If you’re an entrepreneur trying to figure out AI, you my have found Jonathan Masts’ group on Facebook. This collection isn’t comprehensive, it’s curated. These are the prompts Jonathan Mast shared in his group. Join it today and get inspired!
AI Prompts for Entrepreneurs Facebook Group
https://www.facebook.com/groups/77001359440686
Strategic Planning Prompts by JM
Act as a venture capitalist who has reviewed thousands of pitches. Analyze my business idea for a [describe your business] and provide the top three reasons you would not invest, forcing me to confront my weaknesses. Ask me any questions you have.
Analyze the top 5 competitors in the [your industry] space. Identify their key strengths, weaknesses, and marketing strategies, then create a report on opportunities for me to differentiate my services.
StoryPlan Strategic Planning Prompts
Strategic Planning Prompt
Act as a strategic planning facilitator who has led 100+ companies through annual planning. I need to create our 12-month strategic plan with clear goals, initiatives, and accountability. Context: – Current annual revenue: [number] – Revenue goal for next year: [number] – Team size: [number] – Biggest opportunity: [describe] – Biggest threat: [describe] Your task: Walk me through creating a one-page strategic plan that includes:
1. Our 3 strategic priorities for the year (and what we’ll say NO to)
2. Key metrics we’ll track quarterly
3. Major initiatives mapped to quarters
4. Who owns what
5. How we’ll review progress
Before you answer, ask me 3-5 clarifying questions you need to give the best possible response.
Annual Strategic Planning
Act as a strategic planning consultant who has facilitated 200+ annual planning sessions for companies scaling from $2M to $20M.
Context:
– Current annual revenue: [number]
– Target revenue next year: [number]
– Team size: [number]
– Primary offering: [describe]
– Biggest growth constraint right now: [describe]
Your task: Help me create a one-page strategic plan for the next 12 months that includes:
1. Our 3 strategic priorities (and what we’ll stop doing)
2. Key quarterly milestones for each priority
3. Critical metrics we’ll track monthly
4. Resource allocation (time, money, people)
5. Our “definition of winning” for each quarter
Before you answer, ask me 3-5 clarifying questions you need to give the best possible response.
Market Positioning
Act as a positioning strategist who has helped 100+ companies carve out defensible market positions in crowded industries.
Context:
– My business: [describe what you do]
– Target customer: [describe ideal client]
– Top 3 competitors: [list]
– What makes us different (we think): [describe]
– Our price point vs. competitors: [higher/same/lower]
Your task: Analyze our market and help me develop a positioning strategy that:
1. Identifies the specific segment we can dominate (not just serve)
2. Defines our unique point of view (not just our features)
3. Determines our category (are we creating new, or dominating existing?)
4. Maps our competitive alternatives (what do customers do if we don’t exist?)
5. Creates our “only” statement (we are the only [X] that [Y] for [Z])
Before you answer, ask me 3-5 clarifying questions you need to give the best possible response.
Growth Strategy Options Analysis
Act as a growth strategist who has scaled 50+ service businesses from $2M to $10M+ revenue.
Context:
– Current revenue: [number]
– Revenue goal: [number]
– Time frame: [months/years]
– Current acquisition channels: [list]
– Average customer value: [number]
– Team capacity to execute: [describe]
Your task: Generate and evaluate 5 distinct growth strategies, including:
1. The core mechanism (how it works)
2. Estimated investment required (time and money)
3. Realistic timeline to results
4. Risk level and failure modes
5. Dependencies (what needs to be true)
Then rank them by: fastest path, highest ROI, lowest risk, and most scalable. Before you answer, ask me 3-5 clarifying questions you need to give the best possible response.
90-Day Sprint Planning
Act as an execution coach who specializes in 90-day sprint planning for entrepreneur-led businesses.
Context:
– Most important goal right now: [describe]
– Current obstacles: [list 2-3]
– Team capacity: [hours per week available]
– Resources available: [budget, tools, people]
Your task: Design a 90-day sprint plan that:
1. Breaks the big goal into weekly milestones
2. Identifies the critical path (what MUST happen first)
3. Assigns ownership and accountability
4. Builds in weekly review checkpoints
5. Includes “kill criteria” (when to pivot or stop)
Format this as a visual roadmap with Week 1-13 breakdown.
Before you answer, ask me 3-5 clarifying questions you need to give the best possible response.
Systems Prompts by JM
Act as a CEO who has successfully scaled a company from 10 to 50 employees. What are the three most critical systems I need to build right now to avoid chaos as my business grows? Ask me any questions you have.
