Stress Testing Your Strategy Before You Ruin Everything
Your strategy document is probably lovely. Proper formatting, clear goals, maybe even a SWOT analysis. The question nobody asks: what happens when it meets your actual organisation?
As a rule of thumb, a leadership team will spend three months crafting a strategy to let’s say move upmarket. Enterprise customers, higher ASPs, the whole playbook. They will have slides and a lot of conviction. What they rarely will have is a single conversation about what would happen when their best customer success person quit because enterprise deals take nine months and her bonus was tied to quarterly closed deals.
The strategy is fine. The stress test is missing.
Here’s what I mean. You finish the strategy document, send it round for comments, get a few “looks good” replies from people who skimmed it during their commute. Then you jump straight into translating it for product, for sales, for marketing. You write OKRs. You update roadmaps. You create Jira tickets. You’ve gone from strategic intent to tactical execution without checking if the thing can actually survive contact with your organisation.
That gap is where strategies go to die.
The bit everyone skips
Strategy documents assume a clean world. They assume your engineering team will happily pivot from feature work to platform investment. They assume customers will pay more because you’ve decided you’re premium now. They assume your CFO won’t panic when ARR dips for two quarters while you retool.
Reality is more chaotic. Your engineer lead has six months left on her technical debt roadmap and she’s already told her team they can finally fix the authentication system. Your biggest customer is threatening to churn if you don’t build their specific feature. Your board wants growth this quarter, not next year.
The strategy doesn’t fail because it was bad. It fails because nobody checked if it was loadable into your actual context.
This is where stress testing comes in. Not the financial kind, where you check if you can survive a recession. The kind where you deliberately try to break your strategy before you launch it. You poke holes. You surface conflicts. You make the problems visible when they’re still theoretical instead of discovering them six months in when you’re haemorrhaging cash and the exec team is demanding to know what went wrong.
Most teams skip this because it feels negative. You’ve just spent weeks building consensus around a strategy and now you want to... criticise it? Worse, you want to get a room full of people to imagine it failing?
Yes. Exactly that.
What you’re actually looking for
When you stress test a strategy, you’re hunting for three types of problems.
First, the logic gaps. Does this actually make sense? If we move upmarket, do we have the sales infrastructure to close enterprise deals? Do our contracts support multi-year agreements? Can our product handle enterprise security requirements? These are table-stakes questions but they get skipped when everyone’s nodding along to the big vision.
Second, the resource conflicts. Every strategy implies trade-offs but most documents gloss over them. “We’ll focus on enterprise AND maintain our self-serve motion.” Right. With which engineering team? Your five-person product org is already underwater. Something has to give. What gives? And who decides?
Third, the organisational antibodies. Your company has an immune system. It rejects things that don’t fit. If your strategy requires moving slowly and deliberately but your culture rewards shipping fast and iterating, you’ve got a problem. If your strategy needs cross-functional collaboration but your org structure creates silos with conflicting goals, you’ve got a problem.
These aren’t unknowable. They’re predictable. But you have to look.
The pre-mortem that actually works
Forget the complicated frameworks for a minute. The simplest stress test is the pre-mortem. You gather the people who’ll execute the strategy (not just the ones who wrote it) and you tell them this: “It’s 18 months from now. The strategy failed. Completely. Tell me what went wrong.”
I know it sounds grim. It works because it flips the psychology. Instead of defending the strategy, people start spotting risks. Instead of group optimism, you get group paranoia. Which is exactly what you need.
Here’s how to actually run one. Don’t overthink it.
Give people five minutes to write down, privately, why the strategy failed. Actual reasons. Specific failures. “The product couldn’t scale to enterprise loads.” “Sales couldn’t articulate the value prop.” “Marketing got defunded halfway through the rebrand.” “Our best PM quit because they hated enterprise work.”
Then go round the room. Everyone shares one failure scenario. No debate yet, just capture. You’ll notice patterns. Technical risks cluster. Political risks cluster. Market risks cluster.
Now vote. What are the three most dangerous failure modes? Not the most likely (people are terrible at probability). The most dangerous. The ones that would actually kill the strategy.
For those three, you write prevention plans. Not someday. Today. Before you translate the strategy into OKRs or roadmaps. If the biggest risk is “engineering can’t deliver the enterprise features we need”, what’s the mitigation? Do you hire differently? Descope other work? Build in six-month buffer? Partner with someone who has the tech?
The goal isn’t to eliminate risk. You can’t. The goal is to make the trade-offs explicit and manageable rather than implicit and surprising.
When your strategy assumes things it shouldn’t
I ran a pre-mortem once where the top failure scenario was “customer success can’t handle the volume”. The strategy document had us doubling customer count but hadn’t mentioned staffing. When we dug in, turns out finance had already frozen CS headcount. The strategy was relying on an assumption (we’ll hire more CS) that was factually wrong.
We found that in a 60-minute meeting. Imagine finding it six months in, when you’ve already signed the customers and your CS team is drowning.
This is the pattern. Strategies make assumptions. Optimistic ones. The market will respond this way. Competitors will do that. Our team can handle this. Our customers want that. Some assumptions are fine. Some are load-bearing. You need to know which.
Walk through your strategy and list every assumption. Then categorise them. Which ones, if wrong, would tank the whole thing? Those are your load-bearing assumptions. Now test them. Not with research necessarily (though sure, if you can). Test them with the people who’ll actually encounter reality. Ask your sales team if they think customers will pay 40% more for the new positioning. Ask your engineers if they can build the platform features in the timeline. Ask your customer success team if they can support a completely different customer profile.
Listen to their doubt. That’s signal.
The competitor move you’re ignoring
Most strategies have a section on competitive landscape. It’s usually backward-looking. “Here’s what they do today.” Fine. Now tell me what they’ll do when you execute your strategy.
