MASTER Risk Model - Learning Resources - Abilities

Which area or field do you primarily work in?

Strategic Planning

When was the last time your venture goals felt crystal clear—what created that clarity?

Do you think more in terms of tasks or outcomes—how does that shape your planning?

What assumptions are built into your current strategy—are they still valid today?

When has weak strategy undermined strong execution—what exactly went wrong?

Are your long-term goals still connected to your personal vision of startup success?

What drives your strategic choices—data, intuition, pressure, or precedent—and is it effective?

Operational Execution

When did you feel most productive in building your idea—what conditions made it possible?

When has execution failed in your startup—was the cause clarity, commitment, or coordination?

How often do you confuse being busy with being effective—what’s the difference for you?

Are your systems designed for consistency or speed—and does that fit your current stage?

What does “done well” mean in your venture—how clearly is it defined?

When has last-minute work damaged quality—what behaviors caused the pattern?

Performance Monitoring

When have you relied on data to guide a key decision—what made it credible and timely?

Do you rely more on intuition or metrics—how balanced is your approach to performance?

What signals do you ignore because they’re hard to quantify—what might they reveal?

When have you felt blindsided by performance issues—what early signs were missed?

Are you measuring outputs, outcomes, or just activity—what matters most for progress?

How well do current metrics reflect real progress—not just surface activity?

Market Analysis

When did you last feel ahead of your market—what signals gave you that advantage?

How well do you understand the buying process of your audience—what are the hidden drivers?

What hidden biases or assumptions shape your market view—how aware are you of them?

Have you been reacting to your market or anticipating it—how has that shaped results?

When have you misunderstood why a competitor succeeded—what blind spot misled you?

Are you paying attention to market signals or noise—what deserves your focus?

Branding and Positioning

When were you most proud of your brand so far—what design or message captured it best?

Does your audience recognize your positioning—or only remember your logo and visuals?

What’s the gap between how you see your brand and how your audience describes it?

How has your positioning evolved since starting—does it still reflect your direction?

Are you actively shaping your brand perception—or reacting to how others define it?

When did a brand win your loyalty—what can you learn from that?

Digital Marketing Strategy

When did your digital marketing feel impactful—what channels or tactics drove the outcome?

How well do current digital efforts align with your broader strategic goals?

Are you chasing trends or building consistent digital habits that compound over time?

Which part of your digital funnel underperforms—and what root cause explains it?

Do you prioritize producing more content or higher quality—and does that fit audience needs?

What digital experiment failed but taught you something useful for the future?

Negotiation Skills

When have you felt most confident pitching or negotiating—what preparation or mindset helped?

When have you given away too much too early—what fear or assumption drove the decision?

Do you default to creating win-wins or protecting your side—what’s your natural style?

What’s your biggest discomfort in negotiation—silence, pushback, rejection, or something else?

How well do you handle hearing “no”—as a dead end or a path to progress?

What signals throw you off balance most—how could you stay steady next time?

Customer Relationship Management

When have you built the strongest early customer connection—what behaviors created that trust?

What does “trusted partner” mean for you—and do your daily actions reinforce it?

Have you over-contacted or under-contacted a prospect—what did the outcome teach you?

Do you tailor relationship-building to each person—or rely on one-size methods?

Are you better at starting or sustaining engagement—how can you improve the other?

What small gesture or check-in mattered most to a prospect or early user—how could you repeat it?

Sales Strategy and Planning

When has your sales strategy felt most effective—what drove that clarity or focus?

Are you selling reactively or proactively—what forces are shaping your approach right now?

How often do you review and revise your sales plan after new learnings or shifts?

What part of your current strategy relies on old thinking—what needs a rethink now?

Are you chasing volume or quality in sales—does that match your offer and market?

Which internal process slows your execution—why does it still persist?

Talent Acquisition and Recruitment

When have you chosen a great collaborator—what part of the process made the difference?

Does your outreach attract the right potential collaborators or advisors—or just create noise?

What unconscious bias might be shaping your collaborator choices today?

Are your conversations with potential collaborators structured to test potential and fit—or focused only on past experience?