Act as an operations consultant. I want to document the 10 most critical recurring processes in my business. My company does [describe business type]. My goal is to create clear, step-by-step Standard Operating Procedures (SOPs) for my team. Help me identify which processes should be documented first, and provide a simple SOP template I can use for each. Ask me any questions you have.
Act as a process engineer. I’ll describe a recurring task my team performs. I want you to create a clear, step-by-step SOP for it — using active verbs, best practices, and decision logic. Ask me for clarification about inputs, tools, timing, and outputs before writing the SOP.
Act as a process improvement expert. I want to identify the biggest bottlenecks in how our company operates. Our departments include [list departments]. My goal is to spot delays, redundant steps, or inefficiencies that cost time or money. Provide a framework of questions I should ask each department head to uncover operational friction points. Ask me any questions you have.
Act as a business systems architect. I want to create a visual map of my company’s key systems — from marketing and sales to delivery and finance. My goal is to see how work flows between departments. Help me outline 8–10 core business systems and describe the input, output, and owner for each. Ask me any questions you have.
Act as a workflow automation consultant. I want to identify repetitive tasks in my business that could be automated using AI or tools like Zapier or Make. My goal is to increase efficiency and reduce manual work. Provide a process for spotting automation opportunities and suggest 5 tasks we could automate right away. Ask me any questions you have.
Act as a continuous improvement coach. I want to install a system for ongoing reflection and improvement inside my company. My goal is to help teams identify what’s working, what’s not, and what to improve every 90 days. Provide a step-by-step framework for conducting quarterly improvement reviews, including the right questions and follow-up actions. Ask me any questions you have.
StoryPlan Systems Prompts
SOP Creation for Critical Process
Act as a process documentation expert who writes SOPs that employees actually follow.
Context:
– Process name: [what it’s called]
– Why it matters: [business impact if done wrong]
– Current process owner: [person/role]
– Frequency: [how often it happens]
– Tools involved: [software, systems]
– Common mistakes: [what typically goes wrong]
Your task: Create a step-by-step SOP that includes:
1. Purpose & Scope (why we do this, when it applies)
2. Roles & Responsibilities (who does what)
3. Step-by-step process (action verb + expected outcome for each step)
4. Decision trees (if X happens, then do Y)
5. Quality checkpoints (how to know it’s done right)
6. Common mistakes & how to avoid them
7. Resources needed (tools, templates, access)
Format: Easy to follow, not a wall of text. Before you answer, ask me 3-5 clarifying questions you need to give the best possible response.
Process Improvement
Act as a Lean Six Sigma black belt who has eliminated millions in waste from operations.
Context:
– Our company does [describe]
– Our departments: [list]
– Annual revenue: [range]
– Biggest complaint from team: [describe]
Your task: Help me conduct a “waste audit” to identify:
1. Bottlenecks (where work piles up)
2. Redundancies (duplicate efforts)
3. Unnecessary steps (things we do because “we always have”)
4. Communication gaps (where info gets lost)
5. Time vampires (low-value tasks eating high-value time)
Provide: A diagnostic framework I can use to audit each department – The specific questions to ask team members – How to calculate the true cost of each inefficiency – A prioritization matrix for what to fix first.
Before you answer, ask me 3-5 clarifying questions you need to give the best possible response.
Workflow Automation Opportunity Assessment
Act as a workflow automation consultant who has eliminated 1000+ hours of manual work from companies using AI and no-code tools.
Context:
– Our business type: [describe]
– Team size: [number]
– Current tools we use: [list]
– Biggest time-wasters right now: [describe repetitive tasks]
– Tech comfort level: [beginner/intermediate/advanced]
Your task: Identify automation opportunities by:
1. Listing 10 tasks that could be automated (ranked by time saved)
2. For each task: Current time spent → Automation tool → Estimated setup time → ROI
3. Categorizing by: Quick wins (easy, high impact), Strategic automations (harder, huge impact)
4. Providing step-by-step setup for top 3 automations
5. Recommending the automation stack we should invest in
Focus on tools like Zapier, Make, AI, and integrations we already have. Before you answer, ask me 3-5 clarifying questions you need to give the best possible response.
Process Bottleneck Elimination
Act as a Lean Six Sigma expert who specializes in eliminating bottlenecks in service businesses.
Context:
– Process with bottleneck: [describe]
– Where work backs up: [specific point]
– Impact of bottleneck: [delays, costs, customer impact]
– Current capacity at bottleneck: [volume/time]
– Demand at that point: [what’s needed]
Your task: Analyze and solve this bottleneck by:
1. Mapping the current process flow (where work enters, travels, exits)
2. Identifying the true constraint (the slowest step that limits everything)
3. Calculating bottleneck capacity vs. demand (the gap)
4. Generating 5 solutions to increase throughput (elevate the constraint)
5. Evaluating each solution: Cost → Time to implement → Impact → Risk
6. Recommending the optimal solution with implementation plan
Focus on solutions that don’t just “work harder” but actually increase capacity. Before you answer, ask me 3-5 clarifying questions you need to give the best possible response.
