35 Lessons in 35 Years

Andy O’Connor said no the first time his father asked him to join the business.

That’s not usually how a thirty-fifth-anniversary piece starts, but it’s true, and it says something about how the next three and a half decades actually went: mostly figured out one decision at a time.

This year, AJO marks 35 years since he said yes. 

We asked him what he’s learned along the way.

The list ran to 35 items, and almost none of it is about strategy.

Starting late, starting scared

Say no, then let it sit. His father asked him into the business. Andy said no. A year later, his father drove over while Andy was raking leaves and said, “I want you to think about that for a month, and then we’ll talk,” then walked away. “He left me with my thoughts and my leaves.”

Try the work before you commit to it. He asked himself whether there was a way to get a feel for the business before signing on. Three pro bono sessions in, he had his answer: “This is hitting something for me.”

Any experience isn’t wasted. His father’s read on Andy’s fourteen years in law enforcement: “You’ve been getting people to tell you their stories for the last 14 years.” The prior career wasn’t a detour. It was training.

It’s okay to find yourself taking a longer runway. “If I wasn’t working for my father, I probably would have been fired after six months. I needed a long run because I had to learn.”

Insecurity can become a method. He didn’t know the business yet, so he asked people about themselves instead: their families, where they lived. The workaround became the whole practice.

The thing that makes you the odd one out is the thing they want. At an HR conference early on, Andy felt like he didn’t belong in the room. “I don’t belong in this place at all,” he remembers thinking. Every person he spoke to that day told him his law-enforcement background was exactly the fit.

The entrepreneur was there the whole time. Three paper routes at twelve. A landscaping business. A ten-year painting business before any of this. “Maybe I’m more of an entrepreneur than I realized.”

Failure, rejection, and discomfort

Growth lives in the uncomfortable. “When you’re uncomfortable, that’s when you learn the most. When you fail, that’s when you learn the most.”

Rethinking rejection. He used to run pro bono networking seminars, quarterly evenings for people in the middle of a job search. On an easel, he’d put up eighteen no’s, then a yes, circled. Then ten or twelve, and another circled yes. Then eight, and one more. “This is what you need to do to get to where you need to get to,” he’d tell the room. “And once you do, they start coming more frequent. I can’t tell you why that happens, but it does.”

A bad call is data, not a verdict. Building the business in the years before email meant cold calls, ten or twenty a day, and some of them landed badly. He remembers hanging up after one, looking at the phone, and saying out loud, “Well, that didn’t go well at all.” Then concluding, “I had some work to do.”

Relationships over transactions

Partner, not vendor. “We don’t think of ourselves as vendors. We think of ourselves as an extension of the client.” Get called a vendor, and “I’m not sure that that’s the right client for us.”

They remember the favor you forgot. A client once told him, “I always keep you in mind. Remember, you’re the reason I’m here.” His reply: “Oh, I forgot about that.”

Show up early and connect the people in the room. In a client’s cafeteria one morning, Andy found himself introducing three coworkers who’d never met. “This is kind of interesting that the outsider is introducing people to one another.”

Don’t walk in selling. “If you come out with a business card and the opportunity to maybe follow up with a cup of coffee sometime, that’s success.”

Play a longer game than everyone else. “All I had to do was outlast my competition and let them all retire before me. And in a weird way, that’s really happened.”

Touch points, forever. A quarterly check-in. Lunch or coffee a couple of times a year. Some of those relationships run twenty to twenty-five years. “It almost becomes like a friendship because you’re so invested over so many years.”

Someone has to extend trust first. Early on, someone he’d never met agreed to a lunch meeting with him, for no particular reason. “She put the trust out there right away.”

How he led

“That’s just the title.” He was found cleaning coffee stains off the carpet one morning, before eight. “It’s my carpet.”

Indecision becomes the decision. “Sometimes the decision is made for you, and that’s not really leading.”

You don’t need the answer: you need to know where to find it. “I don’t need to have the answer all the time, but I need to be able to know where to go to get the answer.” Strong coaches and consultants are “like having your own library.”

Own the wrong call out loud. “Here’s the decision I made at the time, here’s the information I had at the time. In retrospect I would have done X instead of Y. There’s the learning.”

The best question beats the best answer. At his coach forum, one member would stand up at the end and ask the one thing that made every coach in the room think, “why didn’t I think of that?”

Reward the person who brings bad news. Someone on his team once asked him, in tears, why she was always the one carrying the bad news to his office. “Because you tell me. Other people don’t.”

No trust, no alignment. “You can have all the vision and strategy in the world, but if you don’t have the trust, you come out of the meetings everybody agreeing, and then they go their different directions.”

Zero to a hundred, and back. Fourteen years in law enforcement taught him something no leadership course did. After a high-speed chase, it took five or ten seconds to come back down. “Not staying calm. Getting calm, fast, and getting back in it.”

Family business, succession, the long handoff

Style is personal, not inherited. His father ran the business like the military. “I think it was for him. But that’s not really the way I want to be.” Shannon has said something close to the same thing about her own last few years, figuring out who she is as a leader and how she differs from Andy: “because I’m not him.” Three generations, three different ways of doing it. None of them wrong.

“That’s why we’re here.” The office technically closed at five. One evening, a client working through a job search was still in the back office, on a call to California, in the middle of an interview. Andy’s answer wasn’t to interrupt him. It was to leave him to it. “We’re here for them, that’s why we’re here.”

Go work for someone else first. His advice to a fourth-generation family member entering a business: “Hopefully you get a terrible boss, so you appreciate what you have.”

Coaching feels like nothing until it doesn’t. Andy and Shannon worked with a coach throughout their own succession process, Andy quarterly, Shannon a bit more often. At the end of each session she’d ask, “Was this helpful?” Early on, his answer was, “Yeah, it’s helpful. I’m not sure where we’re going with it.” About a year and a half in, that changed: “It’s kind of like looking through plexiglass, and all of a sudden it crystallized, and now I can see a path.”

Building the business

Hit singles every day. He spent a week at a time on RFPs against firms with far more resources, almost never won, and eventually stopped entering. “Just keep hitting singles, because they all add up.”

Sell what they’ll buy. A client was once furious he’d never mentioned outplacement. “I didn’t, because you weren’t going to buy it from me.” A long silence, then: “That was probably a pretty good decision.”

Answer the question they’re too polite to ask. Early in his career, he needed to signal his age without saying it outright, so he listed his résumé out loud instead: “Here’s this 28-year-old standing in my doorway.”

Build the room where people learn from each other. His coach forum started roughly twenty-five years ago as an informal ask. “Everybody said yes.” Later he invited clients in too. “The more they know about us, the more likely it is they’re going to do business with us.”

What it was all for

Give it back where you can see it. Jaycees, then planning board chair, then town council. Seven years, all unpaid. Then Cornerstone: “take the tour of the neighborhood house and you’ll be supportive of their mission, because the mission is to help people.”

Stand the test of time. What he hopes gets said in another 35 years: “the reputation for good, solid work, being good community people, and being counted on.” Culture, in three words: “collaborative, fun, and a learning environment.”

None of this adds up to a single lesson, and that’s probably the point. Thirty-five years didn’t happen because of one big decision. It happened because of small ones, made on purpose, repeated long after anyone was still counting.

Congratulations, Andy. And thank you.