Letter 010 - Your Calendar Is Your Battlefield & Other Thoughts on Strong Prioritization
Impact = Time (to think) + Energy (to do) + Focus (on what matters most).
Writing this letter while listening to my ol’ reliable late-night work playlist I’ve been refining for 5 years, Strategy Sessions
It has been a looooong day, and I’m taking a brief break to write this letter. After a particularly long day, I’m left to ask myself: “why am I still online?” It’s both an outcome of a genuinely busy time and my failure to adequately prioritize my time over the last couple of weeks (gotta call it like I se it). Therefore, I’m writing this letter to re-anchor to some ideas around prioritization that I think are important.
Below is a view of:
A formula for Impact
Treating your calendar like a battlefield
Strong prioritization / Prioritize With Strength
Think back over the last two weeks. Do you feel like you have worked on the things that are most important? How many times have you looked up after several hours of “work” only to realize you don’t have much to show for those last several hours. Not a great feeling.
While I once had immense patience for this, that’s not the case anymore. I value my time (and the time of others) greatly... Because time is something that is relentless — it never stops moving forward, and I want to make sure I’m spending it in a way that I feel good about at the end of a day/week/month/year/decade/life. And hell, maybe that 30 minutes I just wasted could have been spent doing something nourishing — calling a family member, resting, dancing around like a jackass with our dog Tycho, pretending to not watch the latest season of “Love Is Blind” ….
But getting to that state of “feeling good about how I’ve spent my time” is not easy task. In fact, taking control of your time means being aggressive about time management. This has been a recurring theme of my writing so far, because if you manage time effectively, you create space, and space is where you unlock flow state and quality thinking ====> this is what enables Impact. The attainment of a big move towards a goal. Allow me to create a totally unnecessary, completely mathematically sound formula to bottom-line this a bit more:
Impact = Time (to think) + Energy (to do) + Focus (on what matters most).
(read that in a Yoda voice)
I’m going to focus on Time (to think) and Energy (what to do and not do) in the below sections.
Big Idea 1: The Secret to Time Management is Treating Your Calendar Like A Battlefield.
As your responsibilities grow and grow and grow, so too does the number of meetings you’ll be asked to attend. I remember a time early in my career where I had an ungodly amount of work, but a relatively light meeting load. In that scenario, my impact was dependent upon my ability to use my time wisely to complete various modules of an overarching task. I had more of a “maker” schedule than a manager schedule. In that scenario, I found it critical to plan out the “milestones” i’d hit throughout a day or week, lest I procrastinate and be forced to pull all-nighters to finish work (bleegghhhh I do not miss that). Admittedly, in this “maker” schedule, I didn’t have to be as vigilant on calendar management, but that all changed once I started managing complex projects with many work streams.
If you experience that shift to more of a “manager” schedule, be prepared to aggressively implement guidelines in your calendar…Because if you don’t, you will undermine your ability to really drive excellent results. All of your time will disappear, and you’ll oftentimes look back and have not-enough to show for it. Here is how I structure my calendar to ensure consistent high-output.
Create actual invites on your calendar to block certain activities, and make the invites recurring so that space is always there.
I have my GSD (get shit done), GTD (get thinking done), and GND (get nothing done) meetings with myself every single day throughout the week
Theme your days to create some sense of consistency week-over-week (see my last issue for more on this)
Do not attend a meeting unless you are critical or the information being disseminated is critical. I’m critical if my lack of attendance will lead to a breakdown in progress. Information is critical if me not hearing means I cannot effectively do my job and/or create the best environment possible for my colleagues
Make sure your recurring meetings have an end date. I typically set recurring invites for 1-2 quarters, so that I can regularly revisit if a recurring meeting is serving its purpose.
Challenge people to share information asynchronously using tools like Loom and the beloved “memo”
A great memo (shout out to my colleague Linsey!) follows a clear structure like:
2 bullets on Situation
2 bullets on Problem
2-5 bullets on Go-Forward Options
2 bullets on suggested next steps and/or a clear call to action (CTA) like: “please respond to this message by selecting an above option and providing you thoughts ahead of our decision-making meeting next Tuesday”
Challenge others to think carefully about meeting durations — do you really need 30 minutes? OK, maybe you do… But have a good reason for taking the time of others. I oftentimes do a “salary calculator” in my brain to estimate the cost of a meeting in people time
Challenge others to have a clearly stated Objective and/or agenda for the meeting, even if it is literally developed at the beginning of the meeting
Strive to have a No/Low meeting day during the week. At Microsoft, this is Friday’s for us. This does mean the other four days of the week tend to be a little more crazy
Ensure you have at least one day per month with absolutely no meetings whatsoever. This is when I’ll do “big think” activities or thinks like Press Pause summits (recently did this for channel strategy development — an area that I’m fairly knowledgeable on, but needed to go deeper on)
Last (and definitely not least): set clear start and end times on your days. This is important for your sanity + personal space, but it’s also a really important part of working on global teams. We have colleagues that are all over the world, and the best way to make sure they aren’t having meetings booked at 11pm their time is to just block the hours off that you aren’t working.
I’m based in Atlanta now, but most of my colleagues are in Seattle and India. This single tactic enabled the transition from West to East coast to go over fairly seamlessly… That and clear communications about my new “core working hours”
There are so many other ways to protect your time, but much of how I protect mine comes down to the above. I don’t think anything above is particularly groundbreaking, but executing the above consistently is the key to calendar management.
Big Idea 2: You Should Prioritize With Strength.
Your calendar is simply a reflection of your priorities. I can analyze the time spent on different threads throughout the week and it’ll probably map to the prioritization of the different things I’m working on (it should!).
Prioritization is what allows you to say Yes to what is most important, and No to what is not-critical or “off strategy.”
I’ve spent thousands of hours in a “prioritization” context at work — for a couple of years, I felt like I was doing back-to-back-to-back “prioritization model” and “roadmap development” projects where all you did was choose the most high impact things to work on. I have a bunch of different models and frameworks I’ll share in other letters over time, but this is the one that I deploy on a daily/weekly basis to help me consistently prioritize my work and thus my calendar… to achieve Strong Prioritization.
Here are the questions I ask myself when I am stack-ranking work at the beginning of every week.
A. “If you could only do one thing each day of this week, what would you accomplish each day?”
B. “Do your answers align with the priorities of your role/team/company?”
C. “Do you have the ability to execute these priorities on your own? If not, who else needs to be involved? Do they have the time / will to assist?”
D. “What happens if (activity) doesn’t get done by the end of the week?” (play out what will happen, and assess if it’s something that absolutely must be done this week)
E. “If my competitors saw what I was going to accomplish this week, would my progress make them nervous?” (if is doesn’t, am I helping my company to increasingly put differentiating offerings out into market? Ultimately, everything I do should be contributing to the development of some competitive advantage for my company)
F. “Does what I need to accomplish this week bring me energy / joy?” (if it doesn’t, then I should probably be re-evaluating the scope/focus of my job)
G. When in doubt on any of your outputs, pressure test this with a colleague / your manager
Finally, make sure to rank your priorities. No two things can be tied; your priorities must have a clear rank — 1, 2, 3, 4, 5… This clarity is what drives the tough calls you make about what has to get done and what can be postponed
In summary, your calendar is a reflection of your priorities. Given that your priorities take so much of our time, it is a worthwhile exercise to question whether they are the right priorities.
See ya next week!