How keeping a ruthless calendar makes me a better Product Manager

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Reclaim your time and ship better products

All of the Product Managers I know can relate to a stacked calendar all day, every day. There are many demands on a PM’s time: client research, design reviews, backlog refinement, writing requirements, executive presentations, corralling stakeholders, fighting fires, gathering feedback, and 50 other tasks that it takes to keep your team shipping.

But product management is a discipline built on opportunity spotting, deep thought, and scrappy creativity. If your calendar is constantly full, how do you find time to look up at the bigger picture? This was a question I asked myself after several months of being completely buried by my calendar. I had no good answer. In the wake of this revelation, I decided to run an experiment for a year: during the course of 2018, I resolved to keep between 30–50% of my calendar as unstructured time with the hypothesis that being less “busy” would focus my work and drive better results for the business.

During 2018 my team and I shipped some of the strongest retention gains than during the rest of my tenure at Stitch Fix, which leads me to believe my experiment was a resounding success. But more than that, I experienced a number of unexpected, ancillary benefits that made me and my teams happier, more productive, and just plain better.

In this article, I will outline these benefits and provide some tips for how you (yes you, busy PM) can also reclaim control over your schedule. While this advice is geared towards PMs, I would encourage anybody who feels calendar-swamped to give these techniques a try.

Benefits I have experienced from unstructured time

These are loosely organized in order of the highest impact to my performance.

1. More time to be curious

We are a very data-driven organization at Stitch Fix. But sometimes it is easy to fall into a routine when everything is shipped as an experiment: create a hypothesis, build an experience, measure the results, rinse and repeat. While there is nothing inherently wrong with this cycle (I am grateful that we default to A/B testing everything), it becomes very easy to glance at performance metrics and either roll out the feature or cancel it and move onto the next thing without digging into the why or considering if we have squeezed all of the juice out of this orange before grabbing another.

In freeing up my calendar, I first found myself making time to truly grok test results and and investigate why we were so successful (or unsuccessful) in a given experiment. I would work with our data science team on deeper post-hoc analysis and make time with our UX research team to get deeper qualitative data on how clients perceived a test. My curiosity only grew from there: my team and I started to plan better analytics at the beginning of a test, to spend more time researching up front, and ultimately to articulate and execute a crisper product strategy.

2. Increased team autonomy and distributed decision-making

Part of clearing your calendar means removing yourself from meetings and expecting things to get done without you in all of the weeds. To do this effectively, a few things had to happen: our cross-functional team leads got clearer about setting goals (of all sizes) and expectations up front, we agree on which asynchronous communication tools to use, and we are more comfortable with hallway conversations.

I first started to observe teams exercising this autonomy on small things: taking a stab at draft copy if it was not specified, nudging a story up one spot in the backlog, just handling a bug that seems critical without asking permission. Eventually though, as our trust in each other matured, the decisions got bigger: writing user stories and acceptance criteria without me, de-prioritizing or punting a design task that was not strongly contributing to our goals, looping in a stakeholder that needed to be consulted, accepting work in our backlog, etc. Of course, there are meetings that we have agreed are not cancelable: daily standups (particularly critical for staying in sync), retrospectives (a place to temperature check if we are being too ruthless with calendars), release reviews, OKR planning, and solution ideation. In hindsight, it has been remarkable how many unnecessary meetings we were having.

3. I am more approachable about new ideas or to talk about existing problems

When I was at the peak of my schedule-mania, I once had an engineer on my team tell me he was afraid to approach me with an idea he had because I seemed too busy. That is a serious red flag. If he was afraid to approach me with a new idea, it got me wondering what else people were afraid to approach me with: bugs? good news? bad news?

With more unstructured time I am at my desk more, which means I field more in-the-moment questions from designers and engineers either live or in real time on Slack. Spontaneous coffee chats have also increased for me (one of my favorite kinds of meetings!). Whether it is other PMs wanting to workshop a problem they are puzzling through or an acquaintance from another department who has an idea related to my product area, being available seems to have lowered an invisible barrier that makes me more approachable.

4. Crisper meetings, emails instead of meetings

If you are going to slash meetings, the meetings you keep need to be flawless. In taking a hard look at my schedule, I set the expectation that if I was going attend, I expected an advanced agenda and a stated, desired outcome. This combination seems to encourage meeting facilitators to do the right amount of advanced-prep, whether that was somebody else or me. If we are making big decisions, I will usually prepare or ask for a pre-read as well. Pro tip: if you have a recurring meeting, link to a rolling agenda Google Doc and take live meeting notes in that doc… presto, you have a written record that is easily searchable.

