Succession planning often starts with documents. In reality, it should start with clarity. From a legal perspective, most of the challenges that arise in succession are not caused by poorly drafted agreements. They are caused by assumptions that were never tested, conversations that were delayed, and decisions that were made in isolation.
What’s Commonly Misunderstood
Many business owners believe that once a shareholder agreement or will is in place, succession is “handled.” In practice, legal documents are only as effective as the conversations and intentions behind them. Lawyers translate decisions into enforceable structure. Lawyers do not decide who should lead, how ready someone is, or what family dynamics are at play. When those questions are unresolved, documents become pressure points instead of safeguards.
Where Legal Risk Shows Up
Problems tend to arise when:
- Succession discussions are postponed until a triggering event occurs
- Family expectations differ but are never clarified
- Ownership, leadership, and employment are treated as the same thing
- Agreements are outdated or no longer reflect reality
In these situations, legal tools are often forced to manage emotional conflict. That is not what they are designed to do.
The Role of Legal Support in a Healthy Succession
When succession planning is done well, legal work:
- Protects relationships by providing clarity
- Ensures enforceability of agreed-upon decisions
- Reduces ambiguity during transitions
- Creates confidence for all parties involved
This work is most effective when legal drafting follows thoughtful dialogue, not the other way around.
Why Coordination Matters
Legal structures touch everything: ownership, governance, tax planning, insurance, and leadership continuity. When these areas are not aligned, even well-intended documents can create friction.
Succession planning works best when legal expertise is integrated into a broader, facilitated process that ensures decisions are clear before they are formalized.
X5’s Suggested Resources from Leah Tolton
About Leah:
Leah Tolton practices corporate law with a particular focus on business agreements and commercial contracts, business structures and tax planning, corporate and syndicated lending, equipment leasing and finance, mergers and acquisitions, real estate and real estate joint ventures, partnerships and other co-ownerships. Her practice covers a broad range of clients in the oilfield services, heavy construction, waste management, hospitality and real estate industries.
Leah’s practice has an emphasis on providing legal services to ultra high net worth families and their companies, family-owned businesses and their owners and boards of directors in matters related to corporate governance and succession planning, corporate structuring and sophisticated corporate reorganizations. She has extensive experience with the strategic planning, risk management, mergers, acquisitions and sale transactions of family-owned businesses.
Leah is routinely involved in the negotiation and drafting of commercial agreements relating to the establishment of joint ventures, construction contracts, unanimous shareholder agreements and employee stock option plans for family-owned businesses and for other corporate clients. She also advises clients in lending transactions, from negotiation and drafting of private financing arrangements to sophisticated syndicated financings for a variety of family-owned businesses and other corporate clients in various industries.
Leah’s experience is bolstered by continuous professional development. Further showcasing her dedication to working with family-owned businesses, she earned the designation of Family Enterprise Advisor in 2023. Her appointment to the Board of Advisors of the Alberta Business Family Institute is yet another example of Leah’s commitment to serving as a trusted advisor to a broad range of family businesses.
Resources
Beyond Succession Podcast: Leah is the host of Beyond Succession, a podcast series produced by Bennett Jones focused on succession and continuity in family-owned businesses. Through candid conversations with business owners and advisors, the series explores the legal, governance, and relational dimensions of transition. It reflects Leah’s long-standing work supporting families as they navigate complex ownership and leadership decisions.
Available on Spotify and Apple Podcasts.
For leaders and family business owners looking to go deeper, we recommend the following episodes:
How to Protect Your Legacy When Disaster Strikes
Explore the intricacies of crisis management in family enterprises, where resilience, conflict mitigation and legacy protection are essential to navigating turbulent times. Crises—whether internal conflicts, unforeseen events or leadership disputes—can disrupt critical processes like succession planning and decision-making, challenging both the stability of the business and the harmony within the family. In this episode, host Leah Tolton is joined by Bennett Jones partner James Heelan to share insights on guiding family businesses through these critical moments. At the heart of managing crises is a resilient business culture. Building such a foundation enables family enterprises to face both internal challenges and external pressures with confidence. A key strategy is stakeholder mapping, which provides clarity on the unique family dynamics, ownership structures and business relationships that shape long-term success. Equally vital is the balance between preserving legacy and embracing change, honouring traditions while adapting to new realities to secure the business’s future.Preventative measures, such as regular check-ins with trusted advisors, play an invaluable role in crisis management, underscoring that proactive steps often avert more significant issues down the road. Additionally, private resolution avenues allow families to address disputes discreetly, protecting their reputation and preserving important relationships. These strategies offer family businesses a path to unity and resilience, even in challenging times. X5’s Top three Takeaways from this podcast:
- Culture and alignment matter more than documentation in a crisis: When a crisis hits, the strength of a family enterprise’s culture often determines how effectively it responds. Clear values, shared understanding, and alignment across family and business stakeholders provide stability when formal agreements are outdated or incomplete. Strong culture does not replace legal structure, but it significantly influences outcomes under pressure.
