Why AI Investments Fail
The Actual Intelligence series surfaces themes emerging from The Wisory's exclusive Wise in Five Advisor conversations. Across our conversations with advisors, counterintuitive threads keep appearing, patterns that only emerge when you have access to this many high-level executives speaking candidly in one place. Three Advisors. One theme. Here is what they shared.
Fund Transformation, Not Just Automation
Ryan McManus has spent a decade in the boardroom watching technology reshape entire industries. He founded Accenture’s Digital Transformation Strategy practice and served as COO of Accenture Strategy, a billion-dollar global business. He now sits on public company boards, chairs the NACD’s national committee on technology and governance, and builds AI strategic intelligence platforms for boards and investors at Tectonic.io. He sees the AI decisions companies are making from three vantage points at once: the boardroom, the operating team, and the investor.
In his Wise in Five conversation, Ryan named the single most common and costly mistake he sees companies make with AI. It has nothing to do with technology and everything to do with where the money goes. According to Ryan: “We say we want transformation, but all we do is invest in automation. And that’s exactly what opens up the gap for someone to come in with new pricing, new economics, new services, new business models.”
His point is that automation is the low-hanging fruit in every technology cycle. It is easy to justify, easy to measure, and easy to fund. So companies pour their AI budgets into making existing processes cheaper, then wonder why a competitor has leapt ahead of them on creating value. Ryan has watched this pattern play out for decades.
The answer is not to abandon automation, but to fund both tracks deliberately. Ryan argues that the organization’s most senior people need to ask one question on a regular basis: what is the differentiated value we can bring to market based on these new capabilities? If both conversations, automation and transformation, are not explicitly represented on the roadmap, the company is risking the one where market leadership is actually decided.
For private equity investors, Ryan draws the line even more sharply. As Ryan states: “If you’re not asking these questions before making the investment, you’re by definition overpaying.”
Watch Ryan’s full Wise in Five conversation here
Put the Governance in Before You Scale
Sean Naismith has spent his career at the intersection of data science, AI, and financial services. He led global technical product management and innovation at TransUnion, and before that served as CEO of Enova Decisions, a real-time AI decisioning platform for regulated industries. He has built platforms that supported billions of dollars in revenue by unifying data, identity, and analytics at global scale.
In his Wise in Five conversation, Sean went straight at one of the most expensive misconceptions in AI adoption: the belief that the value comes from building the best model.
According to Sean: “One of the greatest misconceptions right now is that the driver of AI value is going to be building the best model yourself.” In his experience, the value lives somewhere far less glamorous. It lives in the workflows, the operating model that brings the tool to life, and the data governance and compliance that support it. A brilliant AI model with no operating model around it produces nothing durable.
His most practical warning is about the difference between a prototype and a production system. A demo that dazzles in a small test is not the same as something ready to run core systems for millions of customers. His recommended approach is to run two rails at once: a fast track where teams can prototype, learn, and get excited about what is possible, and a hardened track built with the governance, workflow changes, and infrastructure that real deployment demands. Run only the first, and you never scale. Run only the second, and you become a blocker who kills momentum before it starts.
Watch Sean’s full Wise in Five conversation here
Change How People Actually Work
David Edelman has spent 35 years helping companies navigate the exact technology shift they are living through now. He built McKinsey’s first digital marketing strategy practice, served as Chief Marketing Officer of Aetna through its acquisition by CVS, and began his career at the Boston Consulting Group before the internet existed. He has watched waves of companies buy into a new technology expecting it to transform them, and he has a clear-eyed view of why so few actually see the return. He is also the co-author of Personalized: Customer Strategy in the Age of AI.
In his Wise in Five conversation, David pointed to a piece of research that reframes the entire question of why AI investments succeed or fail.
According to David: “I did a study with BCG about what separated folks who were getting more ROI from less, and 70 percent of the value was the difference in the ways of working, as opposed to whether they had data or whether they had technology.”
Seventy percent. Not the tools. Not the data. The way people actually work. The companies getting real returns restructured how their teams operate, moving away from long handoff chains toward smaller cross-functional groups that could test, learn, and ship together. The companies getting lesser results had bought the same technology but did not change how they used it.
As David states: “The hardest thing, no matter company size, is changing behaviors. These tools are incredibly powerful, but it’s not just the tool.”
David is also clear that changing behavior does not mean handing decisions to the machine. He describes keeping human judgment in the loop as non-negotiable. As David states: “You can’t just let these things go on autopilot. You have to put a human in the loop and frankly that’s a responsibility marketing cannot abdicate.” The behavior change he advocates is not automation for its own sake. It is people working differently, with AI as a tool and human judgment still holding the wheel.
Watch David’s full Wise in Five conversation here
The Bottom Line
Ryan, Sean, and David believe failure is driven by a lack of governance, platform architecture, and organizational behavior. AI investments do not fail on the technology. They fail on the decisions around it: funding automation while claiming to want transformation, chasing the perfect model while ignoring the workflow and governance that make it usable, and buying powerful tools while changing nothing about how people work.
And the leaders who develop them, with the right frameworks, the right questions, and the right advisors alongside them, are the ones who will turn AI investments into AI returns while their competitors are still counting efficiency gains.
Wisory members get 1:1 access to executives like Ryan, Sean and David — at the moment a decision matters most, not after it’s already been made. Explore membership at thewisory.com
Ryan McManus is a Wisory Advisor and the founder of Tectonic.io. He previously served as global CEO of Accenture Strategy, where he built the firm’s digital transformation strategy practice. He is a board director, president of the NACD’s New York chapter, and advises private equity investors, boards, and CEOs on AI, business model transformation, and value creation.
Sean Naismith is a Wisory Advisor who has spent his career at the intersection of data science, AI, and financial services. He led global technical product management and innovation at TransUnion and served as CEO of Innova Decision. He advises companies on unifying data and identity, embedding AI into workflows, and building the governance to scale it.
David Edelman is a Wisory Advisor and the former Chief Marketing Officer of Aetna, with 35 years spanning the Boston Consulting Group and eight years building McKinsey’s digital marketing strategy practice. He is the co-author of Personalized: Customer Strategy in the Age of AI and advises companies on AI-driven growth and customer strategy.
Ryan, Sean, and David are available for 1:1 advisory sessions through The Wisory. Members get direct access to executives like these, on the specific challenge, at the moment it matters. Learn more and book time at thewisory.com
