Chip Royce, Flywheel Advisors
If your 2026 revenue plan is going to miss, that decision is probably being made right now, not in Q3 when the board gets tense or in Q4 when an “all‑hands push” appears. It gets made in the quiet moment where you look at a top‑down number, nudge a few cells in a spreadsheet until the math ties out, and decide that with enough effort you can make it work.
Many “ambitious but rational” business plans are already structurally wrong before Q1 even starts. You cannot execute your way out of that design‑time mistake, no matter how hard your team works.
Planning Risk Lives In Your Sales Assumptions
The core issue sits inside your 2026 sales planning assumptions. On paper, your plan looks rigorous. You held a board review, your finance and RevOps teams produced detailed models, and you reviewed slides covering win‑rates, average contract values, sales cycle lengths, and ramp curves for new hires. There may be scenario analyses, sensitivities, and a professional‑looking deck. You felt the rigor.
In reality, most of the risk is concentrated in a much smaller space: the specific assumptions you allowed into the model to goal seek and justify your target revenue.
Individually, those assumptions sound reasonable. You may be expecting win‑rates to rise due to “improved enablement.” You might be counting on average contract values to climb as you “move up‑market.” You may be assuming that sales cycles will compress thanks to “better qualification” or pricing. Marketing is expected to generate more volume with more budget and channels. New sales reps are modeled to ramp faster because you now have a playbook and better on-boarding.
You defend each of these changes in isolation. The problem is that your current go‑to‑market system has probably never delivered all of them together, at that scale, at the same time. When you stack them in a single model and call the result a plan, what you actually have is a multi‑leg parlay bet dressed up as a spreadsheet. That is where the 2026 miss hides.
How “Ambitious but Rational” Becomes an Unrealistic Revenue Target
That is also where unrealistic revenue targets hide. Inside the company, almost no one uses that phrase. Instead, you hear that the plan is “a stretch, but achievable,” or “aggressive, but not crazy.” People reassure each other that if you track tightly and respond quickly, you will fix gaps in‑year. Under the surface, though, a different dynamic is running.
The Number Exists Before the System
In many companies I work with, the 2026 top‑line is set first by investor expectations, long‑term models, or prior commitments that have already been socialized. The planning exercise then becomes an exercise in backing into that number, not starting from what the current GTM system has actually proven it can carry. The question in the room shifts from “What can this system credibly deliver?” to “How do we make this target look achievable?”
That is when sales planning assumptions start getting bent. A 24 percent win‑rate becomes 30 percent. An eight‑month cycle becomes six. A realistic hiring curve is replaced by a version that assumes near‑perfect recruiting and zero bad hires. The spreadsheet still ties out. The system underneath has not changed.
Narrative Gravity Inside the Planning Room
Once you have told the board that you can do $X in 2026, the story locks in. Backing away from it feels like admitting expectations were mis‑set or that leadership lacks confidence. Everyone in the room has a quiet incentive to round optimism up and round risk down, and to let “better execution” function as the glue that holds the story together. In my experience, no one intends to be misleading. They are solving a narrative problem while believing they are solving a planning problem.
Untested Combinations Masquerade as Confidence
Planning decks often show historic performance and then a modest line projecting improvement: slightly higher win rates, slightly larger deals, slightly shorter cycles. Every individual shift looks small. What almost never gets asked explicitly is whether your go to market capacity has ever supported those shifts at this altitude, all at once, in the real world.
If the answer is no, you are not dealing with incremental tweaks. You are dealing with a stack of unearned sales planning assumptions. The risk is not that one of them might be wrong. The risk is that you need most of them to be right, in combination, for the number to hold.
Go To Market Capacity: What Your System Has Actually Earned
This is where experienced operators bring a different lens. When I review annual sales forecasts, I am less interested in whether the math ties out than in what your system previously delivered. I look for proof.
In practice, that means asking if your team delivered revenue within striking distance of this level in any prior period, with anything like the proposed mix of product, segment, and headcount. I look for evidence that win‑rates and cycle times have held at the levels you are now assuming for more than a quarter or two. I compare claimed ramp curves for new hires against your actual history with similar hiring bursts.
The focus here is go to market capacity rather than aspiration. Your GTM engine is not infinitely elastic. It is made of people with specific skills, channels with specific reach, a brand with a particular level of recognition, and processes and infrastructure with specific friction. You can extend that capacity over time. You cannot do it instantly because a model suggests you should.
When a plan quietly assumes capacity that has never existed, or increases that have never been earned, or stability that has never been demonstrated, it concentrates sales plan risk into the design itself. At that point, the miss is less a question of whether it will happen and more a question of when and by how much.
