Prepare your career path session

Ok, as manager we decided to do the big jump and start a career path discussion with our direct reports!

From there, we can roughly be in 3 situations:

  • They don't know at all where they want to be in 5 years (80%),
  • They have a gist of where they are heading to (10%)
  • They have a plan (10%)

They don't know

That's the interesting bit, where we can add the most value. The first step is to understand why they don't know: They have never thought about it before (that raises an important point: before initiating a career discussion, some time should be allowed for the person to think about it. There is no way that somebody will come with a relevant plan on the fly), They have thought about it, but it's so hard that they didn't progress much, They don't believe that's possible to have an interesting discussion about this topic, too many uncertainties in life (in this case you have to convince them to at least give it a try with you and see how it goes)

Depending on their current experience, the discussion will be different (see the different guides for more details). A really good source of insight is any job board. What better than the market can give you what the market wants? As a well known fact, most of the job ads are "profiles" descriptions more than positions in a given company. That makes these ads even more useful to understand what is expected for a given "general" role.

The 3 main steps to define these archetypes of roles are:

  • Find job title patterns in your industry (for tech people in the web industry, that would be CTO, VP of Engineering, Chief of Staff, Principal Engineer, Architect, Expert,...)
  • For each archetype, identify the description of their mission. That would allow us to project ourselves in the future and give us a flavour of our daily tasks. It could immediately raise red flags (VP of Engineer involves people management, and you would like to stay 100% technical for example)
  • For each archetype, gather the requirements listed, which would be essential to plan what should be the next next in people's career to go towards this goal (it will be complicated to switch to VP of Engineering straight away from an IC - Individual Contributor - role, as you don't have management experience. It could then orient you to help them starting their management experience by having one direct report, then 2, then a team, etc.)

You can also try to match these archetypes with personality tests (I really like the one from to help orient the discussion.

From these archetypes, ask them to choose one or two maximum. Their favorite(s) one(s), or their less worse ones, if really undecided.

Then you need to think about which area they should focus on to achieve their goal. It could either be:

  • Something that they would like to focus on first,
  • Something easily achievable on your current company structure,
  • Something you have experience with and will be able to provide them a great support.

Ideally this plan will be part of their quarterly objectives, which means that you allow them to spend some time on it outside of their usual duties.

They have a gist of it

The process used above is still valid. You can just already scrap the parts that have already being identified as not motivating for them and spend more time coming with a plan. I think that's still worth going through the unwanted roles if they don't have strong arguments justifying what they don't like. That could wrongly come: A lack of knowledge on what these roles entail (being a manager? Will I continue to code? Not ready to stop it!), An evolving domain (managing people now has different challenges than 10 years ago, technical challenges are also vastly different)

They know

In this case, that would be more useful to directly concentrate on what they want to achieve. If they are already that self-driven, you can ask them what was their plan in your company? In general? From there, you can support them as much as you can in the direction they want to head towards.

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