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When Your Dad is Your Boss

By Liz (Stewart) DeJesus, Marketing Manager

With Father’s Day fast approaching, I thought it would be a great opportunity to write about what I’ve learned from working for my Dad.

Stewart Transportation Solutions has been a part of my life since I was five years old, and to be honest, I don’t really remember my life without STS. When my Dad would take us out to dinner, we always had to say “Bus!” at the end of the meal. He wanted to make sure we knew that any good fortune my family experienced was directly linked to buses. I wasn’t quite sure how it was related, but I knew buses were an important part of our lives.

I don’t think I ever thought I’d work for my Dad. Sure, I worked a few events for him here and there, but I never saw myself working in the tourism industry. After all, I had a BA in Political Science. I had started building a foundation in lobbying and political campaigns.

Then the recession hit.

After a series of pretty terrible jobs—including a funeral home—my boyfriend at the time (now my husband!) and I moved to Richmond, Virginia, where I accidentally fell into a job helping to plan events with the Richmond Convention and Visitors Bureau.

I was hooked.

When I met my Dad in Seattle in the summer of 2013 to help with a transportation program, we started a conversation I never thought I wanted to have. He wanted to know what I thought about joining STS and helping with the marketing aspect of the company. I definitely had reservations, but they were mostly personal. I knew I had the skills to help him grow his company, but I was worried about what it would be like to work for my Dad. I had heard horror stories about family businesses and I certainly didn’t want to fall into that trap.

For one, I know my Dad better than the average employee. I know what annoys him, what makes him happy, and how to butter him up—every daughter knows that trick! And of course, we have history. He knows my mistakes and I know some of his. All of these factors can certainly have a negative impact on a working relationship, but they can also be helpful.

I’m still learning how to best work with my father, but I have learned a few things along the way that I think would help anyone who is considering working with or for a family member.

Make sure your role is clear. I know my work responsibilities, and so do my coworkers. It’s the ambiguity that can get you in trouble. If my coworkers didn’t know what I was doing on a day-to-day basis, they would be more likely to think that I’m some kind of leech, sucking money out of the company for no clearly defined purpose.

Avoid special treatment like the plague. It is extremely important to me that I am treated like all other employees. I go out of my way to tell our office manager if I’m even going to run a fifteen-minute errand because I don’t want anyone to think that I’m taking advantage of the company.

Boundaries, boundaries, boundaries. We’re still working on this one because we do love to talk about work outside of the office, but setting healthy boundaries is critical to maintaining a good working relationship with family members.

Recognize the common goal. Because of the history I have with my Dad, I know how much time and energy he has put into this company. As a result of my understanding and appreciation for his hard work, I am equally invested in its success. It makes it easier to put petty arguments and disagreements aside when you recognize that we both want to see this company succeed.

Respect. Perhaps the best advice I could give to someone who is considering working for the family business is to respect the authority of those in charge. I have found that treating my Dad like I would any other boss has been a great strategy for me. I respect the rules, his authority and his decisions, even if I don’t agree with them. After all, he’s been doing this a lot longer than I have.

It has been a little over a year since I started working for STS, and it has been different, exciting and very personal. I’ve enjoyed watching this company grow and knowing that I’m a part of that growth. It has been different to see my Dad as the boss—after all, until last year, he has just been my Dad—but it’s exciting to watch him lead his team with so much passion. My time with STS has also been a lot more personal than I expected it to be. I have skin in the game. Not only is STS a part of my family, but now I’m a part of the STS family. And who is better to share that experience with than my Dad?

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