Client Onboarding Process Design
Act as a customer success architect who has designed onboarding systems for 200+ service companies.
Context:
– What we sell: [offering]
– Typical client journey: [from sale to first result]
– Current onboarding process: [if any]
– Where clients get stuck: [common friction points]
– Time from sale to first value: [current timeline]
Your task: Design a structured onboarding process that:
1. Maps the entire journey (day 1 to first major result)
2. Identifies critical touchpoints (when we must engage)
3. Creates milestone moments (celebrating progress, building momentum)
4. Prevents common drop-off points (proactive interventions)
5. Sets clear expectations (what they do, what we do, when)
6. Measures engagement and flags at-risk clients
Include: Timeline, responsibilities, templates, and automation opportunities. Before you answer, ask me 3-5 clarifying questions you need to give the best possible response.
Customer Retention Prompt
Act as a customer success architect who has reduced churn for 50+ SaaS and service companies. Context: – My business: [describe] – Customer lifetime: [average months/years] – Current churn rate: [% or “unknown”] – Main reason customers leave: [if known] Your task: Design a proactive customer retention system that:
1. Identifies at-risk customers before they leave
2. Creates touchpoints at critical moments
3. Builds regular value delivery into our process
4. Captures feedback systematically
5. Measures health scores Provide the framework, timeline, and who should own each part.
Before you answer, ask me 3-5 clarifying questions you need to give the best possible response.
StoryPlan Brand Story Prompts
Core Brand Story Development
Act as a brand strategist who has crafted origin stories for 200+ companies that became the foundation of their marketing.
Context:
– My business: [describe what you do]
– Why I started it: [the real reason, not the polished version]
– The problem I saw in the market: [describe]
– My background before this: [relevant experience]
– The transformation we create: [before and after for clients]
Your task: Help me craft our brand story by developing:
1. The “Before” (what was broken in the market)
2. The “Insight” (what we saw that others missed)
3. The “Journey” (how we developed our approach)
4. The “Difference” (why our solution works differently)
5. The “Proof” (early wins and validation)
6. The “Mission” (where we’re headed and why it matters)
Create this as a 500-word narrative I can adapt for our website, pitches, and content. Before you answer, ask me 3-5 clarifying questions you need to give the best possible response.
Brand Messaging Architecture
Act as a messaging strategist who creates clear, differentiated positioning for companies in crowded markets.
Context:
– Our business: [describe]
– Our ideal customer: [describe persona]
– Their biggest pain: [what keeps them up at night]
– What we’re competing against: [alternatives, not just competitors]
– How we’re actually different: [be honest, not aspirational]
Your task: Build our messaging architecture including:
1. Positioning Statement (We help [X] do [Y] by [Z])
2. Value Proposition (The benefit they get, not what we do)
3. Three Proof Points (Why they should believe us)
4. Competitive Differentiation (Why not the alternatives)
5. Brand Personality (How we sound/feel different)
6. Key Messages by Audience (What each stakeholder needs to hear)
Make this specific enough that our team can write consistent content from it. Before you answer, ask me 3-5 clarifying questions you need to give the best possible response.
Customer Success Story Framework
Act as a case study writer who has turned 500+ customer results into compelling proof stories.
Context:
– Customer name/industry: [if shareable]
– Their situation before us: [describe problem]
– What we did: [our solution/process]
– The results: [quantifiable outcomes]
– Timeline: [how long it took]
– Key insight or turning point: [what made the difference]
Your task: Structure this into a compelling success story that:
1. Opens with a relatable problem (not our solution)
2. Shows the stakes (what was at risk if they didn’t solve it)
3. Reveals the insight or turning point (the “aha” moment)
4. Details the transformation (specific before/after)
5. Quantifies the impact (numbers, time saved, revenue gained)
6. Ends with a future vision (what’s now possible for them)
Format this as: 1) One-paragraph version, 2) Website case study, 3) Social media post. Before you answer, ask me 3-5 clarifying questions you need to give the best possible response.
Founder’s Story for Authority Building
Act as a personal branding strategist who positions founders as thought leaders in their industries.
