How A CEO Spends His Time When Working Remotely

Sean's Shed

Work patterns have dramatically changed since people started working from home. The daily commute has been replaced by sleep-ins, more family time, exercise, or more work.

To get the most out of your time, you need to determine when your energy levels are the highest. I’m an early bird and feel most of my energy in the morning. That said, I find it optimal to get through tasks as soon as I wake up. I always make it a point to tackle my most important (and most dreaded!) tasks first thing in the morning.


How I Structure My Week

Mornings are reserved for deep work and international communications.

Mondays are when we have our weekly management meetings, the first one starting at around 10 am. We like to immediately kick off these meetings by playing the weekly reports as screencasts for everyone to see. This approach means we waste less time waiting for people to start and we stick to the scheduled start time.

Most companies present slides live, but our weekly reports are played asynchronously. This allows managers to go through reports asynchronously, helping them prepare questions and gather their thoughts in advance. For this to work effectively, managers upload their report screencasts on Friday so they’re ready for Monday’s management meetings.

Monday afternoons are dedicated to our weekly finance meetings, ad-hoc meetings, and other deep work. We did try to make our weekly meetings entirely asynchronous, but we found them too complex for such a setup to be feasible. I think asynchronous meetings work best for single topics rather than discussing many areas of interest.

The rest of my work follows a similar pattern. Tuesday through Friday mornings are blocked for deep work and ad-hoc meetings. Note that when I say meetings, these can be live video calls or simply dropping a voice note into a private group.


The Communication System That Works Best

Quick back-and-forth communication like short status updates or quick questions defaults to an async system. Meanwhile, my one-on-ones with line managers remain asynchronous so I’m not interrupting their deep work or customer calls. For this to work, people need to respond in a couple of hours. And if it’s important and urgent, we jump on a call or send an instant message.

Since most things aren’t urgent, a voice note or screencast works well. You get to see when people have played your message. People can like your message and respond in their preferred method be it text, voice, or video.

If we insisted on using more synchronous communication, I would have more meetings in my diary and less flexible work. But using an async system with the help of voice notes, I can drop messages when I’m in the kitchen having breakfast and before arriving in the garden shed where I work.

Now, if I’m needed in the office, I’ll be up at 6.30 am to leave home by 7 am, and I’ll arrive in the office at 8 am. I do miss the commute—listening to Radio 4, grabbing a coffee, and gathering my thoughts—but it’s not great for the environment. Plus, traffic can really be frustrating.


How This System Works Alongside Meetings and Recruitment

Arranging meetings is an overhead in its self, so I use a diary booking system where people can book time with me in 15-minute, 30-minute, or 1-hour slots. This is efficient and negates the need for back-and-forth emails to establish the best times to meet. The problem though is you could end up with back-to-back meetings.

Lots of my time is also spent searching for talent. We are, after all, a people business creating software for our customers. I was using live meeting bookings to conduct 1st round interviews in 15-minute slots. However, this approach often led to filling my diary for weeks on end. You might get occasional no-shows, and I was finding I couldn’t get through the volume of work needed.

Because of that, I now use video messages for 1st round recruitment screening. In the good old days, this used to be a phone call. Now, it’s a video message where candidates explain their skills and experience. If I’m short on time, I can play the video at twice the speed to get through more work. Once I like a candidate, I send them my video callback button so they can call me. No scheduling is needed. The video button is enabled when I’m available and when I’m not, the button is disabled.

Going asynchronous with screening candidates, status updates, and quick-fire questions means my morning is free for deep work. The meetings fit around the work rather than working around the meetings. I have freedom most mornings for thinking time, writing, and sending voice notes of my thoughts. Checking in asynchronously gives me freedom and flexibility. Asynchronous work with video messaging and voice notes is an awesome way of keeping myself connected. Most importantly, it allows me to work on my terms.

Of course, people can still schedule a meeting with me if they need to. But for people who want a quick conversation, I encourage them to use the video callback button on my blog.


How I Work With A Global Team

Now, live meetings on video calls are still undeniably important when working remotely. When you are introducing yourself or escalating an issue, video meetings are unavoidable. But other than that, we try to stick to async communications.

Let’s say I get an idea one evening outside work hours. I’m able to easily relay it (alongside relevant instructions) to my team by sending a voice note in a group. This way, the work is getting done and nothing is lost. My workforce is increasingly going global with people in Asia Pacific and the Americas. Working from the UK, async communication gives me an edge. I can have teams working through the night in Asia and handing over to Europe and the Americas when their workday is over.


Some Parting Words

Gone are the days of the regular 9-to-5. How and where we work have changed. I have adapted how I work and continue to experiment with new arrangements over time. But for now, a blend of synchronous and asynchronous communication works excellently.

Not interrupting my staff with endless meetings and letting them focus on what they need to do has improved productivity and engagement. It’s good to see more and more of my live meetings being replaced with asynchronous ones, particularly when schedules don’t align. My next aim is to educate more customers on the benefits of asynchronous communication for deep work and have them reap the benefits we have been experiencing in our organization.


Sean Gilligan, Founder, Webanywhere
Sean Gilligan, Founder, Webanywhere

About Sean Gilligan

Sean Gilligan is the Founder & CEO of Webanywhere established in 2003. Sean has set up and scaled businesses in the UK, USA and Poland. Webanywhere offers learning solutions, web development and mobile apps to both the corporate and education sectors.

In a remote-first world, Sean is passionate about how you can keep people connected whilst working flexibly. Sean has developed products such as Sound Branch a social podcasting platform, Watch and Learn a social video platform and Event Anywhere a virtual event platform to better connect people online. All 3 platforms include a video-first and voice-first approach to make remote work more collaborative, inclusive and enjoyable.


Useful Links:
Sound Branch
Event Anywhere