Why Do Some IT & Digital Projects Feel Like a Battle That Shouldn’t Be One?
B2B loves structure, but not every problem can be solved with a Gantt chart.
TL;DR
You followed the plan, the tech worked, the budget was there…yet adoption stalled, and resistance crept in to where it all felt like a slow motion disaster. That’s because not every problem is an execution problem. Some are complicated (predictable), others are complex (messy, people-driven). IT leaders get stuck treating one like the other, and no amount of meetings or KPIs will fix it. Call out complexity early, align incentives, and design for iteration.
You ever work on a IT or Digital project where everything looked right on paper, but somehow, it still felt like undertones of the struggle bus?
🟢 You had the right team.
🟢 The budget was locked in.
🟢 The roadmap was solid.
🟢 The tech worked in testing.
But the whole time there was this constant undercurrent of resistance. It’s palpable and everyone can feel it but never outright says it.
Deadlines slipped. The adoption wasn’t there and conversations got harder. You kept running into unexpected roadblocks, and no matter how well you explained the plan, people weren’t fully on board.
If you’ve been there, I want to say something upfront: You’re not crazy.
You’re not imagining things. You’re not missing some secret ingredient that other leaders seem to magically have. You’re running into something deeper than execution. As an IT leader, this drove me insane until it finally clicked (thankfully at a young age).
Let’s solve this riddle.
Not Everything Can Be Solved With a Better Plan
In IT, digital, and business in general, we love structure. We love plans, roadmaps, frameworks, and best practices…and for good reason. They make big problems manageable and bring clarity. In particular for B2B organizations in manufacturing & distribution, structured execution is the default mindset.
That mindset is invaluable in operational areas like supply chain management, procurement, and logistics where process consistency and predictability drive efficiency.
But sometimes, even the best plan doesn’t fix the problem.
Why? Because not every challenge is a matter of execution.
Some things can be solved by breaking them down, assigning tasks, and following a structured approach. And boy do I (and most technical folks) thrive on those types of opportunities. Very analog. These are complicated problems - they might be difficult, but they’re predictable once you understand them. Examples…
Moving data from an old ERP to a new one.
Replacing a firewall with a new one.
Upgrading your fleet of PCs from Windows 10 to Windows 11
If you follow the steps, you get the expected result with minimal variability.
But some challenges are not predictable and they don’t only require technical expertise. They require buy-in, adaptation, and emotional intelligence. These are complex problems, where success isn’t really about execution but about navigating change, resistance, and the unknown. Examples:
Getting customers to actually use self-service instead of calling their rep.
Convincing sales teams that digital tools help them instead of replacing them.
Driving AI adoption in an organization where people don’t trust the data.
See the difference?
One is about doing the work correctly.
The other is about aligning people toward an often uncertain future.
That distinction alone (complicated vs. complex) explains so much about why some projects feel perpetually cursed while others succeed.
Most IT leaders understand this distinction in theory, but it’s not thought of in practice proactively. We treat everything like it’s solely complicated. Thinking about this more hit me like a sack of bricks.
We create rigid project plans. We scope out deliverables. We assume execution = success.
We launch an ecommerce site and customer adoption is meh, we’re confused.
We roll out AI-driven pricing and sales ignores it, we’re frustrated.
We implement a new ERP and business units refuse to change their workflows, we think: What the f*** happened?
When you’ve been a technical problem solver so long, you’re almost preconditioned to only think a certain way.
But…the problem was never only the technology.
This Isn’t Merely a Change Management Rant
Let’s pause for a second. If you’re dealing with a project that feels harder than it should be, ask yourself:
Is this truly a technical problem, or is it a human problem?
Now, before you roll your eyes and say, “No shit, Jacobi. This is basic change management.” - hear me out.
I know change management is a thing. I know that proper communication, training, and leadership buy-in matter. That’s not lost on me and I work my change management muscles daily by nature of the work I do.
What I’m saying is this: what if we’ve been looking at the problem through the wrong lens?
B2B organizations, especially manufacturing and distribution, aren’t new to big, difficult projects. We handle ERP overhauls, warehouse automation, and supply chain optimizations all the time. And when we do, we follow a structured playbook:
✅ Define the problem.
✅ Map the solution.
✅ Assign ownership.
✅ Execute the plan.
✅ Track progress.
And most of the time, this approach works. So when a digital initiative, like an ecommerce rollout or an AI-driven pricing tool struggles, the instinct is to treat it like an execution failure.
❌ “Maybe we need more training.”
❌ “Maybe IT didn’t configure it correctly.”
❌ “Maybe the sales team isn’t trying hard enough.”
What if the real issue is a misalignment of incentives? A loss of perceived control? An unspoken fear that the change is a threat? You can train people all day long, but if they don’t believe the change benefits them, they’ll find a way around it.
And that’s the real problem.
Not execution.
Not process flaws.
Not lack of documentation.
Behavioral resistance masquerading as a technical problem. And you don’t fix that with a fake Gantt chart to fit a certain narrative.
You’re Not Alone in This. We All Get Stuck Here.
I’ve seen brilliant IT leaders, ecommerce directors, and CIOs get completely blindsided by this. People who have led massive, high-stakes projects. People who know how to execute, how to manage complexity, how to keep things moving when everything seems stuck. And yet, when digital transformation, ecommerce adoption, or AI-driven decision-making struggles to take hold, they find themselves in a frustrating loop of resistance and confusion.
Not because they weren’t good at their jobs. Not because they didn’t plan well. Not because they weren’t smart enough.
It’s mostly because no one explicitly tells us that complexity needs to be led differently than complication. It’s a hindsight realization.
