How do I envision my team and plan a roadmap?

Question

I have recently joined an series B startup as their only devOps engineer. I want to build a roadmap on how I want to build things, what are my team priorities and way to measure impact.

Basically, its been almost 3 months now and I have only been doing tasks that my VP shares as a priority, and I want that in next 6 months, I am able to bring in roadmap and the vision that is required for this role. This is also something that my VP highlighted in 1:1 for me to be that senior leader/engineer that he envisions and as a way to get top rating here.

My specific questions -

I am not at all ready, I feel I don't know enough about this field. How do I get over this fear and the thought that I don't even compare to devs in my org?
How do I go about creating the roadmap, what are the points at high level I should think for platforms team?
I haven't done much coding in my life apart from writing scripts in my previous roles in devOps capacity. I am doing more here consciously. So, I am just not sure how to think in Platforms Team/software engineering perspective yet

Alex Chiou · Accepted Answer

This is a good question, but it's rough as this can literally be an entire course on its own 😅

For senior and staff engineers, team roadmapping is important, particularly for staff engineers and senior engineers pushing for staff. Because of this, I did quite a lot of it at Instagram. Here's the process at a high level:

Figure out what the goals of your organization are (ideally you have OKRs and KPIs) for the time period (looks like you run on 6-month cycles which is standard)
Figure out what projects can help your team achieve those goals
For each project, label it with the following:
1. How much it'll contribute to the goal
2. How long it'll take
After you have done #3, you need to do math, particularly addition. You have to come up with a list of projects that satisfy the following criteria when summed up:
1. The total impact equals or exceeds the goal
2. The total time required equals or is smaller than the amount of time you have to execute (6 months)
Socialize your proposal with the team and interested leadership (like your VP) as they might have thoughts on the projects you chose (e.g. they may disagree that a project will contribute that much impact or that a project will only take a certain amount of time)

#3 is the hard part as you obviously don't 100% know how much impact a project will have or how long it'll take until you build and ship it. However, you can make an estimate, and the more senior an engineer is, the more accurate their estimates will be - The mark of a strong staff engineer in particular is that their estimates are 90%+ accurate the vast majority of the time.

For ads, this entire process was relatively straightforward as we just had 1 big revenue goal to work towards. We measure everything at ads, so we also had a lot of historical data on what past projects made what amount of money - This made it not too bad to forecast how much a new ads feature would bring in.

Here's another good related thread: "Should I do a lot of upfront planning around the work I will take on across the half?"

How do I envision my team and plan a roadmap?

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