Why AI Metrics Are Misleading Leaders Every Day with Elaine Barsoom

Transformational change doesn't happen through technology; it happens through people, processes, and culture working in deliberate concert.

In this episode of From the Top with Chad Hesters, host Chad Hesters sits down with Elaine Barsoom, Founder of waveco.ia, innovation strategist, and former AI Center of Excellence leader at Nike, to explore why most AI initiatives stall after the pilot phase and how leaders can architect sustainable transformation across organizations of any size.

What You'll Learn:

- The "Three C's" framework leaders need now: Curiosity (asking better questions), Clarity (defining values and ownership), and Courage (making difficult organizational decisions)—and why skipping any one of these guarantees execution failure

- How to translate strategy into action without creating "innovation theater": Map problems from the 20,000-foot view down to the execution layer, then design repeatable workflows that prevent adoption metrics from masking real business outcomes

- Why frameworks enable flexibility, not limit it: Use consistent evaluation criteria and process mapping to govern 85-90% of decisions, creating guardrails that allow teams to stay agile within boundaries rather than operating in chaos

- The dangerous gap between adoption metrics and actual ROI: Organizations measuring adoption rates (employee logins, tool usage) miss the critical questions: Have workflows been redesigned? Have people been reskilled? Who owns results? Are customer outcomes improving?

- How to scale curiosity and experimentation in large organizations: Build peer-to-peer learning communities, celebrate intelligent failures, and train early adopters to mentor others—creating viral adoption through culture, not mandates from the top

- Why AI is fundamentally a leadership problem, not a technology one: The real decisions—who owns outcomes, what remains human judgment, whether recovered capacity becomes margin or growth—require executive clarity and willingness to restructure incentives and decision rights

- How smaller companies can move faster by "going slow first": Bring in trusted advisors, document tacit employee knowledge, involve your team early, and invest in strategy before execution—counterintuitively yielding higher ROI and faster scaling than jumping straight to implementation

About the Guest

Elaine Barsoom is Founder of waveco.ia, an innovation strategist, organizational transformation architect, and trusted advisor who has helped some of the world's most recognized companies, including American Express, Nike, and Airbnb, turn bold digital transformation and AI ambitions into measurable business results. With an MBA from Wharton and deep expertise in building AI Centers of Excellence and emerging technology organizations, she combines strategic vision with practical execution to help leaders navigate complex change. Elaine also serves as a Venture Partner at Silicon Foundry, where she provides strategic advisory, subject-matter expertise, and access to a powerful innovation network that supports the firm's members and leadership team. Today, through WaveCo.ai, she partners with organizations to accelerate AI adoption through practical, human-centered strategies, helping executives build the leadership, culture, and operating models needed to drive lasting transformation in the age of AI.

Quotes

"It's people, it's processes, it's culture. And unless you have all three, it's really hard to drive a transformation, particularly in large companies." - Elaine Barsoom

"Curiosity keeps urgency from just turning into theater. We are just at a place where the technology is just moving faster than any human can actually move." - Elaine Barsoom

"AI is fundamentally a leadership issue and not a technology one. There are decisions about an organization about who owns the outcomes, what judgment remains human, and how people get through this transition." - Elaine Barsoom

"Go slow to go fast. Curiosity is part of that. Ask the questions. What are we learning? How do we keep the urgency from just turning into theater?" - Elaine Barsoom

"The organizations that struggle aren't the ones that are missing or don't have the budget for the best tools. They're missing the willingness to change incentives, to change the workloads, change decision rights around those tools, and to restructure their organizations." - Elaine Barsoom

"You don't have to be the most technically fluent to be the person that's putting together the AI strategy. You need to be curious, but you need to be able to connect the technical capability to the business consequence." - Elaine Barsoom

"Just because something looks good on paper or strategically makes sense doesn't translate into execution. Everything from strategic fit and alignment to doing the culture and the organizational change is so important." - Elaine Barsoom

"Creating that culture and that community around celebrating folks trying new tools creates a growth mindset rather than it being just something on paper that a CEO is dictating from the top down." - Elaine Barsoom

"You always have to bring your employees on the journey when you're going through this. That's so important in changing the mindset and having that organizational culture." - Elaine Barsoom

"Smaller companies can grow much faster, not bound by a lot of agencies or other outside firms. The things that would normally take 10 people can now maybe take one person or two people." - Elaine Barsoom

Episode Highlights:

[00:05:15] The Three-Pillar Foundation: People, Processes, and Culture – Elaine Barsoom emphasizes that transformation initiatives fail when leaders focus only on strategy without addressing the human and organizational systems that must execute it. For C-suite executives in mid-cap and family-owned companies, this insight directly addresses why AI and digital transformation projects stall after promising pilots. The core challenge is translating grandiose vision into actionable priorities that each functional team, engineering, marketing, and finance, can operationalize and own. Start by mapping how your strategy cascades into specific initiatives for each department, then design an operating model that aligns people, processes, and culture simultaneously rather than sequentially. At Nike, Barsoom designed repeatable workflows and governance structures that prevented siloed AI pilots; at American Express, she created cross-functional ownership models that connected digital initiatives to measurable business outcomes. This integrated approach ensures your transformation roadmap survives the handoff from the C-suite to frontline execution, dramatically improving the odds that strategic intent becomes commercial reality.

