From strategy to execution: Tommy Mayes on what makes family offices work
By Kristen Oliveri
Tommy Mayes is a familiar voice in the family office community, sparking dialogue on LinkedIn about the hard truths behind execution, leadership, and strategy. With years of experience working alongside single-family offices, Mayes has seen firsthand why so many offices struggle to deliver on their goals, and what separates the high-functioning ones from the rest.
In this conversation for Wealth Reimagined, Mayes opens up about why family offices often become a “graveyard of good ideas,” what it takes to empower leadership, and how families can run their offices with the same discipline that created their wealth in the first place.
He also weighs in on one of today’s hottest topics, artificial intelligence, and why the greatest opportunities for family offices may lie not in the headlines, but in the quiet, practical tools that compound value over time.
Q: You’ve said that many family offices are built like professional service firms, not businesses. What do you mean by that, and how does it affect their ability to execute?
A: Yes, this is a theme of mine in many respects. It is not an intuitive concept, but it makes sense right? Almost all wealth comes from a business or business investment, yet the principles do not often translate to the wealth creator’s family office. SFOs are often structured to serve rather than operate and are focused on responsiveness, not outcomes. This makes the team highly tactical and leaves little room for strategy. Without clear goals, accountability, or operational discipline, strategy becomes static. Treating the office like a business with leadership, priorities, and execution authority makes all the difference.
Q: You’ve described family offices as sometimes becoming a “graveyard of good ideas.” What are the biggest barriers you see to moving from strategy to action?
A: Ouch, did I write that? Many offices struggle with ownership and follow-through. Ideas are discussed, even funded, but rarely driven to completion. They are bumped aside by the deal of the day or crisis du jour. This is somewhat a result of the issue discussed above – poor structure. Without clear decision-makers, timelines, and defined success, initiatives fade. Execution needs champions, not committees. It needs clarity of accountability, and the authority to act.
Q: In your experience, what distinguishes a high-functioning family office from one that struggles with execution?
A: First let me say I am seeing examples everyday of enlightened leadership in family enterprises that are inspiring. But to answer the question, it comes down to clarity and culture. High-functioning offices have aligned leadership, a clear mandate, and a team empowered to act. Struggling offices get stuck in ambiguity - too many priorities, unclear roles, and little accountability. I’ve seen offices stall for years on a direct investment strategy because no one owned it. In contrast, one office appointed a dedicated lead executive, set quarterly goals, and executed three deals in under a year. Same resources, different structure.
Q: How can families balance the need for consensus with the kind of decisive leadership a business requires?
A: Consensus should inform, not paralyze. I learned this in banking many years ago, and it applies to family enterprises. Strong governance defines where input matters and where authority rests. Families need to empower leadership to move with conviction toward agreed objectives, not wait for unanimity.
There is this concept of ‘false governance’, where mechanisms and structures are in place to allow for input and discussion. Yet the principal consistently overrides the final decision or dominates the dialog and shuts down the discussion.
Decision-making in a family enterprise context is no different than in a corporate environment. It’s a muscle that needs to be trained and conditioned. If ignored or misused, atrophy or injury occurs. As an example, a family council that has codified responsibility but is never allowed to exercise authority will fail or atrophy and never build the leadership effectiveness necessary to move forward and sustain legacy objectives.
Q: You’ve raised the question: are family offices chasing the AI hype, or investing in its utility? Where do you see the biggest opportunities right now?
A: I do not believe real value is in futuristic bets, although there is money to be made in the right areas. The real value of AI is in solving today’s inefficiencies and improving decision making. AI can streamline research, reporting, and workflows. Offices that focus on practical applications will see faster returns than those chasing headlines or trends.
The key is, and I posted about this the other day, there has to be a strategic framework for AI deployment by an SFO that creates the right privacy and security layers and builds trust across all constituents, especially the principals. Within that framework the team needs to be encouraged if not incented to explore, learn, study and refine ways to improve processes and decision-making. It is clearly a gamechanger.
Q: Can you share examples of how AI can actually improve the day-to-day operations of a family office, beyond the headlines?
A: There is a long list, but in short AI can provide baseline due diligence, draft investment briefs, monitor portfolios for anomalies, summarize legal or financial documents, and automate routine communication. These tools reduce noise, speed decisions, and free the team to focus on higher-value work.
Enterprise versions of ChatGPT are now being utilized in a secure environment, which leverages the power of the language models while keeping the internal data and information private. In addition, platforms like iPaladin are employing these same closed loop AI concepts inside their operating platforms to make the family office OS more efficient and accurate.
Q: How should families think about investing in AI both for their offices and in their portfolio companies?
A: I think most will agree that when investing for return, you focus on fundamentals: real products, proven demand, and clear paths to scale. Many AI startups are still tech in search of a business. The best opportunities solve specific problems in sectors like logistics, healthcare, or compliance, where adoption is growing and margins are defensible. I think we have heard the application layer is where real sustainable value will be created. This remains to be seen.
In the family office, start by identifying pain points. Internally, target tasks that are repetitive or time-consuming. In portfolio companies, focus on AI that enhances core operations, not just valuation.
In either scenario, there should be a strategic focus on developing strategic objectives before executing on the ideas and opportunities.
Q: Before closing, I have to ask: what book is currently on your nightstand?
A: Well, I am guilty of always having a few in process, especially using a combination of a Kindle or Audible. And I have both fiction and non-fiction. Current top of the pile….
THINK BIGGER by Michael Sonnenfeldt, Founder of TIGER 21
Devil in the White City by Erik Larson (third time!)