If you’re a mid-market IT leader, you already know the problem.
You’re buried in tickets. You’re the escalation point. You’re the person everybody calls when something breaks. And the minute you try to lift your head and talk strategy, the business pulls you right back down into the weeds.
That’s how people end up branding you the “fix-it person.”
And once that label sticks, it’s hard to shake.
I’ve spent 20+ years leading enterprise technology, including as CTO at Loblaw and Shoppers Drug Mart. I founded The Narrative Group because I got tired of the old idea that there’s “the business” and “IT,” like IT is some separate country inside the company. It’s not. My paycheck always had the same company name as everyone else’s.
So this article is straight coaching. It’s for the overwhelmed internal CTO who wants to move from reactive execution to being treated like an executive.
Because you can be brilliant technically and still lose the room. You can work yourself into the ground and still be viewed as “cost.”
And you don’t fix that by working harder.
The Fix-It Loop: How Good IT Leaders Get Trapped
I’ll say this upfront. I was never the fix-it person.
But I’ve seen many fix-it people act like firefighters. They spend all their time on urgent problems. They never get the chance to step back and improve the operation. They focus on tactics instead of strategy.
Here’s what it looks like in real life.
A person gets known as the reliable one. The one who can “just handle it.” Then everything funnels to them. They become the human router for every problem. They start protecting their time by skipping “high-level” meetings because those meetings feel optional compared to production issues.
That’s the trap.
I saw a leader do exactly that. He spent his time on immediate, urgent problems. He was always too busy to attend the meetings where priorities and budgets were set. That led to more spending, because decisions still got made. They just got made without him.
If you’re not in the room, you don’t get a vote. You get consequences.
And when you’re stuck in consequences mode, Shadow IT shows up fast. Other departments hire vendors because you’re “too slow.” Architecture becomes accidental. Risk grows quietly. Then one day it’s loud and expensive.
So the goal of IT leadership coaching is simple.
You stop being the person who catches the falling knives. You become the person who removes the reason the knives keep falling. We can help. We coach IT leaders on exactly this!
What Executives Need From You (And It’s Not More Tech Detail)
Most internal IT leaders try to win credibility with technical correctness.
Executives don’t buy correctness. They buy outcomes.
They want predictability. They want to know what’s going to break, when it’s going to break, and what it’s going to cost them. They want to know what you’re doing about it. They want a plan they can understand and defend.
They also want you to speak their language.
That language is money.
At the end of the day, every company on the planet is here to make money. Period. If you want to be treated like an executive, you have to connect your world to that objective.
That doesn’t mean you become “less technical.”
It means you lead with the business model, and you use technology as leverage.
Start With One Question: “How Do You Actually Make Money?”
If you take only one phrase from me, take this one:
“How do you actually make money?”
That question is the fastest way I know to pull a technology conversation back into reality. It forces clarity. It exposes assumptions. It gets you out of tool debates and into value-chain debates.
Once you understand how the business makes money, you can start to see the patterns. When you see the patterns, you can see where technology is in conflict with them. That’s where waste lives. That’s where downtime matters. That’s where customers feel pain.
This is why I push “Financials First” so hard. You can’t pick technology before you understand the business model. You can’t build a roadmap on vibes.
Follow the money. Then map the work.
Your job is to align people, process, and tech to the value chain
When I walk into any transformation situation, I’m thinking about the value chain first. How does work flow end-to-end? Where does it start? Where does it finish? Who touches it? Where does the data move?
Only after that do I care about technical architecture.
Because technical architecture in conflict with the value chain creates operational friction. It creates manual work. It creates ticket volume. It creates mistrust. Then people start saying, “IT is slow,” even when IT is working nonstop.
You don’t fix perception with a new ticketing system. You fix it by removing friction in the value chain.
The Reality Check: You’re Fighting the “70% Problem”
Here’s a stat that should bother you. In a lot of organizations, nearly 70% of IT budgets go to maintenance and operations.
If that’s your world, your calendar makes sense. You’re stuck “keeping the lights on.”
But it also explains why it’s so hard to get ahead. You’re trying to create strategic change with whatever scraps of time are left after operational survival.
Coaching starts by acknowledging that reality.
Then it pushes you to build a plan that changes the ratio over time. Less chaos. More leverage. More strategic capacity. More trust.
Financials First: How to Make the CFO Take You Seriously
If your CFO sees IT as a cost center, your job is to connect IT to the P&L in a way that’s obvious.
I don’t start with security frameworks. I don’t start with cloud maturity models.
I ask one practical question: how much downtime did you have in the past year, and how did that affect productivity?