[00:08:17] Frameworks as Guardrails, Not Straitjackets – Barsoom shares a counterintuitive leadership principle: structured frameworks actually *enable* flexibility by governing 85–90% of decisions, freeing teams to innovate within clear boundaries rather than operating in chaos. Many mid-sized company leaders fear that standardizing processes will stifle entrepreneurship and slow decision-making, but Barsoom demonstrates the opposite through her AI evaluation methodology at Nike. The approach works by asking consistent diagnostic questions upfront, "What problem are we solving?" then mapping workflow design end-to-end before execution begins. This allows different teams (marketing, scaling content production, HR automating recruitment) to apply the same framework to entirely different challenges, creating consistency without rigidity. When you invest time in clear problem definition and process mapping before launch, guardrails actually expand what's possible because teams spend less time debating *how* to approach problems and more time innovating *within* your defined scope. For family-owned and mid-sized businesses with limited resources, this framework-first approach prevents costly pilot abandonment and resource waste while maintaining the agility today's market demands.

[00:11:44] The Three C's Leadership Model: Curiosity, Clarity, and Courage – Barsoom introduces a practical leadership framework that separates executives who successfully drive transformation from those who create "innovation theater" where activity masks lack of progress. The Three C's model requires leaders to lead with *Curiosity* (asking better questions about real business value and frontline needs), establish *Clarity* (defining values, ownership, decision rights, and measurable outcomes), and exercise *Courage* (making the difficult organizational decisions that restructure incentives and redesign roles). For C-suite leaders responsible for AI adoption or digital transformation, this model prevents the common failure pattern where urgency becomes a substitute for rigorous strategic thinking. Barsoom notes that organizations struggle not because they lack budget or access to best-in-class tools, but because leadership fails to align these three elements: curiosity without courage produces endless debate, clarity without curiosity misses emerging opportunities, and courage without clarity creates chaotic reorganizations. By intentionally practicing all three, you build organizational trust and momentum that carries through the inevitable friction of large-scale change, transforming what could be a multi-year stall into measurable progress within quarters.

[00:16:59] Measure Outcomes, Not Adoption Theater – Barsoom critiques the widespread practice of using employee adoption metrics, logins, tool usage, and feature activation as proxies for successful AI transformation, revealing a dangerous blind spot in how most organizations measure progress. Executives at all levels fall into this trap because adoption metrics are easy to track and communicate to boards, but they mask the reality that employees may be performing performative actions ("logging into ChatGPT to show adoption") without actually changing workflows or delivering business value. The right questions to ask instead are: Have we actually redesigned workflows? Have we reskilled people? Who owns results and is accountable for outcomes? Are customer or operational metrics improving? Barsoom uses Klarna's cautionary example: they optimized for cost reduction via AI in customer service but sacrificed the human judgment required for exception handling, ultimately reversing the decision. As a mid-cap or family-owned business leader, auditing your current KPIs is essential; if you're measuring adoption rates without measuring outcome changes, you're likely funding expensive theater rather than genuine transformation. Recalibrate your success metrics to connect technology deployment directly to business consequence: margin, growth, customer satisfaction, or employee capacity freed for higher-value work.

[00:20:35] AI as a Leadership Problem, Not a Technology One – Barsoom's most provocative insight reframes the entire AI adoption conversation: the companies struggling with AI implementation aren't those lacking budget or cutting-edge models, but those unwilling to make difficult *leadership decisions* about incentives, workloads, and organizational structure. This directly challenges the assumption that technology implementation is primarily a technical challenge, when in reality, the hard work is human and organizational. Critical leadership decisions include: Who owns outcomes when AI automates certain tasks? What judgment must remain human (customer exceptions, ethical edge cases, relationships)? Should recovered capacity from automation become margin, competitive growth, better service, or more meaningful work for employees? How do you reskill people whose roles are fundamentally changing? These aren't technical questions; they're strategic choices that determine whether your workforce embraces or resists transformation. For CEOs and boards at mid-sized companies, this insight suggests your AI strategy review should focus less on technical vendor capabilities and more on whether leadership has aligned on these organizational design questions. Without that clarity, even the best AI tools will sit underutilized or fuel organizational friction that erodes execution.

[00:23:10] "Go Slow to Go Fast": The Strategic Advantage of Small Companies – Barsoom reveals a counterintuitive competitive advantage: smaller companies can move faster on transformation *if* they invest in strategy and stakeholder alignment first, rather than rushing straight to execution. While mid-market and large enterprises have more resources, they're often encumbered by legacy systems, organizational inertia, and change management complexity; smaller organizations lack those constraints but often lack the expertise to think strategically. Barsoom's advice is to resist the pressure to "just execute"; instead, bring in trusted advisors to assess your organization, deeply document the tacit knowledge employees possess, involve your team in strategy design, and *then* execute with clarity. This upfront investment pays exponential returns because the entire organization moves together with a shared understanding rather than requiring constant reorientation as execution reveals gaps in strategy. Additionally, smaller teams can now accomplish with one or two AI-enabled people what previously required ten, unlocking competitive leverage if you invest in reskilling your existing team rather than hiring new specialists. For founders and family business leaders, this principle permits you to slow down strategic clarity conversations in the next quarter; the time spent will compress your total transformation timeline and prevent costly restarts that larger organizations can absorb but you cannot.

Episode Resources:

LinkedIn Profiles:

Elaine Barsoom: https://www.linkedin.com/in/ebarsoom
Chad Hesters: https://www.linkedin.com/in/chadhesters/

Websites:

Guest's Company: https://waveco.ai