You’re moving upmarket? Your biggest competitor will probably defend that territory. How? Price cuts? Feature parity? Bundling deals? FUD campaigns about your stability? They won’t sit still.
You’re launching a new product line? Someone will copy it or undercut it or tell customers it’s a distraction from your core competence.
You’re changing your pricing model? Your customers will compare you to alternatives under the new model, not just the old one.
This isn’t paranoia. It’s basic game theory. But I see strategies all the time that assume the market is static. It’s not.
The stress test here is war gaming. Get a small group (three to five people) and split them. Half play your company executing the strategy. Half play your main competitor responding. Give them 30 minutes to sketch the moves and countermoves.
You’ll learn things. Like maybe your competitor has deeper pockets and can sustain a price war longer than you thought. Or maybe they’re distracted by their own strategic mess and won’t react at all. Or maybe the real threat isn’t them, it’s a new entrant you haven’t thought about.
The point isn’t to predict the future perfectly. It’s to stress test whether your strategy is robust to different competitive responses or whether it only works if everyone else cooperates.
The resource conversation most are avoiding
Every strategy requires resources. Money, people, time, attention. Most strategy documents hand-wave this. “We’ll need investment in X.” Sure. From where?
Your finance team has a budget. Your product team has a roadmap. Your engineering team has a backlog. Your marketing team has campaigns planned. Your strategy is now asking all of them to pivot. Something has to give.
This is the conversation that makes people uncomfortable. Because it forces prioritisation. Real prioritisation. Not “let’s do both” or “we’ll work harder”. Actual choices.
If you’re moving upmarket, you’re probably deprioritising features for your current mid-market customers. Are you OK with that? Will they churn? How much churn is acceptable? If you’re investing in platform scalability, you’re delaying new product features. For how long? Will that cost you deals?
The stress test here is making the trade-offs explicit before you commit. List what you’re gaining from the strategy. Now list what you’re giving up. Not in abstract terms. In concrete terms. “We’re giving up feature X, which 30% of customers have requested, to build infrastructure that benefits no one directly for six months.”
If you can’t stomach that trade-off, your strategy isn’t real yet.
The cultural friction you’re pretending isn’t there
Strategies often require cultural change. “We need to become more customer-centric.” “We need to move faster.” “We need to be more data-driven.”
Cool. How?
Culture isn’t a switch you flip. It’s reinforced by structure, by incentives, by who gets promoted, by what gets celebrated, by what gets punished. If your strategy requires behaviour change but you haven’t changed the underlying systems, you’re asking for cultural transformation through sheer willpower.
That doesn’t work.
I watched a company try to shift from project-based work to outcome-based work. The strategy was clear. The exec team was aligned. But the bonus structure still rewarded shipping features, not achieving outcomes. Performance reviews still asked “what did you deliver?” not “what impact did you have?” The Jira workflow was still organised by project.
Six months in, everyone had reverted to project-based thinking because that’s what the system rewarded.
The stress test here is asking: what behaviours does this strategy require? Now audit your systems. Do they support those behaviours or fight them?
If your strategy needs cross-functional collaboration but your org chart creates silos with separate goals, that’s friction. If your strategy needs long-term thinking but your OKR cycles are quarterly with no rollover, that’s friction. If your strategy needs experimentation but your culture punishes failed bets, that’s friction.
You can either change the systems or change the strategy. You can’t ignore the friction and hope it resolves itself.
What to actually do this week
Right. Enough theory. Here’s what you can do before your strategy becomes roadmaps and OKRs.
Block two hours with your core execution team. Not the strategy authors. The people who’ll have to make this real. Product, engineering, sales, customer success, marketing. Whoever touches the work.
Run the pre-mortem. It’s 18 months out. The strategy failed. Why? Capture everything. Vote on the top three killers. Build mitigation plans for those three today.
Then test your load-bearing assumptions. List them. Pick the three that, if wrong, would tank the strategy. Figure out how to validate them before you commit significant resources. Maybe it’s a pricing experiment. Maybe it’s a customer interview sprint. Maybe it’s a technical proof of concept. Small, fast tests.
Finally, audit one system for cultural friction. Pick the most obvious one. If your strategy needs behaviour X but your incentive structure rewards behaviour Y, that’s your starting point. You don’t have to fix everything. Fix the one that’ll cause the most pain.
This isn’t comprehensive. It won’t catch every risk. But it’ll catch enough to avoid the stupid failures. The ones where everyone looks back and says “we should have seen that coming.”
You should have. You didn’t because you skipped the stress test.
The bit that stays uncomfortable
Here’s what nobody tells you about stress testing strategies. It doesn’t make the strategy better in some clean, satisfying way. It makes it messier. More qualified. More realistic.
You start with a crisp vision. Three priorities. Clear goals. After stress testing, you add caveats. “Unless competitor X responds by cutting prices.” “Assuming we can hire five engineers by Q2.” “Provided customer success can scale with us.”
That feels worse. It is better.
Because those caveats are real. They exist whether you name them or not. Naming them means you can watch for them, plan for them, mitigate them. Ignoring them means you get surprised six months in when reality doesn’t match your document.
Most strategies fail not because they were wrong but because they were brittle. They only worked in one very specific set of conditions that never quite materialised. The ones that survive aren’t necessarily smarter. They’re just more honest about what could break them and they have contingencies.
Stress testing won’t guarantee success. Nothing will. But it’ll help you spot the failures that were always coming. And sometimes that’s enough.
Next time you finish a strategy document and everyone’s nodding along, that’s your signal. The nodding means you haven’t found the conflicts yet. Run the pre-mortem. Find them. Then decide if you still want to run the strategy, or if you need to rewrite it before it rewrites itself in production.