Career Progression and Discovery Framework

This is part 2 of a series on managing Data Science teams from the trenches and based on hard won experience running one of the larger data teams in SouthEast Asia from one of its unicorns. YMMV and advice here should be checked to make sure it’s appropriate to both your corporate structure and situation. No solution is one-size,fits-all. This is to guide VPs, CDOs, > and data executives and give them a possible alternative viewpoint on unambiguous wins for our teams (and may help you and your organization.).

Part 1 on how to structure a large Data concerns structurally and can be found here .


Most companies, and particularly most startups, do an inadequate job of discussing someone’s future with the company and, more importantly, coming up with plans for how they should progress and grow. And yet, this is one of the main hygiene points consistently pointed out as being the mark of a good company. We need a long term vision for each person on our team. Figuring out what that should look like is not hard, but it does take work, and a degree of trust and honesty between both the person and their supervisor.

There are 3 Goals to the framework and the conversations surrounding it for your people:

  1. An 18 month plan for skills acquisition and progression plan for the person
  2. Better understand what intrinsically motivates each person and their current basket of skills (even those not used in the role)
  3. Better understand their life goals and how their career can support that

The Framework

Is structured around 3 hour-long conversations you should have with your staff over the course of 3-6 weeks. (I highly recommend taking at least the last 10 minutes to write - even re-write - detailed notes to refer to later).

It centres more on the person than the company and is about getting to know your people, what they want, and understanding what your EVP (Employee Value Proposition) as a company is for each individual and their career.

Keep in mind, these may be awkward, and even difficult conversations to have. Few people actually think hard about their career and goals explicitly (and especially the path to get there), so some preparation and think time is generally needed by people to actually come up with these ideas. Sometimes, peoples’ goals will change as they start to realize a desired future state was not what they imagined when they get there or start working towards it. Part of your job is to facilitate and guide the conversation to try to squeeze intelligence out of the exchange to inform a viable progression plan. This helps get people to where they want to go in life, rather than just giving them a view of the next rung in the corporate promotion ladder.

It all starts with three talks…

Conversation 1: The Origin/Back Story

Every superhero/ine has an origin story. So does each one of your people and it informs, constrains, and influences where and what they may want to do in the future. It’s key for you as their manager to understand where they’re coming from and what motivates them (and quite honestly, knowing more about your people is only going to make you better and them feel more like you understand them.).

There are no definitive right answers or goal to this conversation other than getting to know your people better. What you want to do is get them talking. Do more listening (active listening is ok, if you’re feeding back) but get them to start talking about their life and career. You’re looking for a bit more than just a summary of what they did in their last job. Primarily, you want to get down to:

  1. What intrinsically and extrinsically motivates each person?
  2. Choices and changes they’ve made (or had to make due to external forces) in their lives.
  3. Every person is a puzzle. Try to put together the pieces of the “human puzzle.” How did they get here?
  4. Establish trust and understanding.


These convos can be hard. A lot of companies never, ever really have these conversations with their people and are more focused on what it takes to climb to the next promotional rung. Also, people may be unused to talking about these things, so you may have to do some significant icebreaking here to have some of these chats. If there is a trust bridge between you and your staff or you’re starting off on this conversation after just asking them for status updates in every meeting you’re probably going to have a tougher time on this than usual. Strangely, ice breakers can help.

  1. What was your first job? How did your career evolve after that?
  2. Start with high school (heck, even grade school). What did you love studying the most? Why did you/or did you not, do that post-high school education/work?
  3. Ask about major life events that may have shifted the course of priorities or focus or the course of their lives.

Basically, it’s a “getting to know you” (GTKY) conversation and trying to determine the background of what makes this particular person tick.

Conversation 2: Life Goals and Dreams

The goal of this conversation is to move the conversation from what motivates them, to what they want — out of this job, out of their career, our of their life.

Retention is a byproduct of not just recognition, but of satisfying, meaningful work, and productive relationships (for more on the underlying EVP framework that drives this idea, please read Daniel Pink’s Drive on Autonomy, Mastery, and Purpose.).

