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Ask the Expert: Protecting your family business is more than financial and estate planning

By Lindsay Usherwood
General Counsel

I want to roll back the title of Ask the Expert because I don’t believe anyone can be an expert in family business. It is one of the most complicated relationships, yet family businesses are the backbone of this country. All I can do is share a few tips on how our family makes it work, hoping to give you some ideas to bring to your family business.

When you see family business tips, it is always about sound financial planning and estate planning. These tasks need to be accomplished because, without them, you can’t think about the future with a clear lens. However, they do not necessarily promote happiness or stable growth within your family business.


Any management consultant will tell you that the key to success is effective communication. However, when family dynamics and emotion are involved, it can be difficult to maintain effective communication. To combat this issue, we implemented a weekly meeting called Family Matters. See what we did there? Family has many matters to attend to, and it matters for our business that we keep them straight. These meetings aim to share plans for the week, new projects we are working on, things we feel we can improve upon, and s plans for the future- what we are excited about and what we see as threats to our business. This allows us to be vulnerable and excited about what we are up to individually and as a team. It is an opportunity for us to align, and that’s why we do it every week.

This sounds easy- but believe me, there are times when we leave the meeting feeling frustrated or not well understood. But imagine if we didn’t have this venue? The conversations that happen after are the most

productive to set us up to be one team with a clear path and vision. As a bonus, sometimes these meetings go off the rails, and we spend two hours laughing, which we value as an equally good use of our time as a family.


Family business can easily be hindered by not investing in the future. The two most significant risks are not investing in the next generation of leaders and not investing in your company’s infrastructure.

Not investing in the next generation of leaders is a complicated subject that contributes to why family businesses fail. My firm belief is that having a communicated succession plan will help with the next growth phase for any organization- whether it is a family member or a long-time employee, or someone new to lead the organization into the next growth phase.

The second risk is not investing in infrastructure, and it doesn’t look much different than in the 90’s when my father bought the business from my grandfather. We invested in new office technology: the invention and adoption of e-mail. At the forefront of this investment was technology and hardening our IT infrastructure. The same can be said today. Not only is it what we need to do for our clients to ensure their business is ready for the future, but we must stay ahead to ensure that we can remain fluid for future changes. In 2023, this means that the focus is investment into infrastructure that promotes productivity, communication, and growth while achieving and maintaining compliance in the wake of increased criminal activity in the IT space and the following regulations.

As we start getting ready to celebrate Usherwood Office Technology’s 50th year in business in 2026, we’ve begun to reflect on what has led us here. There have been setbacks and plateaus, but the constant is that we are deepening our familial relationships through communication and vision, and we are deepening our ties to the communities in which we operate by hiring local talent and serving local businesses. This won’t change in the next 50 years because this is our communicated vision for our family business.