One of the greatest challenges for a manager is finding ways to channel the constant pulling into different directions. These days, that pull is likely also true, especially in a distributed team where it’s easy to get pulled into Slack discussions and lose track of priorities. At least that’s been my experience in the past and in the present too, amplified further by now having a management role.

As a manager, trying to balance being there for your team (both for individual team members and the team as a whole) but also finding time to focus on the bigger topics presents a challenge, as the desire is first and foremost to be there for your team to support them, to answer questions, and to get blockers out of the way.

Over the years, I’ve been trying a few ways of handling and channeling the different pulls as well as finding time for focused work, time to ponder and reflect on things and work on the bigger topics that are on my own agenda.

In a couple of recent 1:1s I’ve had, the topic of staying productive came up and I offered to write up a couple of my systems. What I'm outlining below is an overview of the system I'm using (or have used) to structure the time that I don't have directly alloted to meetings or interaction with my team, like 1:1s for example.

Chunks of Focus Time

The core element of all of the systems I have been using is that focused work needs blocks of dedicated time. The best way to manage these that I’ve found is to block them in my calendar. I have a block like that scheduled every morning and about until noon, which means they can’t be booked in any other way unless I choose to.

Those chunks of time I then break down into smaller chunks, e.g. 15 minutes dedicated to a specific task (which can also be scheduled on the calendar to make this approach fully explicit and to force yourself to really think through the work at hand).

I may or may not get the task done in the time allotted but it gives me guidance to think about what needs to happen next to move this particular project or item forward. It also fosters thinking about the smallest possible step, making it as actionable as possible.

During that chunk of time, and in an ideal world, there are no distractions. Either I turn off Slack for a while and try to only focus on the task at hand, removing distractions, but also telling the team that I’m doing so.

Setting these chunks of time for yourself is also about setting expectations for you and your team. If you feel like you need to be available for your team in some capacity, set up an escalation path and communicate that to your team, e.g. that they can text you in case of an emergency.

It doesn’t matter when you schedule these chunks of time, but it does help to be deliberate about putting them in your calendar. And, more importantly, you need to stick to them. Making productive use of these blocks of dedicated time requires discipline and constant adjustment. There are many distractions always at the ready to pull you out of that little bit of time you have. When in doubt, use something like Pomodoro or Hey Focus to focus or remove immediate distractions like chat apps or block social media sites.

You can start each larger block (e.g. when you have two hours) planning out how you’ll make use of the time available, planning out the smaller chunks of time in each block.

Parkinson’s Law

The main driver behind structuring my workday is Parkinson’s Law, and it’s worth mentioning. The law says that

Work expands so as to fill the time available for its completion.

This suggests that unless time is restricted work will expand endlessly. A common feeling and observation is that there’ll always be more work. Unless we limit the time available to it, we’ll spend more than eight hours of work time in a day. It’s too easy to give into that feeling and the desire to get more work done, especially for a manager, where a general feeling is that you don’t have much visible output yet still need to find time to focus on bigger topics.

Setting up chunks of time is one way to make sure that work doesn’t overwhelm. It requires discipline but also the acceptance that not everything that needs to get done will ever get done. There’s always more work to be done.

My favourite corollary to Parkinson’s Law is this, which is more in line with the approach I just detailed.

Work contracts to fit in the time we give it.

The Operating System

This is an idea and approach I’ve gotten from “The Startup CEO”.

The idea is to have a spreadsheet that includes all my current and ongoing projects, giving me an overview of the work I have available for the aforementioned chunks of time or should a window of time suddenly open up (e.g. because a meeting got delayed or cancelled).

Each project includes a list of action items that I could tackle next. These are on-point action items, concrete rather than vague, focused around getting them done in an hour or less than being too vague, which can leave a feeling of never making any progress.

I used to have this operating set up in Wunderlist, like so:

This can also be mapped into a spreadsheet or likely any other task tracking tool. It could also be a simple text file in Markdown.

