Like an Executive | Customers, Etc.

Executive functioning isn’t just for executives.

I debated whether to publish this week—it’s been a long day and there’s a new episode of Ted Lasso on tonight—but I had enough written that I thought I might as well get this thing published. Please excuse grammatical errors (I’m especially embarrassed to be changing between first person and second person so much—thanks for bearing with me).

Part of how I’ve managed teams is treating everyone on the team like an executive. Even if your title was “Junior Support Specialist”, I still wanted you to participate in the work of thinking strategically about how best to serve customers and taking on small projects in that vein. That’s why I made such a big deal about extra-queue-rricular time. Ultimately it’s big win for customers when the people closest to customer problems are also contributing meaningfully to scalable solutions that benefit those customers.

If you’re going to think like an executive, though, you need to function like an executive. We’re talking here about executive functioning skills¹. It’s one thing to crush a support inbox all day and an entirely different thing to function like an executive outside the queue.

You can read entire books about executive functioning, but let’s start with five executive functioning hacks that have been top of mind for me as of late.

16” MacBook Pro with 12.9” iPad Pro, connected via Sidecar with USB-C

Find a “home” to do knowledge work

I wrote recently how in my current moment, I’m settling in at a WeWork so I can do knowledge work outside of the home. I find the change in context to really help in my productivity and brings a lot of focus when I want to sit down and crank.

Similarly, if you have a job doing knowledge work, finding a “home” for different work contexts can be helpful. For example, if your primary responsibility is working with customers, but you spend a day per week working on project work, you might do customer work at your desk and then choose to brainstorm on project work at a coffee shop. The switch in context gets you out of one mode and into another.

Two monitors, even remotely

Sometime in the mid-2000s, LCD monitors (“flat screens”) got cheap enough that they not only regularly replaced bulky CRT monitors, they eventually got to the point where you could reasonably justify getting a second monitor for you PC at work. “Double monitors” was a game-changer for productivity because you could do work on one screen and have another screen up as a reference. Even at a 1024x768 resolution, it seemed like you could unlock so much productivity just by adding another screen.

Fast forward to today and the quality and resolution of screens has improved dramatically. My home office setup has two large external monitors driven by a M1 MacBook Pro. But what about when I’m away from home?

Remote monitors have come a long way. You can get a portable external monitor for like a hundred bucks on Amazon², but if you have a Mac, an iPad will function surprisingly well as an external monitor using Sidecar³. Pro Tip™: Although you can connect an iPad as an external display over WiFi, I highly recommend always connecting over USB-C—sometimes the WiFi connection is wonky and the iPad freezes. Another Pro Tip™: Use the Moom app to quickly move windows between monitors.

Clear your inbox, every day

When I was in the throes of my MBA program, I had three inboxes: personal, work, and school. I mostly stayed on top of my work and school email inboxes, but my personal inbox suffered and grew quite long in the tooth. Now that I’m down to just one inbox, I make it a priority to get to inbox zero—or very close to it—every weekday. It’s just so much cleaner and makes it much more difficult for things to slip through the cracks.

Here’s how I do it:

• Ruthlessly unsubscribe from emails and newsletters that are taking up space in my inbox and that likely I’m not going to read anyway⁴.

• Bundling⁵

• Quickly archive emails that don’t need my attention

• Snooze emails that can or should wait until a later date

• Respond quickly to most emails

• Move emails that represent projects and tasks to an external task list⁶

The “respond quickly” part can be a challenge for me. Some people are really good and sending off quick missives at a blazingly fast pace. I’m more of the slow and thoughtful type. But I try to move it along when I’m clearing my inbox.

Weekly calendaring, weekly

I love that “calendaring” doesn’t trigger a red spell-check squiggly line. It’s such a useful word. “Calendaring” is when you sit down with your calendar, look a week ahead at meetings and priorities, and figure out when you’re going to do things. It’s not rocket science, and the most important part of the calendaring process is that you actually sit down and do it. Let your calendar communicate to yourself and to others your intentions for your future time.

Calendaring is especially helpful for me in this time of sabbatical because it can feel both completely unstructured and entirely too structured at the same time. By planning out my weeks ahead of time, I can more confidently schedule networking calls, make lunch dates with friends, etc. I have a “Weekly Calendaring” appointment on my calendar for every Friday.

One more tip about Calendaring: make sure to leave open space on your calendar to breathe and just in general take a break from meetings. If you find empty space tends to get filled in by people adding time to your calendar, add “[Do Not Schedule]” blocks to your calendar. If you find “[Do Not Schedule]” blocks constantly getting eviscerated because something really important came up, have a serious conversation with yourself—and possible others—about what you consider important in your life such that you consistently renege on your commitment to yourself to take a break.

Figure out your daily routine

Getting good at calendaring naturally invites you to figure out your daily routine. “I seem to be most productive in the mornings right after I work out—I’m going to create a productivity block for two hours first thing in the morning each day to protect that time.”

Figuring out your routine helps you find efficiencies in your schedule, which in turn creates space for what you believe to be important work.

This, by the way, is what I believe to be at the very core of executive functioning: creating space. Space is what allows us to step back, reflect, think, and be intentional about work, but also our lives. By putting effective executive functioning skills into practice, we set ourselves up to do our best work.

1. I recognize that I’m performing a slight equivocation on the word “executive” hear. “Executive” in a business context has its origins in referring to officers of a company, whereas “executive functioning” as a phrase has its origins in neuropsychology. But it’s close enough in meaning that I think it’s fair, helpful, and fun to join the two contexts together.

2. Not an endorsement. It’s literally the first non-sponsored result when searching for “portable external monitor”.

3. When connecting an iPad to a Mac, there’s an option to “link mouse and keyboard”. That’s nice if you want to be able to control native iPad apps from your Mac, sort of like a seamless KVM switch. Personally, I find using the iPad as an external monitor to be more helpful.

4. Should you unsubscribe from Customers, Etc.? I mean, you’re like eight paragraphs in and I’ve now caught you reading the footnotes, so I’d say you’re committed. Merci!

5. I used to use the bundling feature in the Inbox app—which Google created in 2014—but it went away in 2019 when Google killed Inbox. Bundling was incredibly helpful because you could, e.g. put all newsletters in a single bundle that showed up at the same time every day. That way you could keep them in your inbox but only get distracted by them once per day. I hate hate hate that Google killed this feature.

6. I’ve gone back and forth on this over the years. My email inbox has always been a good place to catch generic TODOs and sometimes my inbox has even served as my TODO list, but in the present moment I’m using a system outside of email for my task list.