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Matt Martin of Clockwise: “You compare yourself to leaders you’ve worked with, and that’s just not you”

Every calendar needs long blocks of uninterrupted time for heads-down, focused work. Proactively setting aside time for deeply focused, proactive work prevents you from saying yes to too many reactive requests from others. Set aside at 15–20 minutes at the start of your week to proactively plan what you want to accomplish before the end […]

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Every calendar needs long blocks of uninterrupted time for heads-down, focused work. Proactively setting aside time for deeply focused, proactive work prevents you from saying yes to too many reactive requests from others. Set aside at 15–20 minutes at the start of your week to proactively plan what you want to accomplish before the end of the week and 15–20 minutes at the end of each week to journal what you accomplished and what got in your way. In the first sit-down, write down what you want and need to accomplish.


As a part of our series about the five things you need to successfully manage a remote team, I had the pleasure of interviewing Matt Martin, Co-Founder and CEO of Clockwise.

Matt Martin co-founded Clockwise along with Mike Grinolds and Gary Lerhaupt in 2016. The intelligent calendar assistant frees up your time so you can focus on what matters. It uses AI to understand your work and life commitments and automatically organize your calendar to help you focus on your priorities.


Thank you so much for doing this with us! Before we dig in, our readers would love to get to know you a bit better. What is your “backstory”?

In elementary school I made hyper card stacks with Mac 2s. I loved the possibility of the computer. In school I developed an affinity for history and desire to impact systems at the highest level. Then going to law school and starting in Big Law, where you measure your time by six-minute increments, gave me an appreciation for the preciousness of time.

So, I left law and pursued a career in software engineering in San Francisco. This brought me to several companies, the most impactful of which was RelateIQ. That’s where I met my Clockwise co-founders.

We shared, and continue to share, a common goal: Giving our users more time for focused work, family, and friends. More time that matters to you.

Can you share the most interesting story that happened to you since you started your career?

Shortly after RelateIQ (the startup I was at before I started Clockwise) was acquired by Salesforce, Marc Benioff came down to our office in Palo Alto to attend our quarterly Hack Day. Our offices were in the basement below West Elm on University Avenue. So, first thing, you have to imagine Marc Benioff squeezing into this subterranean startup office and taking roost on a bench at one of the picnic tables in our lunch area — he’s a larger than life character.

As was a personal Hack Day tradition, I presented my demo in character, and this time I had chosen Steve Jobs. Of course, I had no idea when I prepped this that Marc would be there, but every day is a new adventure! So, I was up on stage in a black mock turtleneck presenting God knows what, and here was Marc Benioff questioning me as Steve Jobs (who he knew quite well). It was absolutely surreal and all I remember is him telling me afterwards that I wasn’t quite as good as the real thing, but close. That’s high praise in my book!

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I used to really overthink investor communications. I would ask colleagues to vet drafts of an email to inbound and existing investors. In retrospect, that sounds hilariously overwrought. And it was. It got in the way multiple times because it would delay timelines. Asking three or four people to vet one email draft means it takes three to four cycles to actually send the email. That’s not effective. But it comes from this insecurity and this impostor syndrome around being the leader of the company and wanting to maintain that outward appearance. And once I became comfortable with who I am and my tone of communication I realized that I am more than perfectly capable of emailing investors and giving them responses.

What advice would you give to other CEOs or founders to help their employees to thrive and avoid burnout?

I think the first lesson is just being comfortable in your own shoes. There’s just this innate impostor syndrome around not having credibility to lead the team. You start the company with a set of people that you know and have worked with before. But starting a company doesn’t change who you are. The expectation that it should do so is one that’s completely self-created — I think that most people who start on any endeavor create an expectation around, “I should be a leader now. I should be more commanding. I should act more like a leader.”

You compare yourself to leaders you’ve worked with, and that’s just not you. No leader you’ve experienced before is going to lead in the same way that you lead. It was a journey for me to get more comfortable in my shoes. I can’t say that I’m fully there yet. But, the self-acknowledgement that you’re going to lead differently than anybody else, and that’s okay, has been huge. You’ve got to find what works for you and meld that with what works for the company.

