How to have valuable career growth conversations

Introduction

Most work conversations focus on the immediate: what is being built, what is blocked, and what needs to happen next.

A growth conversation is different.

It is a deliberate step back from day-to-day work to look at how someone is doing, what they have achieved, and where they want to go next. It creates space to talk about progress, direction, and anything that might be getting in the way.

These conversations are simple in theory, but in practice they are often unfocused or inconsistent.

This article outlines a set of questions you can use to run a growth conversation end-to-end, along with the reasoning behind each one so you know what to listen for and where to go deeper.

Question 1: How are you doing? How is work?

This is a general-purpose opening, but it sets the tone for the entire conversation.

You are giving the individual space to talk about their current experience in their own words. There should not be many surprises if you are running regular 1:1s, but occasionally there will be. When you are surprised, it is worth reflecting on why and how you might adjust your 1:1s to prevent this in the future.

Spend time listening. Ask clarifying questions. Do not rush this.

Question 2: How has the last six months gone for you?

This builds on the first question by introducing reflection over time.

You are looking to understand how things have evolved:

• What has been going well?
• What has not?
• Has anything changed meaningfully?

If the first question already covered this in enough depth, you can move quickly here. Otherwise, this is an opportunity to go deeper.

Question 3: Can you list 3 achievements that you are most proud of from the past 6 months to a year?

This question helps you understand both what someone has done and what they value.

You are looking for:

• whether they feel a sense of progress or accomplishment
• what kinds of work they take pride in
• whether there are patterns in the types of achievements they highlight

If someone struggles to name three, that is worth paying attention to. It often indicates a lack of fulfillment or a disconnect from their work.

Patterns here can also inform the rest of the conversation. If their achievements and their future goals do not align, that is something to explore.

Question 4: Describe your current role?

This is about understanding how the individual perceives their role today.

You are looking for:

• how they describe their responsibilities
• what they believe they are accountable for
• how they think they are performing

This gives you a baseline for comparison when you talk about the future. It can also highlight gaps between your expectations and theirs.

Question 5: What do you want your role to look like in 6 months?

Six months is close enough to be concrete, but far enough to allow for change.

You are not looking for a prediction of what will happen. You are looking for what they want to happen. It often helps to frame this as the ideal version of the next six months, not just a continuation of the current trajectory.

For some people, you may need to help them clarify or articulate their thinking. For others, it is better to listen and avoid steering too much.

Question 6: What do you want your role to look like in 2 years?

Two years allows for more ambitious thinking.

You are trying to understand:

• what direction they want to grow in
• how they think about their longer-term career
• whether their goals are coherent with what they are doing today

Less experienced individuals often need more guidance here. More experienced individuals typically have clearer ideas, but may still benefit from discussing possible paths.

This is a good time to describe potential routes, such as a more technical path or a more leadership-oriented one. It is also a good point to link back to the achievements they chose earlier. A career should become an achievement engine over time, and part of the conversation is helping the individual build a path that aligns with the things they value.

Question 7: If you were to leave, what would be the #1 reason to leave?

This question helps surface concerns that might not come up otherwise. Exit interviews are too late to fix issues. This gives you a hook to make changes before it is too late.

Pay attention to how quickly and clearly they answer:

• immediate, specific answers usually indicate something important is already on their mind
• conditional answers such as “if X does not change” point to emerging concerns
• more thoughtful or hesitant answers may indicate lower urgency, but are still useful

You are not actually trying to predict whether they will leave. You are trying to understand what is causing pain and whether you can alleviate it before it hardens into a decision.

Question 8: If you had an infinite amount of budget and my boss’s job, what would you change?

The goal here is to remove constraints and encourage honest feedback.

You are trying to understand:

• what frustrates them
• what they believe could be improved
• what they would change if they had the ability to do so

You can prompt based on earlier parts of the conversation if needed. Often, the answers are more practical than the question suggests. If you hear similar ideas from multiple people, they are worth taking seriously.

Question 9: What haven’t we talked about that we should have talked about?

This ensures the individual has space to raise anything important that has not come up.

Common topics include:

• compensation
• promotions
• specific frustrations

Be prepared to engage with these where appropriate.

What’s next?

Once the conversation is complete, there are a few responsibilities.

Ensure that the issues raised are actioned or at least discussed further. The value of the conversation drops quickly if nothing happens afterward.

Look for patterns across multiple conversations. If the same challenges appear repeatedly, they are unlikely to be isolated issues.

Share your notes. Provide the individual with a summary of what was discussed, and keep a record for future conversations. This makes follow-ups more meaningful and helps track progress over time.

These conversations are simple, but they require attention and consistency to be effective.

Run them fully. Listen carefully. Act on what you hear.