You don’t learn this in a project management course. There’s no section in your PMP certification that covers “what to do when the sales team quietly sabotages ecommerce adoption.” A software vendor doesn’t include a chapter on “how to rebuild trust when AI pricing tools make sales reps feel obsolete.” The ERP migration guide doesn’t explain “how to handle process changes that threaten department fiefdoms.”
So when things start going sideways, what do we do? By default we double down on structure. Psssst, that’s code for more meetings and KPI dashboards.
We tell ourselves, "We need more alignment. We need better tracking. We need stricter accountability."
lol none of that fixes the core issue so let’s see how we can contribute as an IT leader.
What Can You Actually Do? (Without Carrying the Whole Organization on Your Back)
If you’ve ever felt like driving digital adoption or leading IT strategy means taking on the emotional baggage of the entire company, your intuition and feeling is right.
I’m not going to sugarcoat it. B2B IT leaders are put in a strange position. You’re not only expected to execute the technology, you’re expected to change how the business operates without actually being given authority over the people and processes that need to change.
That’s why it’s easy to fall into the trap of owning too much, believing that if you work harder, communicate better, and build a perfect roadmap, things will click into place. For seasoned folks, you already know this, but I’m going to reiterate: You can’t force people to change. (I mean you can but uhh we’re talking beyond short term modification of behaviors)
What you can do is set the conditions for adoption, minimize resistance, and put leadership in a position where they have to engage.
Let’s break this down into three strategies that allow you to lead change without becoming the organization’s punching bag:
#1 - Call Out the Complexity (Early and Often)
The first mistake leaders make is not naming the complexity up front.
IT and digital leaders assume that because they see the challenge clearly, others do too. They expect leadership to recognize that adoption isn’t about training, that digital transformation success isn’t just about platform selection, that digital transformation isn’t just an IT initiative.
Don’t assume this. Feel it out.
So before a project even kicks off, put it on the table. Say it with me:
“This initiative isn’t merely a technical rollout, it’s a behavior change effort. We need to plan for that.”
“Success here depends on incentives and internal alignment, not only execution. We need business leaders involved from the start.”
“If we treat this like a traditional IT project, we will get traditional IT results; functional, but underutilized. That’s not success.”
It’s VERY important that we’re not washing our hands and giving ‘not my business, not my problem’ vibes but this does two things:
1️⃣ It prevents you from being blamed for adoption issues later should they arise. If you flag potential resistance upfront, no one can say, “We didn’t see this coming.”
2️⃣ It forces executives and stakeholders to engage. If they want the project to succeed, they need to take ownership beyond IT.
And if you get pushback? That’s good. It means you’re hitting a nerve that would’ve caused problems later. Trust me.
#2 - Shift from Convincing to Aligning
A lot of leaders spend way too much time trying to “sell” change internally convincing stakeholders why the new system, tool, or process is the right move. That’s exhausting. And it rarely works.
Resistance to change isn’t typically about logic and instead about emotion. As humans, we’re strange like that but that’s how it is.
When sales refuses to use CRM, when customers ignore self-service portals, when employees complain about process automation, it’s usually not because they don’t understand the benefits. It’s because they don’t see how it benefits them.
So instead of trying to convince people why change is good, align the change with their self-interest. Such as:
✅ Sales sees ecommerce as a threat? Make it clear that digital tools will help increase their commissions, not replace them. Show them. The ‘whats in it for me’ is very important.
People don’t resist change. They resist loss. If you can reframe change as a gain, resistance drops significantly.
Do you know what my most successful projects have ever looked like? It’s when employees or consumers of the technology say things like:
“I can’t believe we never had this before” or “Please don’t take this thing away from us, it’s amazing!”
#3- Design for Iteration, Not Perfection
One of the biggest lies in enterprise IT is the idea that you can fully define success before you start.
That’s a comforting thought, but in complex environments it’s nonsense.
The best way to drive adoption isn’t to chase a ‘perfect launch’, it’s to build in flexibility while keeping a clear direction. I’m not saying go full Agile manifesto, but you need a plan that bends without breaking. There’s a fine line between looking adaptable and looking like you have no clue wtf you’re doing. On the flip side, if you come in with a rigid, 'my way or the highway' approach, you’ll bulldoze past real concerns and kill buy-in before you even start.
Instead of launching the a full digital platform on day one…Soft launch it with a controlled group of customers, actively monitor behavior, and refine the experience before scaling. Visibility without chaos.
Instead of assuming employees will magically embrace new workflows…Introduce the change in parallel mode first and let them run the old and new process side by side before shutting the old one down. Gives them a lifeline without stalling adoption.
Instead of rolling out a massive IT-led initiative…Find the natural champions within each department, equip them with the tools and context, and let them influence adoption from within. Top-down mandates breed skepticism whereas peer influence breeds trust.
Rigid, all-or-nothing launches almost always fail when they they are both complex and complicated. Whether you like it or not, these things have to marinate and take time.
Lead Smarter, Not Harder
If you’ve ever felt like IT leaders carry too much of the burden for digital success, it’s because you/they do.
Not because you’re doing anything wrong, but because business leadership defaults to letting IT “own” transformation efforts without fully engaging in the hard parts of change.
You don’t have to carry that weight alone. You don’t have to be the sole champion for adoption.
What you can do is:
✅ Call out complexity before it blindsides everyone.
✅ Align change with self-interest instead of trying to sell it.
✅ Design for real-world iteration, not theoretical perfection.
If you do these things, you shift from being the person responsible for making everything work to being the leader who creates the conditions for success without carrying the entire organization on your back. You’ve got enough to carry already.
You’ve Got This.
If you’ve been frustrated with adoption, culture shifts, or slow-moving change then you’re not alone. Recognizing complexity for what it is doesn’t make the work easier, but it gives you the perspective to navigate it without losing your mind.
That’s what separates tactical execution from real leadership.