When did you rush a collaborator decision that failed—what signal did you overlook early?

How aligned are your collaborator selection methods with your venture’s mission and values?

Performance Management

When have you seen performance surge—what founder habits or management choices enabled it?

What signals do you rely on most to assess performance—are they truly objective?

How do you separate activity from impact—what criteria guide your evaluations?

Have you been clearer about tasks than expectations—how has that affected outcomes?

When have you let poor-performing tasks or approaches linger too long—what were the costs?

What role does trust play in collaborators’ willingness to act on feedback?

Learning and Development

When have you or a close collaborator grown rapidly—what support made it possible?

What prevents you from learning consistently—time, clarity, resources, or mindset?

Are development efforts tied to real venture needs—or just treated as checkboxes?

When did a learning activity feel like busywork—what design element was missing?

What’s the last skill you improved personally—what made it work well?

Do you model continuous learning yourself—or expect it only from others?

Financial Analysis and Budgeting

What’s your role in financial decisions, and where are you over- or under-involved right now?

When have your financial assumptions proven wrong—what lessons reshaped your outlook?

Do you see budgets as constraints or tools—how does that perspective affect choices?

Which parts of your budgeting process are guesswork—what would ground them better?

What metrics do you track, and which ones truly inform smart decisions?

Do your budgets reflect your strategy—or mostly past spending habits?

Risk Management

What financial risks are you comfortable discussing—and which do you tend to avoid?

Have you ignored a risk that later became critical—why didn’t it feel urgent at the time?

Are you more reactive or preventive with financial risk—and what drives that approach?

Do your decisions include worst-case scenarios—or only the expected outcomes?

When do you choose speed over safety—what signals make that trade-off worth it?

What biases affect how you view financial risk—how can you counter them?

Capital Allocation

Do you allocate based on history, urgency, or impact—what drives your current approach?

When has poor capital allocation limited results—what should have been different?

Are your time and energy investments aligned with your most critical outcomes?

What stops you from reducing resources for low-performing activities—habit, assumptions, or uncertainty?

How do you define “return” in your venture—profit, learning, or growth?

Do you feel confident justifying tough trade-offs—why or why not?

Supply Chain Management

Where are you most vulnerable in your supply chain—logistics, sourcing, or communication?

Do you rely on single suppliers for critical inputs—why haven’t you diversified yet?

What would a 10% demand surge break tomorrow—where is your system most fragile?

How often do you update risk plans for sourcing and delivery—what cadence is enough?

Are supply issues usually anticipated or reactive—what explains the pattern?

When did you last fix an inefficiency in your supply chain—what kept it solved?

Lean and Agile Methodologies

How do you usually respond when plans change—resist, adjust, or embrace, and why?

Which daily routine could benefit from iteration or small, low-risk experiments?

Which process over-relies on upfront plans—where would adaptive execution work better?

How often do you reflect on what didn’t work—and turn that into fast adjustments?

Do you delay launch to perfect—when has “just enough” worked better?

What assumptions about customer needs guide you—how often are they tested?

Quality Assurance

When did a small oversight in your venture cause a big problem—what could have caught it earlier?

Do you value speed or accuracy more—how does that choice affect overall quality?

What does “quality” mean for your venture—how do you define and measure it?

Have you ever accepted lower standards to meet a deadline—what were the consequences?

When you find an issue, do you fix symptoms or the root cause first?

What are your blind spots in quality—detail, process, or review practices?

IT Systems Management

Which recurring tool outages block MVP progress—and why haven’t you fixed them yet?

Are you more reactive or proactive maintaining systems—how does that affect trust?

How do you prioritize IT issues—urgency, user impact, or venture risk?

Where is your largest technical gap—cloud, security, scaling, or integrations?

How confident are users in system stability—what would increase perceived reliability?

When did a small oversight escalate into outage—what early signs appeared?

Cybersecurity

When did you last face a phishing attempt—how prepared were you operationally?

Which security steps are habit versus informed by your actual threat model?

Do you know the most likely threats for your stage and industry?

What risky security shortcuts persist—why do people still take them?

What would a 24-hour breach disrupt most—who feels impact first?

