Once in the leadership position, it’s just a matter of time when you will have to address the needs of career growth of your team. This is probably something worth writing a book about, but let us try to go over the most important practical aspects of it in a few sit-downs.

It’s Not About You

Obviously, huh? But this time, this should go to some extreme. To understand all the intricacies of what career path your engineer should be taking, but much more critical why, you have to understand them. Not only from the technical and experience side, this way you’ll get only half of the picture. Personal connection and in-depth understanding of someone’s aspirational desires and motivation are essential in career conversations. That’s one of those aspects of the work why empathy is the crucial skill for a leader. Getting to candid discussions with anybody can’t be done quickly in some forced way and should not be rushed. The better you know them, the better you can lead to the best career outcome.

Forget About What Your Company Has To Offer

Way too often, we start the career talk by laying down what your company has to offer on the table, literally giving a hint of “now, choose.” I think it’s a big mistake right from the get-go and leads to thinking and discussions inside those boundaries only. Instead, the conversation should revolve as long as possible around:

  • What do they love to do?
  • What do they find genuinely interesting?
  • Where do they invest their learning time already?
  • What aspects of (any) work do they find boring or even unpleasant?
  • If we’re talking one year from now, what you think you should be doing by then?

As you see, there’s absolutely no hint of “do you want to do X or Y.” Again, tune in the art of listening, not telling.

Am I Helping My Company Then?

Guiding someone to a potentially “dangerous” situation where you could realize there’s no such a role in your company you could offer can sound counter-intuitive. But, contrary to such a first impression, it’s the best thing you can do for your team your company, not even mentioning the engineer. How so?

Just imagine a disaster you could be walking into if a promotion happens under a false understanding of the role, wrong motivation, non-matching fit. You just turned a happy, motivated great performer who wants to grow into a confused, misguided, not-what-I-wanted 100% underperformer.

It is much better to let people outgrow your organization than poison it with such misunderstandings. When outgrowing happens, you still win: you get a period of outstanding performance, cultivated growth mindset, a person who is undoubtedly going to be a promoter of the company who helped to slingshot them into the career of their dreams instead of selfishly capping the trajectory. You also showed to the rest of the team that no matter what, it’s worth talking about their aspirations with you openly, and both parties can only benefit from such development.

Give Time And Space

Probably there isn’t another more annoying question to anybody than “where do you see yourself in X years?”. So your job is not to press the matter too much: find the right timing, appropriate space, proper wording, and a set of open-ended questions that can help your engineer do open up rather than getting annoyed. If someone doesn’t have any preferences today, that’s fine! If someone can’t make their mind should they grow into one or another direction, let that be! Never impose pressure on such personal decisions, do not force their hand. Just make sure you don’t simply forget about the topic whatsoever and return to it from time to time to sense if there’s some change or conclusion.


This is the stage where knowing caring about someone personally will pay the most significant dividends. Once you know the career direction they’d like to take, make sure you challenge this choice based on your understanding of them. They seem to be utterly disinterested in large architecture topics, but is shooting for an Architect role? Public presentations are something they dread, but considering the developer advocate path? It doesn’t mean you should repell from the choice, instead double-check they thought about various aspects themselves and are aware of what kind of professional and personal stretching they will have to do. If you have people working in this role successfully, it is a brilliant idea to connect them to talk about their daily routine, challenges, and skills they put to use.

In other words, make sure their decision is made based on reality, right intentions, and matching motivation.

3, 2, 1 - Go!

High-five! We’ve got to the bottom of someone’s career aspirations. Quite often, this stage takes the longest, and that’s okay. However, now it’s time to act!

A few hints on how to drive this part of career development - soon!

Part 2 about career development

Photo by Igor Starkov from Pexels