You Only Get One Shot: A Conversation About Farm Succession Planning with Ted Lebow, 26th Annual NODPA Field Days Keynote Speaker

By Ted LeBow, CEO, and Lindsey McDonnell, Business Consultant — Good Roots

Succession planning is one of the most consequential decisions a farm family will ever make — and also one of the most avoided. At Good Roots, we work with farmers and food entrepreneurs every day who are sitting on millions of dollars in land and equipment, dreaming about retirement, and quietly hoping it all works out. It doesn’t always. We decided to sit down together and talk candidly about what we’ve learned: what goes wrong, what goes right, and why waiting too long can cost a family everything they worked to build. The conversation got honest pretty fast. That’s kind of our dynamic.

On Getting Started — The Earlier, the Better
Lindsey: Ted, you’ve been doing this for a long time. What’s the single biggest mistake you see farm families make when it comes to succession planning?
Ted: Waiting. Every single time - waiting. People assume they have more time than they do, and then one day they’re 65 years old, asset-rich and cash-poor, unprofitable, and trying to untangle decades of financial complexity while also figuring out who takes over the farm and whether their marriage survives the process. The farm becomes the retirement plan. The land, the equipment, the livestock — that’s where all the money went. And it makes sense in the moment, because you’re always reinvesting in the operation. But the problem surfaces when the next generation is expected to both run the business AND take on enough debt to financially support the retiring generation. That pressure can cripple a transition before it even starts.

Lindsey: We just lived this with a client. The parents had put nearly everything into the business. They owned a small piece of personal property and had made some modest loans to the operation over the years, but outside of that, almost nothing set aside for retirement. Meanwhile, millions were tied up in farmland and equipment, the operation carried significant debt, and it wasn't generating enough profit to support both generations comfortably. What made it especially hard was that both the parents and the children were deeply motivated to carry on the legacy. The desire was absolutely there. But the financial reality meant the children were stepping into a high-debt situation from day one. Instead of handing over an opportunity, they were unintentionally handing over financial strain.
Ted: Exactly. And hope is not a retirement plan. I say that a lot, but I mean it.

Lindsey: Ted, I hear you say that all the time, but what does "plan early" actually mean? When should someone really start?
Ted: Yesterday. But seriously, earlier than almost anyone thinks. Most people assume succession planning is something you tackle in your 50s or 60s. By then, you're already behind. Honestly? The answer is 18. I know that sounds extreme, but hear me out. A young person who invests $100 a month at 18 and gradually increases that amount to
$1,000 a month by age 30 — and keeps going through age 65 — could build more than
$3 million in retirement savings, assuming historical stock market returns. That kind of financial independence completely changes the succession equation. Parents don’t need the farm to fund their retirement. Successors inherit opportunity instead of overwhelming debt. The business has room to grow instead of being drained by buyout pressure.
Ted: And if they didn’t start at 18 - which, let’s be honest, almost nobody does, the second best time is right now. Not next year. Not when things slow down. Now.
Lindsey: I can attest to that. I didn't start at 18, either. A few years ago I finally purchased my own farm, and it was around that time I was truly able to start contributing to retirement in a meaningful way. That was in my late 30s.

On Building the Next Generation of Leaders
Lindsey: So Ted, succession isn't just about transferring ownership it's also about preparing the next generation to actually lead. What does that look like in practice?
Ted: That's exactly right, and it's the piece that gets overlooked most often. The older generation sometimes holds on too long before giving real responsibility to the next generation. Not because they don't trust them, but because letting go of something you've built and loved for decades is genuinely hard! The result is that successors can be well into their 40s before they've made a major decision on their own. That's not a recipe for a confident new leader.
Lindsey: And I imagine it's not always the person everyone assumed would take over who ends up being the right fit.
Ted: Not at all. We worked with one family where there was a long-standing assumption that the oldest sibling would lead the company someday; that's just how it had always been talked about. But through the succession planning process, it became clear that the younger sibling had both the desire and the aptitude to lead, while the older sibling actually preferred to focus on operations rather than executive leadership. With coaching, mentorship, and real development opportunities, the younger sibling built the confidence to step into the CEO role. It was ultimately a better outcome for everyone, including the older sibling, who was relieved not to carry a role they never really wanted.
Lindsey: That had to require some honest conversations with the whole family.