The key is to keep the list of tasks short and focused only on what needs to happen next. This helps avoid having the task lists grow indefinitely, eventually leaving you feeling like you’re constantly behind.

The focus on projects also provides framing for the work to be done. Some work will always pop up that doesn’t fit into these, but these projects define the work that I should spend my dedicated chunks of focus time on.

Weekly Projects and Daily Tasks

I’ve since abandoned using the operating system and opted for something simpler.

I start every week by writing down 5-6 bigger projects that I’ll focus on. I write these in my notebook, mostly because I like paper and because writing them down forces me to think about the projects more than when I just type them into some task tracking tool. I prefer this kind of magic over tracking things electronically, which ends up just overwhelming me over time.

Every day, I start my day by writing down 5-6 tasks that I want to get done. Some of these tie directly in with the projects for the week (which is the whole point of defining these projects), others are based on work that doesn’t neatly tie into these but that still needs to get done.

The important piece is keeping these tasks actionable. If I need to leave a comment on some GitHub issue, that’s my task. If I need to figure out what my answer should be, that’s the task that needs to come first. If the tasks are too vague or include more than one step, progress on them will stretch over days (or weeks), and it won’t feel like you’re getting anything done.

I also keep a list of tasks that come up out of the blue for each week, or tasks that I need to do at some point, alongside the list of weekly projects, so I can remember to slot them in later.

All this happens in a notebook, so I don’t track these things electronically but rather focus on paper. If you’re looking for a simple methodology to follow, the Bullet Journal is nice. It’s similar to what I’m using but includes a couple of extra features.

Rotating Daily Topics

An approach I’ve recently adopted again is to dedicate certain days of my week to certain areas. Each day has a theme assigned to it that guides my focus further. Here are the themes I’m currently following:

  • Monday: Planning. This is when I go through my own projects, plan out my week, garden the ongoing work in the ELT and determine the projects and work I’m going to focus on during the week. This is also a good day to do expenses for a couple of minutes to make sure they’re up-to-date.
  • Tuesday: Marketing and Partnerships. Here I follow up on conference sponsorships, focus on marketing work, e.g. writing copy, review guest blog posts and follow up on partnerships.
  • Wednesday: Team and Culture. With this team I focus on topics like hiring, following up on or starting new discussions on cultural or company topics (think All Hands, OKRs, and the like).
  • Thursday: Customers. This is usually when I will spend time diving into customer support issues for a while, making sure that I stay in touch with helping customers and continue talking to them. When I have some customers where I’m the main contact for their accounts, this is the day I’ll follow up with them.
  • Friday: Strategy and Writing. Fridays I have scheduled to be out of the office. I’ll try to be mostly offline to spend time pondering larger topics, thinking about strategy and generally leaving slack time that allows me to reflect. I also leave some time on Fridays to write, either internal or external blog posts or to write reflections for myself. I tend to not schedule any company-related meetings on Fridays, too.

The idea for this approach is from Jack Dorsey and how he schedules his week (or how he used to, I can’t be sure). Note that I don’t follow his 80-100 hour work week. My normal work day will have no more than eight hours, with the exception of some of 9-10 hours (usually only one day per week).

The Value of Out of Office Time

Being away from the office and scheduling time to reflect on bigger topics or on yourself (the mark of every leader is to continuously work on themselves, absorb feedback and try to find new ways of approaching problems and questions).

Being away from the office and the usual work environment can help greatly with this, if only it means going to a coffee shop, putting on noise-cancelling headphones and grabbing a notebook to work on an important topic.

The same is true for taking walks, one of my key habits of having time to reflect. The mind wanders when its left on its own, with no immediate task in your head or screen directly in front of you to keep your mind busy.

Once it’s in free-flowing mode it can be nudged into all kinds of directions, by asking myself questions, or by thinking about a random topic. This time is incredibly valuable and is necessary to have dedicated time for reflection and thinking.

Weekly Review

This is something I’ve only recently adopted, inspired by my friend Cate.