Find the ability to separate the short-term wins and losses and long-term wins and losses. If you spend too many emotional cycles down in the nitty gritty you’re just going to wear yourself thin. It gets even more complicated when you attach that emotional connection to it. I think that’s the biggest thing.

Another thing is, you need to make space to feel healthy. If the way you feel healthy is by taking a walk through nature, or by going to the gym and pumping out reps on a cardio machine, or if it’s going for a run or a bike ride, or if it’s just taking a walk and listening to a podcast, physical health, and giving yourself the space to pay attention to that, is really critical. And pay close attention to sleep. The number of people I see give up the long game because they wanna win the short game by not sleeping as much… you’ve got to find your threshold of how much sleep you need and live by it.

Ok, let’s jump to the core of our interview. Some companies have many years of experience with managing a remote team. Others have just started this, due to the COVID-19 pandemic. Can you tell us how many years of experience you have managing remote teams?

This is the first time.

Managing a team remotely can be very different than managing a team that is in front of you. Can you articulate for our readers what the five main challenges are regarding managing a remote team? Can you give a story or example for each? Based on your experience, what can one do to address or redress each of those challenges?

A No Meeting Day can improve focus and productivity

Companies from Shopify to Facebook to Asana have embraced the “No Meeting Day.” Setting aside one day per week to focus on heads-down work without being interrupted by meetings can increase productivity and reduce stress.

Eight hours of uninterrupted Focus Time means less context switching. Context switching is deadly for focus and productivity. When you switch tasks, part of your brain is still thinking about the previous task. It takes some time for those thoughts to quiet down so you can concentrate fully on the task at hand. In the meantime, your performance suffers. Researchers call this “attention residue.” It takes 25 minutes and 26 seconds on average to get back to the level of efficiency you were at before an interruption. This means task shifting, even briefly, can cost as much as 40% of your productive time. Harvard Business Review found that context switching cost one large software company more than 450 hours per year, per manager.

The other big benefit to a No Meeting Day is that it can help cut down on the number of meetings. The average worker attends 62 meetings per month and considers half of those meetings a waste of time.

Heads-down work time really needs to be scheduled

Every calendar needs long blocks of uninterrupted time for heads-down, focused work. Proactively setting aside time for deeply focused, proactive work prevents you from saying yes to too many reactive requests from others.

Set aside at 15–20 minutes at the start of your week to proactively plan what you want to accomplish before the end of the week and 15–20 minutes at the end of each week to journal what you accomplished and what got in your way. In the first sit-down, write down what you want and need to accomplish.

People who write down a specific place, date, and time for a task are more likely to complete it than those who just think about it. You don’t need to think of every possible task. Just pull together a list of everything you might want to do in the next week.

Then prioritize that list. You could use the Eisenhower Method, for example. You can also look at your annual goals and ask yourself what tasks would help you achieve them.

Once you have your prioritized list of tasks, estimate how much time each task will require. If the task will take more than one session, try breaking it into micro-tasks. Or, decide how long you’d like to spend on each session and how many sessions it will take.

Avoid the Planning Fallacy by doubling or tripling your initial estimates. It’s much more fun to finish a task early and take a break or get started on the next task than it is to have to push everything out.

Last, create calendar events and name them after the task you want to accomplish during that time. Creating calendar events with start and stop times for each task helps you battle perfectionism by deciding ahead of time when you need to wrap up a project. Putting your tasks on your calendar forces you to reckon with the finitude of time. Every block is a zero-sum game, which makes it easier to say “no” to lower value commitments. Plus, scheduling your tasks on your calendar means your colleagues won’t schedule over them.

Your workers need mental health resources

COVID-19 is taking a massive toll on workers’ mental health, with 86% of Americans worried about Coronavirus. Workers are busier than ever, especially working mothers. In an April study, 67% of workers reported higher stress, 57% greater anxiety, and 53% more emotional exhaustion. Other studies show higher rates of depression, PTSD, domestic violence, and substance abuse. For 69% of employees in one survey this is the most stressful time of their career while 88% experienced moderate to extreme stress over the past four to six weeks.

