Matt Desilet of SquadLocker: “Be kind to yourself and your team”

Be kind to yourself and your team — Imposter syndrome is running rampant these days, which is not new. With that, we tack on the new rules of engagement during the pandemic. For many of us, face-to-face Zoom is the best we can do — life inevitably happens. We’re all human, and we have to be kind to ourselves […]

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Be kind to yourself and your team — Imposter syndrome is running rampant these days, which is not new. With that, we tack on the new rules of engagement during the pandemic. For many of us, face-to-face Zoom is the best we can do — life inevitably happens. We’re all human, and we have to be kind to ourselves as we work through things. For some, this might truly be a new normal as more work shifts remote. For others, it will be a phase. In any event, there’s no sense in adding extra internal pressure and self-doubt. I make it part of my mission to wrangle up as much joy and positivity as I can and share it with my team.

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 Desilet.

Matt Desilet is Marketing Director at SquadLocker, a company that provides online tools for teams, organizations, and schools to manage custom apparel and equipment purchasing. After his first childhood nickname “Dez” stuck, he never went back. Matt is a growth and engagement strategist experienced in creating digital marketing campaigns, launching new products, and enabling sales + success teams. He is an experienced contributor, manager, and leader on agile marketing teams. Matt likes to focus on delivering data-driven results in a human-centered way. His first startup experience came in the form of gigging and recording with his band full-time. Having a seat on the startup rocket ship gives Matt the same vibe as watching his music take off and get into the hands of thousands of people. To slow things down, he enjoys building and tinkering with guitars at home. A proud Rochestarian, Matt supports the Buffalo Bills, Wegmans, and proper Buffalo chicken wings. Bleu cheese only, Ranch need-not apply.

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”?

I grew up in Rochester NY, which is an amazing place to be a kid. My “plan A” was to be a rock star. While in high school, I used winter and spring breaks to tour with my band, Almost Tomorrow. Once, some of us were 16, of course. After about three years of gigging and recording, I decided to make a run for college and pursue a degree in political science at Northeastern University. After learning that Poli Sci was not at all what I wanted to do for work, I made my second hard pivot into entrepreneurship and startup life. I got involved with NEU’s venture accelerator, IDEA and joined my first startup as employee #1 in 2013. From there, it was all about chasing those big moments in startup life. Think major funding rounds, IPO’s, and acquisitions. It’s not much different from chasing a record deal or a #1 hit.

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

One of my earlier gigs seemed like an amazing fit. I was psyched to join the company. I thought there was a ton of growth there, and it was sort of a shortlist “dream” landing spot for me. Turns out, I would have three successive family emergencies in my first 40 days there, including deaths. Those situations tested both me and the leadership at that organization. I ended up leaving feeling very down about my abilities and self-worth. Looking back though, I realize that company handled the situation in a way I could never get behind as a leader. “There’s a seat for every ass,” was a common saying of my wife’s grandfather. My ass just didn’t belong in that seat.

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?

One of my favorite stories is about an interview I had. I made it passed a phone screen and was interviewing with the marketing leader of a fast-growing Boston education software company. I had tons of HubSpot experience, but no Marketo experience at the time. I did poor research on the subject, and if we’re being honest, I barely thought this would be an issue, even though the JD mentioned Marketo. Sitting down for coffee in this pretty informal interview, the leader asked me about my experience with marketing automation software — and I went on blabbering. When it came time to talk about Marketo, for which I had some boiler plate talk-track about campaigns, I pronounced the platform “Market — to.” As in “I’m marketing to this group.” It got awkward, and she politely said, “Do you mean, Mar-ket-o?” I was pretty sure it was over at that point. Oddly enough, I did get to speak with the co-founders after, but I was humbled by the experience. It was clear I wasn’t ready yet.

So, a tip for newbies — and this is probably the best advice I could give anyone who needs to hear it: “I don’t know” is a perfectly good answer — especially in the business world. We’re not ER surgeons.

