Discussing your career path with your manager is vital for your career, and something that many people avoid because they don’t know how to handle it and fear it might put them under a bad light.

The most common fear is “If I mention something to my boss about a promotion that will be a difficult conversation“. And it’s partially true in many cases, but let me tell you how to structure this conversation and transform it in an opportunity for you.

At Anthropos we believe in career paths and transparency for day 1: we simply believe it’s a tremendous advantage first and foremost for the company. People are excited by that because they see a path and they do their best to overachieve it and do more. It’s also about speed and rhythm, both fundamentals for modern companies.

That’s why all our job descriptions already have an indication of the potential development of that position and we actively discuss that with our candidates in all the steps. Look at an example here for our Product Designer position:

The idea is that you will keep discussing your career path with your manager and ideally plan for it in details. Things will change for you and for the business, so it’s fine to have this conversation multiple times over the years.

Why you should discuss your career path

Because it will help you progress and advance inside the organization. It’s as easy as that.

You should bring up this topic ideally before you accept a new job, but if you haven’t done that, you should make it the topic of the next 1to1.

It’s important for you because it will give you a clear understanding of what your goals need to be and how you can prioritize things in your daily job to reach those goals. People tend to fear this discussion is seen as a promotion ask to their manager: it’s not and you can be upfront about it – it’s a conversation about mutual expectations and alignment on goals.

Great managers know how to motivate people and give them clarity and drive: talking about your career path is a great way to do it. Most managers will expect their people to bring it up in their meetings and in some cases, they will have had some thoughts already to share with you.

How long do you need to wait to discuss your career path?

How long you have been with the company doesn’t matter.

It’s another classic dogma related to this discussion and it’s not true at all.

It doesn’t matter if you have been with the company for 1 year, 1 month or 5 years: you are bringing up a topic that is beneficial to both parties, yourself and the company.

If you have a clear path and understanding of what’s next, you will work toward that and benefit you company as well.

My experience with employees and career paths

Before I tell you more, how do I know about this?

I started a few companies and scaled one of them (Cloud Academy Inc.) to 250+ people in 11 countries. I’ve hired many people across multiple regions and roles, but we also had the opportunity to see many of our early employees grow and progress in their career path.

When our engineering team showed the first signs of struggle, we implemented a well defined career path for them and kept growing the team adapting it to the business and the needs of our people. The same happened across all the other departments, from Sales to Customer Success to Product.

I had this conversation several times with many of my colleagues. As CEO and cofounder I experienced this with two categories of people:

  • My reports (executives, Directors/VPs): as executives they were already at the top of the orgs, but many started as managers or even individual contributors, so we had this conversation multiple times. Sometimes I started it and some other times people came to a one to one meeting telling me “I wanted to pick your brain on what I could do next at COMPANY
  • Colleagues not reporting to me: during my skiplevels people asked me what I thought about their career progression and wanted to discuss what would have made sense for them – from “should I move into customer success?” to “What should I do to be considered in a managerial position?”

In both cases I always tried to point them to specific things they could do to 1) show they were ready for that role 2) if possible, start acting today like they already had that role and show their preparation for it.

Career paths always showed me how confident people were feeling after discussing this and having a clear idea of what they were working toward to – it was also important for us as company, every time we did not spend time “following” someone in his development, that person ended up performing worse than others or leaving.

Career paths are also a pretty unique way to set expectations with your employees and give them feedback on what you expect them to do and learn in order to take more or different responsibilities. Most people, in my experience, want this type of feedback and they will do their best to follow it.

How to start a career path conversation with your manager

Start with context:

  1. If you have been with the company for less than a year: explain how you enjoyed working at this company so far and would like to understand what are potential paths for you. I would say “I am planning to invest in my career here and would like your feedback on where and how I should focus to get to the next steps in my role“. Very simple, right? This is a great hook to let your manager explain what she thinks and then ask “What do you think would be great roles for me in the next years?
  2. If you have been with the company for a while (let’s say, 3 years), I would definitely open this with “I have been thinking about what I can do next here at COMPANY and wanted to pick your brain on a few ideas, and listen to yours as well“. If your company has a career path already defined for your role, that’s easier, if not just start explaining what you could do more in your department or what you feel you have become particularly good at. Your manager will likely tell you how she feels about it and her prospective and you can start the conversation.

Many people want to have this conversation once and close it. It’s impossible: this is a multi-step conversation and you should enjoy the process of confronting your expectations with your manager and discuss with her what’s the best path for you and the goals to get there.

What to do to accelerate your career path

Getting clarity and directions inside the organization is not always as easy as having this conversation. I know this and that’s why you should always consider a very pragmatic approach if you want to step into a new position and be considered for it:

  • Start working like you are in that role already

The easiest trick ever. If you want to be a manager start acting like one today: help your team organize things, step in where nobody else wants and simply show strong commitment, without expecting nothing in return in the short term. Your team will notice this and so will your manager: the next conversation about career path will be easier and smoother.

  • Show your manager your progress and be vocal about results

The best people I had in my team were very vocal about their progress and were constantly keeping me up to speed on results, challenges and major projects. Sometimes it was an email with “What I’ve worked on this week”, and some other times it was a quick slack message. The reality is that I felt up to speed all the times, I trusted these people even more with big challenges and it was absolutely normal for me to start planning their promotion in the next role we discussed. I knew they were ready.

It’s important to remind yourself that growing and advancing in your career path should be a process, it should challenge you and bring you to learn new skills and habits first of all. The discussion with your manager is just one of the many steps, and not even the hardest one. But it’s all worth it in the end: once you have clarity, you know you can grow in your role (and in your organization) you feel more motivated and positive, and that’s how you start enjoying your days more.


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