Underpromise and overdeliver; infinite games
A cool penguin in the 2nd edition.
Welcome to the second issue of Nuanced Experiments. This week I traveled to Boston, MA, USA to check out a couple of games of my favorite baseball team and I also saw penguins for the first time in my life! (I live in the Caribbean 🌴 ).
Hope you're having a cool of a week as Mr. P below. I’ve been waiting to share some career insights and ideas with you, so here goes!
1. Career Insight: When in doubt, underpromise, and overdeliver
Expectation management is a skill most engineers have to learn at some point.
It can be tempting to promise the moon whenever someone is expecting something from you (especially if you're naturally a people-pleaser ✋).
But this strategy can backfire when it turns out that the job you thought you could do this week actually takes you many weeks.
Many things are outside our control but if this happens frequently it could be a sign that you need to know yourself and manage expectations better. Not doing so can risk eroding trust in your manager and peers.
Luckily with experience this is a solvable problem. I'll share three things that have helped me manage this in my career and hopefully will help you accelerate your learning as well:
If you can't generally sketch out a solution for the problem you're being asked to do in your head or on a piece of paper, you probably can't estimate the effort it will take to do it. Instead, spend a day trying to answer as many questions as you can about it, and ONLY THEN, consider estimating. This type of "question answering" pre-work is often called a "Spike" and I still use it whenever I start bigger projects with many unknowns.
If you have never worked on that kind of problem before, you probably can’t estimate it either. I would encourage you to create a spike when possible and aim for estimating at least 3x of your worst case scenario. Only after you’ve done this problem before, drop that 2x. (Ex: If you think it takes you a few hours, make that a full day, etc.)
If you know how to solve the problem and you've done it before, this is the ideal time to estimate. Still, I would recommend estimating 2x of your worst case scenario. (As an aside, your manager may even add a multiple to THAT, as he's also managing expectations upstream).
Overall, the strategy that has served me the most in this area to underpromise (act conservatively and communicate something will take more time → 2-3x), and overdeliver (surprise with how fast you were able to ship it in 1x). In the best case scenario, you're a speedy developer, in the worst case scenario, you’ve just accomplished what you said you would do. Win-win 🙌.
2. What I learned this week
This week I came across the concept of "infinite games". I think it's applicable to an engineering career. Here's a definition by author of “The Infinite Game” Simon Sinek:
An infinite game is one with known and unknown players, changeable rules, and no end. The objective is not to win—the objective is to keep playing.
While I'm not advising that you see everything as an infinite game (this is a nuanced experiments newsletter after all), it can be helpful to frame certain things with different mental models. For example: If there is no game to win (say promotions and raises are not actually winnable states of this career game), and instead the game is simply to be content and in enjoyment, help others, and be better than you were yesterday, does that change anything from your day to day enjoyment of that game (your career)?
3. Nuanced Experiment of the Week
What's one thing in your life that could be framed as an infinite game?
What’s one thing that you can overdeliver on?
Let me know what you choose in your replies!
That’s a wrap! If you made it this far, thank you for reading. If you have feedback or suggestions on what you would like to see in future issues, please reply to this email.
👋 🙏
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