Working with family can be a double-edged sword. On one hand, you have an inherent trust and shared history that few business partners can match. On the other, the lines between professional and personal can blur, leading to complex dynamics and unique challenges.
In a recent episode of Morgan on Purpose: The Podcast I chatted with my sister and long-time business partner, Courtney Ranstrom. We’ve worked together for nearly 20 years, navigating the transition from second-generation employees in our father’s business to co-founders of our own firm, Trailhead Planners.
Our conversation touched on everything from financial literacy for women to the influence of birth order on risk-taking. But perhaps the most insightful takeaways for other business owners were our reflections on the joys and pitfalls of working with family.
Here are a few key lessons we’ve learned along the way:
1. Acknowledge that it’s hard
You know how they say the first step to solving a problem is admitting you have a problem? The same goes for working with family. If you want to successfully navigate the complex dynamics of working with family, you have to start by acknowledging that there are complex dynamics at play. Acknowledge that it’s hard.
Working with family isn’t just about business; it’s about navigating decades of history and established roles. As Courtney noted, “Working with anyone who you know really, really well is incredibly hard.” You have high expectations of each other because you know what the other is capable of, but those same deep connections can make it difficult to separate “work sister” from “home sister.”
2. Communication is key
Clear and open communication is vital in any business partnership, but it’s even more critical when family is involved. For me and Courtney, our Midwestern (North Dakota and Minnesota) upbringing sometimes works against us on this front. We can sometimes fall into the trap of “everything is fine.”
That can sound positive at first, but after awhile “expert conflict avoiders” turns into “passive aggressive resentment. Learning to suck it up and have those tough conversations is essential.
3. Don’t undervalue trust
The biggest advantage of working with family is the unwavering trust. As I said to Courtney, “Even when we’ve had hard conversations… there was always this fallback of, ‘Well, we’ll never screw each other over, though.’” This deep-seated trust allows you to weather the storms and provides a sense of security that is invaluable in the entrepreneurial world.
4. You know each others’ strengths and weaknesses—use them
One reason Courtney and I work so well together is that our skill sets complement each other. Courtney excels in operations, while I lean towards investment and marketing. Recognizing and respecting each other’s strengths allows us to divide and conquer effectively, rather than stepping on each other’s toes.
As always, though, this is a double-edged sword. When you know your colleagues weaknesses, you can cover for them, but you can also become resentful if you feel that they’re slacking. That’s why communication is key. You have to be able to acknowledge what each person is good at and lean into those differences.
5. Find a way to separate work and life
Maintaining a healthy family relationship while running a business together requires conscious effort. Courtney and I often joke that we live in different states for a reason. As much as we love spending time together as a family, when we have to go from work calls to family visits back to work all in a 24 hour period, it can be a lot. (We experience this any time Courtney is back in Minnesota for visits.)
While we cherish our family time together, having physical and mental space between our personal and professional lives is crucial for our long-term success as both siblings and business partners.
Working with family is a journey filled with both unique rewards and distinct challenges. By prioritizing communication, leveraging each other’s strengths, and grounding everything in a foundation of trust, you can turn those family ties into your business’s greatest strength.
Want to hear more? You can find the full episode of “Morgan on Purpose” featuring Courtney Ranstrom on all major podcast platforms. We dive deeper into financial planning for women, the impact of birth order, and our shared journey as entrepreneurs.