Which personal habits increase your cyber risk—public Wi-Fi, reuse, or sharing?

Software Development and Integration

Which module would confuse a contractor onboarding—what makes it hard to explain?

How often does integration testing reveal issues your unit tests completely missed?

Which recurring bugs reveal deeper design debt—what pattern do they show?

What causes handoff friction—tools, boundaries, or unclear ownership?

What’s your new development to bug-fix ratio—what should it be?

How much time goes to coding versus coordination—does that ratio work?

Customer Experience Management

How would a first-time user describe their journey from discovery to value?

Which moment in the journey carries highest emotion for early adopters?

What assumptions about customer wants persist—what evidence supports them?

When were you last delighted as a customer—what precisely created it?

Where are gaps between brand promise and actual customer experience?

How do you define experience success—speed, ease, satisfaction, or emotion?

Service Recovery and Resolution

What’s your instinctive response to complaints—how does that shape recovery and retention?

How confident are you staying calm with upset beta users or buyers?

Do your processes balance resolution speed with empathy during incidents?

Which service failure feels unforgivable—what would repair that perception?

Have you worsened situations by defending instead of listening—what changed afterward?

What does owning the issue mean in your practice?

CRM Systems

How often do you check CRM before outreach—what blocks consistent usage today?

Does your CRM help serve users better, or just add admin work?

What one capability should CRM improve to support founder workflows better?

How do you decide what belongs in CRM and what doesn’t?

Is CRM used mainly for compliance or strengthening relationships—what’s missing?

What customer behavior would truly surprise you if surfaced in CRM?

Regulatory Compliance

Which regulations impact your launch most—and which require expert interpretation, why?

When did you last catch a compliance risk—what cues helped you notice?

Is compliance a constraint or foundation enabling sustainable, trustworthy growth?

Which compliance domain is hardest to track—how do you manage it?

How would you explain key regulatory risks to a new collaborator today?

If rules changed tomorrow, how confident you’d hear and adapt quickly?

Contract Management

How comfortable are you with startup contract terms—what language still feels unclear?

Have you missed a contract detail that created risk—what prevents recurrence?

Which contract terms trigger excessive caution—what’s the underlying concern?

Do you treat contracts as collaboration tools or strictly legal protection?

How aligned are business goals with standard contract clauses in practice?

In your last contract negotiation, what worked and what felt uncomfortable?

Corporate Governance

How does founder decision-making connect to governance, oversight, and accountability?

Have you faced governance gray areas—what principles guided the decision?

Which values guide leadership now—are they consistently practiced under stress?

Is accountability truly clear across your roles and any collaborators—where does it most break?

What does good governance mean for your specific startup context?

Have you challenged a policy—what gave confidence to speak up?

Innovation and Product Development

What prevents you proposing new concepts more often—time, confidence, or validation fear?

Which innovation stage feels hardest now—ideation, prototyping, or validation testing?

When have collaborations improved ideas beyond solo work—what changed?

Are you driven by solving user problems or chasing novelty—why?

How do you balance creativity with feasibility on your current roadmap?

Which innovation do you admire—what lessons from how it was developed?

Research Methodologies

How comfortable are you designing scrappy tests, interpreting signals, and asking sharper questions?

When did you rely on assumptions over testing—what consequence followed?

Which research methods feel natural—qual, quant, or field observation, and why?

Do you over-research or jump too fast—how could you balance better?

How do you distinguish correlation from causation in current analyses?

When has research directly changed product, messaging, or strategy decisions?

Intellectual Property Management

How aware are you of IP risks around names, code, and content?

Have unclear IP rights cost time or money—what weak signals existed?

Do you emphasize protecting value or creating it—how do you balance both?

Which creations would you defend most if copied—why specifically those?

How would you react if others used your work without credit—why?

What’s your attitude toward legal processes—avoidant, cautious, confident, or proactive?

Supplier Relationship Management

Do you treat suppliers as partners, vendors, or risks—does that default help?

When did a supplier relationship materially help or harm launch readiness?

Are you proactive or reactive with supplier issues and emerging opportunities?

How do suppliers likely view you—collaborative, transactional, or challenging?

