6 Reasons Most Success Plans Fail

Hi there,

Seneca once said, "If a man does not know to which port he's sailing, no wind is favorable."

I learned this the hard way.

Early in my Senior CSM role, I kicked off a large enterprise project with what I thought was a solid Success Plan: enable features, train users, track adoption, run check-ins.

But I never aligned with the executive stakeholder on what success meant to them.

Months later, during our first Business Review, the VP asked:

“How is this helping us reduce costs or improve space utilization?”

And I froze.

Because I didn’t know. My plan was focused on product adoption, not outcomes. I hadn’t defined what success looked like, or who cared most about seeing it.

That moment changed everything for me.

It’s not that I wasn’t working hard… I was. But without a shared goal, my efforts were misaligned. And that’s the issue with most Success Plans:

• They focus on the wrong things

• They miss the bigger picture

• They don’t reach the right people

They don’t fail because we don’t care. They fail because no one taught us how to build them right.

So, if you’ve ever wondered if your plan is actually working… you’re not alone.

Let’s break down the 6 most common reasons Success Plans fail—and how to fix them.

#1 – They Focus on Features, Not Business Outcomes

Success Plans often become checklists: enable integrations, complete training, update settings.

But features aren’t the goal, outcomes are.

❌ “Enable badge integration”
✅ “Gain occupancy insights to support a 10% lease cost reduction by year-end”

🛠 Fix it:
Ask: What business problem does this feature support?
If you can’t answer it, go back to discovery.

#2 – The Goals Are Vague

“Optimize real estate.”
“Improve experience.”
“Drive efficiency.”

These sound strategic, but they’re too broad to track. Without clear goals, it’s impossible to prove progress.

🛠 Fix it:
Turn them into SMART goals:

❌ “Optimize real estate”
✅ “Consolidate 3 floors into 2 by Q3 to reduce lease costs by 15%”

❌ “Drive efficiency”
✅ “Enable badge integration by Q1 and cut manual reporting by 80% by Q2”

Ask: How will we know this is working? If you can’t answer, it’s not ready for the plan.

#3 – They’re Too Tactical, Not Strategic

When your plan sounds like a task list, you’re operating at the wrong level. You’re not hired to list features, you’re there to drive outcomes.

🛠 Fix it:
For every action, link it to a business priority.

Tactical: “Enable badge data integration.”
Strategic: “Provide real-time occupancy data to reduce real estate costs.”

Let your plan show why these tasks matter.

#4 – They’re Shared with Champions, Not Executives

You might create a great plan, but if it never reaches a decision-maker, it won’t influence renewal or expansion.

Champions can support you, but executives drive outcomes and budgets.

🛠 Fix it:
Ask: “Who owns this initiative at the exec level?”
Tailor your plan to them. Strip the feature-speak and focus on ROI, business impact, and strategic milestones.

#5 – They’re Built Too Late

Success Plans aren’t rescue tools, they’re the foundation of everything you do. Waiting until renewal is a mistake. By then, the customer’s perception is already formed.

🛠 Fix it:
Start during onboarding, or even earlier. Use discovery and handoff notes to build a draft. Refine over time.

If you wait until a QBR, you’re reacting. Build early so you can lead the relationship with purpose.

#6 – You Build It Alone

If you build a plan solo and email it for review, don’t be surprised when no one uses it.

When the customer doesn’t contribute, they don’t feel ownership. And if you ignore your internal team, you miss crucial context.

🛠 Fix it:
Build your plan with both your customer and your internal stakeholders.

• Share a draft early and ask: “Does this reflect what you want to achieve?”

• Align with your AE and Sales to stay consistent with commitments

• Involve Implementation, Support, and Exec Sponsors where needed

Success is a team sport. The more voices involved, the more likely your plan will drive results.

What You Learned Today:

Success Plans fail when they:

• Focus on features instead of outcomes

• Rely on vague, unmeasurable goals

• Sound tactical instead of strategic

• Never reach executive decision-makers

• They are built too late

• They are created in isolation

A strong Success Plan isn’t just a document; it’s a shared agreement. A strategic blueprint. A tool to build trust, deliver value, and drive growth.

Coming Soon…

The Success Plan Playbook is almost here.

It’s the guide I wish I had years ago:

✅ A 7-step Success Plan framework
✅ Templates, discovery guides, and AI prompts
✅ Scripts to get executive buy-in
✅ Tools to track progress and prove impact

If you’re tired of guessing your way through planning, this playbook will show you exactly how to do it, step by step.

Want early access? Reply back to this email, let me know what your biggest challenge is when building Success Plans.

P.S. What do you think of the ebook cover? If you clicked, you know.

Best,