Avoiding the Second “Oh Shit” Meeting: How to Align Strategy and Execution Early
There are two kinds of “Oh shit” meetings in go-to-market planning.
The first happens in October or November, when the board says, “We need to grow by 50 percent next year,” and the executive team sits down to model how that might happen. It becomes painfully clear that what’s historically been achieved doesn't line up with what's being asked. That moment is uncomfortable, but it’s manageable. There's still time to adjust hiring plans, rebalance pipeline targets, or recalibrate expectations. It's your chance to make the plan real.
The second “Oh shit” meeting is worse. That one happens in June. Pipeline is short, ramped reps are underperforming, and your Q3 target now looks like a stretch. At that point, you're not planning. You’re reacting.
Avoiding the second “Oh shit” meeting is about more than working harder. It’s about building better models, tracking assumptions early, and creating a system of accountability that keeps you from drifting into misalignment. Here’s how to do that.
Understand the Difference Between Top-Down and Bottom-Up Planning
Top-down planning starts with the number. The board wants $50 million next year. The CFO builds a spreadsheet and backfills how many reps you’ll need to get there. It’s fast and often the first input in budget planning. But it assumes a level of control that rarely matches reality.
Bottom-up planning starts with what’s possible. What have your teams historically achieved? What conversion rates can you bank on? How many opportunities does your BDR team actually source in a given quarter? It’s slower to build but reflects the current state of the business more honestly.
The problem is most companies pick one. That’s the mistake.
You need both. And more importantly, you need to overlay them early.
Build your bottom-up model using trailing 12-month data for each segment and channel. Map out conversion rates, velocity, average selling price, and capacity. Then put that next to the board’s top-down number. That’s where the first “Oh shit” moment lives. And that’s good. You want that moment early.
Now you can see the gap and get specific. Is it a pipeline coverage issue? A hiring issue? A velocity problem in enterprise? Are you relying on marketing to deliver 60 percent of pipeline next year but only budgeting for a five percent increase in program spend?
You can’t fix what you can’t see. This process surfaces the gap while there’s still time to close it.
Document Assumptions Like They Matter (Because They Do)
Once you’ve aligned on a plan, the next critical step is documenting the assumptions behind it. This sounds simple but it’s often skipped. People agree in the room and move on. Three months later, no one remembers what they agreed to.
Was marketing supposed to double MQL to pipeline conversion rates? Were you banking on improving SDR productivity by 20 percent through a new tool or certification program? Was expansion pipeline supposed to make up the delta in Q2?
Write. It. Down.
Create a shared document that maps out the big assumptions by team, by segment, and by quarter. Link them directly to the model. If you’re planning to hit $2 million in mid-market pipeline from outbound next quarter, spell out exactly how that happens. How many reps, how many meetings, what conversion rates, and what messaging or campaign changes are expected to drive that lift?
Now you’re not just building a forecast. You’re building a testable hypothesis.
Track Assumptions Like You Track Pipeline
Every company has a pipeline report. Not every company has an assumption tracker. That’s the gap.
Build a cadence where you revisit your key assumptions at least monthly. We recommend using a tool like Domestique’s Demand Council model. It’s a recurring meeting designed to review performance across all pipeline sources, aligned to what each team committed to in the plan. It’s not a data readout. It’s an accountability meeting.
You’re not just asking, “Are we on track?” You’re asking:
Is conversion from MQL to SAO improving like we expected?
Did the outbound messaging adjustments impact demo sets?
Is expansion pipeline tracking with the new CSM comp plan?
And most importantly: If not, what are we doing about it?
This is how you spot slippage before it becomes a miss.
Use Capacity Planning as a Living Model
Most capacity planning models get built, approved, and then forgotten. That’s a waste. Your model should live as a dynamic tool that evolves as your execution plays out.
At Domestique, we recommend treating the capacity plan as a single source of truth. If your outbound conversion assumptions fall flat, update the model. If your enterprise ASP outperforms expectations, update the model. This keeps the plan real and helps teams course-correct without waiting for Q2 surprises.
Final Thought
The second “Oh shit” meeting happens when you ignore the warning signs from the first one. The fix is not magical. It’s about operational rigor, honest math, and proactive tracking.
Align top-down ambition with bottom-up reality. Document assumptions clearly. Revisit them often. And hold your teams accountable to the things they said would be true.
Because if those things aren’t true, the number won’t be either. And by then, it’s not a meeting. It’s a postmortem.