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

I’ve got a five-bullet wish list for all CEOs:

  • Don’t (make us) sweat the small stuff — We all, marketers especially, suffer from “shiny new object syndrome,” and we have to break that habit. Sometimes the thing keeping CEOs up at night shouldn’t, because it has such a small impact on our objectives and key results.
  • Give employees agency — You did not hire people to tell them exactly what to do and how to do it. You did not hire people because everything in that area is being perfectly managed by the resources that you have. If you’re deadly passionate about this area of the business, insist that you, as CEO, are part of the interview process for the department head. Really “marry” this person and their thought process so you can let go a bit. We need you, the CEO, to think bigger and continue to teach us.
  • Always be teaching — Pretty simple one. As a marketer, I want to download the CEO’s brain like a database and reference it all the time. You’re the catalyst, you’re the beating heart. We need you to always be teaching us so that we live and breathe the mission like you do.
  • Communicate clearly — This one is dead-simple. Say what you mean, when you mean it. No pop-quizzes when we’re trying to grow a business. Don’t make folks read between the lines. It’s just a speed bump.
  • Be human — In every single startup I’ve worked for, there’s one consistent moment that rallies a team: when the CEO shows some humanity and humility around the mission of the company. Serious sacrifices are made. Money, time, and memories are traded for lots of hard work and anxiety. Don’t incite fear when times are tough, but don’t be too scared to show some scars. What’s the point of giving out equity opportunities if you don’t share in the struggle?

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?

To be fully transparent, I’ve been managing fully remote teams since the pandemic so about six months. As a startup veteran though, teams have always been at least partly remote. I’ve never really worked for a company where people couldn’t or didn’t occasionally work from home. So, if you’re using that metric: about five years.

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?

Relationship-building is tested like never before:

Say you are stepping into a new role and the position is (now) remote, and the team is remote — but they weren’t always that way. It’s really hard to gain understanding and find common ground without a typical social introduction. There’s no weekly coffee or lunch that is so intertwined into the “normal” onboarding process — so new remote managers have to pay extra attention to this one.

Communication, especially around performance can be indirect, insufficient, and sometimes misleading:

You really want to be clear with regards to how things are going, especially when performance isn’t meeting expectations. I’ve had moments in my career where I’ve had to give tough, direct feedback to a 100% remote employee, and if you don’t set yourself up to have those conversations, you end up surprising people. If you’re surprising folks about their performance and there’s no documentation or history to back up your points, that’s wildly unfair to the person receiving that feedback.

Planning at your org can be inflexible — hard to work inside the lines when the lines outside keep moving:

I’ve been in the nightmare scenario where I keep pointing to data, saying; “This is what’s happened, what’s happening,” and people don’t want to believe it. “Make it better!” It can be frustrating when you show a direct relationship to how things outside of your control impact your objectives and key results.

Accountability can be waning or nonexistent:

Sometimes in the remote environment, you end up with a failure of accountability. Who owns this project? Where was that update? There are lots of habits that lean us into dangerous territory here. Anyone trying to project manage through email threads? No thanks.

People are really hard on themselves right now:

I’ve seen so much of this lately. Folks are wildly unsure of themselves. There’s a lot more folks investing in their personal and professional development these days, which is great, but the “watercooler” talk, at least for me, reveals that people feel unprepared right now, and I’m sure that’s valid.

Based on your experience, what can one do to address or redress each of those challenges?

Rapport matters. Build or strengthen it:

If you are starting from scratch or starting a new gig where you are managing folks remotely, you need to build relationships. You can’t go out for lunch 1:1’s. You can’t really have drinks after work. So how do you fill those gaps? You can’t jump into “business as usual” and forget about the people you are working with. This pays dividends down the road. Inevitably, unintended things happen on virtual meetings. We should not assume that our lives mirror the lives of our reports or teammates. Whether it’s children screaming in the background or dogs jumping all over the computer (guilty), having rapport with your team makes these virtual moments less awkward. You’ll find yourselves laughing about it and moving on quickly.

