Interview with Haley, a VP of Operations shares her stellar remote work strategies

After leading teams for Apple Retail for five years and with a baby at home, it was time for a change.

I loved tech and working with people but knew that the irregular hours would increase stress and limit family time.

I didn’t begin my job search by looking for remote work. I read through job descriptions to find a skillset and passion match. Customer success seemed like a great fit, but as a relatively new job area, most roles were available outside of DC.

That led me to my first remote job at IDoneThis, a team of five that quickly taught me key principles of remote work:

• Structure time intentionally
• Writing > talking: take the time to structure your thoughts to communicate more clearly
• Process > outcome: everything happens intentionally
• Understand how each team member wants to collaborate
• Share what you’re working on proactively to create visibility and make other people’s lives easier
• Make time to learn and think
• Have fun at work

One of the things that struck me the most was our CEO’s belief in the importance of breaks. I went up to the office for a week of training, and after asking what I like to eat, took me to a different ramen restaurant in NYC each day, then proceeded to come back to the office and play video games and/or take a nap. He worked really hard but got his rest in, too.

Without saying “take your breaks” he demonstrated that it’s ok, even good, to be a human with human needs and create a work-life balance that makes sense for you.

As the head of operations for a fully remote content marketing agency, I spend most of my time working with our team and customers. We’re focused on continuing to elevate our employee and customer experience next year, and bringing on awesome new team members obsessed with content to help!

During onboarding, a coworker recommended Maker’s Schedule, Manager’s Schedule. That informed how I structured my time when I started, and how I continue to revisit my schedule today, usually quarterly.

When I started, I was a manager and an individual contributor - the sole person managing customer operations. I’ve always been “good” at context switching, but 9-12 months in, I started to grow weary of it.

Almost everyone on my team is a maker, creating more flexibility than in a meeting centric work environment.

I design each week in a bell curve.

• Monday: ramp up. Dedicate most of the day to planning and thinking. Have meetings that will help me plan for the rest of the week.
• Tuesday: all the meetings (9A-5P, 1 30m break).
• Wednesday: thinking and deep work.
• Thursday: all the meetings (9A-3P).
• Friday: ramp down. Reflect on the week, begin to tee up the following week. Have debrief and blue sky meetings.

I make time at the beginning and end of each day for admin stuff like email, and block time for tasks that I have to do each week like check invoices, prepping agendas, and reviewing customer notes.

I am dedicated to my bedroom. It makes naps easier. 😅

Currently, I either work at my desk in my room or at my kitchen table. I live in a quiet condo on a quiet street, and find that hours easily pass without remembering that I’m working.

I put my phone away, go into full-screen mode whenever possible, and I try really hard to single-task instead of multi-task.

I work in blocks, 1-3 hours before getting my little dude ready and off to school, 6-7 hours during the regular business day, and 1-2 times/week deep work in the evenings.

Most days, I take very few breaks; I like to work very intensely, completely focused on work where possible. Parenting and teaching indoor cycling on the side are great forcing functions for a disciplined work routine; I can’t stay late at work to get stuff done later.

I really enjoy my work and try to be very conscious of whether or not what I’m doing at any given moment is actually the best use of time. I’ve slowly eliminated meetings where I’m not adding value.

• People: Connection to the best talent in the world. I can’t imagine being able to source such amazing people if we weren’t distributed.

• Time: Getting rid of the commute creates time to learn, think, and nap, all of which drive my productivity. I’m able to apply energy and discipline to the highest leverage activities (vs. figuring out where to park, getting annoyed sitting in traffic, navigating office chit chat when I just want to get something done).

Don’t get me wrong — I love people and enjoy the social aspect of work.

Working remote has allowed me to create much deeper relationships though; fewer surface “hi, hey, and hello's."

We get randomly paired with other people on the team for 30 minutes every other week and get to know people on a totally different level than I have in any office environment.

I occasionally miss office snacks, although it’s probably net positive for my health.

We get together as a leadership team a few times a year, and that in-person time to connect and brainstorm is always energizing. I’m hopeful that we can do more of that with the team in years to come.

To-do lists!

I start the week with a big to-do list. Writing everything down and then bucketing into categories: big picture, people, customers, blocking time for each.

I update it throughout the day, and each morning I make a new to-do list from yesterday’s list.

Our productivity stack includes Slack, Front, Airtable and Quip. I usually turn off notifications but always have Slack up and check other systems periodically throughout the day so that I’m not living in reactive mode.

Working remote takes practice, not just in terms of how to be productive. I wrote an article about how to get better at working remotely through the lens of increasing confidence, sense of self, and mastering your schedule.

Our values, our company roadmap, my goals, and my role. It takes some time to figure out what the Venn diagram of what you can do vs. what needs to be done vs. what only you can do looks like, but it’s essential.

Leadership can feel like a choose your own adventure novel; time isn’t structured for you, so it’s important to have a clear sense of where you add the most value.

When I started, I didn’t structure time in intervals to naturally let me push and recover (push: intense calls, big projects, recover: 90% of admin). Now, I try to break up my time to prevent burnout.

There are naturally times after something big is implemented when you’re managing the implementation and kind of waiting to get started on what’s next. This is naturally the time when you need rest, and when it makes sense to start doing the research/learning/prep for the next big push.

FYI ran a remote work report and found that the biggest issues are communication and loneliness. I’d also say that self-awareness creates a lot of issues with remote work.

You have to self manage without someone else watching over your shoulder. It takes longer to see issues than in an office environment, so you have to see them yourself and ask for help early.