A Day in the Life of a Startup CEO

If you run your own business or are considering it, visualizing your typical day can be tough. Explaining it to someone else gets even trickier.

Most people get glassy-eyed when I say my work is in “software” or “online.” The daily tasks associated with running a software company are hard for most people outside of the industry to understand.

As the CEO and co-founder of Hubstaff, I’ve been called Chandler from Friends because no one really knows what he does, either.

So, let’s clear it up. On a high level, I am responsible for the growth of Hubstaff. The biggest question I ask is, “What does Hubstaff need in order to grow?”

I am laser-focused on the items that I believe will lead to the most growth.

That might be marketing, product, support, analytics, culture, hiring, or something in-between. I develop most of the strategy for the company, and how the company operates internally and externally.

The 6 main beliefs that drive my work as CEO

How I approach scheduling and my daily tasks comes down to my personal beliefs about work and productivity.

Knowing this will help you understand why I prioritize some things over others, and how I structure my day.

1. Distractions are the enemy

I hate to be distracted and taken off course, and I try not to distract others. That’s why I try not to schedule meetings or even ask questions when things don’t really need to be discussed in order to move things forward.

When I am in deep work mode, I close down Slack and shut down email.

Nothing is more important than the work I am getting done when in a deep focus mode.

Some people may view this as being cold, but I do it out of respect for my time and everyone else’s. Fewer distractions for everyone means more time for focused, productive work.

I’ve seen a huge rise in my own productivity when I can close down outside distractions and focus on a blank document.

There are many books that have influenced my thinking regarding distractions. Here are a few to add to your list.

Fewer distractions for everyone means more time for focused, productive work.

The CEO’s reading list for focused work

1. Deep Work
2. The Effective Executive (Can’t recommend this one highly enough for managers and execs.)
3. First Things First
4. The 7 Habits of Highly Effective People
5. 4 Disciplines of Execution
6. Most things by Stephen Covey and his son
7. I also love anything by Peter Drucker, especially the Effective Executive

They all present similar ideas:

• Focus on solving your hard problems first
• Avoid distractions
• Carve out intentional time to work on high-impact items

How you can avoid distractions as a leader

Slack is open most of the day because I want to be accessible. If something can be sent over Slack, I prefer that to other channels.

However, it’s not uncommon for a group conversation to be happening where I simply never respond.

I trust my team to make some of these day-to-day decisions, and I pride myself on not needing to have input on every detail.

My willingness to let others decide is due to one of three reasons:

• I don’t have a strong feeling either way
• My brain can only handle so much, and it’s focused on something else
• I want to give my team ownership

This might be misinterpreted by my team at times, but in reality, I am just trying to evaluate things quickly and move onto the next thing.

Because as any CEO knows:

There is always a next thing, and you will be evaluating situations all day long if you’re not focused.

If it’s not a Slack message or a meeting, there’s an email, a customer asking a question, a meeting, a task to do, something to analyze. Fight off distractions as much as possible so you can stay committed to your most important goals.

2. Default to no

Again, protect your deep work time.

I say no all the time, and I am going to need to say no even more in the future.

I’m past the point of doing things in my career because they are best practices, or someone else thinks that I need to do them. I’m sure you’re in the same spot.

Default to no.

Default to doing less, not more.

Focus is more important than breadth. No one can do it all.

Don’t do the project unless it fits your strategy and stop doing things that are not providing value.

I hate wasted work. If you feel what you are doing is not effective, tell me why, prove it with numbers and then let’s stop.

We don’t need to do everything. We need to do what moves the needle.

Here’s how to default to no on a daily basis:

• Turn down meetings
• Delete emails without responding
• Don’t have calls with people to explain why you are not hiring them
• Don’t take sales meetings
• Don’t opt for quick “chats” from cold emails

I cannot let any of the above register in my mind space.

I intentionally design my schedule for three things:

1. ROI
2. Company success (deeper than financial)
3. Personal happiness

If what I am doing doesn’t move the needle on one of the above items, it does not get done.

Default to an empty calendar.

Default to no, and don’t feel the least bit guilty.

Aside from personal contacts, I haven’t answered a phone call from outside of my area code since 2008.

You need to ruthlessly control your schedule. If you let others determine your schedule, they will.

I know CEOs who still take sales calls.

