Leadership in Uncertain Times: Advice From the Boston Tech Scene

by Quinten Dol
March 25, 2020
boston city
Photo: Shutterstock

When a business selects its leaders, a “proven ability to lead an organization during a global pandemic” is not a traditional prerequisite. 

But as the novel coronavirus rattles families, healthcare systems and economies across Boston and the wider world, that’s exactly what executives and team leads are being asked to do. During times of crisis or heightened uncertainty, traditional leadership qualities — communication, influence, team- and culture-building, decisiveness, resilience, problem-solving, curiosity — become more important than ever. 

One thing we can learn from this unfolding crisis is that none of us — as individuals, professionals and companies, but also as communities, nations and economies — are an island. It’s a reminder that, as with all things, humanity is in this together. 

In that spirit, we checked in with leaders across Boston tech to learn how they and their teams are faring, how they’ve adapted and what advice they have to share with other leaders in the Boston area. 

 

As a leader, you are the person who people in your company turn to. Who are you looking to for motivation and support? What advice do you have for other leaders who are walking into a world of uncertainty?

I look to my peers, both inside Hopper and at other companies. This is one of those times it pays to have a network of people you can trust to give you unbiased advice, people who know what some of the logistical, emotional and business challenges you’re going through are. I’ve often said “leadership is lonely,” but it doesn’t have to be.

I’d give other leaders the same advice: Though you may feel alone, you’re not alone. This is an unprecedented situation, and many others are coping with the same challenges. Don’t be afraid to reach out and find a sounding board. We’ll get through all this together. I’d also recommend talking to a leadership coach or someone experienced in helping people deal with change management.

 

Boston is a strong tech community. How do you think we can help each other in times of uncertainty?

I think the main thing is focusing on what we can do to overcome these challenges. Until we find a way out of this pandemic, life won’t really be returning to normal. Right now, we should all be following the advice of the CDC, socially isolating where possible and trying not to panic. I think the other thing is understanding that change is coming and that we should do what we can to help those who are impacted by all of this.

I love the Boston tech community because it is strong and tightknit. We’ve gone through uncertainty before and come out on the other side, and there’s no reason to doubt we’ll be just as successful here.

 

Over the coming weeks and months, what concerns are you anticipating from your team? How are you addressing them?

I think a lot of people are dealing with social isolation and a lot of logistical issues in their personal lives. I have two daughters who are currently out of school, and my family has changed our routine quite a bit. I would expect that to intensify for some of us over the next month or so as social distancing continues. 

My leadership team and I are doing the best we can to gather resources and adapt to this new reality as quickly as possible. We’re trying to ensure we’re available and prepared to help people who are struggling with this new mode of operation.

 

As a leader, you are the person who people in your company turn to. Who are you looking to for motivation and support? What advice do you have for other leaders who are walking into a world of uncertainty?

I’m not sure I’m looking to anyone outside the company for support. We have a pretty seasoned and experienced team, and we end up relying on one another a great deal.

In particular for leaders under 30, what we’re going through today feels unprecedented, as they have no frame of reference. While the nature of this catastrophe is in fact unique, it’s not the first time we’ve been faced with a crisis that’s new and uniquely terrifying. I was on the leadership team of startups on 9/11 and during the 2008 financial crisis, and each of those presented what appeared to be existential threats to the country’s economy and the survival of our company. On both occasions, the prevailing sentiment was, “Things are never going to be the same again.” But we got through them both, and we’ll get through this as well.

I have four pieces of advice. First, the most important thing is calm, steady leadership. Second, communicate constantly and with transparency, and make sure your entire leadership team is in sync. Third, even if we get past this — and we will — it will likely be slower than you think. I can’t emphasize this enough: Prepare for the worst. Start planning ASAP for that. Don’t waste time and be ready to make tough decisions. Finally, focus on preserving cash and reducing burn. To borrow from an old friend of mine, the late great Craig Johnson, “To succeed, you must first survive.” That is your top priority. Do whatever you need to do to ride through this.

 

Boston is a strong tech community. How do you think we can help each other in times of uncertainty?

Remain calm, make sure your employees are safe and batten down the hatches. This too shall pass. In particular for first-time CEOs, there’s often a unique sense of pressure and loneliness. It’s always helpful to share what you're going through with a trusted circle that you can be honest and transparent with. Since we can’t meet in person anymore, I’d recommend having regular group video chats with other CEOs you know.

 

Over the coming weeks and months, what concerns are you anticipating from your team? How are you addressing them?

The biggest challenge the team is facing is fear of the unknown: How long will this last? What happens if I get sick, or a family member gets sick? How much sick leave can I take, and how can I manage my job from home if that happens?

The honest answer is we just don’t know. What I tell people is, “We’re still figuring out what we’ll do. But take a deep breath. We’re all in this together,  and we’ll figure something out that’s fair. In the meantime, try to get as much work done at home as you can, but focus on your family.”

 

Kelsey Steinbeck
Director of Software Engineering

As a leader, you are the person who people in your company turn to. Who are you looking to for motivation and support? What advice do you have for other leaders who are walking into a world of uncertainty?

