A one-on-one meeting with a – subjectively perceived – difficult employee can feel like a game of chess: every move needs to be well thought out, otherwise you end up on the defensive.
No one looks forward to such a challenging one-on-one meeting. But these conversations have the potential to create real breakthroughs. Instead of avoiding conflict, leaders should see it as an opportunity: for clarity, growth and better collaboration – even with the most difficult employees.
With the right strategy – empathy, smart questions and clear expectations – you can conduct the conversation in such a way that both of you win in the end.
Whether in a digital or virtual one-on-one meeting, 1-to-1 meetings offer space for feedback and therefore personal development, which is essential in today's working world. And in this article, I'll give you some good questions that you can use in your one-on-one meeting to have the most productive conversation possible.
First of all: If you're still unsure about what good one-on-one meetings look like, take a look at our guide: The guide with 6 tips for successful one-on-one meetings.
Let's start with seven helpful and practical tips for your appraisal interview.
7 Practical Tips for One-on-One Conversations with difficult Employees
1. "Sit differently – literally."
💡 Tip: Change the seating arrangement. Instead of sitting face-to-face (which often has a confrontational effect), try a 90-degree position or a conversation while walking ("walk & talk"). This relaxes the atmosphere and takes the pressure off.
🎯 Why? People feel less attacked if they are not sitting directly "opposite" each other. This makes the conversation more relaxed.
2. "Say less, ask more – but differently."
💡 Tip: Ask questions that arouse curiosity. Instead of "Why didn't you do that?", ask "How would you solve the problem if you had a completely free hand?"
🎯 Why? Difficult employees often block things out or go on the defensive. By asking open, forward-looking questions, you give them the opportunity to actively develop solutions themselves.
3. "Turn expectations into a co-design project."
💡 Tip: Instead of just setting expectations, ask the employee to formulate their own expectations of the collaboration. "How would you ideally organize our collaboration?"
🎯 Why? When people formulate their own expectations, they automatically take on more responsibility – and find it harder to refuse completely.
4. "Switch from problem mode to possibility mode."
💡 Tip: Turn negative situations into a challenge: "Suppose you were your own consultant – what advice would you give yourself?"
🎯 Why? Difficult employees often resist suggestions from others. By giving them a new perspective, you turn the conversation from problems to solutions.
5 "Talk less, let people write more."
💡 Tip: If conversations are emotionally charged, ask the employee to summarize their point of view in writing – either before or after the meeting.
🎯 Why? This helps to avoid impulsive reactions and forces you to structure yourself more clearly. What you have written can also serve as a common reference later on.
6. "Listen to the nuances – not just the words."
💡 Tip: Pay attention to body language, tone of voice and small reactions. Sometimes there is more information in a shrug of the shoulders or a short pause than in the actual words. Instead of interpreting directly, ask: "I have the feeling there's more – am I right?"
🎯 Why? Difficult employees don't always say what they think directly. But when they realize that you are aware of their non-verbal signals, this often opens up new levels of conversation.
7. "Say what you are NOT going to do."
💡 Tip: Some employees are afraid of criticism or negative consequences. Actively take this fear out of the room: "Don't worry, this isn't about making you look bad. I want to understand what's bothering you."
🎯 Why? This creates psychological security and lowers defensiveness.
Basically, this applies to both you and the employee: Have realistic expectations for the interview and a realistic goal. You can also set out this goal at the beginning of the interview. For example, it can be quite simple:
- Transparent goal at the beginning of the conversationUnfortunately, we will not be able to fulfill your request or resolve the conflict in one step. My goal for this conversation is first of all to understand the situation from your perspective.
This should give you some important basics for your one-on-one meeting with your rather difficult employee. Let's move on to the next step.
A template for one-on-one meetings with difficult employees
The fact that you clicked on this article tells me that you want something like a guide for your one-on-one conversation with a difficult coworker.
That's why you'll find a template here that should accompany such a conversation well. At the same time, the exact format will of course depend very much on your objective –, so please take the tips above into account when designing your conversation with your Direct Report.
You can save the template as a Doc under the actual template, but alternatively also as a PDF or Word document. Simply click on the "Plus" toggle.
🤝 Getting started with empathy
- How are you doing? Is there anything that is on your mind that you would like to share?
- I want this to be an open and constructive discussion.
🗣️ Discussion of concerns
- I would like to talk about [specific topic]. Can you share your perspective on this?
- What do you think contributes to this situation?
- How do you think [team member X] sees this situation?
🔍 Explore solutions
- I believe in small, iterative improvements. How do you think we can tackle this problem together? What could be a first step towards a better status quo?
- Are there any tools, support or other adjustments that could help to improve the situation?
📜 Set expectations
- How can I best support you in achieving the desired changes?
- That's what I need from you in the future.
- Let's set a plan and a timeline to address these concerns.
- Summary: When will we meet again?
- Summary: Who is responsible for which tasks?
🔚 Conclusion
- I appreciate your willingness to support us with improvements.
- What else should I have asked in this conversation?
- Is there anything else that is on your mind?
Download template as printable PDF
Preview: PDF template
If you would like to download the above sample or template as a printable PDF, simply click on the image below. You can then edit or print the template as you wish.
Click image to open ⬇️
Download template as Word document
Preview: One-to-One Meeting Microsoft Word Template
If you would like to download the above sample template as a Word document, simply click on the image below. You can then edit or print the template as you wish.
Click image to open ⬇️
Download template as Google Docs
Preview: Google Docs one-to-one meeting template
If you want to edit the above sample template as Google Docs, simply click on the image below. You can then edit the template flexibly by copying it.