Ted: It did. And it required the parents to set aside birth order and evaluate leadership based on capability. That's not always comfortable, but it's one of the most important decisions a family can make during this process. The goal is to give successors room to develop not just operational knowledge, but the communication, management, and decision-making skills to run a modern agricultural business. And they need space to make mistakes while the consequences are still manageable.
Lindsey: We saw something very similar with another client we worked with closely. They had a succession plan in place, but life happened. The plan centered around their eldest child, but that child ended up pursuing a completely different career path. So the family had to pivot.
Ted: Which is exactly why a succession plan can't just be a document you write once and forget about. Life changes.
Lindsey: For sure. In this case, another child and her husband stepped into the role. She grew up on the farm, so she had that foundational understanding, but her husband came in with no prior production experience at all. So our team went through a real process of assessing their leadership team’s strengths, identifying the gaps, and building a development plan around those. Same concept you were just describing: coaching, mentorship, intentional leadership development to build their confidence in taking on that CEO responsibility. It takes time, but it works.

On Fairness, Sweat Equity, and Difficult Conversations
Lindsey: Ted, one thing I hear come up a lot with farm families is the question of fairness among siblings. How do you even begin to navigate that?
Ted: Very carefully. And very directly. Avoiding it doesn't make it go away. It just means it explodes later, usually at the worst possible moment. The core tension is this: in many farm families, one or two children have spent their adult lives working the operation at below-market wages, carrying enormous responsibility, and building up years of sweat equity. Meanwhile, other siblings pursued careers elsewhere. When it comes time to divide assets, a purely equal split can actually be deeply unfair to the people who made that sacrifice.
Lindsey: So how do you help families get on the same page about what "fair" actually means?
Ted: It starts with open conversation, which sounds simple but is anything but. We worked with one family where the farming children had devoted their adult lives to the operation while their siblings built careers outside agriculture. The parents planned to leave the land and business assets primarily to the farming children and provide life insurance proceeds to the others. On paper, it looked unequal because the farm assets had appreciated so dramatically over time. But once the family openly discussed the years of lower income, sacrifice, and operational responsibility the farming children had carried, everyone came to a much deeper understanding of what fair really meant in their situation.
Lindsey: It sounds like those conversations almost reframe the whole picture.
Ted: They do. What looks unequal on a spreadsheet can make complete sense when you view it through the lens of contribution and long-term commitment. But you have to be willing to have the conversation. That's where a neutral facilitator can be invaluable
— someone who isn't emotionally invested in the outcome and can keep things moving forward when it gets hard.

On Letting Go — The Identity Problem
Lindsey: Ted, I want to ask you about something I think catches a lot of retiring farmers off guard: the idea that for many of them, their work is their identity. What happens when that's suddenly gone?
Ted: It's more common than people expect, and it's often the thing that quietly stalls a transition that looks perfectly fine on paper. For farmers especially, the business isn't just a business: it's their identity. It's how they've defined themselves for 30 or 40 years. And when that goes away, it can be genuinely disorienting.
Lindsey: That's a profound loss, and I don't think we talk about it enough in these conversations. I know you've worked through this firsthand with clients. Can you share what happened and how they worked to overcome it?
Ted: We worked with a multi-generational dairy farm where the retiring owner spent nearly a year negotiating the financial terms of succession while repeatedly delaying the final transition. The family assumed the hold-up was financial. But eventually the real issue surfaced: the owner was terrified of losing their sense of purpose and identity once they were no longer needed at the farm every day.
Once we helped the owner think intentionally about what life after farming could actually look like, travel they'd always put off, volunteer work that had always interested them, a new side venture, the whole dynamic shifted. There was suddenly a vision for the next chapter. And once that existed, letting go of day-to-day control became much less threatening. The transition moved forward pretty quickly after that.
Lindsey: That's such an important reminder that succession planning is as much about the people as it is the business.
Ted: Yup. A good succession plan has to address both. What are you going to do on a Tuesday morning in January when you're not needed at the farm anymore? If you don't have an answer to that, the transition is going to be a struggle, no matter how solid the financial plan is.

