Essy's Essentials

The Working Life Edit

How to Have a Career Development Conversation With Your Manager

How to ask for, prepare and follow up a career development conversation with your manager: what to say, which questions to ask and how to agree concrete next steps.

13 min read

A white trolley beside Esther’s desk holds wrapping paper, notebooks and other supplies.

In short

To prepare for a career development conversation with your manager, decide what you would like to explore, identify your strengths and one or two development areas, collect examples of your work, bring specific questions and ask for opportunities to practise. During the conversation, agree what you will do, what support your manager can offer and when you will review progress.

You do not need to wait for your annual review to talk about where you want to grow. Here is how to prepare a practical conversation about your future, ask for useful opportunities and leave with something more than encouragement.

There is a question I like asking people I manage: what do you actually want from your career? It sounds obvious, doesn’t it? Yet it is remarkably easy to go through a busy working year without stopping to ask it properly.

You do your job. You deal with the urgent things. You attend the meetings. The calendar fills up. And then, suddenly, your next formal review appears and you are expected to produce an answer about your future on the spot.

I don’t think career development should depend on one annual appointment. And I don’t think a conversation about your ambitions should automatically turn into a discussion about a promotion, a salary increase or the things you have done wrong.

As a manager, I want to understand what somebody is interested in, where they feel strong, what they would like to learn and what they are willing to try. That gives us a much better foundation for deciding what comes next. If you are the one preparing to speak with your manager, here is how I would approach it.

What is a career development conversation?

A career development conversation is a discussion about your future direction at work: the skills, experiences and opportunities you want to develop, and the support that could help you get there.

It is different from a formal performance review. A review generally looks at the responsibilities and expectations of your current role (I cover that in how to prepare for a performance review). A career conversation is more exploratory. It might include promotion ambitions, but it can also be about deepening your expertise, changing specialisms, gaining confidence in a particular task or discovering whether a different kind of work suits you.

You do not have to be unhappy in your job to have one. And you certainly do not need a fully formed five-year plan.

1. Ask for the conversation rather than waiting to be noticed

You are allowed to bring up your own development. If your manager has not scheduled a dedicated career conversation, ask for one. Be clear that you want to discuss growth and future opportunities, rather than spending the meeting on urgent operational issues.

You could write: “I’d like to spend some time discussing my development and the direction I could grow in. Could we schedule half an hour to talk about possible opportunities and what I should work on next?”

That is enough. You do not need an elaborate introduction or a dramatic announcement that your career has reached a crossroads.

If you have a regular one-to-one, you can propose putting development on the agenda periodically. If your organisation uses a formal development process, work within it, but do not assume that is your only opportunity to talk.

2. Decide what kind of growth you mean

Before you meet, think about what you actually want. This is where I would begin if I were sitting opposite you as your manager.

Do you want to become more knowledgeable in your current field? Would you enjoy leading a project? Are you curious about moving into a different role? Do you want to become a manager, or are you quite sure that you do not? All of those are valid directions.

Try preparing short answers to these questions:

  • What work do I most enjoy at the moment?
  • What parts of my job would I like to do more often?
  • Where do I want to feel more capable?
  • What kind of responsibility would interest me?
  • What do I want to understand about a possible future role?

If your answer is “I’m not sure yet”, say that. Then choose something to explore. A good development conversation can be about finding direction rather than confirming one. If you would like to turn the answers into something you can keep, how to create a career development plan walks through it step by step.

3. Bring examples, not a sales presentation

You do not need a forty-slide presentation showing why you deserve to be the next senior manager. Bring two or three useful examples of your work. Choose moments that show what you enjoy, what you have contributed or what you want to develop.

Maybe you helped organise an improvement, took responsibility when something changed, supported a colleague or discovered that you enjoy the analytical part of a project. Be specific about your part. Recognise contributions from other people. If the outcome was mixed, explain what you learnt.

One example might sound like this: “I enjoyed bringing people together to solve the handover problem. I liked understanding the different perspectives and turning them into a workable approach. I’d be interested in doing more improvement work, although I know I still need to practise influencing a wider group.” This is an illustrative example, not a description of a specific employee.

That gives your manager something useful to respond to: a real interest, a strength and a development need.

4. Ask what is required, not simply whether you are good enough

If you are interested in a particular next step, ask what it involves. What skills matter? What experience would make you a credible candidate? Which parts of the role are more demanding than they appear? Where does your manager see strengths and gaps?

