Wearing Two Hats: Never at the Same Time

The earlier pieces in this series explored why boundaries matter, how they shape relationships, and the practical tools that make them stick. This fourth article concludes the series on boundaries in family enterprises.

This one is written for advisors.

It focuses on how we hold our roles, when we step back, and when we bring in help.

I work in two domains. I am a CPA who advises on tax. I am also a Family Enterprise Advisor, focusing on governance, roles, and relationships. Both sets of skills help families, but they are most effective when used with clear separation.

Families benefit most when I know which of the two roles I am in, and when I resist the urge to mix them. The temptation to “do both” may feel helpful in the moment, but it blurs boundaries, weakens trust, and can exacerbate family conflict. The stronger and safer practice is to wear one hat at a time.

Why a Policy Isn’t Enough

Consider the case of two brothers in a multigenerational company who disagreed on whether to distribute dividends or reinvest them. To help, their accountant suggested a formal dividend policy. At first, this seemed practical, but the brothers lacked the tools to discuss values and fairness. The ‘solution’ became another point of contention.

One brother confided in his investment advisor, who is also a Family Enterprise Advisor. He referred the family to Blackwood Family Enterprise Services. Through our process, we met individually first and then together. Through our established process, we helped the brothers identify and separate owners’ issues from management issues, coached clearer language, facilitated meetings focused on conflict resolution and shared priorities, and created strategies to protect family relationships when business tensions ran high.

The dividend policy did not disappear. It became one part of a broader system, supported by clear forums and expectations. The family did not need more policy; rather, they needed role clarity, a safe space to talk, and a way to make decisions.

Takeaways:

• Policies and technical solutions are tools, but they rarely solve relational conflict on their own.

• Families need a separate forum and advisor to discuss values, fairness, and priorities.

• Keep technical advice in its lane to make sure it lands in the right place at the right time from the right person.

Knowing When to Refer

One of the hardest aspects of an engagement for a trusted technical advisor is resisting the pull to do more. Families often ask their accountant, lawyer, or investment advisor to step in to mediate disagreements. It feels natural, but it puts both the advisor and the family at risk.

Here are cues that it’s time to step back and refer:

• The conversation shifts from technical choices to fairness or values.

• Two or more family members are talking past each other and looking at you to settle it.

• You feel pressure to keep the peace rather than provide technical advice.

• A policy or plan has been delivered, but conflicts continue or worsen.

In those situations, your credibility grows when you say:

“This is outside my role as your technical advisor. What will help here is a neutral process. I recommend we bring in a Family Enterprise Advisor, like Blackwood, to create that forum.”

By holding your lane, you protect the family from further strain and protect your own reputation. You also create a stronger outcome. When the family works through the relational piece with a neutral advisor, your technical advice has a place to land and endure.

Takeaway:

• If family members are looking to you to resolve disagreements rather than for your technical expertise, your role is being stretched beyond your lane.

• If the conversation is no longer about technical choices but about values, relationships, or what’s “fair,” it’s time to step back.

• If policies, plans, or recommendations are in place but disputes continue or escalate, a neutral advisor can create the forum and process needed for resolution.

  
  

Collaboration That Builds Trust

Advisors worry that inviting in a neutral facilitator will diminish their value. In practice, the opposite happens. Clean collaboration fosters trust and accelerates the decision-making process.

Here is how we partner well with accountants, lawyers, and investment advisors.

• We hold the neutral forum. We create agendas, frame issues by hat, and help the family decide which forum owns which decision.

• We surface themes and timing. We help the family talk about fairness, readiness, and roles, so the technical team has a clear mandate.

• We keep the lanes moving. We equip families with the tools and structure to make informed decisions, enabling their technical advisors to proceed efficiently. Once the technical work is done, we help the family test how the change fits their governance.

The result: technical advisors deliver sharper solutions, and families make decisions that endure.

Takeaway:

• Clean collaboration strengthens trust with both the family and technical advisors.

• Clarify forums, roles, and agendas so everyone knows which decisions belong where.

• Referring to a neutral is not stepping out—it’s stepping up. It ensures your technical advice lands in fertile ground, rather than in the middle of unresolved conflict.

Referring to Blackwood – What to Expect

A clear handoff lowers risk and saves time. Here is how our process unfolds:

• Coordinated intake. We speak with the referring advisor to understand the scope, deadlines, and sensitivities.

• Private conversations. We meet key family members to gather their perspectives and identify areas where forums are missing or unclear.

• Forum design. We help families separate owners’ decisions from management decisions and set a simple meeting rhythm with ground rules created by them and for them.

• Decision support. We facilitate the discussions necessary to develop clarity on roles, priorities, and next steps.

• Stay connected. We check in regularly to confirm the frameworks put in place are holding and recommend adjustments as necessary.

Your relationship with the client remains protected, and you continue as the technical lead. Our role is to create the conditions that enable your sound advice to be implemented and sustained.

Takeaway:

• A clean referral keeps you as the technical lead and strengthens client loyalty.

• Blackwood manages the family forum; you deliver the expertise.

• The family sees you as the professional who brought the right people to the table at the right time.

Speaking Both Languages

I write from experience in both worlds—as a tax advisor and as a family enterprise advisor. I understand how reorganizations, freezes, and ownership changes work. I understand how technical moves affect identity, fairness among siblings, and a founder’s sense of stewardship. I also know that collaboration among technical advisors can produce excellent outcomes, but it can also increase costs and strain relationships if the brief is unclear.

That dual perspective helps me recognize when a family is asking for a solution but is not yet in a place where a durable one is possible. It also keeps me clear: if I am the technical advisor, I cannot also be the neutral. If I am the neutral, I cannot also be the tax planner.

Takeaway:

• Resist the urge to be “everything.” Staying firmly in one role earns more trust than trying to fill two.

• Families don’t need one person to wear both hats at once. They need each advisor to wear their hat well.

• Separation is not a limitation. It is the reason families get better outcomes.

Closing Thought

Boundaries are not about keeping advisors at a distance. They are about giving each professional the space to do their best work. Families need a clear family forum for decisions and precise technical execution. They need advisors who know which hat they are wearing and who invite the right people to the table at the right time.

If you want a neutral partner to help set that structure, refer the family to Blackwood Family Enterprise Services. We protect your relationship, strengthen the forum for decision-making, and support outcomes that last.