How To Have a Career Conversation With Your Boss


We can get a little shy when it comes to talking about careers at work. It’s funny when you think about it. We spend up to 80,000 hours in full-time work over our lifetime and yet, all too often, the conversation about what it is that we are doing there causes a few blushes.

We don’t do this in other important relationships. Imagine if you had a romantic relationship but never discussed where it was going or how it was going!

That would be odd right?

As a career navigation coach, I work with individuals and companies in all sorts of professions to help them have the right conversation at the right time. If you choose your time right and are sensitive and skilled, a careers conversation can unlock all sorts of opportunities in your current job and company.

So let me share with you the three secrets to a good quality careers conversation.

1. Understand that the company really wants to keep you

Consider the time, money and energy spent by your employer getting you into your current position. There was the initial ad, the screening, the interview, the contract, the induction, the training, the management and all the bits and bobs from IT, Division Heads and finance to integrate you into the team, personally and professionally. Over the years, you have accumulated expertise and skills in your area. You hold the history of the projects you have managed, problems you have resolved, campaigns you have run and designs you have implemented. You are very useful.

Your company wants to keep you.

Being mindful of this is important because the first barrier to a quality conversation comes from ‘spooking’ your manager. Without you being clear about it, they may go into a panic, thinking you are planning to leave. You can avoid this by beginning the conversation with a thoughtful and clear intent.

“I’d really like the opportunity to discuss how my future might evolve at xxxx. I really want to be able to add more value and to understand how to navigate the great opportunities that exist here.”

Your manager may worry that you want their job. Or that you want to move on and they would miss your expertise. They are only human too.  Yet a good manager is always committed to the nurture and growth of their people and to that person’s hopes and aspirations. They can help you grow if you let them know what these are.

2. Do your self-reflection and your research beforehand

A job is where you utilise your time and expertise to further the goals of the business or organisation. So you need to be able to map both what your skills and aspirations are and what your employer needs from you right now and in the years to come.

Good career conversations require sensitive preparation on both of these fronts.

Knowing your skills and aspirations

The first thing to do is take stock of your journey so far. What elements of your employment and your latest role have you really enjoyed? What would you like to learn more about? Are there problems or challenges you would love to get your teeth into?

Take time to do an inventory of the experiences you want to amplify and do more of and the elements of your role and experience that you might like to leave behind in the next role. Think about what future success might look and feel like for you and be able to describe it in concrete terms.

“Success for me looks like…

In the next few years, I would love to have the opportunity to…

I see that I could add value to what we are doing on….”

The company wants you to contribute as much as you can

Secondly, take time to look at the company priorities. What are the most important activities or trends related to your organisation and your industry? Is it in a growth spurt? Is it under threat? Is the company managing a lot of disruption and change or is it in a steady state? When you understand the priorities of the business you can bring this insight into your development plan and career conversation.

This sensitivity means the conversation is a win/win. How can the company get value from me and I get satisfaction from the work I do here?

Take time to look around. Are there parts of the company that hold appeal? Perhaps you would like to move sideways, not just upwards? Invest some time to research what is out there. It doesn’t have to be a current vacancy. Your research could lead you to a possibility or a relationship or a new area of work that, over time, you would like to explore.

3. Pick the right time and place

Timing is everything. The right time for a career conversation is a private, ringfenced meeting, where you have space to talk at ease. You want to know you are heard, that your manager is receptive and eager to help.

So don’t dump the conversation on them without booking the time in. Don’t corner your manager at the coffee urn or drop in through their open door and demand they focus on your next steps! Ask if you can schedule a time to get their input on your career direction and next steps. Say you would like time to have an informal discussion. This could be as part of a performance conversation, but I think it is ideal if it is separate.

You might like to ask them to share their own career experience and stories. You can learn a lot from the journey of others. Their track record and history may give you valuable insight on how to navigate the internal recruitment system.

Remember, at the end of the day, you own your career. Your manager is there to support you into getting better and growing as a person. To make the most of this relationship, you need to be open about who you are, what you want and how you see your future. You need to play your part in knowing your options and caring about how you might fit into the company going forward. By taking this time and care, a career conversation with your manager can be exceptionally rewarding.

N.B. I know that not everyone has a manager they trust and have an affinity with. The same approach applies to discussing career moves with internal mobility, HR or a different division in the business.

What career conversation do you want to have and what’s stopping you?

About the Author

Erica Sosna is the career coach for the hero in you. She is the author of Your Life Plan and helps professionals worldwide to make career transitions without taking a pay cut. Find out more at



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