INSIGHT

Six Weeks In: How Kenway's CEO Led Through Crisis by Asking Questions, Not Giving Answers

By Matt Kueker

Matt Kueker became CEO of Kenway in early 2020. Six weeks later, the world shut down due to COVID. Here's how he led through the most uncertain time in modern business—by embracing vulnerability, listening to everyone, and modeling "success in ambiguity."

The Call That Changed Everything

Matt Kueker had been CEO of Kenway for six weeks when COVID-19 hit.

The weight of that responsibility was overwhelming. "I was a new CEO," he says simply. "And I'd never been a doctor."

In that moment of crisis, many leaders would have felt pressure to project certainty. To have all the answers. 

Matt did the opposite.

Listening to the Smartest People in the Room

Rather than pretending to have answers no one could possibly have, Matt turned to the people who might: Kenway's clients.

"Our clients are all incredibly smart," Matt explains. "They were aggregating data and information in real-time about what was working, what wasn't, what they were learning. We listened closely and used what they were discovering to inform our own internal policies."

But he didn't stop there.

"I Made a Point to Talk to Every Team Member"

When asked about offering help during that time, Matt shares a practice that defined his leadership through the crisis—and beyond.

"I made a point to talk to every team member at least once a month, even if there was not a business need to do so," he says. "Just to check in on them. How they were doing. What they needed."

It wasn't about project updates or deliverables. It was about human connection in a time of profound uncertainty and isolation.

"I continued that after COVID," Matt adds. "Now that we've grown, I still do it, but it's quarterly."

Asking Questions Instead of Giving Answers

"Thankfully, we had our Why and our Guiding Principles as a foundation for action," Matt explains. "And then we were very transparent with all of Kenway about what we did not know, the criteria we used for each decision, and in many instances invited them to participate in the decision-making process."

The approach was counterintuitive: lead with questions, not answers.

The result? Not just survival, but deeper connection.

"Not only was our employee base super helpful in crafting our responses to those challenges, but I think we came together even more as a team and garnered a lot of trust for leadership," Matt reflects.

Success in Ambiguity

As Kenway's founder Brian King describes him: "When you meet a colleague who exemplifies work ethic, 'can do' attitude, success in ambiguity and interpersonal relationship skills, you seek them out."

That phrase—"success in ambiguity"—captures something essential about how Matt leads.

It's his comfort with uncertainty, this ability to lead without pretending to know everything, that Matt models for Kenway's culture. COVID demanded it at scale, but it's how he's always operated.

"He has the balance of a tactician and a strategist to not only know where things need to go, but also the ability to bring it there," Brian wrote. 

Brian's assessment of Matt's impact is unequivocal: "Matt's honest, hard-working and passionate approach to his work is one of the primary reasons for Kenway's standing in our industry today. The impact he has had on Kenway employees past and present and on our clients is beyond measure."

During COVID, that strength wasn't about having answers. It was about asking questions, listening deeply, and creating space for others to contribute.

"Help and Be Helped" as Mission, Not Marketing

For Matt, "help and be helped" isn't a tagline. It's Kenway's Why—the reason the organization exists.

"I do not think the philosophy or mission itself has evolved over time, but the opportunities to put it into practice certainly evolve with each passing week, month, year," Matt explains.

The philosophy shapes everything at Kenway, starting with how people work together internally.

"From an internal perspective, our Why is especially powerful because it sets us apart from others in our industry, which can be very competitive between colleagues," Matt notes. "This can manifest in seeking help being perceived as a sign of weakness, which leads to all sorts of challenges."

At Kenway, the opposite is true. "Help and be helped is the foundation of a very teaming, collaborative environment where we value hard work and growth mindset, but also reward seeking help, inclusive of feedback, and all the goodness that comes from it."

A Different Approach to Client Relationships

The philosophy also fundamentally changes how Kenway approaches the market.

"From a market-facing perspective, our Why also sets us apart, because our ultimate goal is not based on revenue, but simply helping as many clients as possible, as much as possible," Matt explains.

"This alleviates the pressure other organizations have to sell, which sometimes leads to overselling or over-promising. We only offer help where we know we will be a great partner for that project, and are happy to refer work out where we are not best suited to help."

Creating Psychological Safety: Being the Last to Speak

As CEO, Matt works deliberately to create an environment where people feel safe asking for help and offering it.

"First and foremost, I try to lead by example," he says.

That means involving employees in significant decisions—not just surface-level choices, but the deep, complex ones that shape the organization.

"We get together quarterly as a whole company and use that time to process and brainstorm key decisions that need to be made," Matt explains.

At a more personal level, Matt has developed a practice that requires discipline: being the last to speak.

"At a more micro level, I not only ask for help, but I make sure I'm the last to speak in most meetings. Or at least I try to be," he says. "I try not to take air out of the meeting room by giving opinions and answers, but add air to the room by listening and asking follow-up questions."

There's one more critical piece: recognition. "We also reinforce positive behaviors publicly when colleagues are not only giving help, but asking for it. I think that is key, because you have to pay closer attention to capture those moments and acknowledge them in a timely manner."

How the CEO Recharges

Outside of work, Matt has a practice that both helps him wind down and brings fresh perspective to his leadership: reading.

"I've always been a voracious reader, but since joining Kenway, I focus on industry, management, leadership, etc. types of content," he says. "I tend to read before I go to bed, which for me is the best way to wind down and help to ensure a good night's sleep, which helps to recharge."

But it's more than relaxation. "It is also very helpful to reframe what is going on at Kenway to bring fresh perspectives to challenges and objectives we are pursuing."

Leading with Questions, Not Answers

Six weeks into his tenure as CEO, Matt Kueker faced a crisis unlike anything in modern business history. He didn't have the answers. He couldn't.

So he did what great leaders do in ambiguity: He asked questions. He listened—to clients, to team members, to the data emerging in real-time. He checked in with every single employee, not for business reasons, but because they were human beings navigating unprecedented uncertainty together.

And in doing so, he didn't just help Kenway survive COVID—he deepened the trust, collaboration, and commitment that define the organization.

"Help and be helped" isn't just Kenway's mission. It's how Matt Kueker leads—in crisis and in calm, in meetings and in monthly check-ins, in certainty and especially in ambiguity.

It's why Kenway is different. And it's why people love working there every day.

Help & Be Helped isn’t just a philosophy — it’s how we lead at Kenway. Connect with Matt Kueker on LinkedIn or read more stories of how Kenway brings Help & Be Helped to life on our Insights page.

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