Every leader needs to make sure they are practicing self-care. We cannot give what we do not have. By keeping ourselves mentally and physically strong, we can provide a strong support system for our teams and others around us. Negativity is coming from every angle right now and it’s important that leadership is that beacon of strength. People are craving familiarity and normalcy, so encourage teams to keep routines, get outside, workout, eat healthy and unplug when possible.

We can lean on each other as leaders right now, so hold one another accountable, check-in often and provide support where you can. We cannot control the world around us but we can control our own actions. By approaching this journey with compassion and true teamwork, we will come out stronger than before.

 

Boston is a strong tech community. How do you think we can help each other in times of uncertainty?

The best way to help folks is to cut them some slack. So many parents now have to run a full-time day care and be a teacher for the next few months — on top of working a full-time job. We all can’t possibly be in three places at once. Empathy, understanding and compassion are the essence of community in times of uncertainty.

We also would love to see the open-source community shine in this situation. Engineers want to help, and this would be a good distraction given the current circumstances. Working toward common humanitarian goals as a tech community could be really inspiring and show the power of open-source. People can really shine in times of crisis, and we would love to see what the tech community as a whole could accomplish.

 

Over the coming weeks and months, what concerns are you anticipating from your team? How are you addressing them?

The prime directive of the agile retrospective has never been more relevant than right now: “Regardless of what we discover, we understand and truly believe that everyone did the best job they could given what they knew at the time, their skills and abilities, the resources available and the situation at hand.” That last part, “the situation at hand,” has many layers of variability right now, and we as leaders need to empathize with that. We will continue to push normalcy and objectives and strive to be the best company we can, but we also understand that folks are doing their best and that is good enough.

One thing we can do to help build resilience during this time of uncertainly and isolation is to double down on remote culture. We have social Slack groups like #cute-animals, #musicians and #fitness. We have Zoom hangout rooms where people go just to recreate the water cooler and digital board games like Jackbox.tv. If you put in the effort to create culture for everyone, when this is all said and done you’ll have built a more resilient workplace and have the ability to hire from anywhere in the world.

 

Heather Hartford
Chief People Officer

As a leader, you are the person who people in your company turn to. Who are you looking to for motivation and support? What advice do you have for other leaders who are walking into a world of uncertainty?

I tap into the power of our internal team at Acquia. We have a widely distributed workforce and many of our team members work from home on a full-time basis. We’ve established Slack channels where colleagues share tips for effective remote working habits, home office set up, staying fit, daily organization, tools for collaboration and more. It’s inspiring and exciting to see strong participation as our team learns from each other.

My advice for other leaders is to promote a positive tone, reinforce the importance of flexibility and self-care, show empathy, be creative and be accessible. Many of us have had the opportunity to work remotely. This situation is different and we may need to shift our thinking. I have always felt remote work was a privilege and have made myself overly accessible, putting all else secondary. This isn’t a privilege you have been given. It’s a requirement to keep our teams and families safe.

 

Boston is a strong tech community. How do you think we can help each other in times of uncertainty?

This situation calls for building connections and resources to support one another. As a community we can come together to create a forum where we share tips, successes and solutions to the issues that arise from the uncertainty of this situation. 

We are stronger together. This situation is going to force us to think differently about how we work together, share best practices and resources. Proactively centralizing our communication, best practices, tips and tools will strengthen us. We are fortunate that in the technology sector our teams are resilient, agile and flexible and are able to work effectively remotely fairly easily.

 

Over the coming weeks and months, what concerns are you anticipating from your team? How are you addressing them?

With regard to social isolation, we are encouraging regular virtual team get togethers and are also encouraging virtual rotating “buddy” pairings for the team to get to know each other through weekly one-on-one meetups. When it comes to general anxiety and fatigue, we are emphasizing self-care with our team, reminding them to take time for themselves. We have a wellness channel where employees can share their favorite resources.

One thing I have been thinking a lot about is the impact on the workforce when we can go back to the office and if folks will want to come back. I believe that many people genuinely prefer working in the office because of the energy, collaboration and learning that colocation brings. That said, I do think people will likely want more flexibility to work remotely because they’ve “built the muscle” to be productive when working remotely. This period of successful remote work should give managers more confidence to approve work-from-home requests because the team has demonstrated that they can be productive from home.

 

Sam Mallikarjunan
CRO

As a leader, you are the person who people in your company turn to. Who are you looking to for motivation and support? What advice do you have for other leaders who are walking into a world of uncertainty?

One of the weird quirks of being a leader that people don’t often discuss is that we don’t get to have “bad days,” or at least we have a responsibility to not let our bad days ruin dozens or hundreds of other people’s days. We have to rely on a greater depth of personal experience to put things into perspective for ourselves and others. I can always reach way back into my past and say, “Well, this isn’t harder than Army basic training at Fort Knox,” but I’ll confess that these past few weeks have been the strangest of my professional career. Nothing prepared me for this.