In this review, I look at the bigger projects I’d scheduled for the previous week and the progress I’ve made on them. Then I write about the projects I’m focusing on next.

In addition I include a section of loose thoughts on different topics, which gives me an outlet for things that have been on my mind during the previous week or that don’t fit anywhere else. They can be related to company culture, personal observation, customer feedback, anything goes.

I like this approach as it gives visibility to the team (whether it’s my direct team or the whole team is something I’m still pondering) what’s on my agenda. Visibility in work is a general struggle for every manager, and a review that’s visible to your team can help increase this kind of visibility.

Your team will generally have more interest in where you are on your bigger projects rather than on every single small task that you check off. A weekly review is a nice approach on giving them insight into your overall progress.

Slightly more than a year ago, I had no idea what a 1:1 is let alone what purpose it’s serves. The idea of talking to one of our team member seemed so foreign at a time when we structured our team around individual autonomy and the assumption that people will speak up when something’s up.

What I quickly learned is that unless you give them a forum and safe space for it, they won’t. They’ll keep their unhappiness, grievances and issues to themselves until it’s too late, and that’s to no fault of their own. When there’s no clear and regular place for you as a person to talk about what’s bothering you, there’s little reason for you to bring it up in any other way.

Since then, 1:1s have become one of the most important interactions we foster with our team at Travis CI. It doesn’t just give a forum for people to talk about what’s bothering them, and to give you (the manager) a place to help them with their personal and professional growth. It gives invaluable face time in a team that’s now about 50% remote.

Granted, one of the most important things about 1:1s is to simply show up, to be there, to listen, to embrace the awkward pause. That alone helps you (the manager) build trust with people on your team.

A 1:1 doesn’t end when the allotted time is up, not for you, not for the person you’ve had the 1:1 with. It’s your job as a manager to figure out what’s moving, motivating and bothering the people on your team, and a 1:1 is a great place to talk about these things.

The conversation, however, has to continue. Whatever issues, questions or problems came out of a 1:1, it’s your job as the manager to follow up on those issues. Whether that happens via email, a brief conversation or in the next 1:1, the medium itself isn’t important.

Following up on things coming out of 1:1 is the single best way for you as the manager to build trust with your team. When you follow up on what you say you will, your team will have confidence in you, they’ll trust you, they know that you care about them.

Scheduling in time for follow up can be challenging, especially with our constant state of busyness, regardless of what our job is. Finding the time for it and following through with it, though, is the single best thing you can do to build trust with your team.

Wait, there’s more. Following up isn’t just important for managers, it’s important for everyone participating in them. Trust goes both ways. When you agree on things to follow up on for both of you, it’s a mutual commitment to each other, to building a trusting relationship.

Credit where credit is due: I’ve learned a lot about 1:1s from Jason Evanish’s posts on the topic and also his recent writing on the Lighthouse blog. Lighthouse is a great tool I’ve been using for the past year or so that helps with tracking notes and action items coming out 1:1s, I’d highly recommend you check it out.

Tags: leadership

About a year ago I met one of our team members in person for the first time. We hung out for the entire day, talking about all kinds of things, problems we were facing with our company at the time were amongst them.

During those conversations he taught me a simple yet rather powerful conversation technique: the awkward pause. It’s since become an important tool for me in 1:1s and conversations with other people.

When you talk about a problematic topic, there tends to be that moment when the other party stops talking. It can happen for lots of reasons. They don’t want to rat someone out, they don’t want to vent, they’re looking for the right words to express themselves, or the topic is so uncomfortable that they don’t want to continue talking about it.

When you’re impatient, it’s tempting to pick up the conversation in those moments. You ask further questions, you start talking about your point of view, you possibly even change the topic thinking that there’s not much more to get out of it.

Our intuition makes the awkward pause weird for both of us. It feels uncomfortable because no one is talking when this entire meeting is about talking, exchanging ideas and thoughts. The temptation to chime in and take over the conversation is big. Nobody likes the awkward pause.