I also put a sticky note on my monitor that said “can this be an email?” Seeing that note every time I was preparing an agenda was an excellent trigger to click the cancel button and to find a more time-efficient way of getting to an outcome (email, Slack, drive-by).

5. Better relationships with close (and distant) stakeholders

I have already mentioned that this new approach to time management increased the level of trust and that stakeholders find me more approachable. This benefit is hard to understate because trust can be a hard thing to foster.

PMs are famous for saying “no.” With more unstructured time, I find myself saying “no” less. Instead, I have found myself saying “can we dive deeper on that?” or “what if we tried this instead?” When you become a collaborative problem solver with your stakeholders instead of a dismissive no-er, trust (and friendships) build quickly. It is a great, virtuous cycle.

6. More time to mentor and be a sounding board for other PMs

Our product team is pretty lean and each of us is responsible for large swaths of the Stitch Fix experience. One thing we are not great at is spending quality time problem solving together: this tends to happen in cross-functional teams instead of amongst Product Managers. Since this experiment began, that has changed. I actively seek out my colleagues’ free time to workshop ideas and have introduced the concept of “product pairing” to better learn from each other (that experiment is still in flight, perhaps I will write another article on that in the future).

I also have the headspace to provide more thoughtful feedback. Instead of just slinging Product Requirement Documents around and giving/receiving cursory feedback, I spend more time investing in Stitch Fix projects outside of my product area. This brings me closer to all aspects of our business and helps me see opportunities I would have missed before. Some of the advice I have given to other PMs has also lead to positive adjustments to their approaches or a scrappier way to solve a problem.

7. I am saving the company money

Or my team is at least delivering greater value for our time to the company. If we are spending less time in a meetings, we all have more time to produce quality work product. And I’m not just saving the value of my own time, I am saving the value of each person’s time who would have been in a meeting room with me.

8. Last but not least, I am a happier human

Being too busy is not fun. Getting to the end of a day of meetings so you are free to do individual contributor work through dinner is not a recipe for quality of life. Now if I stay late, it is usually because I am excited about something, not because I am rushing to meet a deadline. Like most of these benefits, this one also extends to the people I work with.

How to get started

Take a deep breath and center yourself. There are going to be moments where coworkers are not going to understand and it will seem like a meeting is the only way. In most cases, I promise it isn’t. A key principle to success is valuing unstructured time appropriately — treat it as if it is currency because in a way, it is. I have described the benefits I have experienced, so if you are not sure how valuable your time is, let that be a starting place.

Interesting enough, Once I got started, I experienced calendar clearing to be somewhat self-perpetuating: when I started asking hard questions about a meeting, my colleagues did the same. By being more present, small decisions started to be made at our desks or in Slack — the need for one-off meetings fell off sharply as we all got more comfortable making decisions in a less formal, non-meeting setting.

Here are a few tactics that have been invaluable to me:

  • Tell people you are doing this. I found the framing of “hey, I am experimenting with my time right now” instantly made this idea click more for people. Telling people will also reduce the number of inbound meeting requests.
  • Calendar blocking. Block unstructured time and do not let other people schedule over it. I have found it useful to designate what I want to do during that time (e.g. “watch user videos”) or if you struggle with others throwing time on your calendar, just name the events “busy” and folks tend to assume the event is private.
  • Require meeting agendas and outcomes in advance. This one gets uncomfortable until people get in the rhythm of providing them. If I get invited to a meeting I either do not want to go to or that does not have these, I reply with a friendly email along the lines of “I would love to make sure I am prepared for this: can you please include a meeting purpose and agenda?” I will not accept the meeting until it is there. Not showing up is a great motivator for the facilitator to do the up-front work on the next one.
  • Predict incoming questions and concerns. If you have a lot of feedback coming in from leadership, put together an FAQ deck or include an FAQ section in your feature or strategy documents (and link it to your roadmap). Answer the questions you anticipate there and add to it as new ones come in. This helps me decline meetings and instead refer folks to what has already been written down.
  • Do more informal 1:1s. I have come to love having an on-demand chat in the kitchen instead of a formal 1:1 in a meeting room. It feels easier to break when you have covered everything compared to formally getting up from a conference room table. If you are a Fitbit user, walking 1:1s can do the same thing!

Just remember that you AND your team will benefit from you keeping a disciplined calendar. So go free up your time and build great things! If you have other effective time tactics, please share them in the comments.

Customer-Facing Product at Stitch Fix

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