My New Calendar System

Over the past few months I’ve been trying an experiment with my calendar. It’s working and a friend encouraged me to share it. Visuals help so I pulled screen shots of my calendar for the up coming week and the same week a year ago. It’s a holiday week, so not the busiest, but absent some typical breakfasts and evening events it is representative and illustrates the difference.

This was my calendar the Week of Labor Day 2016

To avoid burying the lead, my new system is 4 meetings a day and nothing scheduled more than 7 work days in advance. I have meeting slots at 10:15, 11:15, 2:15 and 3:15. The rest of the day is open for internal meetings and work. Lunches are few and far between. There’re exceptions to rules, (board meetings, the First Round Partner meeting etc.) but this system is the guiding principle and it’s

for me.

This is my calendar for next week, the week of Labor Day 2017:

I made this change because I was frustrated with the product I was putting in the market. I felt busy but not productive. I was waking up every day to a bunch of meetings that did not feel like the best use of my time or the highest value for the people who were giving me their time. Most importantly, I was scheduling things months in advance and struggling to be available to the right people at the right time except in case of emergency. As a service provider, I need to be available when the customer calls. I need to be prepared for the meeting and have the capacity to deliver on my post meeting follow ups in a timely manner. Otherwise I am wasting everyone’s time.

I audited my calendar and I found two major problems:

  1. My time was not aligned with my priorities
  2. My days were too busy for me to get anything done

Root Causes

First point of failure: Aligning Time With Priorities

Commitments were made weeks or months in advance and my priorities were changing day to day. Urgent and important things come up for founders I work with, internal projects wind down or an experiment fails, an investment opportunity arrises and requires a fast turn around — all pulling at my calendar and all needing to be fit into a schedule that was filled 2 or 4 or 6 weeks ago. Time is finite so all I could do is cancel existing meetings or extend my work day to 24 hours. Shit.

Second point of failure: Respect for other people’s time

In the audit, I saw far too many canceled meetings with people I know and respect as well as meetings with these people where I could not hide the fact that I wished I was working on the priority of the day rather than fulfilling the commitment I had made to them a month ago (when they were the priority of the day…). I realized that social norms ossified my calendar and made it almost impossible to align the way I spent my time on a given day with my priorities for that day. I felt terrible about constantly blowing holes in the calendars of my peers, partners and friends. In fact, I found that I was most frequently canceling or re-scheduling on my strongest and most valuable connections because I believed they’d be most likely to understand. This compounded my calendar woes because the only thing worst than an introvert with a completely full calendar is when that calendar is 100% new faces. Shit, shit.

Third point of failure: Overcommitment

I was booked from morning to night and often had an event or a dinner following a full day of back to back meetings. Each of these meetings represent a product that I am putting in the market. Each of these meetings require preparation and follow-up — and the very best first meetings with founders not only force me to get smart on their industry, vision and solution, but also require me to convince them that partnering with me and First Round should be their first choice. My calendar did not allow room for any of this work and the product I offered suffered. When the work happened, it would happen late at night or early in the morning — or would require me to cancel even more meetings. Shit on top of shit on top of shit.

Tactical Solutions

This had to change — so I ran an experiment designed to fix the two root causes of my calendar disaster. Now, 6 months later, I am more available to the founders I have already partnered with and am doing a better job supporting them to maximizing their impact on their company. I have been able to deliver much higher quality first meetings with the time to properly prepare and follow up and, even with way fewer meetings, my investment pace has actually increased — implying that I am getting more out of my time in the new system. But, the most valuable thing is the sense that my time each day is allocated according to my priorities for that day. Very satisfying.

Tactic 1: Setting your limit

The key to aligning your time with your priorities is recognizing how fluid your priorities tend to be. I tried to figure out how many days into the future I could predict my priorities with high confidence. To do this, I wrote down my top 5 priorities each day and realized that within 7 days, none of the original 5 were on the list. This helped me see that if I wanted to align my time with my priorities, I could not schedule anything beyond 7 work days. Now, I manage my calendar by the basic principle of never schedule meetings beyond your ability to predict your priorities.

Tactic 2: Saying no is the key

Reducing the number of meetings I take does mean I have to say no more frequently. This is hard, but it is the only way to make this system work. To get comfortable with this idea of limiting the number of meetings I could take each day and to decide how many meetings I should take, I imagined a success case where I had time to prepare for each meeting and time to do the high value work that a great meeting creates — typically learning more about a new market opportunity or diving in to support a founder I already work with — and found that for every hour of meeting time, I wanted an hour of work time. It’s my calendar, so I created the hour to do the work. Four meetings a day is an 8 hour day, leaving 2 hours for longer term projects and 14 to handle real emergencies as they arise in addition to seeing my family and sleeping.

Tactic 3: Exception Handling

When it comes to saying no, the seven day scheduling limit provides some relief and gives me a legitimate use of “maybe.” When I’m asked to schedule something more than a week out, I now make a habit of asking myself, “How likely is it that this will be a top priority for me on the day the meeting actually happens?” Sometimes it is obvious that it will be and I can break my rule and commit as an exception. Other times it is clear that it will not be a priority and I say, “I’m sorry, I can’t.” But, most of the time, I am not sure and I’ll ask if I can touch base closer to the time requested as my schedule and priorities for the week become clear. Usually this does not put undue burden on the other person and if it does, I can commit or say no today based on my confidence in the alignment of time with my priorities in the future.

Tactic 4: Leave open slots

The calendar audit also showed me that the top priority for any given day was usually less than 24 hours old. This realization helped me limit my set meetings to 4 to allow time to tackle the highest priority stuff in any given day, but also motivates me to try to keep at least one slot open on each day as long as I can. I never know what will bubble up to fill it, but so far my days are full and I feel really good about being able to make the time to handle my top priorities without blowing up previous commitments. It is counter intuitive, but the longer I wait to fill my days, the more productive my days become.

Having “How’s tomorrow?” be my response when someone wants to meet is my new favorite thing to say.


My New Calendar System was originally published in sneakerheadVC on Medium, where people are continuing the conversation by highlighting and responding to this story.