Proactive versus reactive product development

Field notes from an engineering team lead

Intro to the field notes

  • Proactive versus reactive product development (here)
  • Setting up and empowering product delivery teams
  • Reflections from trying Basecamp’s “Shape Up” as an alternative to agile scrum
  • A more personal reflection on where I’ve gotten it wrong and what those experience have taught me

Order versus chaos

From top-left to right: terror; aspirations to unicorn status; a lingering sense that things could blow up at any moment; dollars everywhere; weight of responsibility to investors and employees; and SO MUCH admin to get through.
From top-left to right: A desire for calm and stability; deep, intrinsic enjoyment of creative work; fascination with the rules and logic of complex systems; a commitment to building the stack well, one “brick” at a time.
left blank on purpose 👆
also left blank on purpose 👆

Breaking out of the cycle

  • That thing that feels like a truly existential burning fire that you became aware of a couple weeks ago almost never is. While the founder’s choice to turn the team from the example above may seem like a no-brainer financially, it actually came with huge costs that reverberated through the organization for months. How an engineering team executes over the long-term is far more important than what it builds tomorrow or next week. Executives that can protect their technical teams from day-to-day chaos will reap long-term rewards of software quality and scalability. Those that don’t will create compounding problems for themselves.
  • Doing this requires enormous discipline from founders in particular. It’s hard to accept that 98% of the time the right answer is to take a deep breath, write that hugely important thing down, and then trust your team to finish the build they’re on before mixing things up. To do this you’ll need an outlet on the tech/product side for all your fear, anxiety, and excitement, as well as confidence in your team’s model of execution. I’ll get into that in the next two posts.
  • To the extent possible, avoid making heat-of-the-moment promises to customers or investors that pre-commit your team to building a product or feature on an arbitrary timeline. Just don’t do this. It’s all too common, and artificially manufactures a time crunch that sets you up for the anti-pattern we describe above. You have enough pressure on you without making more.
  • Engineering teams should absolutely be expected to pivot dynamically to support business requirements. The ability to adapt and overcome is a huge part of what makes a startup successful. Tight iteration cycles are critical for engineers to have the confidence that they’re building the right things. The point is that those cycles should be executed in a way that doesn’t give your product builders whiplash and erode trust.
  • Emergencies that warrant an interruption of your engineering team’s “execution model” are rare and expensive, but they do happen. Sometimes you actually do live or die — or make a quantum leap as an org — based on what happens next Friday. It’s the founders’ and executive team’s job to steer the organization through those moments, and when they happen communication is critical. Sit down with the team and give them the why. Take questions and listen. While some engineers may be more unsettled by this dynamic than others, it’s what they signed up for when they joined a startup. Seen in the right light, it’s also part of the fun. Founders and execs who thoughtfully share context during highly dynamic periods will be amazed by the energy that their team will put into supporting them and the new vision. Just make sure that this doesn’t become your MO: If it does, that points to a larger problem.

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Aaron Polhamus

Working with Team Vest to transform how retail investing is done throughout the Americas 🌎