Another year of helping businesses with their tech stacks. Dozens of companies. Hundreds of tools evaluated. Thousands of hours of implementation.

Here are the patterns I keep seeing.

Lesson 1: The Problem Is Rarely the Software

When someone says “our CRM doesn’t work,” the CRM usually works fine. The problem is:

• Nobody owns it
• Training was inadequate
• Data quality is poor
• Processes don’t match the tool
• Expectations were unrealistic

I’ve seen companies switch CRMs three times and have the same problems each time. Because the software wasn’t the problem.

Before blaming the tool, examine the people and process around it.

Lesson 2: Complexity Creeps

Every business I work with has more tools than they need. It doesn’t start that way.

Someone adds a marketing tool. Someone else adds a project tool. Another team needs their own solution. Each addition is justified. The total becomes unjustifiable.

The only defense is active curation. Regular review. Willingness to say no. Someone who owns the overall stack, not just individual pieces.

Lesson 3: Switching Costs Are Always Higher Than Expected

The vendor quote for the new system is one number. The actual cost is five times that.

Migration, integration, training, productivity dip, unexpected issues. Every time.

I’ve stopped being surprised. I now plan for it. Clients should too.

This doesn’t mean you should never switch. But factor in real costs before deciding.

Lesson 4: Free Tiers Create Expensive Habits

Companies start on free tiers. They grow. They accumulate data and processes tied to the free tool. Then the tool raises prices or restricts features.

Now they’re locked in with habits they can’t easily change.

Free is fine for starting. But be intentional about it. Know when you’ll graduate and to what.

Lesson 5: The Sales Process Misleads

Software sales demos show best cases. Reference customers are cherry-picked. Pricing is optimistic.

I’ve seen companies buy based on demos and regret it within months.

The antidote: talk to real customers (not just references). Run real trials with real data. Question everything that sounds too good.

Lesson 6: Nobody Reads Documentation

Every tool has help articles. Nobody reads them.

Result: companies use 20% of their software’s capability because they don’t know the rest exists.

The fix isn’t more documentation. It’s regular training, internal champions, and actually dedicating time to learn tools properly.

Lesson 7: Data Quality Is Everything

Garbage in, garbage out. I’ve said it a hundred times this year.

The best CRM in the world is useless with duplicate contacts and missing fields. The best analytics platform means nothing with inconsistent data entry.

Data quality isn’t a technology problem. It’s a discipline problem. Someone needs to own it.

Lesson 8: Integration Is Underinvested

I consistently see companies with five, six, seven tools that don’t talk to each other.

Staff manually copy data between systems daily. Reports require exporting and combining. Things fall through cracks.

Basic integration, even just Zapier connecting a few things, would save hours weekly. But it’s never prioritized because it’s not urgent.

It’s urgent. You’re just not seeing the cost.

Lesson 9: Annual Contracts Aren’t Always Better

Vendors love annual commits. They offer discounts.

But annual contracts remove flexibility. When you realize the tool isn’t working, you’re stuck for months.

For new tools, I recommend monthly until you’re sure it works. The premium is worth the flexibility.

Lesson 10: The Biggest Tool Isn’t the Best Tool

Enterprise software is designed for enterprises. The features that justify the cost require scale you don’t have.

I regularly see 20-person companies on Salesforce Enterprise or Microsoft E5 licensing. They use 10% of it. They overpay massively.

Right-sizing matters. The best tool is the one that fits your actual size and needs.

Lesson 11: Implementation Is the Hard Part

Buying software is easy. Implementing it is hard.

Implementation includes:

• Configuration for your needs
• Data migration
• Integration with other systems
• Training staff
• Getting adoption
• Iterating based on real usage

Most failed implementations fail in adoption, not technology.

Lesson 12: Vendors Want to Upsell

Every vendor interaction includes an upsell attempt. More seats. Higher tier. Additional modules.

This is fine, it’s their job. But it means vendor advice isn’t neutral.

Get outside perspective before major decisions. Whether that’s consultants, peers, or just thorough independent research.

What I’d Tell Every SMB

Based on everything I’ve seen:

1. Use fewer tools better. Consolidate where possible. Master what you have.

2. Assign owners. Every major system needs someone responsible for it.

3. Invest in training. Not once. Ongoing.

4. Integrate your core systems. Even basic automation saves hours.

5. Review annually. Your needs change. Your stack should too.

6. Don’t overbuy. The right tool is the one that fits, not the biggest one.

7. Fix process before blaming tools. The software usually isn’t the problem.

8. Budget for real costs. Implementation is expensive. Price increases are coming.

9. Prioritize security basics. MFA, password managers, backups. Non-negotiable.

10. Make deliberate choices. Don’t let your stack happen to you. Curate it.

Looking Ahead

The trends for next year are clear: AI tools becoming practical, security requirements increasing, consolidation making sense, costs rising.

But the fundamentals don’t change. Use the right tools for your size. Implement them properly. Keep them maintained.

Technology serves the business. Not the other way around.

Here’s to another year of right-sized tech stacks.