A broken strategy doesn’t always look like failure—it often looks like “we’re working hard” while momentum quietly disappears. In this article, Jef Menguin shows where to start by naming what’s off and asking the right questions before you add more projects. Practice the shift and share it at work so your next quarter runs on clear choices, not heroic effort.
Let me bring you inside a familiar company.
You run an IT solutions firm in the Philippines. You’ve been in the market for years. Clients know your name. Your website says you’re a “trusted IT solutions provider.”
The team is busy.
Sales is chasing RFPs. Engineers are deploying projects. Support is handling tickets and outages.
On paper, things look okay. Revenue is not crashing. But it is not growing the way you expected.
Then something starts to bother you.
A big client renews— but only the basic contract, not the higher-value services you hoped for.
Another client says, “We’re exploring a cloud-first partner,” even though you’ve been handling their infrastructure for a long time.
Your people are working hard. But you feel a quiet truth: this doesn’t feel like winning.
You ask your leadership team one question:
“In your own words, how are we trying to win in the next three to five years?”
One says, “We want to be a one-stop shop.” Another says, “We want to be experts in cybersecurity.” Another says, “We want to grow managed services.” Someone else says, “We want to focus on government accounts.”
All of those can be good. But they are not the same game.
That’s what a “broken strategy” looks like in a trusted IT provider.
Not chaos. Just a growing sense that everyone is rowing hard—but not in the same direction.
How Strategy Breaks in a Growing IT Firm
Strategy usually doesn’t break because people are lazy.
It breaks quietly over time.
You add new services to answer client requests. You accept different kinds of projects “for now.” You chase government bids, then private bids, then SME packages.
Every step makes sense in the moment. But slowly, your choices blur.
Your website still says “trusted IT solutions provider.” But inside, no one can answer, in plain language:
- “Trusted by whom?”
- “Trusted for what?”
- “Trusted in which game?”
You see the signs:
Sales tries to sell everything to everyone. Engineers are stretched across too many technologies. Support is drowning in commitments you made to “close the deal.” Your best people are tired—not because they hate the work, but because the work feels scattered.
The plan is full. The strategy is fuzzy.
You Don’t Fix a Broken Strategy by Adding More Services
When leaders feel something is wrong, the first instinct is often:
“Let’s add a new offer.” “Let’s enter a new vertical.” “Let’s sign a new vendor partnership.”
But you don’t fix a broken strategy by adding more things to sell.
You fix it by going back to choices.
Strategy is not your list of services. Strategy is your small set of linked answers to five questions:
What does winning really mean for us, as an IT provider? Where will we play (industries, segments, geography, problems)? How will we win in a way that makes us the only real choice for the right clients? What must we be very good at (capabilities, strengths)? What systems and habits must support us (processes, tools, culture)?
When your strategy feels broken, at least one of these answers is weak, blurred, or outdated.
Maybe “winning” is still defined as “hitting revenue targets” instead of “owning a specific space in the client’s mind.” Maybe you’re playing in too many arenas. Maybe your “how to win” sounds like every other IT provider’s promise. Maybe you’re trying to be good at everything from cabling to cloud architecture. Maybe your systems reward closing deals, not building long-term, high-value relationships.
Until you revisit those choices, new services will only add noise.
Step One: Face What’s Really Happening in Your Business
Before you fix anything, you have to look at reality—not the deck, not the brochure.
Ask questions like:
Where are we actually winning today? Which clients or segments are easiest to serve and happiest with us? Which deals are profitable, not just big? Where are we quietly losing—renewals, expansions, referrals?
Listen to your frontline teams.
What do clients really call you for? When do they say, “We trust you”? When do they bring in other vendors instead of you?
You’re not looking for a story that flatters you. You’re looking for the story that is actually happening.
If you skip this step, your “new strategy” will just be a more elegant version of wishful thinking.
Step Two: Name What’s Actually Broken
Once you’ve faced reality, you can name the problem.
Sometimes the problem is clarity. Your people cannot say in one clear sentence what game you are trying to win.
Sometimes the problem is focus. You have too many “priorities”: managed services, cloud, cybersecurity, telco, custom development, hardware, government bids, everything for everyone.
Sometimes the problem is work. Your daily operations do not match your supposed strategy. You say you want to be “trusted advisors,” but most of your time is spent on low-margin break-fix work and endless urgent requests.
Sometimes the problem is rhythm. You made good choices once, but you never revisited them. No quarterly check-ins. No learning loops. You’re following a 12-month plan as if the tech and business landscape will stay still.
