The do’s and don’ts of working with family and friends

(Guest post by Deana Ward.) Working with family and friends—like anything in life—can be completely awesome or totally awful. Over the course of my career, I've experienced both extremes (and everything in between). Currently, Gear Five Studio is a Petri dish for personal work relationships. My brother and I are business partners. Our art director

Founder Friday is a weekly guest post written by a founder who is based in or hails from the Silicon Prairie. Each month, a topic relevant to startups is presented and founders share lessons learned or best practices utilized on that topic. March’s topic is working with friends and family.

About the author: Deana Ward is the co-founder of Gear Five Studio.


Working with family and friends—like anything in life—can be completely awesome or totally awful. Over the course of my career, I’ve experienced both extremes (and everything in between).

Currently, Gear Five Studio is a Petri dish for personal work relationships. My brother and I are business partners. Our art director is married to one of our graphic designers. Our sales guy and marketing assistant are siblings. Said sales guy dates our art director’s sister. Our newest developer is a close buddy of the same sales guy.

Last week I ran an anonymous in-house survey around this situation. I wanted to know what our team likes and loathes about working with family members, or around others who are family. I’m pleased to report that our current situation seems overwhelmingly positive.

“I feel that working with family and friends enhances how I get my work done, mainly because I enjoy the environment that working together has created.”

“I really like this close knit community much more than working in other environments…the communication is more honest and direct.”

However, this was not always the case. In the early days of our company, we hired everybody: wives, husbands, best friends from childhood, brothers, sisters, cousins, and uncles. According to Phil Libin, the CEO of Evernote, this is a smart practice because no-one will work harder than your friends or family. Usually.

Our situation turned messy.

The dynamics were awkward and the communication was NOT honest or direct. Issues had to be skirted around as to avoid hurt feelings because we knew we’d have to face each other at events and family gatherings. When it became clear that certain team members weren’t properly suited for their roles, the firing process was excruciating and some relationships unraveled beyond repair.

Today, our team is equally interwoven, minus the drama. We are stronger because of our connectivity. Our lessons were hard-learned and the positivity hard-earned.

Working with spouses

In the beginning, both our spouses (Collin’s and mine) were involved in the business. We also had young families. Guess what we talked about at home and at family gatherings. Work. Guess what ALL of us stressed out about around our kids. Work. Guess what we never escaped – morning, noon, and night. Work.

We are passionate about our company, but there are times when you need perspective that can only be gained by stepping outside the situation.

For our married artists (who are newlyweds and childless), working side by side is awesome.

“When we have disagreements, the end product always turns out better. I also think working together improves our communication all the way around.” – Alice Bolte, Gear Five Studio art director

Spouse tip

Working with your spouse can be an awesome experience. Just be sure to qualify the situation by going through Stephanie’s questions. If you have small kids at home you may want to avoid working with your spouse (especially if you are a startup founder). When the road gets rough – and it will at times – an outside perspective will keep you from feeling like you are drowning.

Working with friends

When we started, our CTO was a good friend of ours. His skills and talents were the perfect fit for the role, but we had microscopic doubts about his availability (which he assured us would not be a problem). Because he was our friend, our personal comfort level with him overshadowed our doubts. It didn’t take long for the honeymoon to wear off and the reality of his availability to start causing problems. Long story short, we haven’t spoken in two years.

Friend tip

When considering bringing a friend on-board, ask yourself: If your friend weren’t your friend, would you think he or she was the absolute best candidate for the job?

Doubt means don’t (even minuscule amounts of it). If you have a millimeter of doubt, don’t hire them. It doesn’t matter that if they will “have your back.” If they don’t have the skills, talent, ambition, and availability to deliver, they will be holding you back.

There is no hiding in a startup environment. If you override your doubts, they will surface sooner or later (typically sooner). Just save yourself the trouble.

Working with siblings

I love working with my brother. He is the yang to my yin. We are opposites in many ways. I tell him to slow down and absorb. He pushes me outside my comfort zone. If he’s rambling, I tell him to be quiet. If I’m being a rag, he tells me to take five. If we were more similar, this probably wouldn’t work. If our individual egos were bigger than our business objectives this definitely wouldn’t work. It’s impossible for us to have big egos because we know too much about each other. (He has photographic evidence of my parachute pants and permed hair and won’t hesitate to expose me).

Sibling tip

If you genuinely appreciate your sibling’s quirks, they possess rock-star talent, and you share the same vision, go for it. Anything short of that, proceed with caution. You don’t want to wind up like two hamsters in a cage – ripping each other’s faces off.

Working with your dog

Always the right thing to do.


Credits: Photos courtesy of Deana Ward.

About the Author: Deana Ward is the co-founder and chief operating officer of Gear Five Studio, which creates interactive software that helps innovative leaders solve their most expensive business problem: employee engagement.

Deana is also the creator of, the online resource dedicated to helping smart, busy women get happier by overcoming their organizing obstacles.


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