Two Must Do's for Executives To Truly Prioritize Their Priorities

Do you find that your calendar manages you? We go in detail on how to make your calendar reflect your priorities and why creating themes throughout the week creates an operating cadence that scales.

When I became the Product Lead for Pro at Thumbtack, running 5 product teams that covered the end-to-end experience of small businesses on the platform, my calendar dictated every minute of my working hours. I spent ~5 minutes every morning working through times when I was double or triple-booked that day, apologizing, postponing, and seeing if async was a possibility. Then, I went where my calendar said I needed to be. And then I’m bored in the meetings I’m at, sneaking glances at my email and Slack messages, and growing more stressed at future work piling up elsewhere.

I was not spending time on the most impactful work. I was being reactive. My meetings didn’t have the right participants, I wasn’t properly prepared, or it was unclear why I was needed. Each meeting spawned more meetings to have follow-up conversations, further booking up my future weeks.

It turns out that falling behind on calendar management is a vicious cycle. As I hopped from one meeting to the next, I wasn’t as prepared as possible for that product review or 1:1. I hesitated on critical decisions, lacked nuanced context, or was simply drained and tired. Each not-as-productive meeting would lead to more meetings. Conversations that could take 30 minutes would turn into five meetings across three weeks, further taking up everyone’s time in addition to mine.

To break this vicious cycle, I needed to get on top of my priorities and my calendar. I needed to truly spend most of my time on my top priorities, come prepared for high-stakes conversations, and reduce context switching as much as possible. Since then, I’ve worked with many executives who also struggle with prioritization and calendar management. If you’re looking for a reset going into the second half of the year, here are two well-tested approaches to implement for your week.

Make a top-down view of time spent that reflects your P0/P1’s

It’s perhaps unsurprising how often we look at our calendar and realize that we’re spending most of our time getting pulled into “random meetings” rather than on work we need to get done. As a leader with unparalleled historical context, high-impact product teams, and a strong desire to help others, my calendar was filled with meetings that others scheduled. These cross-functional partners need a decision to move forward with their work. Recruiting and PR need me for interviews and intro conversations. The VP of Marketing and VP of Operations want to talk about (not enough) progress on shared metrics. A new hire wants to meet me. Then there are about 20 hours of one-on-ones and team check-ins. What’s truly critical?

If you are struggling with time management, the first step is not to open your calendar, but to list out your true priorities. What initiatives, decisions, or strategies are they responsible for driving? What is the change that they need to make happen? Then, divide your list into three sections: P0’s (only I can do), P1 (critical priorities that I cannot miss), and P2 (important to get done). Finally, assign a percentage of your time to each section: If your time spent reflects your priorities, this is what it should look like in aggregate.

Here are some critical watch-outs when attempting this process:

• Start with the P1’s, aiming for a list of 5-8 items. Why? When you start with the P0 section, everything becomes a P0. Once we have the P1’s, then we take 2-3 of the most critical, cannot miss items and make them P0.

• Make sure each item is time-bound (there’s an end date less than 6 months), measurable (you know when it’s done), and concrete (specific actions are clear). “Integrate the newly acquired company” is too vague. “Get executive team buy-in on merged product strategy for current and newly acquired company before Q3 planning” is better.

• It does not include any work that isn’t mission-critical or that only the executive can get done well. Keep a separate list of items where “no active work” or “important but won’t get done”. Realistically, busy executives don’t have time for tasks that are “nice to have” or “would be interesting to try”.

Once you have the top-down view of time spent based on your priorities, then it is time to pull up your calendar to the next month. For each of your meetings, assign it to a P0/P1/P2 or ???. Take a deeeeeeep breath as you assess how big of a difference you have between ideal and reality. This is why you’re so tired.

Then, start working towards the ideal. Remove yourself or delegate meetings where you are not critical. Combine multiple similar conversations on a topic or make one-on-ones a one-on-one-on-one. Shorten meetings from hours to 15 or 30 minutes. Reduce recurring frequency from weekly to biweekly to monthly. Finally, delete…and ask for forgiveness — because you’ll end up asking for it anyway on the day of due to being triple-booked. They’ll thank you for the advanced notice so they can find alternatives. Get ruthless about making your overall time spent as close to the ideal you just came up with as possible.

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Tip #2: Theme Your Weeks

Context switching takes up a lot of mental bandwidth. When you go from meeting to meeting, it can take 10-15 minutes to just ramp up on the topic. In addition, when meetings happen in a random order, you often don’t meet with the right person at the right time.

For example, the team needs a decision where you need to talk to your engineering partner, yet you don’t meet with him for four days. A Product Review happens on a Thursday afternoon, and there isn’t time to get back together before Monday. The sales team needs an update on a product launch on a Monday, but the team check-in isn’t till Tuesday afternoon.

One of the best ways to ensure you stay on top of your priorities is to find an operating cadence throughout the week that you can stick with over time. When I was at Meta as product lead and then as CPO and CTO, I followed a regular pattern in my week. This allowed me to do less context switching, prioritize critical meetings earlier in the week, and have a higher likelihood of meeting the right person or team when I needed them or when I was most useful to them. This cadence also set a helpful cadence for my teams and peers for their work.

Here is an illustrative set of themes for a week:

This general cadence worked well because it allowed conversations to flow the most naturally. Here’s how it worked:

• Each week, I would start with calendar management, emails, and a bunch of logistics work to set myself up for a successful week.

• I ask for written team updates on Friday afternoons. This allows me to review them before the Monday executive leadership meetings without much of a time gap.

• I schedule weekly update meetings with teams on Monday afternoons, after the executive leadership meeting. This allows me to bring context, decisions, and asks from the leadership to the teams immediately.

• Tuesdays are for external and cross-functional meetings. Having these meetings after the team and leadership syncs allows me to bring the latest updates and context to my cross-functional peers and externally.

• Wednesday mornings are for large group decision-making meetings. This gives the team time in the week to prepare and have their pre-meetings. It also allows for any necessary follow-up meetings to happen during the same week.

• After most “work priorities” related meetings Mon-Wed, I like to reserve time between late Wed and early Thur to reflect on progress and shift any meetings around for the second half of the week.

• Thursday is reserved for 1:1s. These are also the most easily moved if urgent, critical meetings come up from earlier in the week.

• Friday is reserved for interviews and org work. There is almost always at least one interview on Friday, and it’s a good time to think about people and culture. Having a day dedicated to this ensures that it is a priority for me and for all my leaders.

• Friday afternoon is when pre-reads, weekly updates, and any critical context sharing material are due to be emailed out for the meetings the following week. This ensures everyone who attends has the time to review and prepare.

While the themes were helpful, it is not meant to be followed religiously. Depending on your seniority, org complexity, and level of influence, you may not be able to perfectly control the timing of group meetings.

At the start, you may need to accommodate other standing meetings (e.g. weekly sales leads sync, legal office hours) where you have little control. As CPO & CTO, I had much more control. But even then, I had to evangelize my working cadence with other key executives so that we held the executive weekly on Monday (instead of Tuesday), and to have external meetings on Tuesdays. Over time, you’ll learn which are truly constraints that cannot be moved, and how you can adapt your cadence to flow better with the constraints.

Remember, the intent is to try to create themes that allow you to better prepare for meetings and have the right information. For example, I would tell my team that if their meetings happened after the weekly executive sync that I would have more context to share with them. I would explain to my partner teams that if we met after I meet with my team, I would be more able to share the latest updates. When the week operates on a loose drumbeat, everyone is better able to prepare and have productive conversations.

That’s all folks! See you next week at 3:14 pm!

Yue