You’ve signed the contract. The new software is live. Everyone’s excited.

Fast forward 90 days. Half the team isn’t using it. The other half is using it wrong. The old spreadsheet is still the source of truth. Sound familiar?

Most software implementations fail not because of the software but because of the first 90 days.

Here’s how to get them right.

Why Implementations Fail

Let me list the patterns I see constantly:

No clear owner. Everyone assumes someone else is managing the rollout. Nobody is.

Training happens once. People forget 80% of what they learned in training within a week.

No consequences for not using it. If the old way still works, people will use the old way.

Too much, too fast. Trying to use every feature from day one overwhelms everyone.

No measurement. Nobody knows if the implementation is succeeding or failing.

Every failed implementation I’ve seen involved at least three of these factors.

The 90-Day Framework

Before Day 1: Preparation

Don’t go live until you’ve done this:

Assign an owner. One person is responsible for implementation success. Not a committee. One person. With authority to make decisions and time allocated to the project.

Define success. What does “successful implementation” look like? Be specific:

• 90% of team logging in weekly
• All deals entered in the new CRM
• Monthly reports running from the new system
• Old spreadsheet retired

Plan training. Schedule training sessions. Multiple sessions. Different depths for different users.

Set a go-live date. Communicate it. Make it real.

Days 1-14: The Launch

Week 1: Go live with core users first. These are your champions who’ll help others. Work out the obvious problems before expanding.

Week 2: Broader rollout. Training sessions. Available support for questions. Daily check-ins to catch issues early.

Critical actions:

• Be available for questions constantly
• Fix configuration problems immediately
• Document workarounds for edge cases
• Celebrate small wins publicly

Days 15-30: Building Habits

This is the danger zone. The novelty has worn off. People drift back to old habits.

Keep pressure on adoption. Check usage daily. Follow up with non-users personally.

Remove the old option. If you’re replacing a spreadsheet, make the spreadsheet read-only. Don’t let people operate in both worlds.

Second training round. People have real questions now. Run a “two weeks in” training session focused on actual problems encountered.

Address complaints directly. Some complaints are valid and need configuration changes. Others are resistance that needs managing.

Days 31-60: Refinement

Optimize workflows. Now that people are using the system, you’ll see what’s clunky. Adjust.

Build automations. Set up the time-saving features that make the new system better than the old way.

Create documentation. Write down how your team uses this tool. Company-specific guides, not generic vendor documentation.

Identify power users. Some people have figured it out. Make them informal mentors for others.

Days 61-90: Normalization

Measure against success criteria. Are you hitting your targets? Be honest.

Address stragglers. Some people are still resistant. This requires direct conversation. Is it a training issue, attitude issue, or legitimate tool issue?

Review and optimize. What’s working? What needs adjustment? What features aren’t being used that should be?

Plan for ongoing maintenance. Who handles questions after the “implementation” is done? This can’t be nobody.

The Owner’s Playbook

If you’re the implementation owner, here’s your weekly rhythm:

Daily (first 30 days):

• Check usage dashboards
• Answer questions and fix problems
• Follow up with non-users

Weekly:

• Team check-in (what’s working, what’s not)
• Usage report to leadership
• Configuration adjustments

Every two weeks:

• Training or refresher session
• Review of adoption metrics
• Planning for next phase

After day 30, daily checks can become weekly.

Dealing with Resistance

Some people won’t want to change. Expect this. Handle it.

The “I don’t have time” objection. Acknowledge it’s real. Then explain that the time invested now saves time later. Be specific about how.

The “the old way was fine” objection. Maybe it was. But the decision was made. Your job is to make the new way work, not debate the decision.

The “this is too complicated” objection. This might be valid. Simplify what you’re asking them to do. Focus on the essentials first.

The “it doesn’t work for me” objection. Listen carefully. Sometimes this reveals real gaps in the tool. Sometimes it’s just resistance in disguise.

The silent non-user. The most dangerous. Check usage logs. Have a direct conversation.

When to Call It

Sometimes an implementation isn’t working, and you need to acknowledge it.

Warning signs at 90 days:

• Less than 50% adoption despite effort
• Key workflows still happening outside the system
• Growing user frustration rather than decreasing
• Business impact from implementation problems

If you hit these, pause. Assess whether the problem is fixable or fundamental. Get help if you need it.

Not every implementation can be saved. Better to acknowledge failure at 90 days than drag it out for a year.

Common Fixes

If adoption is low: Check if training is adequate. Check if the system is configured for how people actually work. Sometimes you need to simplify and restart.

If data quality is bad: Create better input forms. Add required fields. Review and correct data monthly until habits form.

If people are using it wrong: More training on the specific issues. Maybe simplify the process.

If leadership isn’t engaged: This is harder. Implementations without leadership backing rarely succeed. You might need to escalate.

After 90 Days

Implementation isn’t done at day 90. It becomes maintenance.

Create ongoing rhythms:

• Monthly usage review
• Quarterly training for new features or staff
• Annual assessment of whether the tool still fits

The work continues. But after 90 good days, you have a foundation to build on.

Your Homework

If you’re about to implement new software:

• Assign an owner
• Define measurable success criteria
• Build a 90-day plan
• Schedule training (not just one session)
• Commit to daily attention in the first month

Implementation success isn’t about the software. It’s about the work you put into the first 90 days.