May Habib, co-founder and CEO of Writer AI, delivered one in all the bluntest assessments of corporate AI failures on the TED AI conference on Tuesday, revealing that almost half of Fortune 500 executives consider artificial intelligence is actively damaging their organizations — and placing the blame squarely on leadership’s shoulders.
The problem, based on Habib, is not the technology. It’s that business leaders are making a category error, treating AI transformation like previous technology rollouts and delegating it to IT departments. This approach, she warned, has led to “billions of dollars spent on AI initiatives which can be going nowhere.”
“Earlier this 12 months, we did a survey of 800 Fortune 500 C-suite executives,” Habib told the audience of Silicon Valley executives and investors. “42% of them said AI is tearing their company apart.”
The diagnosis challenges conventional wisdom about how enterprises should approach AI adoption. While most major firms have stood up AI task forces, appointed chief AI officers, or expanded IT budgets, Habib argues these moves reflect a fundamental misunderstanding of what AI represents: not one other software tool, but a wholesale reorganization of how work gets done.
“There is something leaders are missing after they compare AI to simply one other tech tool,” Habib said. “This shouldn’t be like giving accountants calculators or bankers Excel or designers Photoshop.”
Why the ‘old playbook’ of delegating to IT departments is failing firms
Habib, whose company has spent five years constructing AI systems for Fortune 500 firms and logged two million miles visiting customer sites, said the pattern is consistent: “When generative AI began showing up, we turned to the old playbook. We turned to IT and said, ‘Go figure this out.'”
That approach fails, she argued, because AI fundamentally changes the economics and organization of labor itself. “For 100 years, enterprises have been built around the concept that execution is pricey and hard,” Habib said. “The enterprise built complex org charts, complex processes, all to administer people doing stuff.”
AI inverts that model. “Execution goes from scarce and expensive to programmatic, on-demand and abundant,” she said. In this latest paradigm, the bottleneck shifts from execution capability to strategic design — a shift that requires business leaders, not IT departments, to drive transformation.
“With AI technology, it could actually not be centralized. It’s in every workflow, every business,” Habib said. “It is now crucial a part of a business leader’s job. It can’t be delegated.”
The statement represents a direct challenge to how most large organizations have structured their AI initiatives, with centralized centers of excellence, dedicated AI teams, or IT-led implementations that business units are expected to adopt.
A generational power shift is occurring based on who understands AI workflow design
Habib framed the shift in dramatic terms: “A generational transfer of power is occurring without delay. It’s not about your age or how long you’ve got been at an organization. The generational transfer of power is in regards to the nature of leadership itself.”
Traditional leadership, she argued, has been defined by the power to administer complexity — big teams, big budgets, intricate processes. “The identity of leaders at these firms, people like us, has been tied to old-fashioned power structures: control, hierarchy, how big our teams are, how big our budgets are. Our value is measured by the sheer amount of complexity we could manage,” Habib said. “Today we reward leaders for this. We promote leaders for this.”
AI makes that model obsolete. “When I’m in a position to 10x the output of my team or do things that might never be possible, work isn’t any longer in regards to the 1x,” she said. “Leadership isn’t any longer about managing complex human execution.”
Instead, Habib outlined three fundamental shifts that outline what she calls “AI-first leaders” — executives her company has worked with who’ve successfully deployed AI agents solving “$100 million plus problems.”
The first shift: Taking a machete to enterprise complexity
The latest leadership mandate, based on Habib, is “taking a machete to the complexity that has calcified so many organizations.” She pointed to the layers of friction which have collected in enterprises: “Brilliant ideas dying in memos, the limitless cycles of approvals, the death by 1,000 clicks, meetings about meetings — a death, by the way in which, that is happening in 17 different browser tabs each for software that guarantees to be a single source of truth.”
Rather than accepting this complexity as inevitable, AI-first leaders redesign workflows from first principles. “There are only a few legacy systems that may’t get replaced in your organization, that will not get replaced,” Habib said. “But they are not going to get replaced by one other monolithic piece of software. They can only get replaced by a business leader articulating business logic and getting that into an agentic system.”
She offered a concrete example: “We have customers where it used to take them seven months to get a creative campaign — not even a product, a campaign. Now they’ll go from TikTok trend to digital shelf in 30 days. That is radical simplicity.”
The catch, she emphasized, is that CIOs cannot drive this transformation alone. “Your CIO can not help flatten your org chart. Only a business leader can have a look at workflows and say, ‘This part is obligatory genius, this part is official scar tissue that has to go.'”
The second shift: Managing the fear as profession ladders disappear
When AI handles execution, “your humans are liberated to do what they’re amazing at: judgment, strategy, creativity,” Habib explained. “The old leadership playbook was about managing headcount. We managed people against revenue: one business development rep for each three account executives, one marketer for each five salespeople.”
But this liberation carries profound challenges that leaders must address directly. Habib acknowledged the elephant within the room that many executives avoid discussing: “These changes are still frightening for people, even when it’s turn into unholy to discuss it.” She’s witnessed the fear firsthand. “It shows up as tears in an AI workshop when someone seems like their old skill set is not translated to the brand new.”
She introduced a term for a typical type of resistance: “productivity anchoring” — when employees “cling to the hard way of doing things because they feel productive, because their self-worth is tied to them, even when empirically AI may be higher.”