Downtime isn’t an “IT problem.” It’s payroll being spent while the business can’t execute. It’s orders delayed. It’s customer experience degraded. It’s staff standing around doing workarounds.
When you frame it that way, you stop sounding like you’re defending a department. You start sounding like you’re protecting enterprise value.
The license-cost trap: “Saving money” that creates expensive labor
Mid-market companies get into trouble when they chase cheap solutions. They cut licenses. They downgrade tools. They outsource to low-cost providers. Then they wonder why everything gets harder to scale.
In my experience, one of the biggest hidden costs of choosing low-cost IT providers is the loss of scalability. You end up paying later in rework. You also miss opportunities because the stack can’t evolve cleanly.
The same dynamic shows up with software licensing. Cutting software license costs often shifts the expense into manual labor. People become the integration layer. They copy and paste. They reconcile spreadsheets. They do work the system should have done.
That slows innovation. It creates complexity. It traps the culture in old patterns.
A real example I’ve seen is a business using an old tool called Mail Manager to save emails into SharePoint, mainly to avoid Microsoft license fees. That decision came back later and complicated system upgrades, including the Windows upgrade.
This is why I’m a fan of being “current.” Mainstream. Not leading edge, not bleeding edge. And I prefer vanilla software whenever you can get away with it. Native functionality keeps you evolvable.
When you’re trying to become an executive, evolvability matters. It’s the difference between a roadmap and a never-ending patch job.
Stop Being the Hero: “Hero Syndrome” Kills Executive Potential
A lot of internal IT leaders have a quiet fear.
“If I’m not the person who can fix it, what’s my value?”
So they become indispensable. They keep knowledge in their head. They take the hardest work themselves. They jump in “just to get it done right.”
That’s Hero Syndrome.
And it burns you out while it stalls your team.
I coached a manager who consistently took over complex tasks from his team to ensure they were done perfectly. He was overworked. His team lacked confidence. The organization became dependent on him.
In a one-on-one, I highlighted the pattern. I said, “I notice you often pick up extra work when the team struggles. Is that fear? Are you worried that if you don’t step in, it won’t be right?”
Once he saw it, he couldn’t unsee it. Because taking over doesn’t let the team learn from their mistakes. It also keeps the leader stuck in execution forever.
If you want to rise, you need to build capability around you.
That means you create standards people can follow. You document the repeatable work. You make escalation paths clear. You train others to handle the issues that currently drag you into the mud. You also accept that sometimes the team will do it “good enough,” and that’s okay, because the long-term win is scale.
Executives scale through people. Firefighters scale through personal exhaustion.
Credibility Comes From Delivery (Not Slide Decks)
Here’s a phrase I live by: talk is cheap. Actions speak volumes.
If you want executive standing, you need to deliver outcomes that the business can feel. That’s how trust gets built. And without trust, strategy is just a document.
This is also why my firm often starts with foundational work. Infrastructure. Connectivity. Cyber hygiene. Devices. Meeting rooms. The stuff everyone complains about, but nobody wants to fund.
I had one customer with six offices. Their primary message was blunt: when people moved from one office to another, they couldn’t connect to the network. Their meeting rooms barely worked. Every time they asked IT for help, security was used as the reason nothing could change.
That’s a terrible pattern.
Security matters. You have to protect people, even when they don’t want to be protected. But you can’t use security as a blocker for day-to-day work. IT is intended to be an enabler, not a blocker.
So we assessed their infrastructure, then stabilized it incrementally. We replaced core switches and network gear across the organization. We replaced outdated servers. We put devices on a lifecycle plan. We improved meeting rooms and communicated how they’re supposed to work so people could use them.
Three years later, I ran into their managing director and asked how we did. He said, “You’ve created a problem for me. Everybody wants the existing office to function exactly like the new office you created because it’s that good.”
That’s what credibility looks like. It’s boring. It’s operational. And it creates the air cover you need to tackle bigger changes.
The Executive Skill Most IT Leaders Skip: Mapping the Work
If your systems don’t talk to each other, don’t start with a vendor search.
Start by drawing the flow.
I mean that literally. Whiteboard it. Map how data moves through the organization. Map who’s talking to who. Map how often. Map where the handoffs are. Map where humans are doing manual bridging.
A picture tells a thousand words, so just draw it all out.
I’ve been in plenty of environments where an e-commerce platform doesn’t match what’s in store inventory. People call it an “integration problem.” It’s usually a business model problem first.