It’s heartening to see that over the past two months many companies have deepened and broadened their mental health and well-being benefits. In fact, just over half of employers in one survey said they’d recently introduced new or improved existing emotional and mental health programs.

Benefits you could offer for free or at a large discount:

  • Online counseling sessions
  • Online meditation classes
  • Meditation apps
  • Mental health apps
  • Remote fitness/yoga classes
  • Coping and stress management virtual classes
  • Well-being coaching sessions
  • Monthly stipend for mental or physical health

Providers include Sleepio, Wellbeats, Modern Health, Thriving Mind, Plum Village’s Zen Meditation app, and Daylight. Making resources available isn’t enough. According to one study, nearly half of workers haven’t heard from their companies about what’s on offer. Workers whose companies have told them are 60% more likely to agree with the statement that their company cares about their wellbeing.

Mental health events and check-ins keep morale high

In an April study, 75% of workers reported more social isolation since the pandemic started. Nearly a third of employees said they haven’t had any informal contact with their team while working remotely. And socially isolated workers are 19% more likely to say their mental health has declined recently.

Companies have an opportunity to create spaces to bring employees together for socialization.

At Clockwise we do Trivia every Tuesday to connect over something that isn’t work. We’ve also experimented with Drawful and other online games. Some companies are holding online events for employees’ kids as well. Whether it’s virtual happy hours or games, it’s important to get employees talking to each other and having fun regularly to boost morale and mental health.

Regular check-ins are also essential. Nearly 40% of workers say that no one at their company has asked them how they’re doing since the pandemic began. Not shockingly, these workers are 38% more likely to agree that their mental health has declined since they went remote.

And they shouldn’t just be about status updates and projects. They should also be about the worker and how they’re doing. And the person to reach out should be the manager, not HR.

In a Qualtrics survey, people listed HR last among those they’re willing to talk to about mental health concerns, after manager, peers, subordinates, and company executives. Employees with a manager who they say is bad at communicating are nearly a quarter more likely to see their mental health decline.

Workers may need mandatory PTO

Clockwise, along with other companies, is implementing mandatory PTO. Most workers are working more hours than ever, and with nowhere to go, they’re less likely than ever to want to take time off. But overwork leads to burnout and depression. Making the time off mandatory and companywide removes any pressure or incentive to work anyway and gives people some much needed rest while also sending a signal that long-term employee well-being is more important than short-term objectives.

We also use Clockwise Slack sync, which adds a symbol next to your teammates’ names in Slack to indicate whether they’re available, in Focus Time, or in a meeting. It’s great for OOO and after hours, especially if teammates are in different time zones.

If you’re out-of-office or otherwise unavailable, it will also automatically turn on Do Not Disturb. Clockwise for Slack will send you a daily forecast of your meetings to help you prepare for your day. And Clockwise will notify you via Slack when your meetings change.

In my experience, one of the trickiest parts of managing a remote team is giving honest feedback, in a way that doesn’t come across as too harsh. If someone is in front of you much of the nuance can be picked up in facial expressions and body language. But not when someone is remote. Can you give a few suggestions about how to best give constructive criticism to a remote employee?

This is so incredibly difficult. First, it’s important to ground all feedback right now in compassion. We’re living through a very strange time and people have many personal circumstances they’re dealing with. So, anxieties can be high and are somewhat unpredictable. Second, to the extent possible, establish a regular cadence of check-ins. One-on-one check-ins are especially important right now and create the space for more casual conversations. I personally like to do these over phone instead of video — it gives both parties the opportunity to get out for a walk and removes the distractions on the computer. Keep in mind, however, that if you know you’ll need to give particularly difficult feedback, you’ll want to do that over video. You’ll be surprised how much you can pick up over voice, especially when it’s a good connection, but you are without body language, which can be critical in sensitive conversations. Third, be yourself, be vulnerable, and feel it out. This is tricky, but that doesn’t mean you have to develop a whole new language — the same niceties and small talk are still welcome here. And if you acknowledge of the weirdness of it all, it creates the space to work through it together.