When you chime in and interrupt the awkward pause, breaking this uncomfortable silence, the topic likely drops off the other person’s mind. Whatever troubles they’ve had, they’re unlikely to come up again in this meeting. They’re more likely to come up in some future conversation, when that person has gotten to a point where the topic has made them so unhappy that it turns into a vent, or maybe even in their resignation.

Interrupting the awkward pause means losing out on invaluable information and insight. What comes after the awkward pause is usually the real issues on that person’s mind. Whether what you’re going to hear is actionable or not, a vent, a personal issue, it’s the underlying issue of everything else you’ve talked about up until this point.

It’s the essence of what the conversation is all about. Breaking out of the awkward pause makes sure that essence is lost forever, possibly never to be seen again.

When you find yourself in a conversation and you can feel that you’re in an awkward pause moment, take a deep breath, focus on the other person and just wait. Resist the urge to continue the conversation and let the other person continue digging up the real issue that’s on their mind. Resist the urge to break out of the awkwardness and just let the other person talk when they’re ready.

Embracing the awkward pause is possibly one of the simplest and most effective tools to make you a better listener. It helps you build trust and develop more patience in conversations with your reports and your peers. I’d go as far as considering it an essential leadership skill.

Thanks, Dan, for teaching me an invaluable skill!

Tags: leadership

Being an introverted person in a leadership position is challenging. The one thing that exhaust you the most is now your main focus, interacting with people.

Personally, I didn’t fully realize that I have introverted tendencies until I read the book “Quiet: The Power of Introverts in a World That Can't Stop Talking”. I’d considered myself shy before then, feeling awkward trying to strike up smalltalk conversations, even just talking to other people, and constantly feeling a need to hide in quiet places to get away from chatter and to focus on my own thoughts.

I chalked it all up to being shy, and it left me in an uncomfortable position. Am I confident enough that I can pull out the relevant skills to be the CEO of an entire company, especially the people part?

Since then, I identified a few routines that helped me balance the needs of being in a leadership position with my introverted nature.

Read every day

Reading has become a very important part of my day and my progression from trying to get a startup off the ground to taking on the role of leading said startup as it matured.

Books have played an important part in helping me shape my own thinking about what I’d like our company to be, and about what I’d like to become. They’ve helped me narrow down on a few problems and helped me focus on solutions for them.

Beyond that, taking time to read is also time to reflect. A lot of books I’ve read have given me one or two key realizations about what I need to improve, what I’m doing well, and what our company can do differently. That one spark is worth reading an entire book for me.

For the introvert in me, reading is quiet time. I usually read first thing in the day, before I do anything else, and before the noise of the day starts crowding my mind, distracting it from the focus required to read.

Take long walks

I started taking walks after I read “Thinking, Fast & Slow”, which was a revelatory book for me, in terms of understanding myself, our customers and my team. Did I mention that reading is amazing, and that you should read every day?

Throughout the day, your brain is busy processing information, impressions, conversations, and adding to that, you’re trying to get it to focus on the work that needs to get done. Giving into this feeling of constant busyness is a downward spiral, leading to even more work, feeling stressed out, and emotionally exhausted.

For me, this ends up with work trickling into my personal life, be it by keeping my mind busy with work topics when I get home or on weekends, or affecting my moods at home.

Beyond reading, the best medium I’ve found to let those thoughts loose is to go on walks. Not just 20 minutes walks, but up to an hour. I walk at a relaxes speed and without any particular place in mind that I want to go. When you walk towards something, your mind is focused on that, and it doesn’t free up mental capacity to think and process. When you walk too fast, you may notice similar things.

I prefer to walk on familiar paths, a sort of roundtrip through the neighborhood, if you will.

After a while, magic happens. My head stops being overly busy, all those thoughts quiet down, and it feels like my head is a lot more responsive to giving it small triggers, like “I wonder what I could write about next?”, or much broader than that, “Containers?” Even small triggers suddenly leave my mind to wander around the topic, looking at different angles, maybe even finding a conclusion. It feels like magic.

