written agreements, procedures, or policy documents;
Anticipate questions and prepare your answers.

When you have your talking points ready, it’s time to schedule the meeting.

Invite the person for a chat

What’s the perfect moment for a tough conversation? The answer is simple: there isn’t one. However, Hedda shared one straightforward rule: the earlier you discuss an issue, the smaller it will grow.

“The common trap is to turn a blind eye to smaller, less essential red flags and hope that they won’t get any worse or save up the feedback to give it only once or twice a year during the performance reviews,” says Hedda.

Such rare feedback will only make employees feel insecure because they don’t understand what they’re doing right.

Invite the person for a chat

It’s important to remember that how a hard conversation goes is partly determined by how you invite someone to a meeting. Instead of the infamous “we need to talk”, you can use less threatening wording, for example:

Do you have a moment tomorrow afternoon? I have some feedback I’d like to discuss with you.
I’d like to get your vision on… Have you got some time on Thursday?
I’d like to see if we can reach a better understanding about… I’m interested to hear your opinion, and I’d like to explain my side. Can we get together early next week?

This way, the person better understands what the meeting will be about.

Another great tip is to keep the time between the invitation and the actual meeting as short as possible, so the other person doesn’t have too much time to worry about the upcoming conversation.

Go into the conversation with an open mind

“Your mindset when heading into a conversation can influence the outcome: if you label it as ‘difficult’, you can start feeling the tension,” says Hedda.

Hedda advises that expectations affect the result — if you go into the conversation with negative emotions, you can get irritable and are more inclined to go on the defensive. And then the conversation will indeed become challenging.

Don’t float around the subject

And here we are — sitting in the meeting room. Your team member already knows critique is coming, and you may feel tension.

“Clear is kind,” says Hedda, “so instead of showering the person with compliments and niceties, just get to the point. Mixed signals will muddle the delivery, and talking about unrelated things may only ease your anxiety but worsen the anxiety of the recipient.”

Don’t leave your conversation partner in suspense any longer than necessary — tell them the news in the first thirty seconds of the conversation.

Don’t float around the subject

After all, your goal is to point out a person’s behaviour and find a way to improve. Here are some tips to get the motivation flowing:

Describe concrete incidents and give specific examples. Hedda says it’s better to avoid words like “always”, “everywhere”, and “never”, anything generalising, and combinations such as “people say” and “I heard that”. She also suggests avoiding accusing the other person of doing certain things (you did, you said, you must have thought) and only focusing on your own experience and feelings;
Use “I” statements. So instead of saying, “You’re doing it wrong”, you can say, “I saw this happening, and that’s not how we agreed to do it”;
Don’t make it personal. Instead of calling someone lazy, say, “Today was the deadline for your report, and for the third time in a row, I’ve received nothing”;
Say “and” rather than “but”. It helps if you see both sides of the story.

Quick check-up: the body language

You’re entirely focused on the conversation — that’s understandable. But do a quick body scan to ensure your body language shows no negative signs.

Here are some tips on proper non-verbal communication:

Sit up straight, at the same height;
Sit next to or opposite each other with nothing in between;
Replicate the other person’s posture;
Speak calmly, with a low voice;
Use supporting hand gestures;
Make eye contact;
Don’t be distracted by any devices — it’s better to leave them at your desk;
Avoid pointing your finger.

Keeping body language in check takes effort. But if you stay calm, engaged, and genuinely curious and watch your non-verbal communication, your conversation partner will also manage to keep calm.

Prepare to listen

After you present your side of things, give the employee a chance to respond. Stay engaged in

what they’re saying as it might detail why problems arise.

Remember that listening is not the same as hearing. When you listen, you show interest and understand what the other person is saying. You let them finish talking, and you’re open to new insights.

“It’s important to ask neutral questions and to be generally curious,” says Hedda. She also shared one well-known technique that helps you to stay engaged in the conversation. It’s called LSD — listen, summarise, and dive deeper. With this technique, you place the focus on your conversation partner and conduct a more effective chat.

When having a hard conversation, observe the other person’s posture and intonation, and make eye contact. You can also encourage the person by showing that you’re all ears by nodding or saying “mhm”.

Be empathetic

Be empathetic

Handling a difficult conversation with empathy and understanding for all involved parties is essential. Try not to take anything personally, and remember that everyone involved has their perspective on the situation. Acknowledge how the other person feels and show them you empathise with their position — even if you don’t necessarily agree.

