You finished your three-year strategic plan. Locked in the budget for next year. The leadership team left the retreat feeling good about the direction.
One problem: your head of IT wasn't in the room.
Maybe they were invited to the "implementation" phase. Maybe they'll see the plan after the priorities are set. Maybe you handed them a budget and said "make it work." Whatever the sequence, you've already made the mistake.
According to Harvard Business Review, 67% of well-formulated strategies fail due to poor execution. Not bad strategies. Well-formulated ones. And one of the most reliable ways to join that 67% is to treat technology leadership as a downstream function rather than a strategic partner.
Let's be clear about what strategic planning actually is. The goal is to define intent....."This is what we intend to do over X period of time." Your departmental strategy plans should align directly with your corporate strategy. The budgets exist to provide the monetary resources to actualize that intent. The whole process is about aligning action with intent.
If you exclude any one of your business units from this process, you are automatically going to be misaligned. And if you're misaligned, you will very likely not hit your targets.
Here's the question I always come back to.... What percentage of your business runs on technology?
If the answer is "most of it" (and in 2026, the answer is almost always "most of it"), then building a strategy without your CIO, VP of IT, Director, or whoever owns your technology decisions is like building a house and inviting the structural engineer after the foundation is poured. You might get lucky. But the smart money says you won't.
BCG found that early technology leadership involvement delivers 154% higher success rates on strategic initiatives. McKinsey's data shows that 57% of top-performing IT organizations have senior leaders very involved in strategic planning, compared to only 17% in bottom-quartile performers. That's not correlation. That's causation.
So why do so many small and mid-sized businesses still keep IT outside the strategy room?
Is it that you feel they're not capable of contributing? That they don't understand the business? That they only think in terms of systems and tickets and uptime? Or is it that you view technology as a necessary burden rather than a source of competitive advantage?
Whatever the reason, it's costing you.
Let me give you an example of what happens when IT gets left out.
I worked with a company that was chomping at the bit to "digitally transform," although they had yet to define what that actually meant for their organization. Their marketing team had a technology idea and jumped over IT to pitch it directly to the CEO. It was out of scope, not part of the strategy. No budget or plan for it.
The CEO was not an operations person. He didn't understand resource balance or project capacity. He green-lit the project with Marketing and then called the head of IT to let him know it was happening. The message was something along the lines of "we need digital transformation, so we're doing this, and I just wanted to let you know." Explicitly, IT was told they were not needed in the project.
Less than a year later, when they attempted to launch a proprietary product visualization tool, guess whose help and budget they suddenly needed? IT.
The tool required extremely expensive and robust computers to operate, specialized headsets, and custom network configuration. IT had to scramble to make it work, which meant diverting resources from other critical projects. They managed to pull it off. But when IT finally got their hands on the tool, they found multiple flaws. Things only their staff would have spotted. But by then it was too late. The tool was put in front of customers within a couple of days.
The result: ,000 in expenses. A couple days worth of usage. Not a single penny in additional sales. Not one. One customer, after trying it out, flat out asked "Why did you do this?" It was a flop.
That's what happens when action is misaligned with intent. And that's what happens when technology leadership is treated as a service desk instead of a strategic function.
Your IT lead (assuming they're beyond general helpdesk) probably knows more about the operational reality of your business than almost anyone else in the building. They see how the systems connect. They know where the manual workarounds are. They understand which processes are held together with duct tape and which ones actually scale. Aside from maybe a CEO, they're the person most likely to see across departmental boundaries.
And even if you don't have a dedicated IT leader, your general IT staff sit in the middle of the day-to-day for every department. They see the friction. They hear the complaints. They know what's actually happening versus what the dashboards say is happening.
Here's another scenario: Your sales team is stuck. Cold calling isn't producing. Your farming techniques are stale. You need to grow revenue by X% over the next twelve months and nobody in the room has a new idea.
Now imagine your IT lead is in that conversation. They ask what data you're bringing to your presentations. How you're sharing it. Whether you've looked at tools that could reduce your operational overhead or automate the grunt work your sales team is doing manually. They mention a platform your team has never heard of that could change the economics of your outreach.
That's not a fantasy. That's what happens when your technology and innovation experts are in the room where strategy gets built rather than receiving a summary afterward.
The inverse is also true. If your IT leader finds out about your growth plans after the budget is finalized, they can't plan the infrastructure to support it. They can't flag the systems that won't scale. They can't budget for the upgrades you'll inevitably need six months from now when you realize the foundation wasn't built for what you're trying to do.
You've just set yourself up to be the CEO who shows up saying "We had a plan, but our systems couldn't support it."
If you've never had technology leadership in the strategy room, here's how to start: Bring them in early. Earlier than the rest of your team. Brief them on the process. Explain what strategic planning looks like at your company and where they can contribute. Let them sit in the thick of the debate. Let them watch how priorities get whittled down.
If you don't have internal IT leadership, hire a fractional CIO or CTO to be part of your discussions. Not after you've completed the strategy. At the beginning. They'll need access to sensitive information, so do what you need to do for NDAs and confidentiality. But get them in the room.
You might be surprised how they change the course of the conversation.
Or you can keep doing what you've been doing. Keep the technology people focused on keeping the lights on. Keep handing them budgets after the decisions are made. Keep wondering why your strategic initiatives stall out somewhere between the retreat and the quarterly review.
Sixty-seven percent of strategies fail. The math doesn't change just because you finished the retreat feeling good about it.
About the Author
Raphael Savastano is the founder and principal consultant of ROFONIC LLC. With 25+ years in IT, 16 years in leadership, including 8 years as CIO scaling technology for a global manufacturer from M to 0M. He now helps growing companies get executive-level technology and operations leadership without the full-time cost. Want to know where your technology actually stands? Take the Founder’s IT Reality Check →
