Abstract: 

Starting a farm's succession plan can feel overwhelming, but the first steps are often the most important, and the most approachable. This guide provides a practical 90-day roadmap designed specifically for Canadian farm families preparing for long-term transition. Unlike high-level explanations of why succession matters, this article focuses on how to begin: clarifying personal goals, gathering essential financial and land information, conducting productive family meetings, identifying intentions for each heir, and assembling a team of trusted advisors to guide tax, legal, and financial decisions. It also explains how to create an initial written plan that can evolve over time as circumstances, markets, or family dynamics shift. By breaking the process into simple, structured steps, this guide helps families reduce stress, improve communication, and build a strong foundation for future transition planning. Whether you plan to retire soon or simply want to prepare responsibly, this starter plan empowers you to begin succession conversations with clarity, confidence, and purpose. 

Starting a farm succession plan doesn’t begin with documents, lawyers, or tax planning, it begins with clarity, communication, and a commitment to preparing the next generation. While many Canadian farm families understand the importance of succession planning, they often struggle with how to start. This guide eliminates that confusion by providing a simple, structured path forward. 

Many families choose to work with Saskatchewan farmland real estate specialists who understand agricultural operations, land valuation, and intergenerational planning, helping ensure early decisions are grounded in both financial reality and family dynamics.  

Key Points: Starting a Farm Succession Plan

• Farm succession planning begins with clarity and communication, not paperwork. 

• The first 90 days focus on preparation, not final decisions. 

• Early family conversations significantly reduce future conflict. 

• Gathering financial and land information creates structure and confidence. 

• Succession planning is a process that evolves over time. 

• Farm-focused advisors help families avoid costly tax and legal mistakes. 

• Starting early provides flexibility, stability, and peace of mind. 

The First 90 Days: A Clear Roadmap for Getting Started

This starter plan is designed to help families move from uncertainty to action, one small step at a time. 

The First 90 Days at a Glance 

• Weeks 1–2: Clarify personal goals and retirement needs 

• Weeks 2–4: Gather financial, land, and ownership information 

• Weeks 4–6: Hold the first family meeting 

• Weeks 6–8: Identify intentions for each family member 

• Weeks 8–10: Assemble your advisory team 

• Weeks 10–12: Create a preliminary written plan 

Step 1 (Weeks 1–2): Clarify Your Own Goals Before You Talk to Anyone

Before speaking with advisors or family members, the exiting generation should privately clarify their personal vision. A succession plan can only move forward once the farm operator(s) understands what they want and what they need. 

Ask yourself: 

• What does retirement look like for me? 

• Do I want to fully step back, or transition gradually? 

• What annual income do I need to feel secure? 

• Am I emotionally ready to give up control? 

• What legacy do I want to protect? 

Write down: 

• Your personal goals 

• The values you want the transition to reflect 

• Any concerns you have about family dynamics 

• Assets you feel strongly about keeping or transferring 

This step gives you confidence and clarity before inviting others into the discussion. 

Step 2 (Weeks 2–4): Gather Key Information

Before calling a meeting, collect the basic information that will support early discussions. This is not about making decisions, it's about being prepared. 

Information to gather: 

Financial Snapshot 

• Current farm income streams 

• Debts, liabilities, leases, or contracts 

• Equipment list 

• Operating loans 

Land & Asset Information 

• Land titles 

• Approximate market values (or recent appraisals) 

• Ownership structure (sole, joint, corporate, partnership) 

Reviewing current Saskatchewan farmland listings can help ground these discussions in today’s market reality and reduce assumptions about value or feasibility. 

Family Considerations 

• Who is currently involved in the farm? 

• Who has expressed interest in farming in the future? 

• Are there children who expect fairness but not land? 

This information reduces guesswork, prevents emotional assumptions, and gives structure to the first family meeting. 

Step 3 (Weeks 4–6): Hold the First Family Meeting with a Script to Make It Easier

The first meeting is not about making decisions, it’s about opening communication. Its purpose is to share intentions, not negotiate outcomes. 

How to prepare the meeting; 

• Choose a neutral location. 

• Share an agenda in advance. 

• Let children know the meeting is exploratory, not final. 

• Set a respectful, calm tone. 

A simple script to start the meeting: 

“We’ve reached a point where we need to start thinking about the future of the farm. Nothing is decided. We want to hear what each of you hopes for, and we want this process to be open, honest, and fair. Today is just a starting point.” 

Topics to cover: 

• Your personal goals 

• Why you’re starting these conversations now 

• The importance of protecting both the farm and family relationships 

• An invitation for each family member to share their hopes and concerns 

Ground rules for success: 

• Everyone gets equal speaking time 

• No decisions will be made during this first meeting 

• Respect differences in perspective 

• Capture notes without assigning obligations 

Starting the conversation early reduces emotional pressure later. 