Most people have a very hazy view of what they want their lives to look like. I actually recommend giving them 2 weeks to think about this after teeing up previewing this talk and after the first conversation and coming up with 3-5 “alternative destinies” for where their lives may want to take them (example convo: “ok, so if the dream of being CTO fails, what else would make your life satisfying? Entrepreneur? Lecturer?). Ask people what the pinnacle of their career would look like (or if they had that and have not changed tacks to something else - what other things have they’ve considered?). Also, ask about what values are important to them in moving that career forward and other life goals they may have, from home ownership, to family, marriage, relocation, and their dreams. Strangely, while it sounds hokey, asking about peoples’ dreams is a surprisingly easy way to push forward candid conversations on what you need to get there.

So, either after the 1st conversation or after this one, have your direct report do some homework and create a document with 3-5 columns listing title/destiny and what skills would be important to each dream and the level of competency they would need in that skill (#protip: for most people, tell them they need to spend some quiet time doing this aside from all work stuff. Like a half day to think really, really hard about this especially if they’ve never done it before.).

As an example, it might look something like this:

PhD Researcher Charity ED Wikimedia CTO Unicorn CDO Consultancy
Skill 1
Skill 2
Skill 3
Skill 4
etc …

The second part of the conversation you need to have is making sure a person’s values align with the values they have expressed are important to them via this chart. Most people want to be rock stars, but it’s surprising how few are willing to put in the hard practice and improving work needed to actually get there. So, put things to the sniff test to make sure this is not purely aspirational thinking and is the result of considered, measured thought (A project without a goal is a hobby. A goal without projects to get you there is a dream.).

Keep in mind, not everything has to be “I want to be king of the world.” Some people want to be an expert in their craft and particular field and get home to have lots of time with their family. There’s nothing wrong with wanting to be a farmer or an entrepreneur or a destiny which has absolutely nothing to do with a future at Company X. These are all valid responses to this exercise and we need to be open and supportive of peoples’ longer term plans (even if it makes them realize they should probably be looking elsewhere to get where they want to go.). Keep in mind, peoples’ times in jobs are limited and part of our value proposition is to keep people interested in working here enough that they don’t churn. Even if they want to be an entrepreneur or a farmer, or just want more money, our role as managers is to help them, within reason, get the skills here that will serve their role and path at Delivery Hero and help them move in the direction they’d like their life heading.

Why is getting this right important? Because now your job is to help them get those skills.

Conversation 3: The 18 Month Plan

The idea of this talk is to plan the next 18 months with DH for this person in terms of the highest priority and value skills to them to be picking up and talking about opportunities we may be able to provide to help them gain those skills.

Get people to ask themselves:

  1. What do I need to learn life goal-wise?
  2. How should I prioritize?
  3. What will also be valuable to the company?
  4. Whom can I learn from?
  5. How can I craft/change my role to learn it?

I’d recommend coming up with 3 goals of 6 months each that, to track quarterly. So, one goal per quarter. It’s often a good idea to sequence them rather than expect progression on all 3 fronts over the 18, but that will depend on the individual and constrained by the fact that everyone on the team should be spending 10% of their time to be working towards these sorts of skills.

I’d recommend a nice one-pager that lays this out so it’s written down. And also, I really like a format that also looks at their current skills and levels (see Part 3 of these posts) in relation to the skills and levels they should be exhibiting at their current level.

From these skills, put together a list for each one of the skills they need, who may be able to teach them/who they may learn from, courses they could take, books to read, training to get, and projects where there may be an opportunity to gain these skills.


That’s it. It sounds simple, but it’s a lot of work and an substantial investment for each individual. Done well, it pays off in increasing engagement and retention.

Once you’ve gone through this with all your teams, you should have a plan for each person that you can both huddle around to see progress, and understand if people are progressing in skills and craft.

For roll out, I highly recommend teaching it to your senior reports and then having them cascade it down with each of their people managers that would be capable of providing this sort of guidance. This also parallelizes the task of developing these plans for your entire group, but as it may be new for a lot of people, and some managers may struggle with this task, it’s important to checkpoint the development of the plans at each stage to see how it is progressing. I’d also review the final plans for quality of insight and making sure someone just hasn’t ticked these off their todo list. You do need peopel to buy in and take this process seriously (as well as the belief that their job as a manager is about people rather than task allocation or expertise.). Good luck!

Let me know what you think about the post @awws or . I’d love to hear feedback about what else or similar thinking about what works for you. Even better, (reasoned) opinions on why I might be wrong and what might make it better.

A framework for doing right by your people and discovering and working on their long term career and a responsible boss and employer.

Daryl Manning


2028 Words

2020-09-12 17:21 +0700