The Data Team That Got Everything…And Lost It

Time to put away childish things

For years, data at Middleton Co was a mess, but it worked. Each department had its own embedded analyst in Marketing, Finance, Sales, and Operations. They pulled reports, built dashboards, and answered leadership’s urgent questions. It wasn’t efficient, but it was functional and people were happy.

Then Steve, an ambitious analyst, convinced leadership that data could be more. Leadership centralized the analysts into a single data team under the CTO. Steve was promoted to Director of Data, given a budget, new hires, and a mandate to modernize.

The goal: a single source of truth, better reporting, and make the company “data driven.”

At first, it felt like progress. They migrated reporting to a cloud data warehouse, standardized metrics, and rolled out dashboards to replace the mountain of spreadsheets. Steve quickly hired data engineers, a platform lead, and a data scientist, anticipating an influx of new, advanced requests.

But eighteen months in, leadership asked: “What are we actually getting from this?”

The dashboards weren’t driving decisions. The self-serve tools went unused. Cloud costs were skyrocketing. The influx of new data science requests never materialized. And despite all the new hires, leaders felt underserved. When asked about it, Steve cited a lack of resources¹ and blamed business teams.

The CFO started scrutinizing the spend. The CTO grew frustrated. Within two years, the budget was slashed, layoffs followed, and the data team, created with much fanfare, was quietly dismantled. Analysts returned to business units, their ambitions reduced to routine reporting. Steve’s position was eliminated, a polite firing.

What had once been seen as a strategic investment was now considered an expensive failed experiment. The business moved on, leadership refocused on more immediate operational priorities, and the vision of a data-driven future faded.

The Three Stages of Data Team Maturity

Data teams evolve much like people. They begin in infancy and youth, stumble through adolescence, and, if they adapt, become mature adults.

Youth: Fast, Scrappy, and Unsustainable

Everything is ad hoc. The focus is speed, churning through as many requests as possible. Process, ownership, and governance are afterthoughts, if they exist at all. And that’s fine. At this stage, the primary goal is proving your value to the business. You’re earning trust with stakeholders as a service, demonstrating that data can solve problems and drive insights.

Adolescence: Budget Arrives, But Strategy Doesn’t

But as the data team and leadership’s ambitions rise, expectations shift. The data team is no longer just a support function; it’s an investment, a financial bet. And like any investment, leadership expects a return, measurable, scalable, and fast. The team, however, is focused on making their own lives easier, throwing tech at internal workflows, and solving cool technical challenges².

Adulthood: Strategic, Disciplined, and Impactful

If data teams successfully evolve and mature, they become true contributors to the company. While they may never fully eliminate reporting and ad hoc requests, these become a minor responsibility. Their primary focus has shifted.

• They don’t just answer questions, they shape decisions.

• They don’t build tech for tech’s sake; they align their work with business priorities.

• They focus on scalable solutions that drive revenue, reduce costs, and embed data into decision-making.

At this stage, the data team earns a permanent seat at the table.

The Adolescence Trap

Adolescence is where teams, like Steve’s, stall. The problem wasn’t lack of resources or bad business partners. It was the way they worked.

• They kept taking every ad hoc request, because that’s what they’d always done.

• They spent months debating tech stack decisions instead of solving business problems.

• They assumed that if they just built enough “data products,” impact would follow.

• They never defined a clear ROI strategy, just “make better data.”

This is the adolescence trap that kills most data teams. They think getting centralized and funded is the goal. But winning funding is easy, creating ROI is hard. They fail because they don’t recognize the change in rules.

The moment you get real money, the clock starts ticking. You have 18-24 months to prove ROI. Or you won’t be around to see what comes next.

In the early days, it’s enough to be scrappy and responsive, delivering dashboards and ad hoc analysis on demand. You are one person, an afterthought in a department budget, working side by side with the business team. Even if the value isn't quantifiable, the team can feel it.³ But the moment you become a stand alone team, the expectations flip. Now those salaries, a rounding error across several budgets, gets scrutinized at every turn. Add in ever increasing cloud costs and leadership stops measuring you by vibes and starts demanding measurable results, in the form of profits and loss.

The unspoken assumption from the team is they only need to be incrementally better to get to the next level. If more maturity is needed it will happen organically. Unfortunately, maturity doesn’t follow growth. This is a new game that requires new, more complex skills to compete in. Young teams have honed their skills for ad hoc and reporting work. They need to expand to work that explicitly drives ROI. Those projects are harder to find and harder to execute. They take deliberate planning and processes. That takes intentional focus to build, something that is in short supply in the whirlwind of ad hoc work.

The Twin Ad Hoc Traps

If you lead a growing data team, you have to face the ad hoc work problem without falling into the twin traps.

Peter Pan Teams: They won't grow up, they don't want to even try⁴

Small teams may be inefficient, but they are nimble and adaptable, often finding ways to get things done despite their constraints. But if teams and leaders over identify with their scrappy roots they become Peter Pan, clinging to the comfort of improvisation and resisting the responsibilities of maturity. They take pride in their ability to deliver quickly without formal processes, believing that agility is their greatest strength. But without structure, a larger budget only magnifies inefficiencies. When leadership and finance start asking tough questions, the Peter Pan team doubles down on “what got them here,” more ad hoc work, more reactive firefighting. They assume the core issue is a lack of resources and staff, while leadership sees unchecked bloat and the glaring absence of a strategic plan.