On the Business Itself — Getting the House in Order
Lindsey: Let’s chat about the business side for a minute. Not every farm is in great financial shape when succession comes up. How do you handle that reality?

Ted: With empathy, but without avoiding the hard truth. Because the kindest thing you can do for a family is be honest with them. Handing someone a broken operation and calling it a gift helps no one. Some successors inherit operations burdened by excessive debt, operational inefficiencies, or years of unresolved financial strain. Strong succession planning means improving the health of the business before ownership changes hands, not after.

Lindsey: So what does getting the business healthy actually look like in practice?
Ted: It's different every time, but it starts with visibility and veracity. Can you think of a client we worked with recently where this was key to understanding their overall operation?
Lindsey: Definitely, and it was no small feat. The client had three separately operating entities rolled into one set of financials. It made it nearly impossible to figure out where profitability was or wasn’t actually occurring. We reorganized their chart of accounts, separated financial reporting across entities, and properly allocated assets. That gave us clear visibility into gross margins by department and entity, along with much stronger insight into cash flow, key financial ratios, and overall net profitability — the full picture.
Ted: There you go. And that changes everything about how leadership makes decisions. Once they could actually see the business clearly, they could run it clearly. And more importantly, the incoming generation had a real foundation to build on instead of inheriting a puzzle they couldn't solve.

On Building the Right Team Around You
Lindsey: Ted, for a farm family who's just starting to think about succession: where do they even begin?
Ted: The first thing I tell people is don't try to do this alone. Succession planning touches family relationships, personal identity, legal structures, tax strategy, and operational complexity all at the same time. That's not a one-person job — or even a one-advisor job.
Lindsey: So who should be in the room?

Ted: At minimum you want an accountant, an attorney, a lender, and a financial advisor. But equally important is having someone who can serve as a neutral facilitator — someone who isn't emotionally invested in the outcome and can keep the process moving forward when conversations get hard. And they will get hard.
Lindsey: What about the emotional aspect of succession? There’s a lot of dynamic, relational history in a family. I imagine some of these conversations require more than legal or financial support.
Ted: Absolutely. Some families benefit from professional counseling or family therapy during this process, and there's no shame in that. Succession touches everything — relationships, legacy, identity. You have to be willing to tend to all of it.

Lindsey: What would you say to the farmer who thinks they can figure it out on their own?
Ted: I'd say I understand the instinct. Farmers are resourceful, independent people. But this is the one time where that instinct can really cost you. Most farmers hope they can sort it out themselves, especially when succession feels years away. Then before they know it, that moment arrives and they're trying to untangle everything at the eleventh hour while the rest of the operation still needs running. You're only going to do this once. Invest in an expert and make sure it's done right the first time.

The Bottom Line
The strongest farm transitions focus on four things: financial readiness, leadership development, business health, and open communication across generations. None of those happen accidentally. All of them take time.
If you’re reading this and thinking “I should probably start thinking about this,” you’re right. Start today. Not because the process is scary — though parts of it are — but because done well, it’s one of the most powerful things a farm family can do to protect what they’ve built and give the next generation a real shot at success.

About Good Roots
Good Roots is a professional services firm building a better food system for people, animals, and the earth by empowering farmers and food entrepreneurs with strong foundations in finance, marketing, and management. The Good Roots team works with farmers, food brands, manufacturers, distributors, hubs, grocers, nonprofits, and more. For more information, visit www.growgoodroots.com.

Posted: to Field Days on Sat, Jul 4, 2026
Updated: Sat, Jul 4, 2026