The new platform gets approved in three weeks. There’s a logo, there’s a roadmap, there's budget available, and there's a consulting deck as thick as Kevlar on a tank. Everyone in the room nods during the presentation because the story's right, the future's here, leadership's got a story for The Street, and we’re moving forward.
Meanwhile, just down the hall, a critical system held together by a patch script written years ago during a fire drill is bumped again to next year's budget cycle. Again.
No one at the opposite end of that hall will tell you the critical system doesn't matter. They all know it matters. But the conversation wasn’t about where investment is actually meaningful, it was about where the status accrues. Which project gets to wear the good suit.
This all came back to me while reading Kiri Masters recent LinkedIn piece about this very same inverted approach and the short cut demons that exist in retail media, although this isn’t limited to retail media by any stretch. Overinvesting 10:1 in CAPEX to OPEX in service of transformation, standing up a CDP with minimal first-party data in it, throwing a sleek new loyalty app over a broken CRM and rewards system. I've seen all three and more in the past 15 years. Fact is, that we've all seen watched permutations of them in nearly every large organization. Company ownership models change. Departments change. Reorgs happen. Technology changes. Acronyms get a fresh coat of paint. And the pattern outlives them all.
Teams spend months on strategic capability discussions while foundational processes, integrations, data sets, and crucial platforms quietly accumulate debt and risk in dusty back rooms no one checks. The new initiative gets an executive sponsor and a kick off deck. The old system gets functional leadership pleading for help while their teams cross fingers hoping it all survives another quarter before imploding.
At first, I attributed this to a budgeting process. Not anymore. It’s a prestige problem.
Most modern corporations built their internal status economy on newness, novelty, and FOMO. Launching the new generates attention; maintaining the old generates reliability. The former gets you noticed; the latter gets taken for granted.
The irony is that most organizations already know where their biggest operational problems live. Marketing knows where the content workflow bottlenecks are, IT knows which integrations terrify every stakeholder who works with them, data teams know which data assets no one actually relies on, and operations teams know which processes require tribal knowledge and a leap of faith. None of this is a mystery. It’s all an open secret everybody’s chosen not to assign prestige and adequate funding.
Stewardship has become low-status work, and the hierarchy it lives in is visible everywhere you look. In marketing, the high-prestige lane is AI, personalization, retail media, whatever trend is included in the latest consulting deck. The low-prestige lane is metadata, taxonomy, content governance, asset management, the unglamorous stuff that makes the high-prestige lane actually work. In IT, transformation captures the spotlight while technical debt, documentation, patching, and integration cleanup gets whatever budgets are left over. In data orgs, everyone wants to build the model, nobody wants to standardize definitions or clarify ownership. The attendant budgets tell you exactly what a company actually values.
This inversion of prestige hasn’t always been true. Some of the most admired companies in business history (Toyota, Costco, Intel, P&G) based most of their value proposition on rigorous operational execution. They got good at the mundane and repeatable: doing more with fewer mistakes, less variation, well-documented systems, and observable processes. They treated reliability like a line item asset on their balance sheet because it is one.
Somewhere along the way though, the rest of the corporate world started to confuse visibility with value. Transformation earned more applause than operation. Innovation outshined execution. Launching something new beat maintaining the old. And the folks building the future became the heroes while the folks keeping the lights on became the cost center.
Then AI showed up and this bluff was exposed.
A disproportionate amount of what masquerades as "AI frustrations" are actually stewardship problems. Organizations want agentic systems, intelligent workflows, autonomous decision-making, the works, while many of those same companies are still fighting basic data quality, documentation, process, and discipline. Feed a model disorganized data and all you've built is a faster way to distribute the same mess, because AI runs a stress test on those neglected low status areas and prints the results in real time.
It's why so many AI projects feel uncannily familiar even with novel interfaces; the technology may have changed but the root cause never did. We've spent years deferring brilliant basics on the foundation and now we’re trying to build a penthouse on top of it. And then when the foundation gives out, we all acted shocked.
We shouldn't because the warning signs have been flashing for years.
Take CrowdStrike's 2024 outage. The company's own root cause analysis traced it to a breakdown in operational discipline; nobody had built an edge-case test for the configuration that brought down a staggering portion of the global internet for a period of hours. Smart engineers, sloppy, underinvested process.
The 2018 Equifax breach is a textbook example of neglecting the fundamentals (and paying a nine-figure settlement for it), ultimately attributing their breach to an expired security certificate that sat idle for 19 months, rendering their low prestige alerting functionality useless for that period.
Southwest Airlines' meltdown over the 2022 holidays was also a predictable, if tragic, outcome of several years of underinvestment. The pilot’s union alerted the company years earlier to major problems with outdated and faulty crew scheduling technology. The company ignored it until it cost them 15,000 canceled flights and over $1 billion in cancelled flights, reimbursements and government fines.
Our story plays out again and again and again. Neglect any issue long enough and it transforms from a deferred investment into a major expenditure, from an operational detail into a PR nightmare. From an ignored problem into a balance-sheet write-off that only makes the balance sheet after a crisis has erupted.
That's the part that really fascinates me the most. None of these fiduciarily responsible companies suddenly discovered that the neglected thing mattered. They already knew. So much for fiduciary responsibility.
What shifted was the neglected thing's status. The maintenance project that couldn't get funded in repeated planning meetings gets funded the day after it lands on the front page of a newspaper. Stewardship finally becomes visible and valuable. It's just a hell of a lot more expensive by the time it does.
This is the point where most organizations misdiagnose themselves. They think they have an innovation gap. Most don't. The real gap is simpler and uglier than that: people are paying attention to the wrong things and rewarding the wrong incentivized behavior.
The stewards who maintain our infrastructure spend their days in the shadows and yet they deliver far more of the value of the business, particularly in areas of intense tech disruption. An AI breakthrough means little if underlying data is poorly organized, a successful automation process relies on clearly defined and adhered to workflows, a personalized recommendation engine requires rigorous governance, and a transformative digital experience depends on a foundational level of operational competency that ought to be readily available.
None of that is optional, and pretending otherwise is how you end up with an expensive penthouse and no foundation.
The companies actually getting value out of AI right now aren't running magic tricks. Amazon, Morgan Stanley, Siemens, and the handful of others actually pulling this off spent years doing the unglamorous part first. AI got the headlines but the stewardship is what made the headlines possible in the first place.
Leadership must start asking very different questions before approving the next transformation initiative. Not just whether the innovation or new capability is impressive or whether it's needed. They need to ask whether the organization has handed enough status to the people maintaining the foundation underneath it to actually make any of these new things work.
*** Views expressed on Push Pull Pivot are personal and shared in an individual capacity. They do not represent those of any current or former employer ***