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“Truth Hurts” Why Your Plan’s Great, Till It’s Gotta Be Great

By Adam Chickman May, 26 2024

Every revenue plan looks solid in December.

You map the number, align the teams, run a few back-of-the-napkin models, and lock it in. Everyone’s fired up.

Then the year starts.

And a few months later, someone’s asking:

“Wait… how are we this far off?”

The truth? Your plan was great—until it had to be great.

Let’s talk about why that happens—and how to build a plan that actually holds up under pressure.

Great Plans Are Rare. Static Plans Are Common.

Planning is essential. It aligns your GTM engine, sets expectations, and keeps Finance and the board in sync.

But most plans aren’t really designed to work. They’re built to look good in a board deck—not to serve as a live system that helps you steer.

And when things go off track (which they always do), there’s no mechanism to see it coming or adjust in time.

Let’s Talk March Madness

Think about your NCAA tournament bracket.

Nobody in history has ever filled out a perfect one. Not once.

Why? Because predicting 63 game outcomes in a row is statistically insane.

Now think about your annual revenue plan.

Twelve months of GTM performance across dozens of channels, regions, and reps?

You’re not going to nail every assumption.

The takeaway isn’t “don’t plan.”

It’s: build your plan with the expectation that you’ll need to adapt. That means crafting it with the right structure and granularity—so you can actually track it, adjust it, and steer in real time.

The 5 Reasons Most Revenue Plans Break

1. You Can’t Track It—Especially the Leading Indicators

Revenue is a lagging indicator. Pipeline? Also lagging if your sales cycle is 30+ days. If you’re identifying gaps after the quarter starts, it’s already too late.

A good plan must be built to track:

  • Pipeline creation rate

  • Win rate trends by stage and team

  • Average sale price movement

  • Lead volume by channel

If your plan doesn’t include this level of detail, it can’t be tracked—and it won’t be corrected until it’s too late.

2. There’s No Timeline Discipline

Planning $10M in pipeline is one thing.

Knowing when that pipeline needs to land is another.

If marketing creates a surge of opps in month three of the quarter, but it takes 60 days to close… you’re missing your number.

A real plan includes specific timing around lead and opp creation, aligned to conversion durations and sales cycles.

3. No KPI-to-Owner Mapping

If you can’t point to who owns a metric, you can’t improve it.

  • Who owns pipeline from outbound?

  • Who’s responsible for win rate on renewals?

  • Who’s watching ASP in SMB segments?

Plans break when metrics float unclaimed. Accountability dies on impact.

4. No Bottom-Up Validation or Capacity Modeling

Top-down planning is common:

“We need $12M. Hire 24 AEs at $500K each.”

But:

  • Can we generate enough pipeline to support that?

  • Do we have the SDRs, the marketing budget, the product maturity?

  • What’s the realistic ramp and productivity curve?

Plans that aren’t rooted in actual capacity, demand, and executional reality are just spreadsheets of wishful thinking.

5. No Granular Source Modeling

Most plans stop at:

“We need $X in pipeline.”

But they don’t break it down:

  • Which channels will drive it?

  • Which sub-channels? Which segments?

  • At what ASPs and conversion rates?

  • By what date?

If your plan doesn’t go far enough upstream, you won’t see risk until it’s too late to react.

How to Make Your Plan Great

“A great plan doesn’t just say where you’re going—it makes sure you can tell when you’re off course, and helps you reroute in time.”

Here’s how to build a plan that doesn’t just survive Q1—it fuels performance all year:

1. Build Granularly Enough to Track It

Include both outcome and input metrics:

  • Revenue, pipeline, opps created

  • Lead volume, win rates, ASP, stage-level conversion

Include timing: when pipeline and opps need to land, not just how much.

Include channel mix: where pipeline is expected to come from.

That level of granularity sets the foundation for real-time tracking.

2. Assign KPI Ownership

Every major metric should have a clear owner.

  • Marketing owns inbound pipeline pacing.

  • SDRs own opp creation by segment.

  • Sales leaders own win rate uplift by team.

No metric should exist without someone being responsible for it.

3. Validate Capacity from the Bottom Up

Before locking your number:

  • Pressure-test quotas against historical rep productivity

  • Model ramp curves, lead flow requirements, pipeline coverage ratios

  • Sanity-check every top-down assumption with bottom-up inputs

4. Model Channels, Sub-Channels, and Timing

Break pipeline targets into:

  • Channels (Marketing, SDR, Partnerships)

  • Sub-channels (Paid Search, Events, Inbound SDR)

  • Timing (which month each needs to deliver what volume)

If you don’t know where it’s coming from or when—it won’t come.

5. Operationalize It in a Revenue Navigation Platform

Here’s the key distinction: your plan won’t track itself.

A spreadsheet is just a model.

But if built the right way—with the granularity, timing, and ownership above—it becomes the foundation for live tracking and dynamic adjustment inside a revenue navigation platform like RevdUp.

  • Reps not ramping as fast as expected? Adjust hiring timelines.

  • Pipeline from outbound down 30%? Shift support to high-performing channels.

  • Win rate stalling in one stage? Diagnose the bottleneck and coach to close it.

Great plans aren’t static—they’re structured to respond to reality.

Revenue Navigation makes that possible.

Bottom Line

A forecast isn’t a plan.

A spreadsheet isn’t a strategy.

And a great plan doesn’t just help you start the year—it helps you win it.

Build your plan the right way, and pair it with a platform that keeps you on course.

Because your plan might look great in the board deck.

But it’s gotta be great when it’s live.

Let’s make sure it is.

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