Frustration mounts as the team feels unappreciated. "We're doing exactly what you asked for," they insist. They blame the business for making the wrong requests and then holding the data team accountable when those efforts fail to deliver impact. Instead of recognizing their need to evolve, they fixate on what they perceive as the downsides of structure and process. The result? They never make the leap from scrappy startup. They cling to their familiar, improvisational tools instead of learning to wield the adult tools of leadership, accountability, and process. And when leadership runs out of patience, the team is left wondering why their once-cherished agility wasn’t enough to keep them relevant.

Technology Tower Teams:

On the opposite end of the spectrum, some teams mistake maturity for purely technical sophistication. They believe they have "graduated" beyond low-value ad hoc work and the operational needs of business teams. They go “all in” purchasing the latest data stack, hiring specialists, and building cutting-edge (and very expensive) data infrastructure. Their focus shifts from business outcomes to architectural perfection, optimizing systems for scale before proving their relevance.

Without a clear strategy, internal pet projects and runaway costs become the norm. When these teams do engage with the business, they prioritize what they find the most interesting or technically challenging, rather than what the business actually needs. Often, they work in isolation for months, unveiling their work (far behind schedule), only for it to be dismissed by the business as irrelevant. Instead of seeing this as a failure in alignment, they view the rejection as proof that the business doesn’t understand the value of data.

As costs rise and frustration mounts, these teams find themselves increasingly isolated, having burned through political and relational capital. Without strong ties to the business, no one advocates for them when leadership scrutiny intensifies. The best they can offer is to slow the rate of cost growth, but by then, it’s too little too late. The leader is typically the first to go, followed by deep cost-cutting measures. Eventually, the team is dismantled entirely, and leadership, burned by the experience, grows hesitant to ever invest significantly in data again. The team never realized that without a plan, their high-end data stack was merely an expensive liability.

The guiding star is ROI, if you can’t demonstrate measurable impact, budgets will shrink, priorities will shift, and as the leader, you’ll be the first on the firing line. Without a shift in mindset, the same team that once thrived in a scrappy startup mode will find itself drowning under the weight of increased expectations, an expanding backlog, and mounting costs. Maturity isn’t a function of size or money—it’s a function of discipline.

The Point of the Game

Not every player can control the opportunities that he gets…because of circumstances, an opportunity arises and then the player does whatever he does with the opportunity. That’s up to each individual player.

That’s why each player needs to always prepare, always be ready, so that when the opportunity comes, he is able to take advantage of it and not miss the opportunity and then that will hurt his chances next time. (emphasis added)

-Bill Belichick UNC Head Football Coach (Also 8x Super Bowl Winning Coach)

In the life of a data team, there are pivotal moments that define its future and, in some cases, the future of the company. These crucible moments arise when everything is on the line, when leadership turns to data as a last resort in a crisis, or when a major initiative depends on the team’s success. You don’t get to pick these moments, but how you respond determines your team’s legacy. All of the discipline and hard work is in preparation for this moment.

Immature teams never get these opportunities; they are too scattered, too reactive, too disorganized. Teams that cosplay as strategic players may get a chance, but they inevitably crash and burn, exposing their lack of substance. True maturity is the prerequisite for a seat at the table when it matters most. This is the moment when a data team can transition from a peripheral support function to a true strategic partner.

Start growing now

Adolescence is a growth phase, but you must get organized and be ready for when the clock starts ticking (remember you only get 18-24 months). As a data leader, that means:

• Define ROI: Understand leadership’s definition and expectations for returns⁵ and aligning your work with these expectations from the outset.

• Identify the business growth bottleneck: Identify what is holding the business back from growing and look for ways data can help remove the bottlenecks.

• Build relationships now: Start selling your team and banking relational capital early with the bottleneck team.⁶ Don’t focus solely on VPs or directors, especially if there’s a power dynamic at play. Instead, start lower, meet with managers and key individual contributors, turning them into advocates who influence their bosses.⁷

• Build your discipline: You can’t jump from a YOLO approach on Slack and email to full-scale maturity overnight. Start by tracking your work (all of it) and use that to look for automation gains.

• Take the plunge: Recognize when the moment has come to make the leap. You will never be fully prepared, but at some point you have to push your chips in.

When that moment comes, teams are either prepared to step up or they aren’t. Those who haven’t laid the foundation will falter, while those who have put in the work will seize the opportunity and cement their place as a critical driver of business success. That is why focusing on maturity isn’t optional. It’s the only way to ensure your team will still be standing when the real opportunities arise.

1. Pro tip, when someone gives you millions of dollars and then asks why they aren’t see more results, don’t say you don’t have enough money.

2. And whining about parents business leaders nagging them to do something productive with their lives money

3. It is all about the vibes. If finance asks about that one data analyst there is an immediate “we couldn’t function without Gary” and that is enough.

4. https://youtu.be/q1YU7

5. I recommend making friends with people on the finance team, they can give a lot of insight into this. Do they expect results within one year or two? Is a break-even ROI acceptable, or do they require a 2x or 3x return on investment?

6. Do you best to be non-threatening, you are looking to partner and help them not replace them. “Seems like you guys aren’t getting the job done,” is a terrible way to get people to want to work with you. Yet this type of approach happens all the time.

7. They will also be able to supply you with valuable intel about what is important to those business leaders.