🚸 Attention: You must be logged in to Google to be able to copy (and thus edit) the template in the menu at the top left.
Click image to open ⬇️
By the way, don't be fooled by the agenda: If your difficult coworker is having a torrent of words, you should tend to let him or her finish and, of course, be prepared to throw your prepared questions overboard.
Although the following picture applies to healthy teams – it does not apply to your one-on-one conversation. Your aim should be to ask questions and let your difficult coworker take the majority of the speaking time.
12 helpful questions for one-on-one meetings with difficult employees
If you are a supervisor in the middle of a battle of words, you may find it difficult to ask good questions.
But of course there are also questions, some of which I would like to mention here.
As you may notice, many of them have one goal: to understand the employee's perspective – and broaden it at the same time.
💬 1 to 1 questions for the course of the meeting with employees
- Thank you for sharing this with me. Let me think about it and get back to you, okay?
- Do I have permission to help you with this?
- How willing are you to do what is necessary to change this situation?
- How much control do you have over this situation?
- How do you know that the problem you think you have is actually a problem – how does it show?
- What would you say to a friend who has similar challenges to yours?
- What would be an alternative way of looking at things?
- What would you do if you didn't reach your goal?
- Do you want to solve your problem now? Right now or this month?
- What advice would the wisest person you know give you in your current situation?
- What have you already tried to solve the challenge?
- That's my biggest takeaway from today's session: [...]. What is yours?
A 1-to-1 template for preventive work
In addition to these questions, another type of template can also be helpful in building a long-term relationship of trust with your employee. It is not suitable for the interview itself, but all the more so as a preventative measure. I would like to introduce you to a special technique for this.
After talking to around 100 managers over the last few months, I have noticed a pattern.
Many bosses occasionally incorporate small surveys into their one-to-one meetings. This means that they simply go through a few questions in a relaxed manner and ask the employee a) whether he or she agrees with a statement (for example from 1 to 7) and then b) why he or she answered in this way.
They expect the following from these micro-surveys in 1:1s:
- More variety and engagement in 1-to-1 conversations
- Taking on new perspectives
- Measurability of (soft) KPIs such as satisfaction over time
And of course you can also use this idea for your one-on-one meetings with difficult employees. I have put together four statements here that focus on you: Your leadership quality. Because this obviously has a major influence on how your employees behave.
You can also download this template as a doc, but even better is the following: In our one-on-one meeting software, we have an integrated tool that visualizes the results over time as a metric and gives you tips with an AI assistant – feel free to take a look without logging in using the button below.
⁉️ Mood check (agreement from 1-7): Leadership quality
- "I'm really happy with my team leader." #JobSatisfaction
- "My team leader regularly zooms out to see the higher-level Team goalsexplain the strategy and the vision."
- "My team leader questions things in a constructive way." #Feedback #Leadership
- "My team leader sets an example of what he expects from us as a team." #Leadership
This is what this survey looks like in Echometer:
Download template as printable PDF
Preview: PDF template
If you would like to download the above sample or template as a printable PDF, simply click on the image below. You can then edit or print the template as you wish.
Click image to open ⬇️
Download template as Word document
Preview: One-to-One Meeting Microsoft Word Template
If you would like to download the above sample template as a Word document, simply click on the image below. You can then edit or print the template as you wish.
Click image to open ⬇️
Download template as Google Docs
Preview: Google Docs one-to-one meeting template
If you want to edit the above sample template as Google Docs, simply click on the image below. You can then edit the template flexibly by copying it.
🚸 Attention: You must be logged in to Google to be able to copy (and thus edit) the template in the menu at the top left.
Click image to open ⬇️
Download template as Google Sheets
Preview: Google Sheets one-to-one meeting template
If you would like a template for weekly check-ins as an editable Google Sheet, simply click on the image below. You can then edit the template flexibly and print it out, for example.
🚸 Attention: You must be logged in to Google to be able to copy (and thus edit) the template in the menu at the top left.
Click image to open ⬇️
Download template as Excel or XLXS
Preview: Excel or XLSX template
If you would like to download the above template as a printable or editable XLSX, simply click on the image below. Then you can flexibly edit or print the template.
Click image to open ⬇️
And, can you hardly wait to ask these questions in your one-on-one meeting? Very good, I'm glad.
If you would like more creative input, I can recommend our corresponding article: 129 Good One-on-One Meeting Questions (by a Psychologist).
15 more Templates for One-on-One Meetings (as Doc, PDF etc.)
You've probably already guessed it. Of course, there are many more templates for one-on-one meetings that you will need sooner or later.
For example, I talk about templates for your one-on-one meeting about salary, your conversation with a difficult employee or with a completely new employee.
We have additional templates for all of these use cases, which you can find in this article: 1:1 meetings: 15 proven templates to edit (free).
Conclusion: See difficult conversations as an opportunity
Once you've had your difficult meeting, it's highly likely that you'll be relieved. And if your meeting is successful, you may even develop something like hope. The questions here should help you. I wish you every success!
But you must not forget one piece of wisdom: There are countless questions you can ask – but the most important thing is that you tailor the interview to your employee.
Our AI meeting assistant for one-on-one meetings can also help you if you regularly hold one-on-one meetings with your team members. If you would like to find out more, take a look at our website: The best 1-on-1 meeting software.
“In my 1:1 meetings, it's annoying to take notes while trying to focus on the employee.”
"Yes, 1:1 meetings with my employees should be my most important meeting – but I need more guidance for that."
"I don't know how I can develop my employees in 1:1 meetings over a longer period of time."
"I don't have time to prepare 1:1 meetings and am therefore unhappy with the results."
