How to make better second-order decisions
Seven easy ways plus a template to help your decisions scale into the future
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In my role as a Sr. Product Lead at Shopify, a big part of my job is making the right decisions today that will allow us to continue to build the product in the way we want years down the road. If I make the wrong decisions today, roll them out to a large community of merchants and app developers, it’s extremely costly or sometimes near impossible to undo later. Now scale this up to hundreds of teams all making decisions daily and the map of your collective decisions becomes a bit of a minefield.
Some of the best builders I know have taught themselves to make the right decisions quickly. As a builder, what you ship is the sum of a million little decisions made from the day you start thinking about an idea to the day you are ready to release it. A few weeks ago we talked about making decisions through the lens of product quality, and how every decision you and your team make compounds to create the high-quality outcome you’re trying to deliver. This week we’re going to develop your “second-order thinking” muscle, so you can continue to deliver products you’re proud of by making good decisions that scale gracefully into the future.
What is second-order thinking?
From the Farnam Street blog: “Second-order thinking is the practice of not just considering the consequences of our decisions but also the consequences of those consequences.” This is the practice of thinking beyond what you’re working on now, to understand how it will live inside of your system for years to come.
To increase your blood pressure a bit. It starts like this:
But really quickly, at scale, it starts to look like this:
Now imagine several teams all making decisions at the same time and it really looks like this:
These decision trees actually deeply oversimplify the complexity of most platforms and systems. In reality, it’s more of a web or even a knitted sweater. If you unravel one piece, you start to do damage that’s very hard to undo. Or if you need to fix a mistake in the middle of the sweater, it starts to look a bit like open heart surgery and never really looks the same again afterwards. (Did I mention I love to knit? 😜)
So you start to understand how aligning teams around shared strategy, principles, ways of working is a necessity – otherwise a series of bad decisions will slow you down and become costly really quickly. So how do you, as Chief Builder, guide your team on a second-order thinking quest?
Seven ways to practice second-order thinking with your team
1. Move slow to move fast
Now, before someone tweets “Nickey told us to move slower!” That is 1000 percent not what I mean here. I like this adage because it helps you, dear Builder, understand that the decisions you’re making today will cascade and impact your team next week, next month, and beyond. Move slow at the right moments, to make sure you’re making the right decisions with the right context. Educate the people around you that when you’re laying the foundation, if you put one down that is crooked or cracked the entire skyscraper is jeopardized. Help your team understand this, print it on a wall, wear it embroidered on a hat on your Zoomz.
2. Share a long-term strategy with the team
Make sure teams know where the product and business is headed longer term. This will help teams make the right decisions today in the interest of getting where you’re going, faster. Beat Walt Disney’s long-term strategy/network effects from 1957. I dare you!
3. Create a culture of socialization
Make sure teams are talking to each other. I’ve seen this done at 30 people product orgs and 3,000 people product orgs and you’d be surprised at how hard this is to execute, especially as organizations grow. If teams are having a hard time finding each other, find ways to force connection. Some ideas:
Having people whose job it is to seek out overlap
Have global demo days where you get to see work outside of your specific team/area
Have a clear articulation in job descriptions that context and socialization is part of your job
Have internal tools and process that push people to sync with relevant stakeholders
4. Know the difference between one-way (irreversible) or two-way doors (can easily change later)
Create a different process around one-way door decisions. Make these a “moment” and get everyone’s attention when you’re walking through it.
5. Know where the dragons lie
Help teams understand where there are already problematic parts of the system. Analyze why they are there and how they got there. This would be a fun blog that I’d love to read: “Shit we shipped that haunted us later!” Learn from your warts!
6. Get the right context
In the world of platform product management, context is queen. Make sure that your team has all the backstory, and understands why things were built the way they are built. Furthermore, create a decision log and write things down for future teams to look back on what you shipped and why you made the decisions you did. I made a quick template for you here, please copy and let me know how you use it!
7. Host a second-order workshop
Recently I hosted a workshop where we brainstormed about the future, to make sure we were making the right product decision on a specific feature today. I can’t tell you exactly what we discussed (secrets don’t make friends!), but I can share the format of our meeting which looked something like:
What does this feature look like in the next 18 - 48 months?
What value does it need to scale up to deliver to our customers?
How do we imagine it changing to deliver this value?
What could other teams ship to block this from being able to happen?
What one-way doors do we need to avoid to make sure our path is clear for the future?
Applying it back home
Now before you get sad because you’re doing none of these things, that’s okay! Even Barack Obama struggles with this! Applying only a handful of these strategies will make a big impact. My challenge for you is to not overhaul your entire process, but to make one change that will help you get better at future-proofing and to refine your process over time. And if you have any unique strategies that you’re already using to be a better second-order thinker, please share them in the comments below 👇