Active Onboarding

Posted on 2023-03-29

Having recently changed jobs, I had the pleasure of onboarding for the first time in four years again, definitely a change of pace. Being quite senior at this point, I have been worrying a bit about how to join a new organisation and perform on my level, not having benefited from working directly on the ground for a long time, thus lacking direct technical experience and also social legitimacy.

Also joining a smaller but actively growing organisation, I expected there not to be a lot of structured onboarding process or guidance, Even organisations multiple times the size of this one had very little in the form of onboarding material, and I would be proven right this time as well. so I decided to take some ownership of the process ahead of time.

Take Notes

Frequent readers of this site will not be surprised that I advocate for writing things down. Not only will there be a lot of new information during the first few weeks that will be difficult to retain, people, services, processes, and so on, but also observations about the onboarding process itself.

I make it a habit to note down any stumbling blocks I encounter, such as access I have not been granted, or documentation that was missing. These notes are invaluable to improve the onboarding process for future joiners.

Capitalise on Those Fresh Eyes

Generally speaking, one is joining an existing organisation from a different context, mostly that of ones previous organisation, maybe also the one before that. This means the circumstances that seem normal and ordinary to everyone else can be contrasted against that prior context, a great starting point to question the status quo. Sometimes there have been conscious, valid decisions that led to it, but sometimes these decisions did not stand the test of time, and even more often, there were no conscious decisions, and the status quo just exists because no one was aware of the alternatives. Of course things can also be surprisingly better than one is used to, and that's worth noting down as well for future reference, or to explicitly hold on to, but in my experience negatives tend to stick out more during first encounters.

Prepare a Plan

I had the luxury of taking a few weeks off in between jobs, which was great for some unwinding, but also gave me some time to come up with a plan for the new job. I started looking at the tech I knew they were using but I was not familiar with yet/anymore, and also prepared a very rough list of goals for my first 30 days. This might sound a bit heavy-handed, but it really just boiled down to:

  1. Agree with my manager on a job description and expectations.
  2. Identify and meet with as many key people as I can, both directors, VPs, and executives, as well as managers, team leads, and product owners in various adjacent domains.
  3. Fill out a list of questions to answer about the current state of things. I stole a large chunk of this from a VP at my last organisation, and a lot of this is quite fundamental, but still a good guideline. Some examples: There are around 200 questions in the actual list, but a lot of them are much more fine-grained, such as "who owns uptime?" or "how is test coverage?" I use these questions during my first (and second) meetings with new colleagues, which give me an automatic agenda past the self-introduction, and can be useful to see how people in different positions think about the state of the organisation. If you're interested in the full list get in touch, and I can prepare an anonymised version of it.
    • What is our mission/vision/problem solved?
    • What is the competetive landscape like?
    • What happened over the last year?
    • What are we planning over the next year?
    • What have been the best decisions so far?
    • What have been the worst decisions so far?
    • What is the organisational structure?
    • What is the technical architecture?
    • How are decisions made at different levels?
  4. Share the results of the survey with everyone else to spark some conversation, and also come up with my own hypothesis of where I can be useful.

Keep an Open Mind

Especially during my first month I am expecting to just soak up information by asking questions and listening to what is said and what is left unsaid. This helps to disconnect from preconceived notions about how an organisation ought to work, because there is no one-size-fits-all approach anyway.

Last but not least, coming in very strong might be acceptable, or even expected from, a new VP or executive, but on a staff engineer level it is an easy way to make enemies within the first few weeks. Things will be different from what one is used to, and in some ways probably for the worse, but such is life.