Checklists & Career Advancement

If asked to distill down the entire universe of advice for early-career engineers into a single atomic principle, my take would be this: use a checklist (and refer to it often).

In managing interns, new grads, & even all the way up to senior engineers, I always share this advice. The checklist is such a simple tool but it can prevent so many issues and help accelerate learning & impact.

In the case of early-career engineers, a checklist sets up a healthy habit of tracking assigned work. Having the understanding of what work is relevant, how much is remaining, and in what order it should be done (or, having to do at least some prioritization within the checklist) all sounds straightforward, but that understanding is frequently missing for early-career engineers. The checklist provides the necessary guardrails around task management so that early-career engineers can focus on the important bits of learning at that stage, which is actually getting their hands dirty with implementation. It eliminates a whole set of variables around the overhead of getting work done, not the actual work itself.

A checklist is also a positive feedback mechanism, where an early-career engineer - often beginning with a thin layer of self-confience - can feel the satisifaction of finishing pieces of work when they’re able to mark them off the list. The act of physically marking something of the list, and eventually owning a checklist with many items crossed off, helps snowball positive momentum and build self-confidence for that engineer. It’s a visual representation of all the effort that they’ve put in.

For more experienced engineers, the checklist is about stabilization and continued alignment with previous decisions. Think of it as dumping state for later. The effect of the checklist for a grocery store run is the same effect during the workday; one can’t be expected to remember everything, so the checklist is a way to communicate from our past selves to our future selves. This becomes increasingly important as one moves through their career: directions get more ambigous, managers / tech leads supervision becomes more hands off, and context switching becomes the norm. In the ever-increasing din of noise, having a steady checklist to set orientation becomes invaluable.

There is a point where a checklist can actually become harmful. Like any tool (Maslow’s Hammer, etc.), overreliance can yield less-than-optimal results. The checklist is fantastic for tactical thinking: what needs to get done in the immediate term & in what order? However, the further along in one is one’s career, the more strategic thinking & creativity is required.

Strategic thinking runs counter to tactical approaches - it extends beyond the short-term, and needs to incorporate the broad array of objectives with a set of imperfect information to build medium- to long-term plans. Checklists are all about rigidity and structure, while broader roles such as Staff Engineer, Tech Lead, etc. need more latitude and creativity to solve broader and more complex problems. In those roles, overreliance on the checklist to do one’s thinking for them can mean that they’ll missing the forest for the trees.

Once the habit of keeping on task is fully embedded in the way one works, the training wheels of the checklist can safely be taken off. Senior+ engineers should throw off the rigid yoke of the checklist (and, if they’re Senior+, likely already have) and embrace a little more gunslinging. However, when the seas become rough and the ship feels like it’s beginning to list (no pun intended), falling back to a checklist to can be helpful to steady the ship and calm the waters.

The checklist is often underestimated as a tool, but proper use of it can yield consistently strong results. For early-career engineers, it’s a secret weapon that provides focus and clarity. As engineers grow in their career, it can continue to be relied on to keep track of context and owed work as ambiguity and context-switching becomes the norm. Eventually, the checklist might become too constraining as longer-range thinking is required in certain roles, but it’s always a helpful fallback to steady things when situations become too chaotic and need structure and clarity.