The Individual Roadmap

Early on I tried forcing our team to take training. That didn’t work well. I’m effectively telling them “you’re not good enough”.

I’ve tried giving an unlimited budget and asking them to tell me what training they want. That doesn’t work well neither. They’re being asked to say what they’re not good at.

Overcoming defensiveness is a big challenge to improving someone’s skills and thus sense of competence.

A better approach combines two questions:

  1. Where do you want to go?
  2. What skills, resources, and knowledge do you need to get there?

These two questions work well in many contexts. It lets the individual identify where they need to go in the future. It lets you check your goals are aligned.

Then it lets them highlight what they think they need to get there.

An easier way to drive deep engagement is to get each person pursuing a roadmap they’ve helped to design. Works as well in your team as it does in your community.


  1. Sarah Hawk says:

    This interests me because it’s not how I feel (I can’t speak for the others in our team). Training is a fundamental part of professional development, as is being aware of areas in which you’re potentially weak.

    One aspect of this is finding time to research what is actually available, but perhaps the biggest sticking point for me is cost. I have a tendency to feel uncomfortable asking for things that have what I perceive to be a high price tag, even though they offer considerable value. I’m aware that it’s a weakness on my part.

    I like the roadmap idea. Does anyone do this in their organisation and is it successful?

  2. Rob Bosch says:

    I find this intriguing.
    What now if the people you want to get to a higher lvl of skills are volunteers as we have in our opensource support community? These people are not bound by the project because of a working contract. The only thing they are bound by is that they want to participate because of their own reasons. Those reasons vary from person to person. Most of the members just want to know how their problems can be solved and with a bit of luck (at least we encourage them) they share there experiences.
    If you look at the 90-9-1 rule, you probably aim at the last 1% and maybe a part of the 9% of the ‘standard’ member population of the project. Those members are more likely to invest time to be able to get better in helping others.
    The question is: would this work in a volunteers community?

  3. Darren Gough says:

    I found this interesting too. As with @HAWK it’s not how I feel about this.

    There’s a huge amount to learn, no matter what you do, constantly and everything evolves. I’ve never had the sense anyone on the team has been defensive or offended. There are, however, a few things that I think do present challenges:

    1. Time. We’re a small company and no matter how well intentioned and appreciative we are of being able to train and have budget to do so, actually getting time to do it when we’re so busy can be tough. We should make time, sure, but the last 6-12 months have been stormingly (is that a word) good at FeverBee - hence we’re now hiring again. This all takes commitment, investment and time and responsibility to making things happen. It’s great that the team is so focussed on making us a success - it’s just not always practical to stop, think, research and train. This brings me to point 2…

    2. Good training. Honestly, I’ve done a lot of training over the years at a variety of places and most of it is poor. It’s systematic, laborious and unproductive. Maybe I’ve been unlucky multiple times but I inevitably leave with a feeling that “I could have done the best bits of that in an hour and then got back to my FeverBee task list”. This isn’t to say there isn’t some incredible trainers and courses out there (like ours!) but finding them again takes time and a certain amount of serendipity.

    3. Knowing the roadmap. I think a bigger question than “where do I want to go” is “what skills will be needed in the future”. I just listened to the Tim Ferriss podcast with Naval Ravikant and he makes some really good points around the fluid, flexible nature of this. Training for skills can sometimes be redundant also. Do I want to learn to code? Not really - we can find someone who can do that for us cheaper, quicker and more effectively than I want to learn it.

    None of the above is true 100% of the time and, of course, we CAN make time, there ARE courses and a roadmap CAN be useful. At this point though I’m not convinced we’re looking at the question in the right way. Perhaps a more useful approach is to create a completely abstract approach to this. Force people to take a day off every month, scheduled in, when they work on a completely different project.

    They can write a short story, learn to play power chords on a guitar, volunteer at a charity or do anything to have a unique experience they learn from. Sometimes the best ideas for work come when you have your eyes opened or are challenged in a completely unique way. Be interested to hear if anyone else has done anything like this

  4. Priscilla McClay says:

    Rob – When you say that you want to get your volunteers to a higher skill level, does that mean the issue is that they themselves aren’t interested, or don’t feel they need the training?

    I have done some training for volunteers before, but it was based on their feedback, so we knew that they did want to learn.

  5. Rob Bosch says:

    Hi @Priscilla. Thank you for your response. Maybe I should elaborate a bit on the community I am involved in. It is an opensource community for a specific opensource product: A Linux operating system for a server that is typically used in home, small business and small enterprise environments. Members are users of the software which is available for free (it is opensource, which means that the code is freely available.)
    There is a company behind the software that has several developers on the payroll and a community manager (hi @ale_fattorini).
    Now the community members are very diverse in skills and interest. Several are skilled system administrators. Some of them know a lot about networks, but nothing about Linux. Some are just plain home users and have absolutely no clue what they are doing.
    Fortunately there are quite some (very) active members that help anyone when questions are asked. Our policy is that no question is a ‘dumb’ question. If a member has any problem with the software, because he or she doesn’t understand what is happening, we encourage them to ask in the forums (we also use discourse). The big plus for these less advanced questions, is that they also will be archived and available for future members so they can search the forums and find solutions for their questions.
    Besides the forums we have official documentation and a wiki. Of course we direct members as much as possible to these sources of information, but still some questions need discussion or just aren’t answered in docs or wiki.

    Now the goal: I would like to see that
    a) The community as a whole gets more knowledge. We do this by providing documentation and wiki. We also encourage every member to experiment with the software so they get a better understanding and new features are tested.
    b) The ‘veteran’ users can help even better. I think that if an investment should take place, it should be in these members. My gut-feeling tells me they are likely to commit themselves more than any ordinary member. They already have shown they want to spend time and effort on the community.

    My inspiration on this I got from a cartoon that might be known in several different appearances:

  6. Alessio Fattorini says:

    Thanks for your recap Rob :slightly_smiling: the question here is, how much time should we expend in such individual roadmap? The idea is great, but how much is it time-consuming?

    • Ask info
    • Collect them
    • Discuss individually with the members
    • Pursuing a roadmap they’ve helped to design

    Does it appear hard just to me? How to obtain the best result “reasonably achievable”?

    Edit: I should like to mention this old but always helpful post:

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