Step 4 (Weeks 6–8): Identify Intentions, Not Decisions, for Each Family Member

At this stage, you’re not choosing successors. You are simply uncovering interest and gathering clarity. 

Ask each child or stakeholder: 

• Do you want to be involved in the farm in the future? 

• In what capacity; ownership, management, part-time, or not at all? 

• What questions or concerns do you have about the future? 

• What does “fairness” mean to you? 

• What support would help you feel prepared? 

Why this matters: 

Clear intentions prevent future misunderstandings such as: 

• Unspoken expectations 

• Assumptions about inheritance 

• Surprise decisions after illness or death 

This stage is about listening, not promising. 

Step 5 (Weeks 8–10): Build Your Advisory Team

Once early conversations are completed, it’s time to bring in the professionals who will guide the technical aspects of the plan. 

Your advisors should be agriculture-specific, not general practitioners because farms have unique tax, legal, and operational structures. 

Your succession advisory team may include: 

1. Accountant (tax strategy)

• Explains rollover options 

• Identifies potential capital gains exposure 

• Helps structure staged ownership transfers 

• Advises on income planning for retirement 

2. Lawyer (legal documents & title changes)

• Updates wills and powers of attorney 

• Drafts shareholder or partnership agreements 

• Ensures land titles reflect the succession plan 

• Designs co-ownership structures 

3. Financial Planner (retirement & risk planning)

• Calculates income needs 

• Builds retirement income portfolios 

• Ensures both generations are protected financially 

4. Farmland Specialist / Realtor (valuation & market strategy)

• Provides accurate, data-driven land valuations 

• Supports buyouts, sales, or partial transfers 

• Helps families understand the market value of assets 

In some cases, selling farmland as part of a succession strategy plays a role in funding retirement or balancing fairness 

5. Succession Planner or Mediator (communication & structure)

• Facilitates difficult family meetings 

• Helps transform intentions into documented plans 

• Ensures planning stays on track 

Bringing in professionals early keeps the process objective, structured, and future-focused. 

Step 6 (Weeks 10–12): Create a Preliminary Written Plan

Your first written plan should be simple but clear. It will evolve over time, but documenting early decisions creates accountability and shared understanding. 

Include in your preliminary plan: 

• Emerging goals for the farm 

• Potential successors 

• Preferred timeline for transition 

• Early ideas for ownership transfer 

• Retirement expectations 

• Concerns that need professional guidance 

• A plan for the next family meeting 

This document becomes the blueprint that your advisors will refine. 

Step 7 (Ongoing): Make the Plan a Living Document

The biggest mistake farm families make is treating succession as a one-time event. In reality, it is a process that adapts with: 

• Market changes 

• Health changes 

• Marriage/divorce 

• Successor development 

• New children or grandchildren 

• Land acquisitions or sales 

Review the plan annually and update it as needed. These touchpoints keep communication open and ensure the farm transitions smoothly over time. 

The Most Important Step Is Simply Beginning

No farm transitions smoothly by accident. The earlier your family begins succession conversations, the more options you will have, legally, financially, emotionally, and operationally. These early challenges are common and frequently discussed in real-world farmland transition cases. Explore farmland transition insights featured in the media. 

By following this 90-day plan, you create a calm, structured foundation for every decision that comes next. 

The Cawkwell Group has supported hundreds of farmers through valuation, transition planning, and generational change. We’re here to make the journey clearer, easier, and more secure for your family. 

📩 Ready to start your farm’s transition? Contact The Cawkwell Group today. 

Frequently Asked Questions: Starting a Farm Succession Plan

How long does it take to start a farm succession plan?
The initial planning phase typically takes 60–90 days. Full implementation may take several years. 

Do I need lawyers and accountants right away?
Not immediately. Early clarity and family discussions come first. 

Is it too early to start if I’m not retiring soon?
No. Early planning increases flexibility and reduces stress. 

What if my children aren’t sure they want to farm?
That uncertainty is common. This stage focuses on listening, not deciding. 

About the Author

Ted Cawkwell is a Saskatchewan-based farmland specialist with decades of experience working directly with Canadian farm families. As a key member of The Cawkwell Group, Ted specializes in farmland valuation, farm real estate transactions, and advisory services related to estate planning and farm succession. 

Ted has guided hundreds of producers through early-stage succession planning, helping families structure conversations, understand land value, and build practical transition roadmaps. His experience-driven approach reflects a deep understanding of both the business realities of modern agriculture and the family dynamics that shape successful farm transitions. 

This article reflects Ted Cawkwell’s firsthand experience advising Canadian farm families on farmland transitions and succession planning.