The solution is not to look away. “We must design latest pathways to affect, to indicate your people their value shouldn’t be in executing a task. Their value is in orchestrating systems of execution, to ask the following great query,” Habib said. She advocates replacing profession “ladders” with “lattices” where “people must grow laterally, to expand sideways.”
She was candid in regards to the disruption: “The first rungs on our profession ladders are indeed going away. I do know because my company is automating them.” But she insisted this creates opportunity for work that’s “more creative, more strategic, more driven by curiosity and impact — and I consider quite a bit more human than the roles that they are replacing.”
The third shift: When execution becomes free, ambition becomes the one bottleneck
The final shift is from optimization to creation. “Before AI, we used to call it transformation after we took 12 steps and made them nine,” Habib said. “That’s optimizing the world because it is. We can now create a brand new world. That is the greenfield mindset.”
She challenged executives to discover assumptions their industries are built on that AI now disrupts. Writer’s customers, she said, are already seeing latest categories of growth: treating every customer like their only customer, democratizing premium services to broader markets, and entering latest markets at unprecedented speed because “AI strips away the friction to access latest channels.”
“When execution is abundant, the one bottleneck is the scope of your personal ambition,” Habib declared.
What this implies for CIOs: Building the stadium while business leaders design the plays
Habib didn’t leave IT leaders and not using a role — she redefined it. “If tech is everyone’s job, you is perhaps asking, what’s mine?” she addressed CIOs. “Yours is to supply the mission critical infrastructure that makes this revolution possible.”
As tens or lots of of 1000’s of AI agents operate at various levels of autonomy inside organizations, “governance becomes existential,” she explained. “The business leader’s job is to design the play, but you could have to construct the stadium, you could have to write down the rule book, and you could have to ensure that these plays can win at championship scale.”
The formulation suggests a partnership model: business leaders drive workflow redesign and strategic implementation while IT provides the infrastructure, governance frameworks, and security guardrails that make mass AI deployment secure and scalable. “One cannot succeed without the opposite,” Habib said.
For CIOs and technical leaders, this represents a fundamental shift from gatekeeper to enabler. When business units deploy agents autonomously, IT faces governance challenges unlike anything in enterprise software history. Success requires real partnership between business and IT — neither can succeed alone, forcing cultural changes in how these functions collaborate.
An actual example: From multi-day scrambles to easy answers during a market crisis
To ground her arguments in concrete business impact, Habib described working with the chief client officer of a Fortune 500 wealth advisory firm during recent market volatility following tariff announcements.
“Their phone was ringing off the hook with customers attempting to determine their market exposure,” she recounted. “Every request kicked off a multi-day, multi-person scramble: a portfolio manager ran the show, an analyst pulled charts, a relationship manager built the PowerPoint, a compliance officer needed to review all the things for disclosures. And the leader in all this — she was forwarding emails and chasing updates. This is the highest job: managing complexity.”
With an agentic AI system, the identical work happens programmatically. “A system of agents is in a position to assemble the reply faster than any number of individuals could have. No more midnight deck reviews. No more days on end” of coordination, Habib said.
This is not about marginal productivity gains — it’s about fundamentally different operating models where senior executives shift from managing coordination to designing intelligent systems.
Why so many AI initiatives are failing despite massive investment
Habib’s arguments arrive as many enterprises face AI disillusionment. After initial excitement about generative AI, many firms have struggled to maneuver beyond pilots and demonstrations to production deployments generating tangible business value.
Her diagnosis — that leaders are delegating slightly than driving transformation — aligns with growing evidence that organizational aspects, not technical limitations, explain most failures. Companies often lack clarity on use cases, struggle with data preparation, or face internal resistance to workflow changes that AI requires.
Perhaps probably the most striking aspect of Habib’s presentation was her willingness to acknowledge the human cost of AI transformation — and demand leaders address it slightly than avoid it. “Your job as a frontrunner is to not look away from this fear. Your job is to face it with a plan,” she told the audience.
She described “productivity anchoring” as a type of “self-sabotage” where employees resist AI adoption because their identity and self-worth are tied to execution tasks AI can now perform. The phenomenon suggests that successful AI transformation requires not only technical and strategic changes but psychological and cultural work that many leaders could also be unprepared for.
Two challenges: Get your hands dirty, then reimagine all the things
Habib closed by throwing down two gauntlets to her executive audience.
“First, a small one: get your hands dirty with agentic AI. Don’t delegate. Choose a process that you simply oversee and automate it. See the difference from managing a fancy process to redesigning it for yourself.”
The second was more ambitious: “Go back to your team and ask, what could we achieve if execution were free? What would work feel like, be like, appear to be if you happen to’re unbound from the friction and process that slows us down today?”
She concluded: “The tools for creation are in your hands. The mandate for leadership is in your shoulders. What will you construct?”
For enterprise leaders accustomed to viewing AI as an IT initiative, Habib’s message is evident: that approach is not working, won’t work, and reflects a fundamental misunderstanding of what AI represents. Whether executives embrace her call to personally drive transformation — or proceed delegating to IT departments — may determine which organizations thrive and which turn into cautionary tales.
The statistic she opened with lingers uncomfortably: 42% of Fortune 500 C-suite executives say AI is tearing their firms apart. Habib’s diagnosis suggests they’re tearing themselves apart by clinging to organizational models designed for an era when execution was scarce. The cure she prescribes requires leaders to do something most find uncomfortable: stop managing complexity and begin dismantling it.