The best life advice I’ve ever received has come from airline safety videos: Secure your own mask before assisting others. It’s not because you’re placing your own safety above the child sitting next to you, but that those who rely on you for help won’t get it if you don’t first help yourself. 

 

Boston is a strong tech community. How do you think we can help each other in times of uncertainty?

I was in Boston during the marathon bombing, less than half a mile from the finish line. Bostonians are some of the most irascible and ornery people on Earth sometimes, but they’re also the most caring and resilient. We’re seeing people come together to support those they have absolutely no connection to, like those laid off by Wayfair and Lola. We’ve even mobilized support for our local health professionals, connecting with people all over the world to get them the masks and other protective gear they’re currently lacking.

My first piece of advice for the tech community is to continue to use our inherent drive to find innovative solutions to new problems. I’m seeing people create Google Docs to help laid-off employees, creating their own ad hoc delivery networks to support the elderly and 3D printing components needed by healthcare professionals. 

My second piece of advice is to double down on empathy. If you manage a team, program open-ended questions that can’t be blown off into all of your conversations. We need to be okay with investing in the mental and emotional health of our people, in addition to their professional growth, and be intentional about providing the support structures they need. 

My third piece of advice is to avoid making assumptions. This is the time to over-communicate and to not be afraid of sharing “obvious” information. Add captain obvious to every team meeting.

 

Over the coming weeks and months, what concerns are you anticipating from your team? How are you addressing them?

Some people don’t have internet access at home that’s up to par with the office, and we need to help them upgrade. People also need help setting up firewalls and VPNs, while some have to buy desks. My wife and I live in a studio apartment, and she’s always worked from home full time and has dibs on the one desk we already have.

 

Matt Gay
Director of Engineering

As a leader, you are the person who people in your company turn to. Who are you looking to for motivation and support? What advice do you have for other leaders who are walking into a world of uncertainty?

I’ve been leaning heavily on my friends for support. Over the weekend, I had a “Zoom and gloom” session with a friend where we drank scotch on a shared Zoom session. She’s also an engineering leader, so we spent some time talking about managing teams during this scary period. This was far less awkward than I expected it to be and just the chance to socialize with someone had a noticeably positive effect on my mood.

I’ve also been making heavy use of private Slack groups for company alumni. Connecting with former co-workers is comforting and provides a safe(er) space to talk about these times with people who know me well.

 

Boston is a strong tech community. How do you think we can help each other in times of uncertainty?

While the obvious effect of this is that a bunch of people are suddenly being forced into working from home, we need to remember that there’s far more to this challenge than just moving into a new, lonely office complete with substandard coffee, beer and snack selection. This is also a very real crisis that is weighing heavily on all of us. As much as I’d like to solve this by deploying better work-from-home technology, there’s a human element which can’t be ignored. All of us are scared and worried and will respond differently, so we’ll need to manage through that.

I’d encourage all leaders to remember that they’re dealing with people under high levels of stress — including themselves — and to adapt expectations accordingly. Along the same lines, different people are going to need different types of support, so remember that there are no one-size-fits-all solutions to this.

 

Over the coming weeks and months, what concerns are you anticipating from your team? How are you addressing them?

As an organization that provides an essential service to educators and business, we have a responsibility to keep our service up and running. We take that responsibility very seriously as a team, so figuring out how to handle emergency-reactive work when people’s workday availability is more random than usual is going to be a challenge. So far we’ve handled this on an ad-hoc basis, but we’ll need to figure out how to gracefully assign and hand off work when there are emergencies.

I suspect that combating loneliness is also going to be a major challenge for my team. To that end, I’ve been looking for additional opportunities for socialization. We’ve already had an online social event where we played party games — Jackbox.tv. is great for this — and I’ve been more aggressively reaching out to people on my team to just say “hi” as a way to compensate for the lack of random desk conversations.

 

Ashley Paradela
HEAD OF CUSTOMER SUPPORT

As a leader, you are the person who people in your company turn to. Who are you looking to for motivation and support? What advice do you have for other leaders who are walking into a world of uncertainty?

I look to the professional community, the local Boston community, customers, friends and family for support and motivation. In today’s uncertain world, the advice I would give is to try to focus on what you can control and to maintain culture and a sense of normalcy as best you can. Take walks, breaks and remember your neighbors.

 

Boston is a strong tech community. How do you think we can help each other in times of uncertainty?

Do your best to create a virtual sense of community by sharing learnings, best practices and attending remote group events. Engage and stay connected with colleagues via LinkedIn and social media. Again, try to maintain as much normalcy as possible and remember, we’re all in this together.

 

Over the coming weeks and months, what concerns are you anticipating from your team? How are you addressing them?

I expect lead flow to slow down, which will allow us to improve our current process and be better prepared for when things are back to normal. Customers turmoil could also be an issue, so I’m advising my team to reach out to at-risk companies and ensure we’re there to provide support in any way possible. Not just monetary support, either, but a human interaction to create unity. Then there’s uncertainty. As an agile organization, we are used to iterating and learning from unknown situations, and by applying agile principles we are able to continue to improve as a company and as individuals during this trying time.

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