“The Business” split from everyone else. Image via Midjourney from an author prompt.
The challenges to upstream thinking in large legacy organizations
Over more than 20 years in tech consulting, I’ve consistently seen the value user-centric design has brought across every engagement I’ve worked on.
I’ve been fortunate to work alongside some great Design people, and by bringing Product and Tech perspectives into the mix, we’ve collaborated to successfully solve some incredibly tricky design challenges for clients:
- Complex mobile prescription refills for one of the largest pharmacy chains in the country
- Mobile checkout for a premier global luxury brand
- An end-to-end thought leadership management solution for a renowned international strategy consultancy
- And many, many more
The focus on UX went away after nearly every engagement
Over time, I found it curious that after we’d delivered the product and moved on to our next engagement, it seemed many larger organizations couldn’t sustain the high level of user experiences we’d given them.
Increasingly accustomed to a higher bar for software usability, users will actually leave for better-designed experiences elsewhere. What was it that Enterprise software decision-makers were missing when it came to UX?
This bothered me for years, but since spending more time in the Enterprise, I’ve come to recognize two fundamental reasons preventing larger legacy organizations from getting and sustaining the value of design:
- Reason #1: They tend to focus predominantly internally & analytically on planning & execution
- Reason #2: They’re not organized for client-centric value delivery
I’ll follow up these two reasons with a path for fixing them.
Reason #1: They tend to focus predominantly internally & analytically on planning & execution
Enterprise software decision-makers are evaluated on one thing:
How quickly their teams can get as many features as possible in front of their users.
Code it fast, get it out there fast, and make sure it has all the functionality it could possibly ever need. The main focus is on all-out “productivity,” keeping developers coding with “hands on keyboards” as fast as possible.
How it looks is seen as secondary to how it works.
Quick, design this…
When design is needed, a developer goes to the design team and asks for any designer to quickly create an interface.
The designer is at a disadvantage in this dynamic, as all functionality and element placement decisions have already been made.
And there’s no incentive to improve the situation.
For many software decision-makers, when you’re being judged on the quantity of features and functionality your teams can get out the door, design is seen as something that gets in the way, slowing down feature delivery.
“The Business” leads
Much of this comes from a fundamental split that exists in most Enterprises between a dominant group, known as “The Business,” who “theoretically” represent the needs of “all stakeholders.”
It’s a challenging role for business people to juggle different stakeholder needs, but there’s a deep-seated focus on emphasizing shareholder value above all else through revenue and profit maximization. It’s also easy to fall into a perspective where the business comes to see themselves as the customer, confusing their own Business Impact needs with actual user needs.
There’s no better example of this than the ongoing obsession with chatbots. Regardless of their underlying technology, these efforts end up offering sparse customer value, as their main focus is clearly cost reduction.
What customer would voluntarily choose to interact with a bot instead of a human?
IT is responsible for Execution
Typically subservient to The Business is the IT group.
They’re tasked with the grunt-work “execution” of taking fuzzy business specifications, and “manufacturing” the software.
But because of this split, “IT” is viewed as a “Cost Center,” and everything they do is viewed as “overhead,” subject to efficiency and cost-saving measures.
This extends to the point where I’ve heard people on the business side openly question what the Return on Investment (“ROI”) of good User Experience design (UX) is.
But it might be as relevant to ask what’s the ROI of Strategy, or Product Management.
The split focuses everyone downstream
Strategy, UX, and Product Management are all client-centric activities focused upstream on collaboratively influencing something that’s inherently outside of the organization’s control — client behavior.
While most people in the Enterprise focus downstream on accelerating the pace of execution, this over-obsession on “doing” ignores the power of upstream thinking to positively impact user experiences.
It’s been estimated there’s less than $1 spent on Strategy and Design for every $1,000 spent on execution. At the same time, as many as 80% of tech projects fail to provide their anticipated benefits.
And I think this is another of the fundamental differences between tech-native and Legacy organizations.
How Silicon Valley approaches work differently
Newer organizations don’t have this fundamental split between thinkers and doers, and integrate thinking and doing more effectively.