Why in the world would you let a salesperson direct your schedule, just to waste 30 minutes and get sold something you don’t want or need?

Focus on what matters to you and your success, not theirs.

Default to an empty calendar.

Is that mean or harsh? Maybe. But I’m willing to deal with those consequences. I believe in being focused on my team, job, family, and self. Defaulting to no is how I stay true to that.

3. Embrace being alone

As you can probably guess, my best work is done alone in a room, not talking to anyone, and without any distractions.

I’ve accepted this as a truth and have begun to embrace it more and more.

This is when I can be in creation mode, and create value for the world or my organization.

As a CEO, you’re going to be creating something that does not exist. This type of work takes time, thought, and focus.

4. No more meetings

As you start defaulting to no and working alone, you need to avoid meetings.

In a remote company that is operating over many time zones like Hubstaff, this is an important skill. It allows everyone to work on their own time.

It’s also important because you never know when these productive pockets are going to hit, and you don’t want to spend highly productive time in a meeting.

I generally agree with what Basecamp believes regarding meetings.

Be upfront with your team and say: If you need a meeting with me, please make it short and let’s get an action item from it. Then follow up later regarding the action item when it is closed.

My average day includes about two hours of meetings, and I would like to reduce that. These meetings are Sprint calls, planning sessions, numbers meetings, talking about structure, strategy, product, and one-on-one meetings.

The first thing I do is look at these meeting times, and try to structure my day around them. I figure out when I am going to get to my work, and I design what I am going to do. The “when” is based on meeting times, and the “what” is largely determined by my task list.

5. Trust the data

I believe in data more than opinions or theories.

I believe that analytics, numbers, or KPIs should be the way that we judge performance.

It makes management easier, more efficient, and more accurate.

Check out the 4 Disciplines of Execution from the reading list for more on this.

6. People don’t change

I don’t spend lots of time trying to change people’s minds. I don’t spend lots of time giving second and third chances.

I believe that lazy people are lazy and hard workers are hard workers. I believe that people who generally make good decisions will make good decisions.

I believe that people are mostly self-driven. If anyone requires micromanaging, you have the wrong person or a situational issue.

How I prioritize the right work

One of the things that I enjoy most about what I do for a living is that every minute of every day is a choice. I am lucky enough to choose how I spend time.

Some days are spent writing blog posts, some days are spent managing people, others are spent building plans or doing admin work. Most days are a mix of all the above.

The basis for what I am working on is a combination of two things:

1. How I am feeling?
   Am I feeling highly productive or not? If so, then it’s time to drop all else and get into deep work. These days, I do not feel highly productive 24/7. I used to in my 20s and early 30s but that has changed slightly.
   Now, I am noticing that I have highly productive pockets of time. These can last for days, hours, or minutes. If I hit a productive pocket, then I go to deep work. If I am not in one, then I move to some kind of simple work like answering emails, entering stats, looking at funnels, looking at trends, management, or accounting.
2. What is going to provide the most ROI for the business?
   Sometimes this means revenue growth, but most of the time it does not.
   This can mean that a team member needs extra attention, coaching, or motivation. It could be that the team needs structure. It could mean that payroll needs to be done or the KPIs need to be entered so we can analyze them.

How I organize and manage my work with a project management tool

My task list is organized in Hubstaff Tasks, which is an Agile project management tool we built over the past four years.

It uses Kanban-style project boards so you can see everything in one view. I really love this style of task management because it reduces the brain power I need to spend on organization.

If I have an idea, it goes on my list. Each task item gets a description, and then I can prioritize super easily using drag-and-drop. I constantly have this ongoing list of ideas and I pick which to work on based on priority.

I don’t spend a ton of time putting down too many details here. This is enough for me to bring back those general thoughts and dive into the work.

The individual tasks are created weeks or months in advance, so I sleep on these larger project-level items for weeks.

I like this method because around 50% of the time, my ideas and tasks just don’t get done. Over that period of weeks sleeping on items, some remain top of mind and others sink to the bottom. At that point, I adjust the priority.

One of the most important questions is, “How do you get the ideas for what gets added to the task list?”

I would say, this is the single most important activity that I do as a leader. I wrote about this process of defining and prioritizing goals back when we had 99 customers, and it really has not changed. It’s loosely based on the Theory of Constraints and basically is built to uncover the blockers in a business, and knock them out.