Can you specifically address how to give constructive feedback over email? How do you prevent the email from sounding too critical or harsh?

If it’s significant constructive feedback, try not to. It’s really not that difficult to at hop on a phone or video call, and it avoids the coldness of written communication alone. One tactic I (try to) use: write the feedback out and then try to put yourself in the shoes of the recipient; if it feels likely to generate a negative reaction, try to hop on a call.

Now, there’s still a time and place for feedback via email (or chat). Make the effort to give small points of written feedback (both constructive and positive!) regularly. Doing so creates the expectation that written feedback is normal and defuses the feeling that something is really wrong when that small piece of constructive feedback comes through. It’s helpful to (a) keep the feedback concise, (b) avoid generalizations, © ground the feedback in specific actions, (d) give specific examples of ways to improve, and (d) try to reorient away from “you” statements to statements about how the action impacts others (e.g, “I feel like you’re not considering my viewpoint when you cut me off in meetings” instead of “you always talk over other people). And remember the positive feedback! Keep the positive feedback separate from the constructive, when possible.

Can you share any suggestions for teams who are used to working together on location but are forced to work remotely due to the pandemic. Are there potential obstacles one should avoid with a team that is just getting used to working remotely?

Coronavirus wreaked havoc on workers’ calendars. Our data showed workers became busier, we worked longer hours, and we saw their calendars get more chaotic after our employers started mandating that we work from home. Specifically, we found that people are spending a lot more time in meetings — an extra 1–1.5 hours per week in team sync meetings, a 29% increase, and 24% more time in one-on-one meetings.

To take back control of your day and improve productivity, it’s a good idea to audit your calendar. Prioritize meetings that you need to attend, vs. those that can be canceled or pushed back. When needed, push back in a nice way to see if you’re truly needed. Learning how to better train your team and delegate, will open up more opportunities for your team to grow while giving you more tools on how to juggle expanding responsibilities.

What do you suggest can be done to create a healthy and empowering work culture with a team that is remote and not physically together?

There are endless possibilities to bring your team closer together while working remotely. If your company culture was collaborative and fun spirited before the pandemic, then shifting activities that co-workers can do virtually will be less challenging.

There are several ways to build camaraderie while working apart, at Clockwise, we take pride in celebrating our employees and milestones reached. At the end of each week, we gather on Zoom for “demos,” where employees present their accomplishments of the week and if we reached a particular milestone, we’ll celebrate by wearing silly party supplies like hats or sunglasses.

We also host virtual weekly team lunches for co-workers to chat and catch up. We’ll break up into smaller groups to facilitate conversation and bring everyone together. It’s also important to get employees together off the clock to form bonds and boost morale. Consider organizing a virtual happy hour, game night or some other event that your team will enjoy.

In a remote environment, it’s more important than ever to check-in with your employees and normalize the new landscape as much as possible. For example, we continue to make welcome care packages for our new employees as part of the onboarding process and mail them to their home. Something as simple as this can go a long way to show the company values them.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

Well, there are movements of critical importance to society like that are far beyond my area of expertise. If I could inspire any movement at all, it might be to restore the importance of the scientific method, to see the corrosive flaws in our criminal justice system, to create a healthy space for fact based reporting, or to inspire everyone to embrace government’s role in capturing economic externalities. But, grounding this question to areas where I have some expertise with which to inspire…

I would love to inspire a movement that asks everyone to take back control of their time. To inspire people to question how you really want to spend your days, and empower them to make more informed, more considered choices around how to invest their most precious resource.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“This is water.” David Foster Wallace’s 2005 commencement speech is a piece I return to often. The speech, which you really should read in its entirety, is a critical, always relevant, reminder of the central importance of empathy and the very real choice we have in choosing how to engage in the world around us.

Thank you for these great insights!

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