Own your calendar
Tere maailm! (“Hello World!” in Estonian)
It’s the last newsletter of 2024! I hope you have had a peaceful end of the year and are looking forward to 2025 and what it will bring (professionally, at least). If you haven’t done a personal retrospective of your 2024 and have thoughts about next year's professional goals, now is the time to do it! Pat Kua shared a great retrospective form in his newsletter this week. I’ve used his year-end retro and the ones from the Ink+Volt blogs to help me build one for myself. You can find many others online or even use an LLM to generate some prompts if you want a place to start.
In creating a personal retrospective process, having something like these templates is just a good first step. Add some final questions after the end, such as “What did I like about this process?” and “What would I change about this process for next time?” You can build your template and iterate on it every year. That is how I evolved my process over the years. If there ever was an official motto of this newsletter and podcast, it might be “One size never fits all.” (I wish I’d thought of that earlier…)
If you are new to the newsletter, please check out the archives on Substack. Of course, you can always buy the book.
New Blog Post
Creating the newsletter or podcast every week and promoting the book have seriously impacted my blogging frequency, but I published a new blog post last week: “The CTO’s Guide to Crafting a Technology Leadership Resume.” I wrote it after reviewing multiple resumes of senior engineering leaders I mentor who are considering switching roles in the next year and finding that I was giving the same advice to all of them.
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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 section 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 sequential; each 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 “Thoughts on emulating Spotify’s matrix organization in other companies.” I talk about the Spotify Matrix Model, some of the benefits we saw, as well as some of the cultural challenges we had within Spotify in our adoption of it. I talk a bit about the model's legacy and reflect on why Spotify has largely moved on from it as it has grown.
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).
About this week’s chapter
This week’s chapter is relatively short, but its advice is particularly timely. It discusses the process I use in my retrospective to de-frag my calendar twice a year and how I monitor how I use my time week-to-week between retrospectives. My current company is much better about meeting creep than previous ones. However, I still notice that if I don’t actively review and eliminate unnecessary meetings, my calendar can still get overwhelmed by them easily. Before you get back into the whirlwind in January, now is the perfect time to review your recurring meetings, reschedule the critical ones to give you larger blocks of work time, decline (or cancel) the ones that aren’t useful anymore or delegate the ones that might be an opportunity for one of your team to step up.
This chapter was also featured on the podcast in March.
This is chapter 6 of It Depends.
OWN YOUR CALENDAR
Originally published on July 20, 2021
Every six months, I take a day to review and reflect on how things have been going and the changes I want to make moving forward. This day is my personal strategy off-site.
As part of the process, I think about what I want to do more of, what I want to do less of, and how much time I should allocate each week toward my professional goals. I then create a sample of what a perfect day would look like and a mockup of what an ideal week would look like apportioning my time in alignment with my goals.
With my review and planning done, I go to my work calendar and clean it up to make it look like my ideal week. I delete or stop attending meetings that are not useful. I block out time for focused work on my goals. Then, to give some flexibility for the things that arise, I make sure that I leave some gaps or mark some of my project-work time as “free,” allowing others to schedule it if needed.
Each week has unique challenges: unforeseen work appears, a critical customer meeting dominates, or a work emergency takes over my calendar.
At the end of the week, I look back at the calendar and figure out how much of my time spent maps to my planned time allocation.
Often, I find that new things are creeping in if I am not attentive. As my time diverges from my ideal allocation, I must decide if I change my plan based on my new reality (and possibly adjust my goals) or re-assert my plan and delegate or drop the new constraints on my time.
I track each week’s time allocations in a spreadsheet. It helps me understand where I am spending my time over the year. In addition, it makes it very clear if I am spending too much time on low-value work. The spreadsheet also shows if I am unrealistic about how I allocate my time in a week which is helpful for the next six-month planning.
This process may seem very rigid, and in many ways, it is. However, I’ve come to it over the years through iteration after finding myself feeling very busy but not making meaningful progress toward my personal or professional goals.
As we grow in our roles, new opportunities and responsibilities appear. Our peers, team, and others want our input and time. This activity gives us the impression that we are doing necessary, valuable work. We may look at our full calendars at the end of the week and wonder what we accomplished. If this situation feels familiar to you, it may be worth adding some rigor to understand how you want to spend your time and how you actually spend your time.
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