Sales Plan Risk Lives in Design Time, Not In‑Year Execution
Most CEOs I speak with do not see this as a design problem. They experience it within the fiscal year as an execution problem. Risk feels real when Q1 comes in light, when pipeline quality looks off, or when forecast calls get harder. It feels real when the Q2 board deck is harder to write than expected. So, the natural belief is that you are missing because execution is off, and that the controllable variable is effort: more activity, faster response, better focus.
By the time those symptoms are obvious, the real decision that created them is months behind you.
In Q1, early gaps are easy to rationalize as seasonality, deal slippage, or timing. No one wants to reopen the 2026 plan in February, so you tell yourselves that you will make it up. In Q2, you move to a familiar set of “execution fixes.” You turn up outbound activity, fund more demand generation programs, pull promotions forward, revise compensation to “incentivize focus,” and spin up enablement sprints and more deal reviews. Those moves can help at the margin. They cannot conjure a version of your GTM system that has never existed.
By Q3, the pattern is usually set. Pipeline numbers may look large on paper, but late‑stage quality is suspect. Managers spend more time defending and adjusting forecasts than coaching. Functional leaders have competing explanations, ranging from product gaps to pricing, from pipeline mix to macro conditions. Internally, the story tilts hard toward execution. Marketing hears that it is not producing enough qualified leads. Sales hears that it is not pushing hard enough or using the playbook. Customer success hears that upsell and expansion should be contributing more. Energy drains as people debate who is underperforming rather than whether the 2026 plan was ever structurally sound.
In Q4, triage takes over. You strip future quarters to pull every deal you can into the current year. You offer discounts to accelerate decisions. You freeze non‑essential spend and pause hiring. You spend more time managing expectations and rewriting the 2027 narrative to absorb the miss. You may claw back some ground, but you are not fixing 2026. You are managing the optics and consequences of a decision that was effectively locked in the day the plan was signed.
The Hard Physics Behind “You Can’t Execute Your Way Out”
The belief that you can “fix it in this quarter through execution” runs directly into hard constraints that no amount of pressure can quickly change.
Hiring and ramp have real limits. Even if you find excellent people, they can only be recruited, onboarded, and made productive at a finite speed. Demand generation cannot double overnight without running into channel saturation, audience fatigue, or brand recognition issues. Sales cycles only shorten sustainably when there is a structural reason for them to do so, such as better fit, clearer value, or a materially cleaner buying process. They do not shorten just because the plan assumes a one‑month compression.
On top of this, the GTM system has lag. Many of the decisions you make early in the year will not be fully visible in the numbers until later quarters. By the time that lag catches up to you, your degrees of freedom are narrow.
This is why you cannot execute your way out of a plan that was structurally wrong on day one. It is not a question of motivation, discipline, or willpower. It is a question of physics inside your particular GTM system.
The Human Cost of a Plan That Was Wrong on Day One
The consequences for your teams are not abstract. When a plan is structurally wrong, your people carry the cost.
When you sign an unrealistic plan, a quiet deal gets made. Leadership knows the number is aggressive. The board hears a confident story about execution upside. The team is told that the plan is ambitious but achievable. Everyone walks away slightly uneasy, yet aligned enough to move forward.
Then the year happens. Sales teams grind through quotas that were rooted in assumptions the system had not earned. Marketing is asked to deliver demand at a scale the current brand and channels struggle to support. Revenue operations spends the year trying to reconcile volatile forecasts with a model that assumed away most of that volatility. Almost no one says out loud that “the 2026 plan was poorly conceived.” Instead, postmortems frame the miss as a story about effort, focus, or speed of response. The year becomes, in effect, a morality tale about execution, not a structural lesson about design.
People remember that. They remember the feeling of spending a year pursuing a number that, in hindsight, was never realistically on the table. They remember being told that the plan was real, then watching leaders explain the miss in terms that never acknowledge that original design error. That memory changes how they respond to the next stretch plan you bring them. They will nod in the meeting. They may not truly believe you. One structurally wrong plan can quietly erode trust in every future plan, even if you eventually fix the underlying architecture.
How Leaders and Operators Read the Same Plan Differently
Against that backdrop, it is useful to contrast how a typical leadership team reads a plan with how an experienced operator reads the same document.
Most leadership teams focus on whether the model ties out mathematically, whether the narrative aligns with strategy and investor expectations, and whether the assumptions feel “within reason.” The questions are often about whether the plan is too conservative, whether enough is being asked of the field, or whether you are taking enough risk. The plan is treated primarily as a story to be sold and defended.
An operator treats the plan as a system to be stress‑tested. I care less about the polish of the deck and more about where the GTM system has actually demonstrated capacity at or near the proposed altitude. I look for assumptions that are truly earned versus those that are aspirational. I look for places where the model is effectively borrowing from the future and labeling that gap “execution.”
