Since launching onShore Security, a Chicago-based cybersecurity company, Stel Valavanis has experimented with several leadership styles. “I’d say I started with pacesetting and found that it doesn’t scale, then shifted to authoritative to get things done, but now see that as a last resort,” Valavanis said.
Three decades after launching onShore, Valavanis has settled into a democratic leadership style. “It gives the highest buy-in and the most informed decision, but it can be slow and inefficient too,” he said. For example, he recently took team input on product-features bundling, which involves demand, value, operations and economics, yet “pretty much calls the shots” when it comes to design, tone and language of marketing materials. “Consistency and speed would suffer if it were done by committee,” he said.
The 2 Main Types of Leadership
- Primal leaders: Focus on employees as individuals and do their job with emotional intelligence and empathy. Leadership styles: Democratic, transformative, affiliative, collaborative, visionary, servant and coaching.
- Dissonant leaders: Focus on the goals of the company, often to the detriment of employees. Leadership styles: Transactional, pacesetting, commanding and authoritative.
As onShore grows, Valavanis coaches managers into leadership styles appropriate for their responsibilities and departments. “I keep my management team tight knit and democratic while also working one-on-one with them in a coaching style and getting them to help each other,” he said.
Leaders might be born. They might be made. But as Valavanis’s experience demonstrates, leaders most definitely evolve. Professionals new to leadership think they need to be extra tough to earn respect, said Andrea Kayne, associate professor and leadership program director at DePaul University in Chicago and a senior advisor at edtech company Otus. “That’s a myth,” Kayne said.
On the flip side, she’s seen new leaders become too friendly with staff, a situation that makes it difficult to set boundaries or deliver constructive feedback. “What’s really important is to figure out who you are and be consistent,” said Kayne. “Consistency and authenticity is really important to the people who are working for you.”
The Personal Approach
It took a while for Nathan McKelvey to find his authentic leadership style. Earlier in his career, McKelvey ran a private jet charter company. McKelvey describes a pressure cooker overflowing with wealthy, demanding clients and VC backers hungry for revenue. McKelvey, in turn, pushed his 50 employees to perform, and the situation created “a lot of burnout,” he said. “It was not a fun day-to-day environment.”
That lasted 10 years, and instilled in McKelvey an appreciation for how leadership styles can affect a company and its employees. In 2019, with the private jet experience firmly in mind, he launched Army8, a Boston-based tech-industry marketing and consulting firm. The company, by design, is not VC backed. McKelvey and Army8’s five full-time employees (he has another 100 or so contractors) hold a team check-in at the end of every week, sharing challenges and mistakes to learn from them and moving on.
“I am not afraid to talk about the times I’ve screwed up. It’s okay to make a mistake, learn from it and move on.”
The intention? A low-stress, productive workplace. “You need a creative mind in marketing and you don’t get that in a high-stress environment,” McKelvey said.
McKelvey calls his leadership style “personal,” with a massive amount of trust among him and his staff. “I am not afraid to talk about the times I’ve screwed up,” he said. “It’s okay to make a mistake, learn from it and move on.” The management style, he said, doesn’t work for everyone. “You have to be open to sharing,” he said, noting that he interviews all new hires, asking probing questions, sometimes personal, to see if the trust level is there. One drawback: “It can be difficult to scale, because you need to find the right personalities,” he said.
The two-way trust makes for happier, more relaxed employees. “Nate always gives us the benefit of the doubt,” said Carla Higham, Army8 communications strategist. “When we screw up, it’s not because we lack skills or drive. He knows that something is happening beyond that.”
Michael Golden and Thad Wong, business partners for 25 years, have had to develop their leadership styles in tandem. The two formed @properties, a tech-focused, Chicago-based real estate company, in part as a counterbalance to having been inadequately managed in the past. “We wanted a supportive work environment, and for people to feel they were part of something that mattered, and that they were appreciated,” said Golden, who with Wong is co-CEO of @properties. (The company also has a COO, Joni Meyerowitz.)