Are you fulfilling from stores? Are you fulfilling from a distribution center? Are you doing click and collect? Are you picking from the store and shipping from the store? Those are different operating models, and the data needs to move differently for each one.
Take Amazon. They don’t pick out of retail stores. They pick from distribution centers. Their model is centralized in a way that fits that reality.
Now take a large grocery chain that wants convenience and uses retail locations to pick. Now you’re merging store-level inventory management with the e-commerce experience. Inventory has to be accurate by location. If the customer changes which store they’re picking from, the inventory needs to update. The website needs to communicate with the material management system for the physical location doing the pick.
If you don’t have those flows mapped, you’re going to have problems. And you’ll spend money fixing symptoms.
Mapping turns symptoms into root causes. Executives love root causes.
Business Rules: The Thing That Breaks Rollouts on the Front Line
When tech rollouts become a disaster, it usually comes back to definition. A lack of understanding of what the business process is intended to do. A lack of clarity in the business rules inside that process.
People under-define the rules. Then they roll out a system that has no chance of behaving correctly.
If you’re trying to become an executive, you become the person who forces business rules into the open. You don’t do it to be academic. You do it because frontline pain is expensive.
Self-checkout taught me more about leadership than most board meetings
Self-checkout is a simple story with a brutal lesson.
In retail, your number one expense, other than goods for resale, is labor. If you want to take labor out of a store, you get the customer to do it. That’s why self-checkout exists.
But the whole model depends on interventions. When a scan doesn’t come up with the right price or the right item, staff have to intervene. The industry tracks interventions because that’s where cost and frustration show up.
At Shoppers Drug Mart, we piloted self-checkout in two stores. It went really well. The user interface was friendly and easy to use. After a three-month pilot, we decided to launch it into 150 stores in the next fiscal year, and that grew to 400+ stores.
At Loblaw, the self-checkout experience presented far too many interventions so we had to rewrite the entire front-end interface. The intervention rate was too high. Instead of one cashier supporting 10 self-checkouts, you needed two or three. Now the “labor-saving” technology is adding labor.
That story is about UX, master data, and business rules.
It’s also about leadership. You don’t win by deploying tech. You win by making the business model elegant in the real world.
Innovation is making the operation of a business model elegant. That’s it. It doesn’t need to be complicated.
Pilots, Performance Testing, and Being Honest About Pain
Another misconception you’ll hear a lot: the rollout will be flawless.
That’s fantasy.
Large-scale change has pain. The job of an executive IT leader is to manage that pain, reduce risk, and keep the business running while you evolve.
This is why pilots matter. Lab testing helps, but real world experience is the most valuable thing you can have.
I was involved in rolling out a large-scale loyalty program. You can build the technology and make it work with 10 users. Then you have to scale it to ten million people hitting the same endpoint on a Saturday morning. That’s a different universe.
In that rollout, we got delayed by roughly three to four months because of performance testing. We had to measure behavior at scale and make changes in the back end to handle it.
That delay wasn’t failure. It was reality.
If you hide reality from executives, they stop trusting you. If you bring them reality early, and give them options, they start treating you like a partner.
My tactic is always to give executives enough information to make decisions. Leaders make decisions every day, often without all the information they want. Your job is to reduce that fog and put them in a position where they need to own the decision.
That’s executive work.
AI: Use It Like an Adult
Right now, “AI” is the buzzword that makes me nervous.
AI is immature. It doesn’t know what it doesn’t know. It’s a very good liar. Left unsupervised, without oversight, it would be a complete disaster.
So if your CEO is chasing AI because it sounds like labor reduction, you need to ground the conversation.
I’m optimistic about AI when it’s applied to long-running workflows, exception handling, and improving data quality. I think generative AI can help create standardized data with strong business rules that can be reused over and over again. That’s practical. That’s measurable.
I’ve also seen automation used to crush cycle time. In one case, an e-commerce product setup process that used to take weeks of elapsed time and a huge amount of manual effort got reduced down to hours.
That’s the point. You remove tedious work. You redeploy people into higher-value work. You reduce the overall cost to operate.
But you have to earn the right to do it.
Garbage in, garbage out. You can’t just codify broken business processes in the interest of doing everything at once. Go find the boring foundational functions and start small. Once the foundation is solid, then you do the high-visibility projects everyone wants to show off.
That sequence is how you keep trust.
The People Side: Listening Is a Power Move
A lot of store managers, plant managers, warehouse leads, and frontline supervisors have the same reaction when IT shows up.
They get scared. Or they get angry. Or they vent.
Most of the time, they’re not anti-technology. They’re sick of being let down by it.