They tend to tackle risks collaboratively, up-front, in consistent, structured, and scientific ways that allow them to put better-quality work in front of their customers.
Unfortunately, when the only mental model is based on a dominant/subservient, business vs. IT split, software itself isn’t seen as a strategic enabler and primary channel for value creation.
It’s seen as a necessary evil that can be designed and manufactured by interchangeable “doers,” outsourced either internally or externally.
Reason #2: They’re not organized for client-centric value delivery
“If a client came into your company and saw your org chart, would they believe you were organized with their interests in mind, or your own?”
Rich Mironov
If the thinker/doer split wasn’t challenging enough, Legacy organizations are also still organized largely on outdated manufacturing-based industrial models.
This encourages the creation of silos patterned on internal ways of dividing the organization, each with its own division lead. The end result of this internal-centric, siloed functional focus is that no Portfolio or Program can own the end-to-end creation and delivery of any piece of software.
Worse, they frequently won’t even know who they have to reach out to to get some critical piece of work done.
Being big should be an advantage
Larger organizations should be able to take advantage of their size, providing greater value than the sum of their parts, giving them unprecedented reach and scale.
But with these internal divisions, more people and processes are required to orchestrate work so it can move across the necessary silos to eventually deliver value to an end-user. This reduces many people’s full-time jobs to figuring out how to get something done when their needs may be blocked by an external dependency on some other team.
Will that other team “prioritize” what’s needed so that piece of work can get finished and find its way in front of a user in some reasonable timeframe?
The all-consuming internal focus
But the internal focus needed to deliver on business requests ignores a very simple fact:
You can’t make your clients DO anything. You can only create amazing experiences, and they’ll want to come, stay, and hand over their money.
Once you’ve set up a structure that forces people to spend all their time downstream trying to navigate the organization, and the fact that design is seen an additional cost, something to “sprinkle in” at the end, how likely is it that teams will be able to collaborate to design and deliver the intuitive, “sticky” user experiences to solve crucial customer problems?
Have organizations set this up as a “winnable” game for their people?
What to Do Instead: Start from Client-Centricity
Like it or not, if you serve a customer, the minimum standard has been raised to the point that the only choice you have is to play or be left behind.
The best companies have client-centricity woven into their core structures and operating cadences. They take advantage of the compounding effect of a collaborative upstream focus on strategy, design, and product management.
They’ve effectively organized into teams of teams around delivering “flows” of value to specific end-users.
What the Enterprise can do
People in the Enterprise can start taking gradual steps towards client-centricity and upstream thinking by:
- Cross-functionally and collaboratively designing a strategy based on working backwards from actual client problems
- Being crystal-clear who your target customers are (and aren’t)
Reorganizing around Value can be approached gradually through:
- Making existing Dependencies visible
- Using collaborative planning events to manage Dependencies
- Impact Mapping and Value Stream Mapping
- Looking for ways to pull some of the main Dependencies into the Portfolio and Program structures
- Establishing a regular cadence of touch points
- Experimenting with reorganizing around Value Streams on a smaller scale before broadening out to other areas
- Tracking Flow metrics to understand the effectiveness of these efforts
Making User Experiences a priority
As part of their long-term, multi-year effort to move from a Project to Product focus, Ford Motors has gradually built a world-class design capability.

Once considered one of the worst examples of legacy American Enterprise excess, ineffectiveness, and bad user experiences, Ford’s success is the result of a massive, focused, and consistent effort to reorganize and operate differently.
This has allowed them to innovate and provide new products to customers, resulting in considerable top-line revenue growth.
It takes time
As with any focus on client-centricity and upstream thinking, these kinds of changes are hard to start and implement, and can take years to pay off.
Again, it comes back to the same thing: Understanding your job isn’t to serve “The Business,” but to collaborate with them to serve your customers.
And the fact that you can’t make your customers “do” anything.
Yes, execution and delivery remain important capabilities.
But only by prioritizing more higher-quality upstream thinking on Strategy, Design, and Product Management, and reorganizing in ways that allow for collaboration, will organizations be able to solve the right client problems both efficiently and effectively.
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