One of the things that I love most about being a CEO is how different my days can look. I can go from a meeting, to thinking strategically about what the business needs, to an interview, to a website review meeting. The days are full, and I love the variety.
I find that one of the hardest parts about being a CEO is managing your emotions. There are good days, and there are bad days, but you always need to project the positive aspects of the company. I think I’m particularly good at compartmentalizing. For example, if it was a hard day, I can still go home and be present with my family. I can put whatever’s going on at work into a box and then come back and deal with it the next day. I think that’s a pretty important skill for a successful executive.
Morning Routine: Wake Up, Work, Weights
So, let’s dive into what my actual day looks like.
I often find myself waking up early in the mornings, so my rule of thumb is if it’s before 5:00am, I try to go back to sleep. If it’s after 5:00am, I wake up and start working.
I actually love working in the mornings. That’s probably my most productive time, especially if I have something hard or complex to work through. I tend to be a little bit sharper in the mornings, so if I have something that’s more important, I’ll prefer to put it earlier in the day if possible.
Around 6:30am or 7:00am, I work out. I work out almost every day. I have a trainer twice a week who comes to the house, and the other days I work out in my home gym. Sometimes I go for a run, and every once in a while, my wife and I will go to Barry’s Bootcamp. I can’t imagine starting my day without a workout.
Then, I’m usually in the office around 8:30am.
Death By Meetings: My philosophy on Meetings
I have my executive team meeting on Mondays, but otherwise, I try to spread 1:1s throughout the week to have balance.
I follow the Patrick Lencioni “Death by Meeting” framework for running most meetings. This means that we have a weekly tactical with an agenda, a monthly strategic, and a quarterly off-site to work through longer-term issues. The idea is that a news bulletin is different from a 30-minute sitcom, which is different from a feature film, which is different from a mini-series.
Here’s how that translates to meetings:
Daily Check-in (news bulletin): 5-minute stand-up meeting with the team to discuss schedules and pressing deadlines.
Weekly Tactical (sitcom): 60-minute meeting to report on two major issues. The team should develop the agenda for the majority of the meeting.
Monthly Strategic (feature film): 2-hour meeting with the entire team to discuss a few key topics. Individuals come prepared with data, anecdotes and pertinent research, ready to have an in-depth discussion.
Quarterly Retreat (mini-series): 1- or 2-day long offsite with the team dedicated to critical conversations about the business. This could range from competition, to team dynamics, to performers, to customer satisfaction. The idea is that these items can’t be covered in weekly or monthly meetings.
The bottom line is that you must really be thoughtful about allocating the meetings to different purposes as opposed to just shoving everything inside one meeting.
For my 1:1s, I always prefer to walk. This is more about me – I find that it’s good to get out and get some fresh air. I like to change the dynamic. When you’re walking, it encourages more free-form thinking and discussing top-of-mind items. This is opposed to sitting in a room looking at a screen, which is much more focused on a specific agenda and planned topics. Sometimes, you have to have those 1:1s sitting in a room or looking at your screen, so keeping a mix is best.
For me, in a given month, I go for walking meetings for three out of four 1:1s, and then do more of a detailed deep dive once a month.
Never Eat Alone: A Principle of Leadership
I’m a big fan of the thesis behind the book Never Eat Alone. I try to schedule lunch meetings as much as I can. I love getting to know our new employees, so as part of the onboarding process, new hires will book a time to have lunch with me. It’s literally an item on the checklist for new hires to set up a 1:1 lunch with me. This is a great way to get to know everybody and their different personalities. Then, I try to fill up the other lunch slots with 1:1 lunches with colleagues, friends, etc.
Occasionally, when I’m too tired or need a break, I’ll eat by myself, but I love to take a real lunch and use it to talk to people, and I encourage everyone at Engagio to do the same. In fact, we have a perk that enforces this – if you get lunch with someone outside your department that you don’t regularly get lunch with, you can expense it.
Afternoon Routine: More of the Same
To be honest, my mornings and early afternoons don’t look that different. They both consist of a mixture of meetings, 1:1s, working sessions, interviews, etc. However, as it gets later in the afternoon, I don’t do any highly demanding or creative tasks. As I mentioned, I do my best work in the morning when I’m fresh, so I’ll save those tasks to tackle first thing in the day.
Towards the end of the day, before I head out, I try to catch up on things, like following up on a meeting or sending emails. I usually leave work sometime between 6:00pm and 7:00pm. Sometimes that’s managed by the fact that I have to pick up my daughter from one of her activities, like gymnastics.
Evening Routine: TV and a Cocktail
I don’t have any routines per se, but I make a cocktail almost every night to relax (I make everything, but I mostly tend towards Manhattans because they’re good and relatively easy). I also like to watch trashy television with my family. It’s a great way to wind down and spend quality time with them. I try to get into bed no later than 9:30pm, which is pretty early, but that’s what you have to do if you’re waking up at 5:00am the next morning. I’m one of those people who wants close to eight hours of sleep a night to work at my best.
Other CEO Success Secrets
I’m a part of two different CEO groups. One is called 10X CEO, which is focused on working with other top CEO’s of similar stage companies to talk through complex business problems. I’m also a part of something called a T-group pop up, which is really focused on interpersonal dynamics in leadership. Having this strong network to support not only the work I do on the business, but also work on myself has been incredibly valuable, and I highly encourage other people to do the same.
Often, there is spillover work that lands on the weekends. I’m the dad of a 13-year-old and a 10-year-old, which means that a lot of weekends end up being the daddy Uber service. Oftentimes, I drive them to their activity, drop them off, go to Starbucks and work for an hour or so, then pick them up and drive them to the next thing, then work for an hour somewhere else. That time on the weekends in between the kids and the errands is pretty productive.
That’s just a glimpse into a day in the life of a CEO. It’s a demanding job, but I wouldn’t trade it in for the world.
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