What EAs taught me as an operator

Issue 155: Lessons learned from some of the best people I’ve worked with.

The executive assistant (EA) is part curator and part club bouncer—the filter of prioritization for the departments and execs they support. This has tremendous company impact. Though I don’t have an EA in the new role, I notice myself picking up habits I learned from some of the best people I’ve worked with. as I onboarded to a new company a few months ago, I found myself assigning colors to Google calendar events:

• Purple (external meetings)

• Tangerine (commute blocks)

• Gray (work bocks)

• Yellow (personal/breaks)

• Light green (meetings)

• Dark green (1:1s)

• Blue: Other meetings

I texted a redacted version of this to Kelly. I was as proud as a kid at shoe and tell; sharing with her what I learned from how she managed my calendar. She was so proud! Over the years of working with executive assistants with with those on my own team. EAs are the glue that connects departments. The lessons span beyond tactical calendar management, which is crucial. It is also strategic and psychological in how to work with some of the busiest people on earth (including myself). This reflection isn't only for people managers or people who deal with executives, it's also for individual contributors who work on strategic projects. We'll look at the tactical optimizations of running the week(s), strategic thinking like an EA, and EQ/relationship building.

Make the calendar work for you, not the other way around

I started working with Kelly during my third year at a previous company. She started supporting me, our VP of Product, and VP of Engineering. Before Kelly, my calendar was a mess. Not only was I leading the largest org I've ever had in my career, I spent a lot of time with many directors and executives. In our first meeting, Kelly brought a spreadsheet of my calendar and she went to town; slashing unnecessary meetings, renaming calendar events to be consistent, and 1:1s in a more sensible cadence and consistent time blocks. In the first few days of working together, entire week had a predictable cadence.

Yes, I could have done this myself. However, working at a company that was 2-3x'ing is the same feeling of not realizing how tall you may be growing during the peak of maturity. Things change drastically without you realizing it. This is what happens with your operating cadence. The color coding of my calendar and defragging Kelly did allowed me to think more methodically about the current week and beyond as opposed to the current day, or worse, the very next meeting. I remember an exec telling me once she relied on her calendar managed by her EA as if her life depended on it. In a low risk way, it did, and I understand that now.

The other power move Kelly (and later on Claire) did was putting work blocks and breaks in the calendar. I vividly remember moments where I thought to myself that I wish I had time to go on a walk, run to the bathroom, or even breath. It was such a delight to look up and see the next block on the calendar was actually a break! Calendar management was not about managing events and meetings, it was ensuring you could prioritize and do your best work throughout the weeks.

Optimal decisions at optimal times

EA's are good at so many things. The two at the top of the list are understanding how to work with other executives and their own. It goes beyond the executive, who is the proxy for the department. The EAs and execs are important to levers in how cross-department collaboration works. The EA often knows the most crucial information with their executive and others. A good EA won't tell you what those things are and will clearly communicate how to approach your need.

I once worked with an EA who knew the exec she supported got hangry. If you're familiar with the Hungry Judge Effect, then you know how important this small detail it. I remembered never to schedule a serious meeting about any ask for team dysfunction until he ate some food. There are a multitude of situations like this your EA knows how to navigate. Understanding how to deal with a hangry exec is good EQ. You might think something like this is ridiculous or unreasonable, but they are small details of reality one may encounter.

I’ll share an example of what EAs did for me. When it comes to recruiting, I like to debrief on my own before attending the interview debrief with the rest of the team. In my earlier career as a manager, I often got too excited and wanted the candidates to crush it. Giving me a buffer to be in a place of objectivity put me in a better headspace to make the right decision. This is a habit I’ve instilled on myself to this day.

Prioritizing what’s important

The EA has a great view of what is being prioritized across the company, not only what is prioritized for you. We always think our priority is the most important. As a leader of a design org, I always think that my roles are the most important to get reviews approval for. However, when it’s being prioritized against that crucial Site Reliability Engineer, it’s a completely different story—the greater good of the entire company.

Prioritizing is crucial to getting things done. If you surface a low priority need when the leadership of a company if prepping for an exec meeting or the board meeting, you’re going to lose credibility based on what yiu surface.

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Conclusion

This post personified my appreciate for all the EA’s I’ve worked with. They are the true MVPs in getting stuff done. Whether I have an EA or not, I’ve taken these lessons with me as they’ve made me a much better operator.

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Hype links

Collection of what I read and related to this week's post

• The Cloud Is a Prison. Can the Local-First Software Movement Set Us Free? → I believe in the cloud and also local-first—very interesting read

• Oh to Be a Fly on the Wall During the Conversation Where Elon Musk Asks Tim Cook to Help X Corp Replace iOS as the Bedrock Everything Platform →

• The No Code to Know Code Manifesto → Huge congrats to Mason Poe of Edgar Allan on this new direction

• Stashpad

  ¹
  → I use Obsidian for Galaxy Brain and Stashpad for Gravity Brain—when you need to get stuff done

• Levi Jones is open to new roles → Finally, a designer who finished their portfolio

• Defining your own “success” by Kyle Lambert → As I’m headed to go on vacation, I’m always reminded by my friend Kyle that success is not only career-oriented. A great reminder

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Job opportunities

• We're hiring at Replit

  • Lead Brand Designer

  • AI Engineer

  • Product Engineer

• Linear is hiring a Head of Product Design

1. I am an angel investor in this company