I was recently asked if I thought estimating is a valuable skill for a software engineer to develop. This is a deceptively simple question that everybody is quick to affirm. One of my favorite parts of Stripe is that our operating principles are practiced and it’s encouraged, when reasonable, to pause and reason through from first principles. I’m also heavily influenced by the Toyota Production System which tries to tie every action into value for the end user. I reframed the question to “Why are accurate estimates valuable to our users?”
Recently I had the opportunity to interview for a manager of manager role. This caused me consider more deeply what I really want for my own career. The process helped me clarify what's most important to me and where I find the most enriching experiences in my job. In this post I write out the interfaces to support a team that I feel valued in and brings me tremendous happiness.
I've been working remote for 12 years now, starting with my first kid. It was really important for me to be there with my kids as they grow up and it's been well worth it. I'm amazed I have an amazing job at an amazing company (ps., we're hiring). I'm amazed I'm effective outside of our engineering offices (San Francisco, Seattle, and now Dublin). Today's opportunities in tech allow me to work in a large, growing and high impact company outside of an office. Sometimes I forget the benefits this brings and that it enables some special experiences. Such as working from Japan for 6-8 weeks every year. This post is how I’ve structured my work and temporary-home life to support it.
Yesterday my son and I were out shopping for his science experiment and he got distracted by some of the wood assembly kits. He said, “I really like building things!” I agreed and asked why he didn’t spend more of his time building things. He really does enjoy it and when he is doing it he obviously enjoys himself and he loves to show off what he created. He doesn’t start projects very often, though.
I realized I’m the same way about feedback cycles. I love feedback, reviews, and really love getting helpful feedback. But every time feedback cycle rolls around I drag my feet. This is a good signal that something isn’t aligned in my head. If I value giving and receiving feedback what is the reason the current structure isn’t motivating me to act?
I was talking about this feeling and came to the conclusion that it’s because I feel the people I choose to give me feedback are likely to either confirm my strengths or my weaknesses. The process will not grant me insights into how people see me and my work. Many feedback questions focus on areas of strength and the kindly named “growth areas”. As I advance in my life and watch others do the same, I've noticed the ability to be more self-aware of strengths and growth areas improves. Feedback at this point is a useful tool to verify the accuracy of my self-awareness but rarely provides new insights.
In talking more about this, my friend and I came up with a few questions that will hopefully provide new information. Not just any new information, but the most wonderful of new information: how others see me. I think these questions are also more lightweight than the typical feedback questions that happens during a performance cycle at work. They're also not bound by work! Friends can also provide very interesting insights here.
What motivates me?
I know what I’m motivated by, but I’m guessing most other people don’t quite think about it as much as I do. This question I think is especially important because I’m sure there are moments where someone thinks we’re motivated to get to the same point and perhaps competing with each others. We may be, but we may not — knowing this for sure would be helpful.
Most importantly, though, is that this question invites the discussion about my goals so the people around me can help me succeed. Or they can say my goals are dumb and I should do something different. Either way, everybody wins (by everybody I mean mostly me).
How predictable am I?
I firmly believe in a culture of no surprises. At work, at home, everywhere. Birthday and Christmas surprises are ok. I have the benefit of being inside my own head so, obviously, I am never surprising. Turns out I’m wrong.
My wife has expressed many times that she usually becomes frustrated when car shopping with me. I love cars and love getting new cars. When choosing my current car I went around and drove nearly every 4 door sports sedan on the market. This went on for weeks and weeks, then I sat in my car and drove it for 3 blocks and decided it was the car I wanted. So I got it right then and there. She was surprised and couldn’t see how I leapt from just browsing to buy, buy, buy! In my mind, all I was waiting for was that one car that felt just right. She can’t feel my just right and the entirely opaque process was frustrating purely because of the surprise. She was perfectly fine with the car and it was in our budget. She was unhappy feeling left out and surprised. That lesson sticks with me and I don’t think many people in a work setting would talk about feeling left out and the negative experience of being surprised at a decision.
Am I doing what you think I should be doing?
This one may be a bit slanted towards work but I think it can be adapted to friends fairly easily.
If someone sees my strengths and skills in a different way they may know of an opportunity better suited for me. This is almost an extension to being predictable, though, because if I’m working on something others don’t see the value or connection to my goals I want to hear about it. That means something about my behavior and choices is surprising and I should understand what that gap.
This also opens up a conversation about what I'm doing to improve and grow. Often times feedback has questions along the lines of, "What could this person do better?". Carrying this sentiment up I think brings us to this question. I may be willingly giving up on something so I can do better in another area that is higher priority or more urgent. Or maybe I don't see the importance and that information will help. I believe understanding what others think I should be doing that I'm not it will help me and mitigate problems that I may be entirely unaware of.
There is no perfect success, nor absolute failure. Getting closer to perfect success is like accelerating in a car. The amount of energy to accelerate from 50mph to 60mph is significantly less than what is required to from 100mph to 110mph. The environment works against you, which is why perfect success requires expensive engineering and significant time investment.
For every percentage closer to perfect success, it requires an increasingly greater amount of energy and focus. We don't need success at those levels and rarely, if ever, do we ever encounter it. Even Steve Job's Apple design rigor had glaring faults that were overlooked not because they were perfect, but because they were better. There is definitely acceptable failures.
How many times do we react, loudly, to distant potential threats around us? Kids do this a lot, my son in particular. It burns out those who support them and even they themselves. They get stuck in a pattern of reacting to everything to their own detriment. Prioritize based on the real dangers and consequences, and take action to get to an ideal outcome.
Why do we care about what other people think about our hobbies? Well, they probably don't. They may think it's funny or unusual, but they don't care. I care, though. Why am I willing to sacrifice my enjoyment over an imaginary judgement?
We learn from everybody around us, but only if we open ourselves up and trust the teachers around us. My son was incredulous that I could learn from him, and when I explained how I was surprised that he felt our conversations were merely "practice". Now I worry I am failing as a parent to think my most precious interactions are seen as only practice.
What's the difference between recognition and achievements? How do the two motivate differently, or worse, demotivate. What can be taken away and what stays with us? I have a lot of questions here.
I've previously talked about the Eisenhower Matrix of Important vs. Urgency, and now I'm talking about how to work towards those identified goals. This involves asking important questions to know who benefits and how, and finding ways to strip out anything unnecessary so most of your effort creates value.
It's a terrible feeling to remember some exciting bit of knowledge but forget entirely where you read it or who wrote it. After years of being angry at that feeling, I began applying different techniques to what I read to help remember more about what I read. These are my top 3 techniques that helped.
The environment is the medium in which we exist. It is the canvas we paint our life's work on, but it is not immutable. We can change our environment, and changing our environment changes the situations we experience in our daily life. What can we do to improve our situations and problems? We can try to fix the situations themselves, but they're bound to return again and again. Change your environment for long lasting happiness and peace.