So when you walk in, you don’t start by telling them what’s wrong. You start with empathy. You say, “Show me the day in the life. Show me what’s happening. Where is this frustrating?”
And then you deliver.
If someone takes the risk to show you the pain and you don’t fix it, they’ll mistrust you forever. If you include them in the solution, they become your advocates. They’ll even help you make the business case for investment, because now it’s their problem too.
That’s how you bridge Operations and IT. You stop treating the frontline as “users” and start treating them as the best source of truth you have.
Your Next 30 Days: How to Start Acting Like an Executive
If you’re overwhelmed, you don’t need a massive transformation program next week. You need a shift in how you operate.
Start by protecting a block of strategic time every week. Put it on your calendar. Guard it. If you can’t protect two hours, you’re going to stay in the loop forever. You need space to think.
Then build a one-page financial story for your CEO and CFO. Keep it simple. Talk about downtime and what it did to productivity. Talk about the biggest manual workarounds you see and why they exist. Talk about the foundational risks that will bite later if you ignore them. Add the first small set of fixes you can deliver fast, because quick wins buy you oxygen.
Next, pick one “boring” foundational problem and fix it end-to-end. Network stability, device lifecycle, identity and access, meeting room reliability. Choose something the business feels every day. Deliver it. Communicate it. Make the improvement visible. That’s how you build trust without begging for it.
Then run one controlled pilot for a higher-value change. Keep it small. Test it with real users. Measure what changed using the business’s own metrics. If it’s a process, measure the time it takes to execute. If it’s customer-facing, measure interventions, errors, and rework. Show the results, even if they’re messy, and use what you learned to shape the next phase.
Finally, get yourself back into the meetings where decisions are made. You don’t earn that by demanding a seat. You earn it by showing up with clarity and options. Executives respect people who help them make decisions.
Where Coaching and Outsourcing Fit (And Why It’s Not a Failure)
A lot of internal CTOs avoid outsourcing because it feels like an admission of weakness. I see it differently.
If you’re spending all your energy on commodity work, you’re spending your executive potential on tasks that don’t require an executive. You’re also training the business to see you as the helpdesk.
Sometimes the smartest career move you can make is to offload the “keeping the lights on” work so you can lead what actually matters: the roadmap, the architecture, the business rules, the prioritization, the financial narrative, and the change management.
At The Narrative Group, we can act as a full IT department for smaller mid-sized organizations, or we can provide fractional CIO/CTO support. The point isn’t to replace you. The point is to give you breathing room and executive air cover, while we help stabilize the foundation and build a plan that leadership can fund.
Because when your environment is stable and your story is clear, you become very hard to ignore.
The Bottom Line
If the business thinks of you as the fix-it person, your job is to change the narrative.
Follow the money. Understand the value chain. Map the data flows. Define the business rules. Start with boring foundational functions and deliver. Pilot the risky stuff. Measure productivity in real terms. Keep your stack current and evolvable with vanilla patterns. Use AI with supervision and discipline.
Do that, and something shifts.
People stop calling you only when things break.
They start calling you before decisions get made.
Frequently Asked Questions
Why is it so hard to find time for strategic planning?
It is the ‘70% Problem.’ Industry data reveals that nearly 70% of IT budgets are consumed by maintenance and operations. You are stuck keeping the lights on. Leadership coaching focuses on reversing this ratio – stabilizing the noise so you can finally buy back the bandwidth for innovation.
How do I stop being seen as just the ‘fix-it’ person?
You must break the ‘Hero Syndrome’ loop. If you personally catch every falling knife, you train the organization to view you as a firefighter, not an architect. Credibility shifts when you stop reacting to symptoms and start mapping the work to remove the root causes of the friction.
How do I justify IT investments to a skeptical CFO?
Adopt a ‘Financials First’ mindset. Executives do not buy technical correctness. They buy risk reduction and outcomes. Stop talking about server patches and start translating downtime into lost payroll or delayed revenue. When you connect technical debt to the P&L, you stop defending costs and start protecting enterprise value.
Does outsourcing support mean I have failed to manage my team?
No. Hoarding commodity work is a trap that kills executive potential. Smart leaders offload the ‘keeping the lights on’ tasks to managed services to free up mental space for high-value strategy. It is not an admission of weakness. It is a deliberate decision to focus your leverage where it matters.
Why does ‘Shadow IT’ keep growing despite my security policies?
Shadow IT is a speed signal. It rarely happens out of malice. It happens because the business views IT as too slow or bureaucratic. You cannot fix this with policy documents. You fix it by mapping the value chain and removing the operational friction that forces departments to work around you.