I notice when the plan assumes multiple improvements that have never co‑existed in your environment: better win‑rates, faster cycles, higher ACVs, and higher volumes all moving in the right direction simultaneously, without any structural change that would justify that combination. I look for capacity cliffs where revenue curves rely on new hires producing at near steady‑state levels far earlier than your own history supports. I pay attention to constraints such as segments, channels, or territories that the model treats as infinitely scalable even though the last 18 months of your own data say otherwise.
The conclusion, more often than not, is not that the team simply needs to work harder. It is that the company is about to sign a plan the current GTM system cannot carry. If you do that, the miss is largely pre‑decided.
The One Question Most 2026 Planning Decks Never Answer
All of this leads to a simple, uncomfortable point: many 2026 revenue misses will not be caused by Q2 or Q3 execution failures. They will be caused by architectural mistakes embedded in the plan at design time. The rigor of your spreadsheets is not the same as the reality of your system. If the plan itself is structurally wrong, your people are about to carry a year of pressure for a miss they never had a fair chance to avoid.
Before you head into Q1 with full conviction in your 2026 number, it is worth asking a question that most planning decks glide past: if you stripped out every sales planning assumption your GTM system has never delivered, every unproven uplift in win‑rate, ACV, cycle time, volume, and ramp. What number would actually be left on your 2026 plan? And if that number is meaningfully different from the one you have already shared with your board and your team, is the gap really an execution problem, or is it an architectural one?
As CEO, you are the only person in the room who can insist on that level of honesty before the year begins.
Are You Willing To Find Out If Your Sales Plan Was Ever Real?
This is for the small group of CEOs who already suspect the 2026 miss won’t be decided in Q3, but in the plan you’re about to sign.
If you want an operator’s read on whether your current GTM system has actually earned the sales planning assumptions inside your 2026 number, and whether the miss is already baked in, then we should talk.
FAQ: Structural Risk in Revenue Plans and Sales Planning Assumptions
How do I know if our annual sales plan is actually unrealistic versus just “a stretch”?
The fastest tell is whether your 2026 target is something your current GTM system has ever come close to carrying in real life, even for a quarter. If the answer is no, and the only way you get there is by stacking several positive shifts in your model at once – higher win‑rates, bigger ACV, shorter cycles, faster ramp, more volume – then you are not looking at “a stretch,” you are looking at an unproven configuration that lives only in the spreadsheet.
A stretch plan still has some proof at altitude: you have seen parts of it before, together, in your own data. An unrealistic plan is one where the model relies on combinations your system has never demonstrated. When the story on the slide depends on your best‑case for almost everything happening at the same time, you should assume you are dealing with formalized hope, not earned capacity.
If most of the risk is baked in at design time, what is the point of all the execution work we do in‑year?
Execution still matters; it just cannot compensate for a plan that was architecturally wrong on day one. In‑year execution is how you discover how far off the original design was, and it is how you recover as much ground as possible without breaking the system or the team. You will see pockets of improvement, local wins, and places where better management genuinely tightens things up.
What execution cannot do is rewrite the physics of hiring, ramp, demand generation, and sales cycles on the calendar the board would prefer. If the 2026 model assumed capacity that doesn’t exist, or multiple performance improvements that have never co‑existed in your environment, then “push harder” turns into a year of pressure with limited structural change. The real leverage lives before the year starts, in whether the plan respects what your GTM engine has actually earned the right to assume.
We did a detailed bottom‑up model. Isn’t that enough to de‑risk our annual sales plan assumptions?
A detailed model is necessary, but it is not sufficient. Models are very good at tying numbers together and very bad at telling you whether the underlying system has ever behaved the way the model now assumes it will. In most planning cycles I see, the real danger is not that leaders skipped bottoms‑up work; it is that they treated “the math ties out” as proof the plan is real.
The real proof comes from system performance, not spreadsheet structure. The question is whether your historic data shows this GTM configuration – this mix of segments, product, headcount, channels, and process maturity – carrying anything close to the 2026 number with the win‑rates, ACV, cycles, and volume you are now assuming. If the answer is no, then the model is an elegant story about what you hope the system will do, not evidence of what it can currently do.
If I’m worried our 2026 plan is structurally wrong, what is the right conversation to have with my team and board?
The conversation you want is not “Can we work harder?” or “Which lever should we pull first?” The conversation you want is, “What has this GTM system actually proven it can carry, and where are we asking it to behave in ways it never has before?” That shifts the focus from fault‑finding in Q3 back to design‑time reality in January.
With your team, that sounds like being transparent about where assumptions are unearned, and about the difference between stretch and fantasy. With your board, it sounds like being explicit about the structural risk embedded in the current plan versus the capacity the system has already earned. The goal is not to lower ambition; it is to stop asking your people to spend a year chasing a number the system was never designed to hit, and to reserve “execution pressure” for plans that are at least structurally real.y too early.