Walking, all by myself, has turned out to be an important tool in processing information collected throughout the day, week and month, and working on extracting the patterns, the bigger picture, and what I could do about them.

Schedule time away from the office

As a leader, it’s likely you have a strong urge to always be around your team, being ready to jump in and help them at any time. You may also experience the fear of missing out, always wondering and curious what’s going on in your team, in team chat, and around the company.

That fear and the constant hovering adds to the emotional drain, contributing to a constant feeling of burnout, yet you feel guilty about not being there when your team needs you. It’s too hard to disconnect and focus on yourself and your own work, so that starts slipping and adds more to the constant state of busyness.

The above scenario isn’t an introvert’s problem, it’s the disease that our modern work day has become. In addition to feeling like I’m not progressing on my own work, this situation added to my own feeling of work topics trickling into my personal life, as little time was left to process all that information and recharge.

I started scheduling in weekly time away from the office, time that I spend in a coffee shop or elsewhere, noise-canceling headphones plugged in, working on bigger topics or just letting my mind wonder.

Initially, this didn’t feel like work, and I felt guilty, even selfish, for taking this time. But then I realized that I’m actually getting results from this time away from the office. It allows me to progress on important and bigger company topics, yet it gave me the isolated space that my introverted self needs to focus.

Taking walks, reading and spending time away from the office have become important stop gaps for me. They give me the time and space to process, recharge, figure out the bigger picture and come up with solutions for problems a crowded brain might not otherwise be able to extract.

Write every day

I sometimes struggle forming thoughts into concrete sentences when I talk to people. Part of that is because I’m having trouble forming a complete picture in my head, which I feel I need before I can say something. This reflects in how I approach thinking about bigger company topics as well. I need time and space to form my own opinions on things, and there is one tool that’s been the greatest help for me in this, writing.

I try to write, every day. Whether it’s working on a blog post, whether it’s writing an internal proposal, a summary of a call I’ve just had with someone to send around to the team, or simply writing a journal.

I’ve done the latter every day for almost two years now, and it’s become an essential part of my every day work. I’m using Day One whose reminders pop up multiple times throughout the day to help me capture what I’m thinking. Longer prose also goes into Day One at times, as some situations warrant a longer thought process, which is effectively reflected in what I write. For anything else, I’ve started trying out Ulysses, before I’ve used NValt and Byword for writing. I enjoy the simplicity of a full screen app with just a cursor.

It doesn’t really matter what tool you’re using, what matters is that you get beyond that moment of utter fear instilled by a blank screen with a blinking cursor on it and just write down what’s on your mind.

Writing requires me to focus, and it allows me to make sense of all the noise in my head. It’s my one outlet of processing all the information I collect, consciously or not, throughout the day.

Take your time in making decisions, but follow up on them

I need time to process information, to figure out any patterns and to come to my own conclusion on it. That process can involve writing, thinking, walking or listening to more opinions, gathering more insight from our diverse team.

That can sometimes be frustrating for others, especially when they want to move forward with something quickly. There are situations where I can just say “Sounds good.” and trust them with all my heart.

In other situations, I make a commitment to get back to them in a certain amount of time. The more you define that amount of time and keep your commitment, the more trust you can build with people over time. When they know that you do follow up and keep your own commitments, they’ll get more used to this being your mode of making decisions.

I found those two to be a good balance between making sure things don’t get stalled all the time and my own need for thinking things through a bit longer before I can come to a conclusion.

Beyond reading, writing, walking and spending time at the office, I’ve started meditating daily to try and tackle another issue I’ve mentioned earlier. Oftentimes I find my mind thinking about work things when I’m at home. I get distracted playing with my daughter, reading a book to her or over dinner, and I have an immediate urge to work on the thing I just thought about. I found that rather frustrating, and I’ve noticed that meditation helps me focus a lot more on the moment rather than have my mind wander endlessly.

What helps you foster your introverted nature as a leader? What helps you lead introverted people on your team? I’d love to hear about your experiences.