Some mistakes I see once. Others I see constantly. Here are the recurring patterns that cost businesses time and money.

Mistake 1: Buying for the Company You Hope to Be

A 15-person company buys Salesforce Enterprise because they plan to be 150 people someday.

Three years later, they’re still 20 people. They’ve paid enterprise prices the whole time. They use basic features.

The fix: Buy for today’s needs with 12 months of growth buffer. Not three-year projections. You can upgrade later.

Mistake 2: One Person Making All Tech Decisions

The CEO picks the CRM because they liked a demo. Nobody else was involved. The sales team hates it.

The IT person picks the project management tool. Nobody else uses it.

The fix: Involve actual users in selection. Their buy-in matters more than feature lists.

Mistake 3: Skipping the Trial

“The demo looked great. Let’s just buy it.”

Demos are controlled performances. Trials reveal reality.

The fix: Always trial with real data and real tasks. Never buy based only on demos.

Mistake 4: No Renewal Calendar

The contract auto-renewed. At a higher rate. With a 60-day notice period that passed unnoticed.

The fix: Maintain a calendar of every renewal. Set reminders 90 days before. Review every renewal intentionally.

Mistake 5: Death by a Thousand Subscriptions

$15/month here. $30/month there. Nobody tracks the total.

Until someone looks and finds $2,500/month in subscriptions, half of which are barely used.

The fix: Complete software inventory. Quarterly audits. One approval process for new tools.

Mistake 6: No Integration Strategy

Five tools, no connections. Data copied manually between systems. Errors accumulate.

The fix: Before adding any tool, ask how it connects to what you have. Build integration from the start, not as an afterthought.

Mistake 7: Training Once and Done

Two-hour training session during implementation. Then nothing.

Months later, half the team has forgotten. New hires were never trained.

The fix: Ongoing training. Refreshers. New hire onboarding. Internal documentation. Regular reinforcement.

Mistake 8: The Shadow IT Problem

Someone signs up for a free tool with their personal email. It becomes essential. Now your business data is in a personal account.

The fix: Centralize purchasing. Make it easy for people to request tools. Have clear ownership of all subscriptions.

Mistake 9: Ignoring Security Basics

No MFA. Passwords written on sticky notes. No offboarding process for departing employees.

The fix: MFA on everything. Password manager. Offboarding checklist that includes system access removal.

Mistake 10: Confusing “Hard to Use” with “Bad Software”

“This software is terrible.” Actually, the software is fine. Training was inadequate. Adoption was never enforced.

The fix: When a tool isn’t working, diagnose whether it’s the tool or the implementation before deciding to switch.

Mistake 11: The Free Tier Trap

Business builds critical processes on free tool. Tool changes free tier limits. Now business is stuck paying unexpected fees or scrambling to migrate.

The fix: Know the limits of free tiers. Plan for when you’ll graduate. Don’t build critical processes on shaky foundations.

Mistake 12: No Owner

Every tool needs an owner. Not a user. An owner.

Someone responsible for:

• Data quality
• User access management
• Configuration
• Training
• Evaluating ongoing fit

Without owners, tools drift into disrepair.

The fix: Assign explicit owners. Include system ownership in job descriptions.

The Common Thread

Most mistakes aren’t about picking the wrong software. They’re about:

• Poor planning
• Inadequate implementation
• Lack of ongoing maintenance
• Missing ownership

The same businesses that fail with Tool A would fail with Tool B. Because the failure isn’t in the technology.

Prevention Checklist

Before any new tool:

• Who will own this?
• Who will use it? Are they involved in selection?
• Have we trialled with real work?
• How does this integrate with existing tools?
• What’s the training plan?
• What happens at renewal?
• Is this right-sized for our current needs?

Answering these questions prevents most mistakes.

When You’ve Made the Mistake

Already made one of these mistakes? Options:

Fix it: Clean up data. Improve training. Build missing integrations. Assign owners.

Replace it: If the tool genuinely doesn’t fit, switch. But be honest about whether switching will solve the real problem.

Accept it: Sometimes the cost of change exceeds the cost of the problem. Document the limitation and work around it.

Not every mistake needs immediate correction. But understanding where you’ve gone wrong helps you avoid repeating it.

The Meta-Lesson

Tech stack management isn’t a one-time activity. It’s ongoing.

Regular review. Active maintenance. Deliberate decisions.

The businesses that avoid these mistakes aren’t lucky. They’re attentive. They treat technology as something to manage, not just something to buy.

Treat your tech stack with the same attention you give other business assets. That’s what separates companies that get technology right from those that don’t.