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“Why a manager should always work on empathy” With RescueTime CEO Robby Macdonell

You can always work on empathy: You don’t need to try to be best friends with everyone on your team, but try to stay aware of their experience at work and listen for ways you can improve it. Sometimes, you’ll find ways to show you care that aren’t obvious. For example, I noticed that a […]


You can always work on empathy: You don’t need to try to be best friends with everyone on your team, but try to stay aware of their experience at work and listen for ways you can improve it. Sometimes, you’ll find ways to show you care that aren’t obvious. For example, I noticed that a few of our employees found the expectations of our open vacation policy frustratingly vague after dealing with a death in the family. By adding a (generous) bereavement policy, we were able to remove a source of stress in an already trying time for our team members.


I had the pleasure to interview Robby Macdonell, the CEO of RescueTime

Thank you so much for doing this with us! What is your “backstory”?

I started my career as a freelance graphic designer and eventually moved into the startup world where I spent several years as a user experience developer. The work was great, but the days would often fly by in such a blur that it was difficult to feel like I was being productive. A few of my friends and I got sick of always feeling behind, so we wrote a small script that would run on our computers and tell us how much time we spent in different applications. When we saw the results, we were amazed at how different our perceptions were from reality. It really helped me make positive changes, and eventually, we turned that idea from a scratch-our-own-itch project into a company. Now we help thousands of people make better use of their time and do their best work.

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

About 5 years ago, my father started having health issues, and I decided to move back to Tennessee to be closer to him. I was sure I would have to quit my job, but we decided that we would try working remotely instead. It was a huge mental shift to go from being at our headquarters in Seattle every day to working from home in Nashville. As I grew more comfortable working remotely, I started to see the advantages. There are fewer interruptions and not having a commute is really nice. Staying connected to my colleagues wasn’t as difficult as I expected, thanks to video chat and Slack. I missed seeing people face to face, but the tradeoff was that I got to be near my family when they needed me, and continue doing the job I really love. I’m not sure I could easily go back to working in a “normal” office environment now.

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 learned the hard way that when you work with someone in the opposite hemisphere, daylight savings time shifts two hours, not just one. We hired an amazing content manager in Melbourne, Australia. The time difference was a challenge, but we were able to find a small window of overlap that worked for both of us. We didn’t consider daylight savings time, however. All of a sudden, a 15-hour time difference became a 17 hour one. We had to quickly reschedule a bunch of meetings when that happened. Lesson Learned: The world is a big place! Time zone mathematics helps.

How do you synchronize large teams to effectively work together?

Because we are a distributed workforce, the challenges are not limited to size but geography. We use video chat to work together. Video allows us the benefits of face to face and is far better than email or simple chat when we need to work together. We also strive for the right balance between process and getting lost in the minutiae of detail. Finally, we break down large problems into smaller chunks that can be handled by one or two people which enables everyone to be more efficient.

What is the top challenge when managing global teams in different geographical locations? Can you give an example or a story?

The biggest challenge is maintaining a human connection between your people. When everyone is in a different location, as ours are, it’s so easy to only focus communications on work and miss out on the normal small-talk and open-ended conversations you’d have in a centralized office. Not having unstructured time to bond, explore, even argue with each other really robs a company of one of its best assets–diversity of thought. As a remote team, that’s one of the areas we have to work much harder to maintain than a more traditional office environment.

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

How you communicate is as important as what you communicate.

With limited face-to-face time, your emails and Slack messages become the pulse of your company culture. As CEO, however, it’s important to be very intentional about how you communicate, because you’re leading by example, whether you mean to or not.

At RescueTime, having a culture that promotes balance and focused, deep, work is really important to us — particularly given the data that shows that only 30 percent of us are able to get an hour of dedicated focused work time in a given day due to the constant onslaught of communication technology distractions. That means I have to keep my own urgency in check. If I send a few frantic, late-night emails asking people to drop what they’re doing because I need something right away, I start to chip away at that part of our culture. Instead, I lead by instilling digital wellness best practices to encourage better work-life balance and productivity for every employee as well as myself. This is an essential practice at RescueTime that unfortunately, most workplaces de-prioritize in favor of always-on responsiveness.

Most times when people quit their jobs they actually “quit their managers”. What are your thoughts on retaining talent today?

If you want people to stay, make them feel safe and confident that they’ll be able to focus on their most important work.

‘Psychological safety’ is one of the most important factors for a successful, high performing team, and ensuring that the company culture supports people’s efforts to do their best work is the most important thing a leader can do.

People should feel safe to take risks and make mistakes. They should also feel confident that the work that’s on their plate really matters. If you can create a supportive environment and not yank the rug out from under them with shifting priorities, you’ll create an environment that people won’t want to leave.

Based on your personal experience, what are the “5 Things You Need To Know To Successfully Manage a Team”. (Please share a story or example for each, Ideally an example from your experience)

You can always work on empathy: You don’t need to try to be best friends with everyone on your team, but try to stay aware of their experience at work and listen for ways you can improve it. Sometimes, you’ll find ways to show you care that aren’t obvious. For example, I noticed that a few of our employees found the expectations of our open vacation policy frustratingly vague after dealing with a death in the family. By adding a (generous) bereavement policy, we were able to remove a source of stress in an already trying time for our team members.

Give your team members the space to be experts: Chances are, you can’t do every job in your company better than anyone else. It can be tempting to weigh in and second guess other people’s efforts but resist that where you can. Your team members should be better in their roles than you are. But if you never let them lead, they’ll never build confidence and you might as well be doing all those jobs yourself.

Get comfortable asking “what can I do to help?”: A big part of leadership is giving your team the resources to do their best work. Don’t assume your team members will ask for help. They may think you’re busy with ‘more important’ things or think they’ll be judged if they speak up. I try to make a habit of asking how I can help as often as I can. When someone gives you an opportunity to help, make it a priority and follow through on it.

Be open to feedback, even when it’s negative: It’s fun to hear people say nice things when you’re doing a good job, but be open to negative feedback as well. Even if you disagree with the person giving it, there’s almost always something to learn, and your team will appreciate the safe environment where they can speak up.

Don’t be afraid to be a human being: You’re not going to know all the answers all the time, and you’ll feel like an imposter in your role as a leader from time to time. It happens to everyone. Sometimes a fake-it-till-you-make-it approach works, but it’s ok to admit when you’re struggling. Your team doesn’t expect you to be perfect, and they’ll appreciate it when you show some vulnerability.

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. 🙂

Everyone would go through their phones and turn off the default notifications for all their apps. Without all the distractions, there’s no telling what we’d accomplish!

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

Happiness is not a matter of intensity but of balance, order, rhythm and harmony. — Thomas Merton

My father’s illness forced me to shift my location — physically and mentally. We commonly wave the banner of drive and intensity but happiness and fulfillment is so much more than that.

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