Context:
– My background: [education, career path, key experiences]
– Why I’m qualified to solve this problem: [relevant expertise]
– My unconventional insight or approach: [what I believe that others don’t]
– Biggest failure/lesson that shaped my methodology: [turning point]
– The change I want to create in my industry: [mission]
Your task: Help me craft my founder’s story that:
1. Establishes credibility without being boring
2. Shows the personal stakes (why this matters to me)
3. Reveals the contrarian insight (what I see that others miss)
4. Demonstrates hard-won expertise (not just credentials)
5. Connects my story to client transformation (how my journey helps them)
Create: 1) LinkedIn “About” section, 2) Speaking bio, 3) Podcast introduction. Before you answer, ask me 3-5 clarifying questions you need to give the best possible response.
People Prompts by JM
Act as an HR systems strategist. I want to create a standardized onboarding system for new employees. My goal is to document what every new hire needs to learn, read, and complete during their first 30 days. Provide a 4-week onboarding plan and checklist that I can adapt by role. Ask me any questions you have.
Act as a knowledge management expert. I want to create a searchable internal knowledge base for our company using [platform]. My goal is to organize all our SOPs, FAQs, templates, and tools in one place. Provide an outline for how to categorize and tag content so it’s easy to find and maintain. Ask me any questions you have.
Leadership Prompts by JM
Act as an EOS-style integrator. I want to create a rhythm of accountability across my company. My goal is to establish weekly, monthly, and quarterly meetings that keep everyone aligned to our goals. Provide a meeting cadence with agendas and what metrics or dashboards should be reviewed in each. Ask me any questions you have.
StoryPlan Leadership Prompts
Delegation Framework Development Prompt
Act as a leadership coach who teaches founders to delegate effectively and reclaim 20+ hours per week.
Context:
– Current role: [CEO, Founder, etc.]
– Hours per week: [working time]
– Time spent on: [breakdown if known]
– What I should be doing: [strategic work]
– What I’m actually doing: [operational/tactical]
– Team capability: [describe who you have]
Your task: Create my delegation strategy by:
1. Auditing my current time (urgent vs. important, $10/hr vs. $1000/hr work)
2. Identifying “only I can do this” tasks vs. delegable work
3. Prioritizing what to delegate first (biggest time savings + team can handle)
4. Creating delegation packages (responsibility + authority + resources + outcomes)
5. Building the hand-off process (how to transfer without dropping balls)
6. Establishing the checking system (how to monitor without micromanaging)
Goal: Free up 15+ hours per week for strategic work. Before you answer, ask me 3-5 clarifying questions you need to give the best possible response.
Priority Management System Prompt
Act as a productivity strategist who helps leadership teams focus on what actually moves the needle.
Context:
– Current state: [overwhelmed, reactive, too many priorities]
– Team size: [number]
– Strategic goals: [if defined]
– Typical distractions: [what pulls focus]
– Decision-making style: [how we currently prioritize]
Your task: Create a priority management system including:
1. Priority framework (how to decide what matters most – impact vs. effort)
2. The “Rule of 3” implementation (company, department, individual priorities)
3. Quarterly “Rocks” definition (3-7 critical objectives per quarter)
4. Weekly WIG focus (Most Important Goal this week)
5. Daily MIT (3 Most Important Tasks per day per person)
6. “Stop Doing” list (what we’ll actively eliminate)
Build in a weekly review process to keep priorities current and relevant. Before you answer, ask me 3-5 clarifying questions you need to give the best possible response.
Team Performance Dashboard Creation
Act as a business intelligence consultant who builds executive dashboards that drive better decisions.
Context:
– Company type: [describe business]
– Key metrics we care about: [revenue, profit, client satisfaction, etc.]
– Current reporting: [what we track now, if anything]
– Decision-making gaps: [what we wish we knew]
– Tools available: [spreadsheets, CRM, project management]
Your task: Design a performance dashboard that:
1. Identifies the 8-12 key metrics (leading and lagging indicators)
2. Organizes by category (financial, operational, customer, team)
3. Sets targets and thresholds (green/yellow/red zones)
4. Determines review frequency (daily, weekly, monthly)
5. Assigns ownership (who’s responsible for each metric)
6. Creates the actual dashboard template (visual format)
Make this simple enough to maintain, powerful enough to drive decisions. Before you answer, ask me 3-5 clarifying questions you need to give the best possible response.
Decision Making Prompt
Act as a CEO coach who has helped founders make high-stakes decisions under uncertainty. I’m facing a major business decision about [describe situation].
Options I’m considering:
1. [Option A]
2. [Option B]
3. [Option C]
Your task: Help me think through this strategically by:
1. Identifying what I’m really optimizing for (it’s usually not what I think)
2. Exposing my hidden assumptions
3. Mapping second and third-order consequences of each option
4. Identifying the “reversibility” of each choice (one-way vs. two-way doors)
5. Recommending a decision framework specific to this situation
Before you answer, ask me 3-5 clarifying questions you need to give the best possible response.