In 2025 Choose to Work Deliberately
こんにちは、 世界！ (“Hello World!” in Japanese)
It’s the second to last newsletter of the year! You may already be deep in the process if you do yearly performance reviews tied to the calendar. If the process hasn’t started, now is a perfect time to get ahead. Let me remind you of the four-part performance review series: Assembling the Data (podcast), Evaluating the Data and Writing the Review (podcast), Making a Raise Recommendation (podcast), Delivering the Review (podcast).
I’ve blocked out a day for my half-yearly personal retrospective before the end of the year. It’s a chance to reflect on what has been going well and what I want to change about how I work and lead. I also consider what new things I want to learn in the coming year. Even though I have been doing this job for a long time, the constant change and opportunities to grow still excite me. While I have developed a fairly structured process for myself (podcast), you don’t need to do something so involved. Just taking time to think about where you are and where you want to be is valuable, and the end of the year is as good a time as any to do it.
If you are new to the newsletter, please check out the archives on Substack. Of course, you can always buy the book.
Reader Survey
I’m thinking about what happens to this newsletter and the podcast after we complete the book. I want your help! Please complete a very quick and anonymous survey to help me out.
Send me your questions about being or becoming a CTO
Do you want to know what it is like to be a CTO? Are you already a CTO and having some challenges? Do you want to understand the C-level career path better? Please send me your questions! contact@itdependsbook.net You can also add them to the chat on substack or in the comments for this post.
About this newsletter
What makes this newsletter unique is that every two weeks, I share a chapter from my book It Depends: Writing on Technology Leadership 2012-2022, which Unit Circle Press released in March. These chapters are not in sequential order; each one is a standalone piece. In addition, a podcast serializes the audiobook in order, released alternate weeks from this newsletter.
The Latest Podcast
The latest episode of the podcast is “The Spotify model: how to create, dissolve, and remix teams to be more dynamic and more innovative.” This is one of my most widely read and shared articles. The chapter was written in 2015 while I was still working at Spotify. It covers one specific strength of the Spotify organizational model: the dynamic nature of the squads within a tribe. In the podcast, I talk more about the influence that having worked at Spotify has had on my leadership style, why Spotify doesn’t do the Spotify model anymore and why I don’t implement the Spotify model in the technology teams I lead since I left the company.
You can download the episode from Apple Podcasts, Spotify, YouTube, directly via the RSS Feed, or wherever you listen to podcasts (see pod.link for a more extensive list).
Drop me a line
I’m always eager to hear from you. If you have questions, want a signed copy, or simply want to say ‘hi!’, please email me at contact@itdependsbook.net. You can also share your thoughts on Substack or the various podcast platforms. Your feedback is invaluable, and I look forward to hearing from you.
About this week’s chapter
As the title makes obvious, this chapter was written at the end of 2017. The title includes the year but isn’t about a specific time. The advice is evergreen. Some themes recur in my writing, and one of the most central ones is being deliberate in your actions and decisions. I write about it often because I wasn't intentional when I started my leadership journey. I went with my gut and was proud to do so. My gut instincts got me pretty far. Until they didn’t. The realization that I needed to be more thoughtful in my approach to management unblocked my career development.
Now that I’ve been a CTO for almost nine years, my biggest fear is becoming complacent. I’ve got enough experience to get away with going with my gut instincts and be right more often than not. That is dangerous for someone in any role and at any level of knowledge work. Our industry evolves quickly, and becoming complacent means becoming out of date, even when talking about team problems instead of technical ones.
This chapter is a plea to approach your work with intention and thoughtfulness. It is short, but hopefully, you find it convincing.
This is chapter 7 of It Depends.
In 2018 Decide to Work Deliberately
Originally published on January 1, 2018
“I went to the woods because I wished to live deliberately, to front only the essential facts of life, and see if I could not learn what it had to teach, and not, when I came to die, discover that I had not lived.”
Henry David Thoreau
You may have heard this quote before. Maybe it resonated with you, or maybe not. What does it mean to live (and work) deliberately?
I’ve thought a lot about this over the last few years.
Earlier in my career, I certainly wasn’t deliberate. I “went with my gut” a lot. Some of it was my lack of experience, and some was an overinflated ego.
As I got more experience, I looked back at earlier decisions that I had made as a leader and realized how poorly considered some of them were. I could have put myself and my team in a much better position with more thought. I’ve also been lucky enough to work with people who have modeled what approaching work thoughtfully can look like.
Consider all the decisions you make in a day at your job. You work on this project instead of that one. You choose the opening phrase you make in your pitch to a customer. You attend this training or decide to skip it. You invite one colleague to lunch and not another. You hire this person instead of that one. How much thought do you put into each of these decisions? Do you know why you made this choice? Do you ever evaluate what worked well or poorly and what you might do differently the next time?
Some of these decisions might seem obvious in the moment. Next time you encounter a decision that appears trivial, take a beat, and just think about why the choice is so clear. Every choice you make means that you are also choosing not to do something. Have you considered both options? Every decision is the start of a chain of events. What are the assumptions you are making about the effects of this choice? Later, return to your decision and test if your assumptions were correct. Was it still the best option? What did you learn from this that you will bring forward?
Thinking strategically is thinking through your assumptions and the implications of a decision and evaluating the outcome. Being strategic is critical for big company decisions but is also valuable in the decisions you make all day.
It does take a bit of practice to do this, but as with anything you practice, it gets easier. It will eventually become second nature.
So, next time you make a hiring decision or decide to work on project X tomorrow so you can do project Y today, ask yourself, “Why is this the right thing to do?” If you can’t answer immediately, spend a minute and consider. You may realize that it isn’t the right choice, and the next time you may spend more time making that decision.
“Look at every path closely and deliberately, then ask ourselves this crucial question: Does this path have a heart? If it does, then the path is good. If it doesn’t, it is of no use.”
Carlos Castaneda
Thanks again for reading! If you find it helpful, please share it with your friends.
Buy on Amazon | Buy on Bookshop.org | Buy on Audible | Other stores