Care personally, so you can challenge directly — and ask for direct feedback (Radical Candor callout):

After you have an established relationship, you have to show that you care about the things impacting people’s lives. Support these folks like the human beings they are within the purview of accomplishing company goals, of course. I’m fully swiping this from one of my favorite reads, Radical Candor by Kim Scott. This is an extension of the “building rapport” advice; it’s crucially important to connect the dots between rapport and reporting. In order to effectively manage folks tied to goals and objectives, we have to have some way to evaluate performance against goals. If you take the humanity that would normally exist out of that process, people won’t feel cared for and they will go find other places to work. Once you have that relationship and have shown that you care about a person’s performance and quality of live, you’ve earned the right to challenge them directly on established and agreed upon objectives. Pro tip: Ask this of your direct supervisor and frequent collaborators as well. This direct feedback against the critical objectives of your role will only help you. Speaking of objectives…

Build flexible, scalable plans to meet and exceed your goals:

The plans we make now need to be flexible. Plans need to account for varying levels of success (100% attainment, 90%, 75%, total failure). Missing consistently? Re-forecast! Change the plan to adjust to what’s really happening. Build objectives with realistic wiggle room so that you can see how capable your team is at this time. Our plans must have built-in learning opportunities so you can fix things fast. They also need to scale up. It’s forgivable to be surprised by success, less forgivable to be incapable of capitalizing off of it.

Hold yourself and your team to those plans:

This answers the question “to what end?” Your team just did all this great work building with flex and scalability in mind so that you can look hard at results later.

Be kind to yourself and your team:

Imposter syndrome is running rampant these days, which is not new. With that, we tack on the new rules of engagement during the pandemic. For many of us, face-to-face Zoom is the best we can do — life inevitably happens. We’re all human, and we have to be kind to ourselves as we work through things. For some, this might truly be a new normal as more work shifts remote. For others, it will be a phase. In any event, there’s no sense in adding extra internal pressure and self-doubt. I make it part of my mission to wrangle up as much joy and positivity as I can and share it with my team.

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 may not be a popular opinion amongst managers, but I do think you need to earn the right to challenge directly. Establish rapport and make sure your team knows that you care personally so you can challenge directly. Having documentation and record of expectations, performance, etc., can make this a LOT easier for you as well. Surprising people isn’t fun, and I’m of the opinion that pop quizzes ended in high school.

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

Potentially a hot take — if the constructive feedback is foundational, I don’t give that over email… period. If it’s a small thing like — “Hey, this punctuation looks off,” or “Our messaging doesn’t feel aligned with this brand guideline doc, what do you think?” That’s cool. But if someone is really misaligned then I think we need to be at least on the phone, Zoom/video preferred. If it’s way off-hours, I might send an email that sets up a call but putting substantial constructive feedback that provokes reflection and critical thinking in an email has a way of stewing.

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?

Try and replicate or maintain the rituals in some way to keep the cadence going. Regular lookbacks and check-ins are important. Cut some fat in terms of meetings — you need time to get stuff done.

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?

This is a good exercise, remote or not. Outline what everyone owns and broadcast that to the larger team or company. It’s crucial that people within and without know who owns what on your team. This exercise lets folks on the team triage when requests come in. Taking these steps also helps guide ownership on project management within the team. Giving your team ownership also gives them agency. Empower your reports to take control of what they can so that their performance is in their hands.

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. 🙂

There are many famous ways to say it, but I’m a big fan of the golden rule. Treat others as you would like to be treated. As an extension of that, I’ve always loved Dr. King’s ideology that we should judge people by the content of their character. I think that helps the most people with the smallest number of steps.

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

An indirect leader at a college internship once told me that my kindness would take me very far, and that it can’t be taught, only learned through experience. And I think that’s proven to be correct in my experience.

With that, I am a big fan of the 14th Dalai Lama and many of his teachings. I think kindness and compassion are key elements to happiness. Happiness is the key ingredient to achieving my definition of success. An easy favorite — “Choose to be optimistic, it feels better.”

Thank you for these great insights!

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