Question 1 of 16
Strategic Clarity
Do you know what you're building and for whom?
QUESTION 1 OF 16
We chase opportunities (deals, markets, partnerships, features) that don't align with where we're trying to go long-term.
For example: Pursuing enterprise deals when your strategy is SMB, building one-off features for big customers, exploring new markets before winning your current one, or saying yes to partnerships that distract from core business.
5Never, everything ladders to clear strategy
4Rarely, mostly disciplined
3Sometimes, occasional distractions
2Often, frequently off-strategy
1Always, no strategic filter
Strategic Clarity
Do you know what you're building and for whom?
QUESTION 2 OF 16
If you asked 10 employees "what's our 3-year goal and why it matters," you'd get 10 different answers.
5Never, everyone knows the North Star
4Rarely, strong alignment
3Sometimes, some confusion
2Often, widespread confusion
1Always, nobody can articulate it
Strategic Clarity
Do you know what you're building and for whom?
QUESTION 3 OF 16
Leadership debates the same strategic questions quarter after quarter without resolution.
For example: Enterprise vs SMB, product vs services, pricing model changes, or go-to-market strategy—the same debates resurface every quarter without getting settled.
5Never, decisions stick
4Rarely, mostly settled
3Sometimes, some rehashing
2Often, constant redebating
1Always, nothing gets resolved
Strategic Clarity
Do you know what you're building and for whom?
QUESTION 4 OF 16
Our product roadmap is driven by whoever screams loudest (customers, sales, execs) rather than strategic priorities.
5Never, strategy drives roadmap
4Rarely, mostly strategic
3Sometimes, reactive decisions
2Often, very reactive
1Always, completely reactive
Organizational Alignment
Is everyone pulling in the same direction?
QUESTION 5 OF 16
Sales closes deals that create problems for CS/Product, or Product ships features Sales can't sell.
For example: Sales signs customers who aren't a good fit and CS struggles to retain them, Product builds features no one asked for and Sales doesn't know how to position them, or Sales promises capabilities you don't have yet.
5Never, tight alignment
4Rarely, good feedback loops
3Sometimes, some misalignment
2Often, frequent friction
1Always, constant cross-functional fires
Organizational Alignment
Is everyone pulling in the same direction?
QUESTION 6 OF 16
Different departments have goals that conflict with each other.
For example: Sales compensated purely on bookings regardless of customer fit, CS measured on retention of customers that shouldn't have been sold, Product rewarded for shipping features not revenue impact, Marketing measured on lead volume not lead quality, or Finance focused on margins while Sales pushes for growth at any cost.
5Never, goals are fully aligned
4Rarely, mostly aligned
3Sometimes, some conflicts exist
2Often, significant conflicts
1Always, everyone optimizing different things
Organizational Alignment
Is everyone pulling in the same direction?
QUESTION 7 OF 16
When we say something is a "top priority," nothing actually changes—the same work continues.
For example: You declare "customer onboarding is our #1 priority" but don't add headcount there, don't pause other projects, and don't reallocate budget—so nothing actually shifts.
5Never, priorities drive resource shifts
4Rarely, resources usually shift
3Sometimes, priorities are loose
2Often, priorities are meaningless
1Always, priority = lip service
Organizational Alignment
Is everyone pulling in the same direction?
QUESTION 8 OF 16
Important decisions get delayed for weeks because we keep debating or waiting for someone to weigh in.
5Never, decisions are fast
4Rarely, mostly timely
3Sometimes, some delays
2Often, slow decision-making
1Always, decisions take forever
Execution Predictability
Can you deliver consistently or is everything heroic?
QUESTION 9 OF 16
When a key person goes on vacation or leaves, their area falls apart.
For example: Deals stop closing when your top rep is out, implementations fail when your best CSM leaves, or you have no idea how someone did their job because everything was in their head and nothing was documented.
5Never, documented processes
4Rarely, mostly documented
3Sometimes, some dependence
2Often, very hero-dependent
1Always, completely person-dependent
Execution Predictability
Can you deliver consistently or is everything heroic?
QUESTION 10 OF 16
We're surprised by business results (missed forecast, unexpected churn, sudden pipeline gaps) because we don't have early warning signals.
5Never, strong predictive signals
4Rarely, good visibility
3Sometimes, some surprises
2Often, frequent surprises
1Always, constant firefighting
Execution Predictability
Can you deliver consistently or is everything heroic?
QUESTION 11 OF 16
Deals require heavy discounting, executive involvement, or last-minute heroics to close.
For example: You personally close deals every quarter, reps routinely give 20%+ discounts to hit targets, or every deal needs a custom proposal and pricing negotiation to get across the line.
5Never, consistent value-based selling
4Rarely, clean deals
3Sometimes, some heroics needed
2Often, most deals need help
1Always, every deal is a battle
Execution Predictability
Can you deliver consistently or is everything heroic?
QUESTION 12 OF 16
New hires take 6+ months to be productive because we lack clear onboarding/training.
5Never, fast ramp (1-3 months)
4Rarely, mostly fast
3Sometimes, varies by person
2Often, slow ramp
1Always, very long ramp times
Growth Sustainability
Does the business model actually work?
QUESTION 13 OF 16
Customers churn or don't expand because they never fully adopted the product or realized value.
For example: When you dig into why customers left, they were only using 30% of features, never had a success plan, or couldn't articulate the ROI they got from your product.
5Never, strong adoption and value realization
4Rarely, good adoption
3Sometimes, mixed results
2Often, adoption struggles
1Always, poor adoption/value realization
Growth Sustainability
Does the business model actually work?
QUESTION 14 OF 16
We don't actually know our customer acquisition cost or payback period with confidence.
5Never, we track this tightly
4Rarely, mostly clear
3Sometimes, somewhat fuzzy
2Often, unclear metrics
1Always, no real visibility
Growth Sustainability
Does the business model actually work?
QUESTION 15 OF 16
Customer implementations frequently go sideways, requiring major intervention to save them.
For example: CS routinely pulls all-nighters to fix implementations, you personally jump on calls to rescue projects, or "90-day onboarding" regularly stretches to 6+ months with lots of firefighting.
5Never, smooth implementations
4Rarely, mostly smooth
3Sometimes, some issues
2Often, frequent problems
1Always, implementation chaos
Growth Sustainability
Does the business model actually work?
QUESTION 16 OF 16
We're burning cash and not confident we can reach profitability or successfully raise our next round.
5Never, strong unit economics or clear path
4Rarely, good trajectory
3Sometimes, some concerns
2Often, worried about runway
1Always, cash is a major stress
Scale-Ready
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