One of the most useful questions you can ask is: “When you look at the kind of role I’m interested in, what would you need to see me demonstrate before I’d be ready to apply?” It moves the conversation away from vague encouragement and towards something you can practise.

Your manager might not have all the answers. That is fine. Perhaps they can introduce you to someone who does the role, suggest a colleague to shadow or help you find the correct job profile.

Do not confuse an honest answer about a gap with a rejection of your ambition. If a skill genuinely matters, knowing about it gives you the chance to develop it.

5. Talk about confidence without making it the whole problem

A person can be good at something and still find it uncomfortable. Perhaps you want to speak up more in meetings, give presentations or handle difficult conversations. As a manager, I would want to understand what makes that difficult and which opportunities would help you improve.

But I would not make “be more confident” the entire development plan. Confidence is easier to work with when we connect it to an actual behaviour. For example: “I’d like to contribute more often in larger meetings. Could I prepare and present one short recommendation at our next session, and could we review afterwards what worked?” That gives you practice, a clear action and feedback.

Coaching or training may help, and sometimes external learning is appropriate. But do not assume that buying a course is the same as giving somebody a chance to use what they learn.

Also, development should not mean forcing everyone into the same personality. Someone can lead through clear writing, technical judgement, thoughtful listening or well-prepared decisions as well as through confident public speaking.

6. Make a specific request for support

A conversation that ends with “keep doing what you’re doing” can feel reassuring. It may also leave you with no clear next step.

Before you go into the meeting, identify a request that could realistically help you develop. Perhaps you need a chance to lead a small project, access to a colleague with specialist expertise, time to attend training, feedback after a meeting or an introduction to another team. The table below gives a few examples.

A manager may have to consider workload, budgets and available opportunities. Ask for an alternative if your first idea is not possible. And be prepared for your part of the commitment: if an opportunity is offered, you need to engage with it, prepare and follow through.

What to ask for, depending on what you want

Examples of a specific support request for different development aims.
You could ask…
Explore a different functionCould I speak to someone who works in that area about their day-to-day responsibilities?
Get better at presentingCould I present a short update and ask you for feedback afterwards?
Develop technical knowledgeIs there a project or experienced colleague I could learn from?
Prepare for more responsibilityWhat would be an appropriate small stretch assignment to start with?
Improve stakeholder managementCould we discuss an upcoming situation where I can practise this with support?

7. If you want a promotion, say so, but ask the next question too

It is perfectly reasonable to say you are interested in progression. You do not need to disguise ambition as a vague wish to take on “more challenges”.

But do not stop at “I’d like a promotion.” Ask which responsibilities the next role involves, how vacancies are filled, how readiness is evaluated and what evidence would make your application stronger.

I think it is important for managers to be candid here. They can support someone’s development and still be unable to guarantee a future vacancy or selection decision. An encouraging conversation should not quietly become an implied promise.

If there is no opportunity right now, you can still develop transferable skills, meet people working in the area and explore where else the work might exist. And if you eventually conclude that another employer offers a better fit, finding that out through thoughtful conversations is better than staying frustrated indefinitely.

8. Leave with two-sided commitments

For me, this is one of the most important parts. A useful career development conversation should finish with clarity about what happens next. Write down:

  • Your action: something you will try or prepare.
  • Your manager’s action: feedback, an introduction, time, information or an opportunity they have agreed to provide.
  • The review date: when you will discuss what happened and decide the next step.

The example below is deliberately small. Career development is rarely the result of one enormous leap. More often, it is a series of opportunities where you find out what you can do, what you enjoy and what you still want to learn. To keep those agreements visible afterwards, you could create a simple career development plan.

Example: a small set of agreements

An illustrative set of agreements after a career conversation: what, who and when.
OwnerWhen
Draft an improvement proposalEmployeeBefore next month’s meeting
Review the proposal and arrange presentation timeManagerThe following week
Discuss feedback and next practice opportunityBothAt the next development check-in

Questions to ask your manager about career development

You do not need to ask every question. Choose the ones relevant to your situation.

When exploring direction: “Which strengths do you see me using most effectively?” “Where do you think I could contribute more?” “What type of work might suit the things I enjoy?”

When interested in a particular role: “What would I need to demonstrate to be a credible candidate?” “Which skills or experiences am I currently missing?” “Who could help me understand the role better?”

When asking for development opportunities: “Is there a project where I could practise this skill?” “What support could be available?” “Could we agree how to review the experience afterwards?”

When the opportunities are limited: “What is realistically possible in the next three months?” “Are there other ways to gain the relevant experience?” “When would it make sense to review this again?”

