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When the Kid Becomes the Boss
Published Friday, February 10, 2017

(Editor's note: Since this article originally appeared in print in the December issue of Business NH Magazine, Jane Oneail has left the League of NH Craftsmen.)

Jane Oneail took over as executive director of the League of NH Craftsmen in 2015 and regularly deals with members and employees who are senior to her by three decades. Recognizing that many of these people are the same age as her parents, Oneail, 37, approaches her job with a mix of humility and confidence to convey she is in charge but also open to listening and other people’s ideas.  

“My approach to it from the beginning has been to listen, to honor people’s experience, particularly at an organization like the League, which has this incredible history,” she says of the 84-year-old organization. “I mean, honestly, no leader, no matter their age, could come in here with the arrogance that they know better than everybody else.” And while she says humility is an incredibly valuable quality to have in her position, she still has to lead, and she says that’s just as important. “The advice I would give to anyone my age who is running an org would be to have some humility, but you also have to strike a balance because people do want leadership, they do want confidence, they do want somebody to strike a tone,” she says.  “It’s definitely a tightrope.”

And it’s a tightrope more young CEOs and managers will face as they move up the ladder and boomers remain in the workforce longer or keep working part time. This creates a new work dynamic where the person on top is sometimes young enough to be the son or daughter of the people they oversee.

“The hierarchy used to be you started young out of college and worked your way up,” says Sheila Kabat, vice president and COO of human resource and organizational development services for Snowden Associates in Portsmouth. “We are evolving through that right now. And I think in some of the industries, you will see seasoned employees—as I like to call them—working for younger people. And a lot of this has to do with the breakthrough industries, the ones disrupting the norm, that it’s more typical. I think we are very much in a transition.” Kabat says, noting this is especially evident in the tech sector.

While it’s very human for both employer and employee to have some trepidation about these situations, Kabat says  these situations can be rewarding for everyone involved. She says industries led by younger bosses “are much more tolerant, and older workers are eager, very often, to work in that environment because it’s often an energetic environment.”

Goodbye Hierarchy
The new generation of younger bosses, by and large, are much more interested in creating collaborative, egalitarian environments devoid of the employer/subordinate dynamic, says Jim Kimberly, president of Sapphire Consulting in Amherst. “The younger leaders today are more collaborative, are more interested in open communication,” he says. “They don’t care about hierarchy as much as the other generations. And because of that, they just feel like everyone is equal, and why can’t people just share?”

Nick Soggu is one of those leaders. Soggu started Silvertech, a digital marketing firm, in the late 1990s when he was just 23 years old and did not consider the age of his employees particularly relevant. He was, and is, more interested in their career goals and skills. “I think it’s really just about defining what their goals are, what they are looking to get out of the employment period that they have and making sure that as a company and as a leader that you are able to cater to their needs,” Soggu says. “The way I think about people and work is that people are here on borrowed time. We employ them, but in some ways we are sort of borrowing their expertise and their time, and so we owe them and the team as much as we owe our clients and our company.”

Soggu says he doesn’t see any downside to younger bosses and older employees, having employed a variety of age groups. “I think we offer a flexible work environment that caters to all generations,” he says of his workers who range from just out of college to those over 60 years old. “My biggest challenge as a boss has been in the hiring front. We are constantly looking to grow and want to have team members that are growing along with our clients’ needs. Recruiting has been a challenge for us and will probably continue to be for the near future. We just aren’t graduating enough individuals with the right skill sets in our own education systems.”

Dealing With the Downside
But there can be a downside for older workers, says Kimberly. A younger boss may disregard some older employees who are not used to that style of management.

“If I’m an older employee, and my last boss was older than me with old school philosophy, you know: speak when spoken to only, need-to-know information sharing, not into open sharing—now I’ve got a boss that shares everything with me, I don’t know how to react to that. I don’t know what to say or do.”

Kimberly says that’s why it is so important for young leaders, particularly ones new to their positions, to have a conversation early on to get to know each other’s styles. “The key to any good relationship amongst members is to develop strong relationships with all workers. So spend time with each of your direct reports to understand their motivations and their desire to be as successful as possible within your team. Make sure you schedule one-on-one time as well as team meetings,” he says.