If your conversation partner gets emotional during the meeting, don’t comfort or soothe someone immediately: give the other person time to let the news sink in.

“In any stressful situation, it’s not helpful to ask the person to calm down,” says Hedda, “but rather to tell the person that you see them getting emotional and to ask if they want to take a break or if they’re okay with continuing the conversation.”

Listen, observe, and show genuine interest if the other person says something. Say that it’s perfectly alright to be sad or angry.

However, no matter how emotional the person gets, try not to end up in a trap where you sprinkle on some niceties to cover up your initial message. “Whenever you want to say something nice or to be pleasant or polite, ask yourself this question — will this increase their sense of clarity and comfort, or will it only increase my sense of comfort?” says Hedda.

Speaking of emotions

During the conversation, we may be so afraid of the other person’s reaction that we forget about our own emotions.

If your body is giving you signals that you’re getting too emotional, for example, you get a lump in your throat or your hands start shaking, take a quick break. It won’t help anyone if you lose it during a conversation. Deep breaths in and out of your abdomen can help you better manage your emotions.

But there’s another pitfall hiding here: “Don’t make it about yourself,” Hedda warns. It’s especially relevant when you’re delivering bad news. For example, when telling the person they didn’t get the promotion they’ve applied for, you shouldn’t be talking about how difficult this decision was for you.

“If you need to get these emotions off your chest, talk to your manager or People Partner, but during the conversation with your employee, always keep it about them,” says Hedda.

Offer a solution

What’s the use in delivering critique if you offer no remedy? You can’t barrage your employee with negative news and thoughts and consider the meeting a success. You must explain the reason for the one-on-one conversation, detail your critique, and suggest improvements.

For example, if you’re declining a raise request, let the employee know what you expect or need them to achieve and a timeframe for that raise to transpire. Your employee should always leave these difficult conversations at work thinking they can do better and be motivated to improve.

However, before suggesting further steps, ensure the recipient has accepted the bad news or critique. You’ll know they’ve processed the information when they start looking for solutions.

Offer a solution

“We always give employees a chance to work with feedback, and as a company, we make sure that we’ve done everything we can to help our employees improve,” says Hedda.

Unfortunately, you can never force anyone to learn, improve, and work on their development. That will always be up to the employee.

Is there a need for a follow-up meeting?

“It heavily depends on the content: if it’s a performance issue, it’s common that you draft a performance improvement plan, and in that plan, you agree on how often you’ll be revisiting it,” shares Hedda. “If you can do it once a week, the employee will have many feedback points they can work on.”

“It might also be that the performance points may require a longer time to make improvements,” says Hedda. “In those cases, scheduling follow-up meetings every other week may be more appropriate.”

When it comes to other topics like conflict or compensation, it depends on the conclusion you reached during the meeting: “If we’re talking about conflict, you can ask if the person wants to meet again to talk about how they feel after some time has passed,” says Hedda. “Parties may have resolved the conflict immediately, so there’s no need for a follow-up.”

Regarding compensation, Hedda says that when a manager has made a decision, it may not be helpful to schedule a follow-up chat — it may give an employee a false feeling that the final decision hasn’t been reached yet. It’s essential to be clear about when the topic is closed. You can always follow up with the employee about how they feel about the situation in your future 1:1’s without making it too focused on the compensation topic.

In any case, it’s always better to stay on top of the issue, so everyone feels like things are improving. Without scheduling a follow-up conversation when it’s necessary to revisit the problem, the team member could grow isolated and wonder if you took your discussion seriously.

Let’s sum it up

Difficult conversations at work are an unavoidable part of being a manager, but they don’t have to be intimidating or overwhelming if approached correctly.

Let’s sum it up

Prepare ahead of time, listen intently, and demonstrate empathy during the conversation, so both parties feel heard and respected. Doing this will go a long way toward ensuring successful outcomes.

Emotions transform ordinary conversations into laborious discussions, but practice makes perfect. The more often you have a difficult conversation, the better you’ll learn to deal with your emotions: “You’ll get the most input from practice. However, hard conversations are not something you seek out — they come to you, and you probably shouldn’t try to provoke them just to practice,” Hedda smiles.

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Managing difficult conversations at work

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