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The Art Of The Shepherd


In Aussie rules (Australian football), a shepherd is a team mate who runs beside the player with the ball and legally clears the opposition out of the way. The shepherd never touches the ball. That is the whole discipline, and it is a better picture of generational family advisory than any flock of sheep.


The picture matters because advisers are so often cast as the one who carries the ball. They draft the plan, make the call, run the meeting and hand the family the result. It looks like service and it builds dependence. The family watches the work being done and never learns to do it, and the day the adviser leaves, the ball is dropped.


Giving Them The Ball

The first act of a shepherd is to trust the carrier with the ball. In a family that means the decision, the conversation and the responsibility belong to the people who will live with them. The adviser does not hold them in reserve, and does not hand them over only once the family has been proven ready. Readiness is built by carrying, not waiting.


That is uncomfortable for everyone. Senior generations find it hard to release a decision they have always held, and younger members find it hard to be handed one in front of their family. A good shepherd makes the handover deliberate, names it plainly, and runs alongside it.


Room To Run

A carrier who is crowded cannot see the field. Room to run means the family sets its own direction, at its own pace, and makes its own mistakes within sight of someone ready to help. The shepherd does not choose the destination. The family does. The shepherd's job is to keep the lane open long enough for the family to find it.


Moving With Them

Position is the shepherd's whole instrument. Close enough to matter when pressure arrives, far enough to leave the carrier alone. A shepherd who stands back and watches offers no protection. One who clings to the carrier's hip restricts the very movement they were there to enable. The skill is staying level with the run, matching pace, and adjusting as the field changes.


Protection & Guidance In One Movement

Protection is what the shepherd does with the body. It means taking pressure so the family can decide without being rushed, cornered or exploited. In family work that pressure comes from deadlines, from outside parties with an interest, from the louder voices inside the family, and sometimes from the family's own history.


Guidance is what the shepherd does with position and voice. It rarely sounds like instruction. It sounds like calling what the carrier cannot see: an opening on the left, someone closing from behind, a clearer option ahead. And then it lets the carrier decide.


Peeling Away - What The Shepherd Does Not Do

A shepherd does not take the ball. The moment the adviser starts making the decisions, the family has stopped running and started watching. A shepherd does not protect so completely that the carrier never feels contact. Protection mistaken for preparation leaves the next generation with a clean jumper and no experience of being tackled. The shepherd does not promise that no tackle will land. Some will. The aim is that when one does, the carrier is back on their feet quickly and the ball is still in their hands.


Knowing When To Peel Away

The best shepherding ends with the carrier in open space and the shepherd no longer needed. That is the defined point at which the family no longer needs the adviser, and it is the real measure of the work. an adviser who cannot peel away has been playing a different game.


Families do not need advisers who run for them. They need someone who trusts them with the ball, gives them room, stays level with the run, takes the pressure that does not belong to them, and calls what they cannot yet see. The family runs. The shepherd makes sure it can.


It begins with a conversation and ends with alignment.





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About the Author

Damien Lipp

Damien provides guidance, support, and strategic advice to multi-generational families and their advisors on the complex human dynamics that influence wealth transition, succession, governance, and legacy planning.

His work focuses on strengthening the emotional capital within a family, by ensuring the relationships, communication, and decision-making processes are as robust as the financial strategies designed by their advisors.

His expertise is grounded in lived experience. As a third-generation member of a family business, a family office, and a blended family, he understand first-hand the challenges, frustrations, and nuances that shape family-enterprise environments. This allows him to connect authentically with family members, particularly next-generation leaders and to share relatable examples, stories and case studies that resonate.

He helps the voice of the next generation to the current generation and their advisors, creating clarity, alignment, and trust across the family system. Through a unique advisory approach, he works closely with each family member to support their personal goals while aligning them with the broader aspirations of the family regarding wealth transfer.

His focus is always on the health of the relationships because he believes sustainable governance and successful transitions start with strong family foundations.

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