What if the conversation does not go as you hoped?

Perhaps your manager sees a development gap you disagree with. Ask for a clear example and explain the evidence behind your own view. You do not have to agree immediately, but understanding the expectation is useful.

Perhaps the team is under pressure and there is no space for a new project. Discuss when the situation might change or whether a smaller opportunity is possible.

Perhaps your manager does not seem particularly interested. You can still ask for a specific follow-up or seek information through appropriate internal career or learning channels.

I would not treat one disappointing conversation as proof that your entire future is closed. But I would pay attention to whether clear requests and agreed actions are repeatedly left unsupported. The purpose is to learn what options exist, not to win a debate in a single meeting.

What your manager should bring to the conversation

Because I write from a manager’s perspective, I think it would be unfair to place all responsibility on the employee.

A manager should make time to listen without deciding the answer in advance. They should help clarify expectations and distinguish what is possible now from what remains uncertain. They should offer honest feedback, consider access to learning and experience, and follow through on their own commitments.

They should also avoid assuming that everyone wants the same career. More senior does not automatically mean better. An excellent specialist should not need to become a manager to be taken seriously. And when someone chooses a development goal, the manager should help make room for practising it, where the realities of the job allow.

The employee owns their learning. The manager is accountable for providing appropriate clarity and support. Both matter.

A five-minute preparation sheet

If you are preparing for a meeting this week, write down these answers on a single page:

  • What I want: one sentence describing a direction or area to explore.
  • What I bring: two strengths supported by real examples.
  • What I need to learn: one or two skills or experiences.
  • What I would like to try: one practical development opportunity.
  • What I want to ask: two specific questions for my manager.
  • What we will agree: my action, their support and a date to revisit it.

You can take that page into the meeting. You do not need a sophisticated template.

What I hope you leave with

I want people to know what they are good at, what is expected of them and where there is room to grow. I also want them to know that they can ask for opportunities rather than hoping somebody will spot their ambition from across the office.

As a manager, it gives me genuine pleasure to see someone develop and eventually make a space their own. But the most useful conversations are the ones where that wish becomes something practical.

One clear direction. One opportunity to practise. Honest feedback. A next conversation. That is how a career development discussion becomes more than a pleasant half-hour.

Pair It With

Frequently Asked Questions

How do I ask my manager for a career development conversation?

Ask for a dedicated half-hour to discuss your interests, development goals and potential opportunities. Explain that you want to focus on future growth rather than the day’s operational tasks.

What should I say in a career development meeting?

Explain the work you enjoy, where you would like to grow, a few examples of your current strengths and what you want to practise next. Ask for honest feedback and a specific next opportunity.

How do I discuss career goals if I don’t know what I want?

Be open about exploring. Ask what strengths your manager sees and whether you can learn about other roles, shadow a colleague or take part in a small project before choosing a longer-term direction.

How do I tell my manager I want a promotion?

Say clearly that you are interested in progressing, then ask about the role’s requirements, readiness criteria, available vacancies and opportunities to build relevant evidence. Development support is not a guarantee of promotion.

What questions should I ask my manager about career growth?

Ask which strengths they see, what skills would matter for a role you are exploring, where you can gain practical experience, what support is possible and how you will review your progress together.

Is a career development meeting the same as a performance review?

No. Performance reviews typically focus on current responsibilities and results. Career development meetings explore future direction, skills, experiences and opportunities. You can connect them, but the purpose of each is different.

What if my manager says there are no opportunities?

Ask which constraints apply and whether there are smaller or alternative opportunities, such as shadowing, mentoring or cross-team learning. Agree when to revisit the issue and assess your wider options if growth remains unavailable.

Who should follow up after a career conversation?

Both people. The employee should follow through on agreed actions and learning opportunities; the manager should deliver the support or feedback they committed to. Put a review date in the calendar.

About Esther

Written from Esther’s perspective as a practising manager and founder of Essy’s Essentials. The sample questions and examples are general guidance. Follow your employer’s policies for formal reviews, promotion, training and confidential information.

Related reading: How to Prepare for a Performance Review: A Manager’s Perspective · Career Comparison: What I Can Learn From Someone Else · Ambition and Staying Myself

Further reading: CIPD: Coaching and mentoring · CIPD: Learning needs analysis · Prospects: How to choose a career

Esther, founder of Essy's Essentials

Written by Esther

Esther is a photographer and storyteller, and the founder of Essy's Essentials - a seasonal home for stories, rituals, recipes and everyday luxuries.

More about Esther →