There is a version of a career conversation that most managers will happily have with you, covering how your current work is going and whether you are on track for your next review.
What these often miss, unless you steer it there, is where you actually want to be in the next two years and whether your current role is giving you what you need to get there.
The longer that version of the conversation gets skipped or postponed, the more your career trajectory ends up being shaped by other people’s assumptions about what you want rather than anything you have actually said.
In this post
- Why this conversation tends to get put off
- What to bring into the room
- Reading what your manager does not say
- A pre-meeting checklist you can use
- Making it a habit rather than a one-off
Why this conversation tends to get put off
There is a structural reason and a personal one that explains why this conversation doesn’t always happen.
Structurally, the formal review cycle does the heavy lifting in most organisations, which means there is rarely an obvious prompt to schedule something else. Diaries are busy, and the conversation that should have happened in March has somehow still not happened by November.
The personal reason runs deeper. Asking for time to talk about your career can feel exposing, particularly if you are not yet sure what you want, or if you are worried about signalling something to your manager that you have not fully decided yourself.
So you wait and you tell yourself you will raise it at the next one-to-one, then the one after and before you know it six months pass. Meanwhile your manager has been building a picture of where they think you are heading based on signals they pick up rather than a direct conversation.
What to bring into the room
So instead of putting the conversation off, book a time with your manager to explain what you want and where you want your career to go.
Then once have the meeting scheduled, you need to go in with the right material, which can do a lot of the legwork of the conversation for you.
This includes:
- A short summary of what you have been delivering, particularly anything that shows you operating at a level above your current role or scope
- A working view of where you would like to be in twelve to eighteen months
- Any gaps in experience and the exposure you would need to close them
In addition, it’s important that you have the specific ask of your manager. That might be a project you want to get involved in, an introduction to someone in another part of the business, exposure to a particular client or board paper, or sponsorship for a development programme.
Vague requests get vague responses, and “I want more development” puts the task in your managers hands to figure out how to give you this – since they are busy without a clear ask it may get left to wayside.
The more concrete your ask, the easier it is for your manager to actually do something about it. The career tracking post covers how to keep the kind of running record that supports this preparation, and it is worth having that in place long before you sit down for the conversation.
Reading what your manager does not say
During your conversation, pay attention to what is left unsaid.
If your manager responds enthusiastically to your trajectory but cannot identify a single specific way they are going to help, that tells you that there may not be the growth opportunities you are seeking in your current organisation.
If they redirect the conversation back to your current performance instead of engaging with where you are heading, that is telling you that you are not meeting expectations somewhere, and you need to understand how you change this. Either through improved performance or a better understanding of what’s important to your manager and the business, so you can align your efforts to that work.
The willingness to invest in your development tells you a great deal about whether your manager is going to function as a useful sponsor for the next stage, or whether you will need to look elsewhere within the business for that support.
Research from McKinsey on Women in the Workplace consistently finds that women receive less specific, actionable career advice from their managers than their male peers, even when their performance is rated similarly.
Knowing this makes it easier to recognise when a conversation has been polite but not useful, and to adjust your strategy instead of assuming the absence of specific feedback means everything is on track. The managing up post gives more on how to read and shape this dynamic over time.
A pre-meeting checklist you can use
If you are about to schedule the conversation, run through this list in the fortnight before, then in the meeting, then in the week after.
In the two weeks before the meeting:
- Create a one-page summary of what you have delivered in the last six to twelve months, with measurable impact where possible
- A clear view on the role or scope you are working towards in the next 12 to 18 months
- An honest assessment of the gaps between where you are now and where you want to be
- Two or three specific asks of your manager that would help close those gaps
- A view on the wider context, including team changes, budget timing, or any restructure noise that might affect timing
In the meeting:
- Open with the framing that this is a forward-looking conversation, separate from a review
- Share your view of where you are heading first, then invite theirs
- Get specific commitments before the conversation closes, with a date attached to each
- Agree when you will check in next on progress
In the week after:
- Send a brief written summary of what was discussed and what was agreed, by email
- Add any agreed actions to your own tracking
- Diarise the next conversation, ideally within three months
The point of writing it down afterwards is partly for your own record, and partly so that any commitment your manager made is on the page, not only in their memory of a Wednesday afternoon meeting.
Making it a habit rather than a one-off
A single career conversation, however well prepared, tends not to move very much on its own. What moves things is having a version of this conversation a few times a year, each time with an updated view on what you are working on and where you are heading. Three a year is the rough cadence I would aim for, spaced so they happen outside the formal review process.
This rhythm builds a record in your manager’s mind of someone intentional about her own development, which makes it considerably easier for them to advocate for you when an opportunity comes up internally or a decision is being made about scope, headcount, or promotion. It also lets you make small adjustments before they become large problems.
If a project you were promised has not materialised after six months, that is a conversation to have at the next check-in, well before the end of the year when it has already affected your trajectory. The board of directors post covers how to build a wider network of advisors who can help you read whether things are on track, particularly when your manager’s view and your own start to diverge.
The point is to put this conversation back on the calendar before someone else decides what your next year looks like for you.
Continue Reading
- How To Manage Up: A Practical Guide To Getting Recognised For Your Work Once you have had the conversation, this is how you build the relationship that makes it count
- The #1 Simple Thing You Should Be Doing To Get A Promotion How tracking your achievements gives you the evidence base for every career conversation you will ever have
- Is Your Job Worth It? The Learning vs Earning Framework A framework for working out whether your current role is still giving you what you need
- The 4×6 Method: Your Strategic Roadmap To Career Acceleration How to think clearly about where you are going before you sit down to talk about it with anyone else
- How I Increased My Salary by 75% in 2.5 Years What happened when those career conversations led somewhere, and how to make sure yours do too
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- Coffee Meeting Guide and Conversation Starters ties directly to the one-to-ones and informal relationship-building advice in the post
- Networking Tracker supports the stakeholder mapping and relationship-building sections
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