What’s your biggest challenge right now?

The biggest challenge right now is preparing to go into the slower season and sort of trying to do right by our employees and keep their hours up and stay efficient. That’s probably my biggest challenge as a new business owner, trying to strike that balance. There’s built-in seasonality to the hospitality business. Coming into a winter is definitely a slowdown. We’ve been very lucky in that the construction (the reconstruction of the Maine Avenue and Bridge Street bridges) hasn’t really impacted us negatively, at least not in the way that we can measure. So it really is just the season that we’re shifting out of summer and into winter, and there’s all kinds of change that comes along with that.

One year after you bought the diner, how’s it going?

It is exactly one year today (Thursday). It’s an interesting time of year to have our first anniversary, with Thanksgiving, because I think even without the holiday we would reflect back and say, “Wow, we are so thankful for this moment and that moment, (and) of this person and that person.” One year in, we recognize that we’ve been so, so fortunate to have so many great staff members that helped us transition, customers who were appreciative of what we were trying to do — keep the diner the same, keep the quality as high as it’s always been. I’d say that what I’m feeling most right now on this one-year anniversary is just a whole lot of thanks for all the people that made it possible. Because it certainly wouldn’t have been possible. If it was just my wife and I trying to keep all the oars going, it just, we wouldn’t be here. So yeah, we’re just very fortunate.

What’s the biggest difference between being an employee and an owner?

I think the biggest difference is as a team member and employee, you can report to a higher-up who then deals with a problem. That can be staff issues. It can be anything. Right? And, as the employee, you feel like you’ve done your job: You’ve reported to the big boss and they’re going to take care of it. The hardest part for me has been recognizing that, especially in terms of staff issues, I am the boss, and I’m not doing anyone any favors by not setting clear expectations. So that’s really been difficult, to make that transition. But like I said, I’m very, very lucky that my staff are so great. There haven’t been many instances where I need to, and my employees call me out on it. They say, “Hey, you know, you’re the boss.”

You need to set the expectations. And so that, I think, is the hardest thing — understanding that the culture that you want in a business isn’t just going to make itself. As you try to make a culture, not every moment is warm and fuzzy. You have to find a balance between not being hard on people. You have to find a balance between laying out what you want and still being friendly. That for me was interesting — making that transition because I don’t want to be anyone’s boss. You know, I don’t feel like I am. I feel like more (of) my job is to facilitate putting my employees in a position to do what they do, right? I’ve hired them to do the job. I should get out of their way and enable them to be successful by giving them the right tools and let them do what they need to do, but at the same time, let them know what I expect them to do. So, I guess the short version of that is adjusting to a very, very high level view of everything altogether and understanding the role that you serve as an owner is different than just doing the nuts and bolts of the (being) the best employee. You know, the best employee does a great job at everything, but never has to have that 30,000 foot view, as the owner that you need to.

How do you foster creativity in yourself and your staff?

I basically let them know they have power in certain circumstances. I’ll just give you a direct example. A lot of times we get catering orders, where they’d just say, we have this many people, we want to do sandwiches and wraps, so just give us what you think. One time in particular they said, we’ve got five people who are vegan and we need a vegan option. I thought, well, this sounds like a fun little challenge. One of my cooks who is an excellent chef, he does a great job on the line, didn’t get to do as much work in the back as he’d like to over the summer because it’s so busy. I thought he’s going to love this.

I said, take a couple of hours on your shift today and I want you to menu plan this. You tell me what I need to get for you to do this. You’re basically just giving someone license to be as creative as they want. You’re saying, “Hey, I want you to show me how awesome you are. I know you’re awesome. This is a very important thing. You know how important it is to us that we impress our customers. I want you to just nail this and knock it out of the park.” And he did. I think that you have to create time for your staff. And so in this case, I just pulled him off of his regular hard work, and said I know you can do this.

I think that he understood what was happening and he took advantage how as far as making the business bigger. That has been a real challenge.

I think that our goal in the first year wasn’t necessarily to make the business that much bigger. It was really more to just learn as much as we could about what it means to own the business and what kind of flexibility we have and what restrictions we have. I didn’t really put that stress on myself, and (as a) matter of fact, it was better for me probably to be immersed in the grind and kind of have my head under water a little bit.

But now going into year two, I think it’s just important that you have kind of a meeting of the minds at the beginning of the year.

This year we’re going to put more energy and effort into expanding (catering) and just try to keep that as a marker in your mind. Everything you do that year, you just want to make sure you’re moving toward that goal. It’s always kind of there.

The other thing I think that’s been really important is my wife (Sarah Harris) is my partner in all of this. She has been doing an outstanding job managing our social media, responding to people who request charitable contributions, keeping the diner fresh with new flowers and seasonal changes, and engaging with our Facebook fans. So we’ve created some clear lines, so that stuff that is creative and needs to happen in the business, that’s her role. So that is her day to day. That is how we’re finding the time — she just has to do that. She’s not doing the operational stuff in the restaurant. She’s doing that creative stuff, and then bookkeeping and making the paperwork happen.

Where will the business be in five years?

In five years, I hope that we will be sitting on a brand new bridge with a beautiful new stretch of road in front of us and that the diner will look sort of the same. But we’ll be doing more in terms of catering and offering some of the things that we have here, like some of our stuff for dessert, as options for people to have for takeout items. Not catering, necessarily, but custom desserts for people. I think we’ll do more of that.

We’re going to try to refresh (the diner) and restore it to some extent, a little bit of the time, and be true to the history of the building. Not many of these buildings are left, and it really is kind of a local treasure. I think it’s important to serve as a steward of the place, because I hope that it’s here longer than I am.

So that’s what I think our five-year plan looks like right now. Just keep things in the house looking very much like they are, keep our menu creative, and maybe do a little bit more in terms of catering and to-go and make the diner structure kind of fresher, bring it back to where it needs to be and have it look more like it did in the ’60s than you know, than it has recently.