- Understanding stakeholders early prevents escalation: Crises expose misalignment around who owns, leads, and benefits from the business. Mapping stakeholders—including family members, owners, employees, lenders, and external partners—creates clarity and reduces unintended consequences. Many disputes escalate not because of bad intent, but because assumptions about roles and interests were never examined.
- Proactive advisory relationships protect legacy and relationships: Regular check-ins with trusted advisors help families identify risks before they become crises. Thoughtful planning, private dispute resolution mechanisms, and post-crisis reflection allow businesses to protect both reputation and relationships. Proactive guidance supports resilience while preserving dignity, legacy, and long-term continuity.
The Legal Labyrinth of Family Business Succession
Whether you are a family business owner, stakeholder or keen entrepreneur, this podcast is a valuable tool that addresses topics around navigating the complexities of the family enterprise. Join Leah Tolton, a seasoned family enterprise and corporate lawyer who is passionate about helping family enterprise businesses, as she explores topics of governance, succession and growth. In this episode, Leah is joined by Barbara Kimmitt KC, a partner in Bennett Jones’ Tax group, as they discuss the intricacies of family business ownership transition planning and estate planning for entrepreneurs. They cover topics such as the differences between wills, enduring powers of attorney and advance directives, and how these documents play a crucial role in the smooth transition of family businesses. The episode also delves into the importance of having a comprehensive succession plan in place, including the use of trust structures and unanimous shareholder agreements. X5’s Top three Takeaways from this podcast:
- Succession requires coordinated legal documents, not standalone solutions: Wills, enduring powers of attorney, advance directives, trusts, and shareholder agreements each serve different purposes and operate at different times. Problems arise when these documents are created in isolation or are outdated. Effective succession planning depends on ensuring all legal instruments work together and reflect the current reality of the family and business.
- Who makes decisions matters as much as what the documents say: In family enterprises, appointing decision-makers without considering business acumen and family dynamics can unintentionally create conflict. Powers of attorney and estate plans can place unprepared or unintended individuals into positions of control. Thoughtful selection, role-specific authority, and alignment with shareholder agreements reduce risk and preserve continuity.
- Succession planning is an ongoing process, not a one-time event: Family structures, ownership roles, and personal circumstances change over time, making regular review essential. Periodic check-ins and coordinated advisor involvement help ensure plans remain relevant and effective. Treating succession as a living process supports smoother transitions and reduces the likelihood of disputes when change occurs.
Mastering Succession and Emotional Dynamics in the Family Business
Succession planning is vital yet delicate for family businesses, impacting relationships and emotions alongside strategy. Exploring the intricacies of succession planning in family businesses, Beyond Succession delves into the sensitive balance between family dynamics and strategic decision-making. In this episode, Mike Mack of X5 Management sits down with host and Bennett Jones Partner, Leah Tolton, to explore how succession dynamics create ripples across family and business relationships, influencing the enterprise’s trajectory. We dive into the complex and nuanced interplay between succession planning, family ties, emotions and objectives.
Discover how thoughtful transitions and targeted coaching can both maximize leadership potential and foster family unity through organizational change. Here are X5’s top three takeaways:
- Succession is a people issue before it is a legal or strategic one: In family enterprises, succession decisions ripple through relationships, history, and identity. When emotional dynamics and family roles are left unexamined, even well-structured plans can create conflict. Successful succession starts by acknowledging and addressing the human side of transition.
- Early, structured conversations reduce risk and preserve relationship: Families that engage in open dialogue years in advance are better positioned to align expectations and develop future leaders. Waiting until a triggering event forces decisions increases tension and limits options. Clear, facilitated conversations create the foundation for smoother transitions.
- Leadership continuity depends on intentional development and shared buy-in: Identifying a successor is only the beginning. Future leaders need time, support, and real responsibility to grow into the role, and other stakeholders need clarity on how and why decisions are made. Buy-in is built through transparency, shared principles, and consistent communication.
These conversations explore the legal, governance, and relational realities of succession, with practical insight drawn from real family enterprise experiences.
