Employee development conversations: 40+ questions and examples

One-to-ones held every other week reduce the risk of burnout by 84%, according to a Forbes survey of 20,000 employees. Yet in many Swedish organisations, the formal development conversation between manager and employee (in Sweden, the medarbetarsamtal) still happens once a year, from a template nobody has looked at since the last time. The gap between those two realities is where engagement quietly leaks away.

The quality of a development conversation comes down to the questions you ask, and how prepared both sides are. This article gives you a practical bank of questions: more than 40 concrete questions sorted by conversation type, an example of what a good exchange sounds like, and a preparation checklist for both manager and employee.

What is a development conversation, and why the questions matter

A development conversation is a structured, recurring one-to-one conversation between a manager and an employee, covering the work situation, wellbeing, performance, development and what the employee needs from their manager. It is not a status update on tasks, and it is not a salary negotiation, those are separate conversations with separate rules.

The evidence for doing these conversations well, and often, is unambiguous. According to the research summarised in our guide to the different types of development conversation:

• Only 51% of employees say their employer listens to them well.
• 24% of employees would leave an employer that does not give them sufficient feedback.
• 68% of employees who receive regular feedback say they are satisfied with their workplace.
• 94% of employees prefer real-time feedback from their manager, according to a Wakefield Research study, and over half of office workers want performance conversations at least monthly.

In other words: the annual ritual is out of step with what employees actually want. A better rhythm is quarterly formal conversations plus a short check-in every one to two weeks. The question bank below covers both.

Before the conversation: a preparation checklist

A development conversation fails or succeeds before it starts. Both sides should prepare, and both should know the agenda in advance. We cover preparation in more depth in our article on preparing for a development conversation, but here is the short version.

For the manager

1. Book the conversation at least a week ahead and share the themes you want to cover. Surprises kill honesty.
2. Review what was agreed last time. Nothing signals "this doesn't matter" like forgotten commitments.
3. Look at whatever data you have, engagement or pulse survey results, goal progress, recent feedback, so the conversation starts from evidence, not memory.
4. Choose five to eight questions from the bank below. Depth beats coverage.
5. Plan to spend most of the conversation listening, not talking. The conversation belongs to the employee.

For the employee

1. Write down two or three things that have gone well since last time, and why.
2. Note one thing that is making work harder than it needs to be.
3. Think about where you want to be in one to two years, even a rough direction helps.
4. Prepare one piece of feedback for your manager. Good managers ask for it; great employees bring it anyway.

40+ questions by conversation type

Different conversations need different questions. Below, the bank is sorted by the four themes most development conversations cover: development, goals, wellbeing and career, plus the short recurring check-in.

Development and performance (10 questions)

• Which results from the past quarter are you most proud of, and why?
• Which goals did you reach, and which did you not? What made the difference?
• What has been your biggest learning since we last spoke?
• Where do you feel you are growing fastest right now?
• Which parts of your role feel too easy? Which feel too hard?
• What skill would make the biggest difference to your work if you developed it this year?
• What kind of feedback do you get too little of?
• What can I do better as your manager to help you reach your goals?
• What do you need from me that you are not getting today?
• If you could change one thing about how we work together, what would it be?

Note the last three: asking for feedback on your own leadership is not optional. Research cited in our conversation-types guide shows employee engagement increases dramatically, by as much as 1,250%, when organisations use active listening methods, and listening starts with the manager inviting critique.

Goal conversations: goals and direction (8 questions)

• Do you understand how your goals connect to the team's and the organisation's goals? Where is the link unclear?
• Which of your current goals feels most meaningful to you? Which feels least?
• What bottlenecks are preventing you from reaching your goals?
• What resources, tools or decisions do you need that you don't have?
• If we could only achieve one of your goals this quarter, which should it be?
• What would "exceeding expectations" look like in your role, in your own words?
• Which of your goals should we adjust, given what has changed since we set them?
• How will we both know, concretely, that you have succeeded?

Research published in the Journal of Applied Psychology, referenced in our guide, shows employees perform better when they understand the significance of their work, which is why the first two questions on this list matter more than the goal itself.

Wellbeing and work environment (10 questions)

• On a scale of one to ten, how are you doing at work right now? What would move that number up one point?
• What gives you energy in your work at the moment? What drains it?
• How is your workload, sustainable, tight, or too much? For how long has it been that way?
• When did you last feel genuinely proud at work?
• Is there anything in the team dynamic that makes your job harder?
• Do you feel you can raise problems openly here? What would make it easier?
• How well does your work fit with the rest of your life right now?
• Is there anything happening outside work that you would like me to be aware of?
• What is one thing I might not know that I probably should?
• What are we not talking about that we should be?

Career conversations: career and future (8 questions)

• Where would you like to be in two years, role, responsibility, or type of work?
• Which parts of your current job would you like more of? Which less?
• Is there anyone in the organisation whose role or path interests you?
• What experience are you missing to take the next step?
• Would you rather deepen your expertise or broaden your responsibility?
• What would make you stay here for the next three years? What might make you leave?
• Is there a project or assignment you would love to try, even outside your role?
• What should we do in the next six months to move you towards where you want to be?

Check-ins: the recurring conversation (5 questions)

• Tell me about last week, what stands out?
• What are your priorities for the coming week?
• Is anything blocking you that I can remove?
• How are you doing, honestly?
• Is there anything you want to put on the agenda for our next longer conversation?

An example: what a good exchange sounds like

Questions are only half the craft; the follow-up is the other half. Compare a typical exchange with a better one. The weak version: "How's your workload?", "Fine, a bit busy.", "Good, let's move on." Nothing was learned. The stronger version digs one level deeper:

Manager: How is your workload, sustainable, tight, or too much? Employee: Tight, but manageable. Manager: How long has it been tight? Employee: Since March, honestly. Manager: What is the one thing that, if we removed it, would make the biggest difference? Employee: The weekly reporting. It takes half a day and I'm not sure anyone reads it. Manager: Let me find out who actually uses it. If nobody does, we cut it. I'll come back to you by Friday.

Three follow-up questions, one concrete commitment, one deadline. That is what turns a conversation into change, and it is why every development conversation should end with the same closing question: "What have we agreed, and who does what by when?"

One annual conversation is not enough

Even a brilliant annual development conversation cannot compensate for eleven silent months. Problems with workload, team friction or motivation build over weeks, not years, and by the time the annual conversation arrives, the employee may already be halfway out the door. That is the case we make in why annual development talks should be replaced with regular check-ins.

The practical model is a layered one:

1. Continuous listening: short, frequent pulse measurements that show how each team is actually doing between conversations.
2. Biweekly check-ins: a short, focused conversation using the five check-in questions above.
3. Quarterly development conversation: a deeper conversation drawing on the development, goal, wellbeing and career questions.

Pulse data and conversations reinforce each other. If the temperature on workload drops in the survey data, the manager knows to open the next check-in with the wellbeing questions, instead of discovering the problem months later. This is where a platform like Winningtemp helps: not by replacing the conversation, but by telling managers which conversation to have, with whom, and when.

What to do on Monday morning

• Pick your rhythm: a quarterly development conversation plus a biweekly check-in. Put the next three in the calendar today.
• Choose five to eight questions from the bank above for your next conversation, and send the themes to the employee in advance.
• Ask for feedback on yourself in every conversation, "what can I do better to help you succeed?" is the single highest-value question on this page.
• End with commitments: what was agreed, who does what, by when. Review them at the start of the next conversation.
• Add continuous listening so the data between conversations tells you where to focus, because the development conversation should confirm what you already sense, not surprise you.