Coworking with the CEO: Five Lessons Learned

Bethany Crystal
6 min readSep 30, 2021


Even if you don’t have a permanent office, you can co-work with a colleague from just about anywhere

In the “before times” (that’s to say, the pre-pandemic era), employees used to get access to “business lessons by exposure” all the time, whether we knew it or not.

In the office, we’d overhear conversational snippets from that meeting down the hall where someone left their door open or spoke a little too loud. We’d laugh at the animated way that our executives greeted investors prior to a board meeting and clock that it meant something important was going down. Maybe we’d plan our midday watercooler check-ins right after important meetings in an effort to maximize that precious “edge time” where so much of the formative processing and synthesizing work gets done. (Or maybe we’d just make sure to grab beers with the sales team every now and then to get a real read on how things were going.)

But in a work-from-home era, it’s been a lot tougher to observe and model behaviors. (When you’re rarely in the same space, what does it mean to “observe” someone else?) After nearly a year of working at Bolster, something was starting to feel funny to me about this whole thing. I realized what I wanted was more learning by osmosis.

Once I was able to articulate this request a bit more clearly, I asked our CEO Matt Blumberg to test it out with me: Could I spend a day coworking with him? Essentially, I wanted to just to “be around” during his workday, maybe listen in on some calls and have pockets of debrief time. To his credit, Matt didn’t look at me sideways or call me crazy. To my surprise, he said yes.

So I spent an entire day this week co-working alongside our Matt. I sat in on a few meetings, I listened in on a few others, and I got the incredibly rare benefit of immediate reactions and real-time synthesis on a variety of business topics. Here’s what I learned.

Five Lessons Learned from Co-Working with the CEO

  1. It’s really hard to get a broad business perspective when you’re in every conversation.
    The main way that I interact with colleagues today is through Zoom meetings.This means, to some degree, that every interaction I have has one thing in common: Me. Because of this, I rarely get to understand how people think or what they talk about when I’m not in the (virtual) room. This is actually a pretty mentally screwy way of getting a sense of a broader business context. After all, while we all like to think our jobs might be the most important thing going on, that’s rarely the case. That’s why it’s helpful to just “be around” people and know how they are spending their time and their days. This mental calibration reminds you that maybe the thing you’re working on, while important, isn’t the most important thing. It also helps you internalize that cadence of focus and prioritization across an entire organization. Honestly, perhaps the best thing about this exercise was a simple business reset of seeing the company through someone else’s eyes. Understanding how someone else prioritizes their day teaches you a lot about how you might look at your own.
  2. The job is largely about finding the signal through the noise.
    I’ve known this in theory for many years: The best executives and senior leaders are ones who can read through an entire strategy doc or board deck and ask the 1–2 most important questions. I know this because for five years in VC, I heard the one-liner outputs on the other side of conversations, board meetings, and strategic business shifts. But what I rarely got in that job was the in-depth “other side” of the coin: What was the long conversation that led them to that particular conclusion? Most important: What else was discussed in that conversation that was eventually deemed irrelevant, noisy, or distraction? It’s a lot easier to practice this skill yourself when you get to watch how someone else processes a large amount of information and reduces it down to a single action item or takeaway.
  3. Figuring out your efficiency life hacks is essential.
    Everyone has their own life hacks that get them through the day. Whether it’s a Trello board, meeting chunking, or a particular way of taking notes. And “growing up” in your career is all about figuring out the hacks that work best for you, then doing them consistently to keep yourself moving quickly in and out of one business context into the next. None of this is earth-shattering stuff, but after a year and a half of being stuck in my own vacuum and self-orbit, it was kind of nice to see how someone else approached this. A couple of things I learned from Matt included: If you know you’re going to need to email the notes from the meeting to someone else, start typing those notes in an email compose window so you can send it off without a second thought. Also, it’s a good thing to ask for 3–5 minutes at the end of one meeting to make sure you go in prepared for the next one.
  4. Hearing someone else tell the company story helps you enhance your own.
    This was the beauty of working on the sales floor. You take sales calls right next to other sales reps in the middle of their own pitches. This helps you pick up on snippets of the pitch or latch onto the way someone else explains a certain product concept and you build that into your own approach. Over time, your own version of the story becomes a collage of bits and pieces you’ve taken from everyone else and optimized for your own “best version.” While I’ve certainly gotten good at speaking to what our company does, it was incredibly helpful just to overhear it from someone else, a few different ways, to totally different audiences than I usually interact with on my day. I came away with a couple of different perspectives to try on for my next “at bat.”
  5. Coworking builds connection.
    No matter how efficient and effective your Zoom meetings have become, there’s no replacing the feeling of energy you get when you work in the same place alongside someone else. Even if you aren’t in each other’s meetings. Even if you’re just doing your own thing while they are doing their own thing. There’s a feeling of connection and meaning you can only get when you share a space in real life. In my time working out of a coworking space 4–5 days a week, I can’t tell you how nice it’s been just to be able to say, “See you tomorrow” to a couple of other regulars. To know someone else out there is working on the same things as you, working toward the same objectives, is just a really good feeling. It might be intangible, but that doesn’t make it any less powerful.

Why we need to co-work with our coworkers

When I worked at Stack Overflow, I was rarely in any meetings directly with anyone on our engineering team, but I nearly always knew what was on their minds, what they were working on, and what was keeping them up at night. How? The ping pong table.

The fact is: I’m terrible at ping pong and rarely even played. But I participated in ping pong games nearly every day just for a chance to interact with this part of the business. From my desk, I’d listen for the distinct tap-tap-tap of the ball against the table for a signal that it was break time. Then, I’d dart in that direction, prop myself up on the pillows along the windowsill next to the ping pong table and watch the game…and listen to the chatter. All this time, throughout these 18 months of COVID-era working, I’ve been wondering: Where’s the ping pong table? How do I get that same fringe benefit of just paying attention?

One of the biggest benefits of the COVID era style of work has been the increased accessibility of everyone, all the time, all over the world. In many ways, the universality of Zoom and video conferencing has made it easier than ever to get in touch, to work from anywhere, and to access anyone. But I think we’re just scratching the surface about what it means to feel the heartbeat of a business in a world where we rarely convene in person, and how we help people internalize real priorities in the absence of context clues we’d grown to rely on from every prior job.

Co-working with colleagues — even in a one-on-one capacity — might be one way that we get there. I plan to do this even more.

Originally published at Dry Erase.



Bethany Crystal

A little bit web2, a little bit web3… Today’s projects: @Bolster & @Zeitgeist_xyz , board @CompSci_High ; ex @USV , @StackOverflow , alum of @Northwes