This is the process that I use to come up with the projects that our teams work on. A project is usually around 30 days of work, but sometimes more. Then we break down the projects into smaller tasks, and these tasks are what gets entered into Hubstaff Tasks and managed.

I also add a ton of ad hoc tasks. These are things that only I know about and can be done in less than about 16 working hours. Most of them can be done in less than 2 hours.

My typical week

I like to work around 40 hours a week, from 7am until 5pm, with some breaks throughout the day.

I’ll fit in answering emails on the phone during the night and weekend. I spend a lot of time thinking about the business in addition to that, as I’m sure you do, too.

Most of my work week includes:

• Answering questions and looking up data points. This is time spent trying to track things down for different people. I’m often a sounding board or second opinion for tactics and plans.
• Solving problems. I like to look for inefficiencies and then jump in for a short period of time. I’ll work on correcting a problem that I see, put it in the right hands, and then get out.
• Working on projects. Sometimes this list of projects comes from things that I would be the best to tackle, and other times it comes from not having anyone else available to work on it.
• Strategy work. Trying to figure out where the company should go, why, and how to get there. I’d like to focus here more in the future.
• Accounting. I run the accounting for Hubstaff. This generally takes about eight hours a month. I have not been able to outsource it yet but probably should soon.
• Roadmaps. From a high level, I make sure that marketing, support, success, and development are on track with the quarterly roadmap.
• Putting out fires. This takes quite a bit of time, and is usually spur-of-the-moment. I really never know what it’s going to be but it tends to relate to organizational needs.
• Admin work. This includes drafting contracts, payroll, legal, access, and other administrative tasks.

That’s my week at a high level. Now, let’s look at a typical day.

Daily schedule of a CEO

Morning

I wake up between 6:30-7am and get dressed in workout clothes. This forces me to get up and exercise right away.

I spend 15 minutes at the computer just so I can quickly see if there is anything urgent on email or Slack.

Sometimes this leads to a longer work session and exercise gets delayed. But since I have the workout gear on, it gets me to move over to the exercise room sooner or later.

I usually just run on the treadmill while watching some type of documentary on Netflix. I enjoy war strategy, true crime, that sort of thing.

If I’m running outside, I listen to an audiobook on business or self-help. I run for about 30 minutes, tracking the time and my heart rate on an Apple watch.

I exercise first thing in the morning because usually it won’t happen later in the day.

I’ve learned over time that it’s important to invest in yourself, and this is how I do that. You want to create these investments first, not last. This is a common theme in terms of how I run my life.

I try to get done with exercise by 8am so I can play basketball or have breakfast with the kids before they head to school.

I have 8- and 9-year-old boys, and I realize that they will soon be 13,16, and 18 in no time. These next few years are critical for me to give them a lot of attention. It’s a win-win because I truly enjoy doing things with them, like playing sports or biking.

For breakfast, I have something very quick. Usually toast and fruit or cereal and fruit with an americano.

I make the coffee on a Breville espresso machine. It may seem like $500 is expensive for a machine, but have two espressos a day, and I never go out for coffee. I value my time too much for this.

Starbucks would be $4/day ($1,460 annually), but the bigger problem is time.

I’ve known from a young age that time is my most valuable resource, so I try never to waste it.

That doesn’t mean that I work 24/7. It just means that I multitask a ton, and that I value my time above pretty much anything else.

My kids get on the bus at 8:24am, and then it’s straight to work in my office. By this time, I have a good idea of what’s going on for the day because I’ve seen all my emails, Slack messages, and I rarely allow meetings on my calendar that are not scheduled.

I’ve known from a young age that time is my most valuable resource, so I try never to waste it.

Office hours

A good practice for CEOs is to start with a scan and analysis.

Some questions to ask yourself:

• When can I fit in deep work?
• Can I fit in deep work at all today?

If so, I schedule it on my calendar and I try to stick to it.

If I have three or four meetings scheduled, then I don’t schedule any deep work. The reality is that I won’t end up getting to it. Being realistic about this fact helps me to stay structured and it helps me to realize every day what the meetings are costing me in terms of deep work.

By 8:30am, I get my email inbox knocked down.

I encourage close customer contact, so I answer anywhere between 15-25 customer emails per day.

If the question is technical, I simply pass the question on to the support team. I answer myself if it’s about product feedback.