Golden handles finance and operations, and Wong, marketing, innovation, creative efforts and growth, with their duties crossing over in several departments, including managing the 4,000 agents who are contractors with @properties. “We are fundamentally very different people,” Golden said. “But we work very, very well together.”
As a team, they identify as visionary leaders investing in tech and tech solutions for the company and its 400 payroll employees. They also identify as servant leaders to support the 400 people on payroll and more crucially, those 4,000 agents. “They’re only here because they want to be here, so we’ve always viewed ourselves as serving them,” Golden said. Their servant leadership has become more empathetic over time, he added. “If someone’s going through a difficult time, with a health or personal struggle, our goal as a company and as leaders is to be there for them,” Golden said.
They work collaboratively on company challenges, with Wong taking a more aggressive approach and Golden, a more conservative tack. “He makes me take far more risks than I would have on my own, and I probably temper some of the risks that he would take if I weren’t there,” Golden said. When they face tough decisions around finance or other sensitive matters, “we just do it, and in as soft a way as possible,” Golden said. “It’s not about squeezing out every dollar that you can. It’s about running a business that can survive and thrive and provide value and service to our people.”
Their two approaches also work well with employees, some of whom gravitate toward Golden’s more laid back approach and others, to Wong’s more assertive style. “Everybody can find leadership they identify with,” Wong said.
Visionary and Collaborative
Luke Switkowski, CEO and cofounder at digital workplace consultancy Kognitiv, once reported to managers who seemed open to ideas, but who in reality were not. “You’d have a great idea and bring it to the manager and they’d say no,” he said. “They didn’t let you pursue something you see as an opportunity.”
That experience informed Switkowski’s own style, which he characterizes as empowering employees to do their best work. “People deal with a lot of stuff that they bring to work every day, and we have to have a sensitivity to that,” he said. “We are not micromanagers.”
He describes his leadership style as visionary and collaborative. “Just because I have a clear idea doesn’t mean it’s going to translate well downstream,” he said. Switkowski said that letting employees into his thought process has served the company well over the years.
For instance, five years ago, Kognitiv wanted to create its own SaaS tool that would integrate with Workday. Kognitiv employees talked to clients, who asked for an interview-scheduling tool. Kognitiv built Rooster, a scheduling app that integrates with Workday. “You trust that you have experts on your team,” Switkowski said. “When we started exploring the idea of Rooster, I trusted them to give me the most truthful answer.”
Switkowski encourages employees to act like owners, which is one of Kognitiv’s values. “We try to instill that and let people run with ideas,” he said. His style, he added, might not work well at a startup fast-tracked to be acquired. “If we were working on a quick exit, we’d be more tactical and maybe less creative,” he said.
Transforming to Transformational
Before joining the world of tech startups 13 years ago, Peggy O’Flaherty worked for United Airlines and raised five children. She describes her earlier leadership — definitely informed by her parenting style — as a touch authoritative and mostly transactional: Identify goal, make checklist of steps to complete goal, complete goal.
“People deal with a lot of stuff that they bring to work every day, and we have to have a sensitivity to that.”
“When my children were young and I was a young manager, I laid out the plan and expected everyone to march to my orders,” O’Flaherty said. “It doesn’t work that way.” The approach (for employees) worked at times, but at other times, O’Flaherty felt like she was dragging people along, without successfully communicating a vision or a plan.
As cofounder and chief community officer at Mavely, a startup that matches influencers with brands, O’Flaherty now aspires to transformational leadership. “I understand my own strengths and weaknesses and can see other people’s,” she said. “People deal with a lot of stuff that they bring to work every day, and we have to have a sensitivity to that,” she said.
Transformational leadership starts with making sure the 10 Mavely employees have the right skills for the roles they fill. “When I see people struggling, it’s usually because they’re in a role that doesn’t play to their biggest strengths,” she said. “I always try to figure out a way to work with them.”
Her own desire to be more than a taskmaster, plus the counsel of a mentor, helped with the evolution. The mentor is Tim Connors, founder of VC firm PivotNorth Capital, who is also an investor in Mavely. Connors, O’Flaherty said, modeled transformational leadership and demonstrated how to “truly act within our core values,” she said.