Having difficult conversations with employees is an inevitable — if uncomfortable — part of people management. Whether it’s about performance, workplace conflict, sharing negative feedback, or discussing personal issues, being able to address sensitive subjects is an essential part of supporting employees.
Yet according to data from Officevibe’s Pulse Survey software, 24% of employees do not feel that their direct manager is aware of employee pain points.
Nearly 1 in 4 employees do not feel that their manager is aware of employee pain points.Officevibe Pulse Survey data
Effectively carrying out a hard conversation in a one-on-one meeting contributes to the continuous development of your employees and your team. Our step-by-step framework and advice from experts can help you make any challenging discussion productive and solution-oriented.
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Tough talks will always remain a challenge for managers, but these difficult conversation tips can help to make your discussion easier, while supporting effective conflict resolution.
1. Set the talking point in advance
One-on-one meetings are a good moment to carry out tricky discussions. It’s important for you to prepare for the difficult conversation, but remember that communication is a two-way street. Giving the other person advance notice of what you’d like to discuss allows them to prepare, too, and establishes clear expectations for you both. Add the talking point to your shared one-on-one agenda or send your team member a quick message to give them a heads-up in a way that’s both clear and neutral in its tone.
Instead of saying: “We need to talk about what happened in the team meeting.”
Try saying: “I’m curious to hear your thoughts on the different opinions that came up in last week’s team meeting. Can we chat about it at our next one-on-one?”
If you're not sure how best to plan for the discussion, Officevibe has an editable agenda template for difficult conversations at work. Plus, there are dozens of suggested talking points and questions you can choose from if you need more inspiration. Meeting agendas are collaborative, so you and your team member can both prepare for a chat ahead of time by adding your own talking points.
2. Focus on facts, not feelings
To prepare for a tough one-on-one meeting, dig a bit into what you’re feeling so you can understand and share your thoughts clearly. Try to separate what you know from what you think or feel. You can do an objectivity exercise to eliminate what might be an assumption or projection. One such exercise is to consider what advice you’d give a friend in your position, or even in your employee’s position. Rachel Kent, a former Camp Director, shares:
Gather all the facts, then consider the outcome you want. Build the conversation backwards once you know the desired outcome. Make some notes ahead of time of things you don’t want to miss and bring them with you.
For some difficult conversations, having tangible support can help keep the focus on facts rather than gut feelings. This tactic can be particularly useful when it comes to offering negative feedback to employees.
Put together some notes with numbers, specific examples of peer feedback, documentation, or other resources that can help you ground a tough conversation.
🧾 Don’t ambush someone with receipts: Preparing with concrete supports is one thing, but pulling up screenshots or compiling a file of evidence against someone is quite another. Be mindful in what you put together and ask yourself how you see it contributing to the discussion.
Talking about a difficult topic or having an otherwise challenging conversation can evoke some emotion from even the most regulated among us. When it comes to managing your emotions, it’s important to find a good balance between being composed and being authentic. Brendan Collins, an experienced Mental Health Worker supporting people from vulnerable populations, shares:
Don't be too calm, be calm enough. If you’re overly calm it might give the impression that you don't care, or that you think you’re better than the other person.
3. Create an environment for trust and honesty
It’s important to foster a sense of trust and mutual respect with employees, to encourage them to come to you with tougher topics. Having regular feedback exchanges helps people feel comfortable to be candid with you, and maintaining recurring one-on-ones with each team member makes these discussions feel less daunting when they do pop up. When facing a tough talk, ask questions during your one-on-one to open up the conversation and show that you want to hear what the other person has to say.
One way to break the ice for having more difficult conversations at work is to state directly that you’re open to them. Tony Ticknor, a manager of 15 employees at Irish Titan, uses his one-on-one conversations as an opportunity for more awkward discussions. He shares:
I sit down with people and I say ‘I want these one-on-ones to be awkward.’ I want people to come tell me when something’s hard, or they don’t want to do something, or they’re having a conflict with someone on the team.
To learn more about how Tony uses Officevibe to have more meaningful one-on-ones, read his customer success story.
4. Aim for understanding above consensus
The ultimate goal when addressing a difficult situation isn’t necessarily seeing eye-to-eye, but rather finding a sense of understanding between two people. Sometimes conflict is rooted in misunderstanding, and you want to be sure you’re not missing some vital information. Be empathetic and give your team member space to share their perspective before you offer your own.
In the moment is not always the time to share your policy explanation or feelings. It can be about letting them express themselves, not about giving them information.Brendan Collins, Mental Health Worker
Remember there’s a difference between acknowledgment and agreement; you don’t have to validate an employee’s point of view to make them feel heard. According to Officevibe’s Pulse Survey data,
17% of employees don’t feel that their direct manager cares about their opinion.Officevibe Pulse Survey data
This sentiment has implications beyond the manager-employee relationship — we see a strong correlation between whether employees feel their manager cares about their opinion, and whether they feel they’re part of a team. So listening is very important! Being open enough that people not only feel comfortable to be honest with you, but believe that you care personally, is key to cultivating a supportive, collaborative team environment.
5. Find a solution together
Every one-on-one meeting should wrap up by setting clear action items, and this is especially important when you’re discussing something like a disagreement between colleagues, unmet employee expectations or poor performance, or someone’s mistake. One or both of you may come to the meeting with action items in mind, but take the time to discuss them, build on them, find common ground, and decide on a path forward together. A successful conversation means finding the most productive solution, not being right or proving a point.
Offer help and support where you can: Acting as a team player and contributing to the solution when employees are having a tough time shows leadership, and helps build a stronger, more supportive team.
The most important part of setting action items is following up. Set a talking point for your next one-on-one to revisit your established plan and ensure you’ve both followed through your commitments and achieved the desired outcome. Officevibe’s one-on-one software does this for you, so every meeting drives real results.
Handle difficult conversations at work with confidence
Handling difficult conversations can be challenging, but having these tough talks ultimately leads to growth on your team. By approaching sensitive subjects with empathy and care, you can make an umconfortable discussion productive, and come to a positive outcome.
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