I’ve spent a lot of my “time as an entrepreneur” dealing with the so-called “generation gap,” the temperamental disconnect between young bosses and even younger employees. Or young bosses and older employees. Or middle-of-the-age-range bosses and both younger and older employees.

I’m sure that generation gaps have always been an issue in the work force. But in the past 15 years, with technologically savvy twentysomethings launching companies in droves, age gaps have become a concern for entrepreneurial businesses in particular. In 1991, I was one of those geek-founders; I am now a middle-of-the-age-range boss. In both situations, I’ve managed up and down the generational ladder, gaining from my experiences a smattering of well-honed skills that go to the heart of this issue.

What follows are four experiences that stand out, along with the lessons I’ve learned about managing the age gap.

Down the Ladder

When my partner and I started Net Daemons Associates Inc., a computer-consulting firm, our employees were young enough to create an age gap. We were both 28 years old; they were fresh-out-of-college graduates who had figured their bosses would be adults–and who defined “adult” as someone closer to their parents’ age than their own. But we were young people managing even younger people, and they suspected that we might be doing things in ways that either weren’t quite right or were just wrong. For our part, we, in management, knew we were feeling our way.

Was this bad? Wrong? Unintentional? No, no, and most importantly, NO, I would respond (and I suspect our employees would now agree). We certainly knew it would be easier to be led by an older, seasoned manager. But we also knew that part of NDA’s je ne sais quoi was that we were driving off the beaten path. In our mind, younger managers were more likely than older managers to do that.

Point One:

Managing down a generation enables the blazing of unique paths.

Down and Up the Ladder

We grew and aged, we continued to hire young employees, and the generation gap grew wider. We also began hiring managers and employees who were older, some by as much as a generation. We figured experienced people would save us time because they knew the ropes.

As we mixed generations, however, we discovered that the groups spoke in different languages about experiences. They had different ideas about how things worked. They handled authority and reacted to management differently. Older employees, for instance, were more likely to defer to authority and less likely to question and prod at issues. At the same time, they were inclined to doubt that someone a generation younger than they could manage a company.

Point Two:

Mixing generations means that preconceptions and expectations are in different places. If you want to make things work, you’ll need to tear down disparate pasts and build a common base of understanding grounded in your company’s values.

In the Middle

When NDA was acquired by Interliant Inc. earlier this year, I became a middle-of-the-age-range boss, sandwiched between managers and employees in their twenties and those older experienced people. Sitting in the middle, I now see the generational issues from both sides.

Younger managers who are intelligent, quick, creative, and good at what they do nonetheless have a hard time gaining a voice because they lack experience. And experience does indeed matter. I don’t think, for example, that you can determine whether your company’s policies are too rigid or too lax unless you’ve experienced the pinch and pull of managing from policy. Although learning through trial and error undoubtedly makes sense, I would argue that for entrepreneurial companies, leveraging rather than recreating people’s knowledge makes greater sense.

At the same time, too much experience with a single previous employer is equivalent to inexperience. Believing that it really is hard to teach an old dog new tricks, I question whether people fitting that profile can handle the chaos, rapid change, fluid work force, and new and evolving policies that define today’s emerging companies.

Point Three:

In managing up and down the generational ladder, a level of experience that is neither too little overall nor too much in one place is what trumps age at every turn.

Up and Down the Ladder

In addition to my job at Interliant, I am an active player in the outside business world. Through my involvement on boards, professional associations, and nonprofit groups, I run into generation gaps all of the time.

Each person I interact with and work with, no matter what his or her age, has something for me to learn. “Old-school” managers bring a consistency that is both applicable and comforting in today’s go-go global economy. “New school” managers exhibit flexibility and creative thinking, as well as the realization that the world is changing and we need to move with it. What’s important is knowing when to listen and when to contribute.

Point Four:

Generational issues can be mitigated by living your entrepreneurial life with values, integrity, respect for others, and the gift of listening.

. . . . .

It’s important for entrepreneurs to be aware of generation gaps, whether the gap is 5, 8, 10, or 20 years. Those years can create huge communication issues that could be attributed to the wrong root problem. Recognizing that a skewed view has taken hold because of mismatched expectations rather than something being wrong with you or another person is critical. Being aware of the fact that an age gap might be an issue allows you to solve root problems.

I don’t spend my time looking for diversity to be an issue, but the reality is that diversity can cause interesting situations. It’s always smart to understand the terrain so that I can traverse it with ease. I’ve learned that gaps can be bridged with an open mind, a respect for differences, and an understanding of everyone’s level of experience.