What supplier behavior do you reward most—low cost, flexibility, or innovation?

Have you measured your supplier ecosystem’s strategic value recently—how?

Logistics and Distribution

Do you view logistics as differentiation or invisible plumbing—why for your venture?

What was your largest logistics breakdown—what did it teach immediately?

How does distribution directly shape user experience for your early customers?

How flexible is your system if a supplier or route fails suddenly?

Do you measure environmental impacts of distribution choices and routes?

Do you clearly see logistics’ impact on timelines and goals?

Cost Management

Do you cut costs reactively or manage runway strategically—what drives that habit?

How often do you consider cost impact in daily founder trade-offs?

When is spending more justified for long-term value versus wasteful overspending?

Which area is most vulnerable to chronic cost overruns—and why?

Have past budget cuts hurt service, delivery, or momentum—how?

How confident are you explaining ROI for major purchases or investments?

Data Analysis and Visualization

Do your charts clarify the insight or overwhelm—what causes that recurring outcome?

How often do you ask whether the dataset truly answers the question?

What frustrates you most about shared data—structure, visuals, or missing context?

Which problem would a simple trend line clarify immediately for your audience?

Which data source do you trust least—and why specifically?

How confident are you communicating insights visually to nontechnical audiences?

Predictive Analytics

How comfortable are you separating correlation from causation when forecasting early demand?

When have forecasts helped or hurt—what improved calibration afterward?

What assumptions sneak into interpreting model outputs—how do you check them?

How do you balance model complexity with interpretability in decisions?

How do you communicate uncertainty in predictions to key audiences?

Which data quality issues most harmed forecasting accuracy this quarter?

Business Intelligence

How often do you use BI over gut when prioritizing experiments?

What’s the biggest gap between data available and decisions actually made?

Which BI metrics feel redundant or unused—why do they persist?

How do you balance reporting speed with accuracy and useful context?

Which audience questions recur that BI still doesn’t answer well?

When did BI insights actually change a priority or core process?

Enterprise Risk Management

How do you assess risk now—intuition, checklists, or structured frameworks?

When did an overlooked risk trigger issues—what early practice helps?

How comfortable are you escalating broader risks that affect others?

What’s the balance between risk appetite and avoidance across your venture?

How well do risk practices align with overall strategy and appetite?

How confident are you risk information flows adequately across your workstreams?

Crisis Management

When was the last operational crisis—what worked, and what failed under pressure?

How confident are you leading decisively and calmly during intense pressure?

What is your biggest weakness in crisis readiness and practice?

How effectively do you learn from crises and near misses?

How clear are roles and decision rights during emergencies for you and any collaborators?

What’s the impact of crises on trust—and how can recovery improve?

Regulatory Compliance 2

How confident are you about compliance duties before launch and after revenue?

When did you last spot a compliance risk before escalation?

Which compliance areas feel ambiguous—what support would increase confidence?

Which compliance area feels most complex or difficult to monitor?

How would you explain compliance risks in plain language to newcomers?

How quickly do regulatory updates reach you—and is that sufficient?

Product Lifecycle Management

How well do you understand lifecycle dynamics from MVP to maturity today?

When did lifecycle stage directly shape a key product decision?

How do you adjust marketing and support as products mature?

How proactive are you at sunsetting products—what triggers retirement?

How do customer needs evolve across lifecycle, and how do you track?

What lessons emerged from recent launches or retirements—be very specific?

Market and User Research

How do you validate market assumptions before product changes—what evidence qualifies?

When have research findings surprised you and overturned prior beliefs?

How often do you include real users in ideation and testing cycles?

Where are your market knowledge gaps—how will you fill them?

How effectively do you communicate research to influence decisions?

What biases might skew your interpretation of user data or trends?

Go-to-Market Strategy

How well does your GTM plan address real needs and competitor pressure?

When have you adapted your launch plan based on early feedback?

What assumptions guide channel selection and messaging—are they validated?

How aligned are product, marketing, and sales on current launch goals?

Which GTM metrics truly drive action—what gets changed because of them?

How do you balance speed-to-market with thorough testing and preparation?

MASTER Risk Hub