Much of this has to do with business owners trying to find a solution for their unique needs. I’ll show them where they can find the solution in our product, break down pricing, and try to save customer relationships.

These emails are sprinkled in throughout the day. I try to get these done first thing in the morning because many of our customers are in Europe, Asia, and Australia and the email has been sitting in my inbox for hours already.

I encourage close customer contact, so I answer anywhere between 15-25 customer emails per day.

By 9:15am, I am ready to get into deep work if I don’t have meetings. Since I took the time to scan my day at the beginning, I already have this block of time scheduled for deep work.

I have standing meetings on three weekday mornings so I only have two days to get into the deep work right away.

Early lunch

I have an early lunch around 11am.

For lunch, I usually have a quick sandwich, and again, 95% of the time it’s at home. Lunch only takes me about 10 mins, and I then spend a few minutes getting my mind off work somehow. This could be going to the grocery store, messing around in the garage, or picking weeds.

If it’s during summer, I play with the kids for a while, and I’m back into work by noon. Then, I’ll answer Slack messages and email for another 30 minutes.

Afternoon

If I didn’t get in a deep work session in the morning, now is the time: 12:30 to 2pm.

Most days, I have a meeting scheduled, but after that, it’s deep work for the rest of the day. I tend to shut off email and Slack during this time.

From whenever that afternoon meeting ends until around 4:45pm, I answer questions or work on smaller admin tasks such as contracts, metrics, accounting, and hiring. I like doing these items towards the end of the day because they can pile up. I knock them out once per day vs. dealing with them multiple times during the day. Sometimes I can get a smaller project knocked out during this time.

Evening

Around 4:45pm, I stop working and start cooking. I cook for the family a lot, and we eat early because of baseball, basketball and after-school activities.

We eat and then I run the kids around for a while. Sometimes I’ll go surfing on the boat, play piano, split a bottle of wine with my wife, or hang out with friends.

Then it’s TV time, where we’ll watch kids sports movies like Sandlot or Miracle. I use this time to hang with the kids and relax with them.

We go to bed early, like 8:30 or so. I love my sleep. I’ve always needed a lot of sleep in order to feel good during the day.  Here’s what my sleep looks like.

List of responsibilities

Like many CEOs, I am getting questions from every department, involved in decision-making, having things run by me, and participating in meetings. But really, I am thinking about next moves, looking at trends, trying to determine where we are going to go, and how.

• How we are going to get customers
• How we are going to answer questions on the support team
• How we want to operate

Really, I stay aware of anything and everything in the company, right down to the bookkeeping.

I am officially responsible for two departments: Marketing and Support. This means that I do a lot of the high-level planning and look into results for both of these teams. It’s up to me to figure out what we are going to do, who we need to hire, how we are going to operate, how we are going to adjust, how we are going to grow, and more.

One of the things that has largely fallen off is the amount of tactical work that I do. For example, I don’t really work on ads, copywriting, or SEO. I do look at the reports, though, and provide direction. One of the tactical things that I do still do is write posts like this. I’ve spent all day straight on this post that you are currently reading.

Here are some other areas and responsibilities I have as CEO.

Administrative work

• Timesheet approvals
• Accounting
• Weekly and monthly metrics
• New hire account access
• Paying for subscriptions
• Contracts
• Legal

Strategic

• Strategic planning
• Project planning

Tactical

• Project work

Whirlwind (from 4dx)

• Meetings
  • Strategy
  • Quarterly planning
  • Product and marketing numbers updates
  • Sprint planning
  • Check out our post on how our remote team operates.
• Podcasts
• Customer emails: Time here varies but usually around 20 emails per day. If it’s a busy time, I can spend almost all day doing these activities between other meetings, lunch and questions from team members.
• Hiring
• Questions from team and collaboration work

My takeaways for structuring your day

As you can see, my daily schedule follows what I believe about work and productivity as a CEO.

1. I try to put first things first and hard things first. Check out the first book on my reading list for more on this.
2. I say no a lot.
3. I work alone and focus on the work that I enjoy (which tends to be the same work I am good at).
4. I try to structure my day around productivity and enjoyment.
5. I double down on what I see working and try to look for trends. It’s much like playing chess, and always trying to think a few moves ahead.

This gives our company the ability to be in good positions because things have been thought through and analyzed on a regular basis. And it helps me as a CEO stay on track with my goals for myself and the business.

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