Often, two or three of these are tangled together.
Naming them turns “our strategy is failing” into something more useful:
“Our choices are fuzzy here.” “We’re trying to win in too many places.” “Our work hasn’t shifted to match our promises.” “We’re not learning fast enough from execution.”
Step Three: Go Back to the Five Questions—with New Eyes
This is where you reuse 5 Strategy Questions for Leaders Who Play to Win, but with the truth on the table.
For a trusted IT provider, that might sound like:
What does winning mean for us now? Is it “grow revenue by any IT project,” or “become the go-to partner for mid-market companies in specific industries who need ongoing, secure, cloud-first operations”?
Those are different games.
Where will we play? Are we serious about a few industries (for example, healthcare, logistics, or finance) and sizes of clients? Or are we still saying yes to every RFP we see?
How will we win? Is our edge speed? Deep specialization? Security? Integration? Local presence with global standards? We can’t be number one in everything.
What must we be very good at? Is it 24/7 managed services? Modernizing legacy systems? Securing hybrid environments? Supporting specific business apps?
What systems must support us? Do our sales incentives, delivery methods, documentation, and support processes actually reinforce our choices—or do they pull us back to “project of the month”?
You don’t need perfect answers on day one. You need sharper, more honest ones than you have now.
Step Four: Build a Simple Game Plan for the Next 12 Months
Once your choices are clearer, you don’t need a 100-page rollout.
You need a simple game plan that says:
“For the next 12 months, these are the three to five plays we will run to express and test our strategy.”
For example:
We will focus on becoming the most trusted managed services partner for mid-sized companies in two industries. We will reduce low-margin, one-off break-fix work that does not build long-term value. We will invest deeply in one or two capabilities that match our way of winning (say, secure cloud migrations and ongoing monitoring).
Then you ask:
Which clients do we double down on? Which kind of deals do we stop chasing? What needs to change in sales, delivery, and support so this game plan is real—not just talk?
The game plan does not replace your strategy. It gives your updated strategy a body to move with.
Step Five: Let the Team Feel the Shift
A repaired strategy that stays in the boardroom will break again.
Your engineers, project managers, salespeople, and support staff must feel the change in their day-to-day work.
That doesn’t mean a three-hour lecture on strategy frameworks.
It might sound like this in a team meeting:
“Before, we tried to say yes to almost every IT project we could handle. That helped us grow, but it also stretched us thin and confused our message.
From now on, our game is different:
We want to be the most trusted managed services partner for mid-sized companies in [chosen industries]. That means:
- we design offers that keep clients with us for years,
- we say no to projects that distract us, and
- we invest our energy in the systems and skills that support this.
Here’s what that means for your role…”
Then you connect for each group:
For sales: which opportunities to prioritize, and which to walk away from. For engineers: which certifications and technologies matter most now. For support: what “trusted” means in handling tickets and communication.
They don’t need the whole story of your strategy repair. They need to know what game you’re now serious about—and how they can help you win it.
Step Six: Protect a Rhythm That Keeps You Honest
If you stop here, the old pattern will quietly return.
So you build a simple strategy rhythm for your IT firm.
Every quarter, you and your key people ask:
Is this still the right game, given what we’re seeing with clients and competitors? Which plays are clearly working? Which are not? What will we adjust in the next 90 days based on what we’ve learned?
You don’t throw away your strategy every quarter. You let it learn.
You treat each quarter as a test of your choices—not as a race to finish a to-do list from last year.
Over time, this rhythm does something important: it keeps you from becoming “just another IT solutions provider” who promises everything and stands for nothing.
You Don’t Need to Burn Everything Down
Fixing a broken strategy for a trusted IT solutions provider doesn’t mean:
Firing half your team. Dropping every service you offer. Rebranding every six months.
It usually means something simpler but deeper:
Facing what is really happening. Naming whether the problem is clarity, focus, work, or rhythm. Revisiting your choices using the five questions. Building a clear game plan for the next 12 months. Helping your people see the new game in their daily work. Protecting a rhythm so your strategy keeps learning.
Piece by piece, your strategy becomes something you can explain, your people can execute, and your clients can feel.
So if you’re looking at your IT business today and thinking, “We’re busy, but I’m not sure we’re really winning,” the next step is not another service to add to your website.
It’s a quiet, honest question:
Where, exactly, is our strategy broken—and what is the first conversation we need to have to fix it?
If you’re building a business and you are playing to win…
Let’s install one shift that moves metrics.
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