Make sure to discuss how each does their work, the processes and systems they use to conduct business as well as their preferred communication style, Kimberly says. “Sometimes you’ll have generational differences of communications, but it’s actually pretty universal, people just have different styles. So if we just call it generational issues—and people generally want to pin it on the millennials versus the rest of us, I think it’s too simplistic. I think it’s more important to talk about: Are people having the conversations right away when you get a new boss, regardless of their age? Are we having conversations that look at work styles and communication styles, and can we have open conversations about what those are?” he says.

A talented, seasoned individual could become defensive or overbearing in their behavior with a younger boss, Kabat says. “Crucial honest conversations that build this new relationship will be vital to the future success of everyone involved,” she says. “Be clear in your dialogue with your boss, younger or older, about your desire to contribute using your best talent and past contributions. Assumptions are usually founded on lack of knowledge and information. Sometime a shared cup of coffee or lunch can enable an informal exchange to build that boss relationship.”

If a younger manager senses tension with an older worker, do a gut check and ask a colleague about your behavior on the team, Kimberly says. “Are you respecting their experience and input? Are you just pushing your ideas on them? Make sure you’re balancing your advocacy with inquiry,” he says.

If an employee thinks a younger boss is making assumptions based on age, Kimberly says to first check with coworkers to verify perceptions. “If you are spot on with the assumptions, you have to check them out with the boss. Again, it’s about the relationship. Are you approaching with ideas and input? Have you made assumptions about your boss that may be incorrect? Bite the bullet and have a candid conversation with respect,” he says.

One way to avoid such situations is provide managers with leadership development opportunities that deal with diversity in the workplace, including generational influences, cultural awareness and potential age and gender bias, Kimberly says.

“With the evolving diversity of our workforce and the promise of ongoing change, all managers need the support of the appropriate information to set them up for success while leading,” Kabat says. “Human Resources might help to create development plans for the younger managers that include in-house mentoring with experienced leaders and more structured development designed to ensure learning that is necessary for their role.”

Know Your Employees
Kimberly says it’s paramount that the leader take the lead on this dialogue, since the employee may feel the conversation is not appropriate or may be uncomfortable broaching the topic with his or her boss. For example, Kimberly says he’s coaching a leader who is in his 30s who went from managing three people to 200, with nine managers reporting directly to him and layers of employees beneath them. “And now he’s got to adapt to working with a wide variety of people with lots of experience,” he says. “It’s really incumbent on the leader to set the tone, to try to engage in conversation about how the team will work together, can work together and what people’s strengths and weaknesses are.”

Oneail oversees a staff of 16 who range in age from mid-30s to mid-60s. She focuses on team building, being transparent about the challenges facing the organization as well as the opportunities within it, and finding ways to thank her team. “The team at the League works so hard, so I have tried to thank them as often as possible. Group lunches go a long way,” she says.

As fundraising is always a challenge for any nonprofit, Oneail works with her diverse team to come up with creative solutions. “One of the ways to address the need to increase earned and contributed income was the development of an Innovation Team—a group of creative thinkers on the staff and board that are tasked with solving two problems: increasing our service to the craftsmen and generating income for the League,” she says.

Kabat says respect is key to cultivating a positive relationship that can bridge most age gaps. “Respect goes a long way,” Kabat says. “If I respect somebody, it’s not an age thing. If I don’t respect somebody, it’s not an age thing. It has to do with their authenticity. So I think the younger person working through and being genuine will see that seasoned employee as a resource. That person may have been working for the company, and they do have a lot of institutional or company knowledge that the young person might not possess.”

The younger boss should go to the more seasoned employee and ask for his or her counsel and generally engage them in valuable ways that will lead to respect on both sides. Kimberly adds that both the younger boss and the older employee will continue to build that relationship as long as each approaches situations with an attitude of inquiry, such as asking questions like, “How do you work? How is work done in this group? I’m not familiar with or I don’t know this particular product line, or tell me a story about when you are at your most effective and what does that look like for you?”

“I think if you can adopt an attitude of inquiry and curiosity instead of ‘I have expert knowledge that I am now going to pass on to you,’ it really, really will go a long way to have everyone hopefully share in a more open environment,” he says.

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