Diagnostic Questions

🎯 Business Goal Alignment: Questions for Founders

🧭 Vision & Direction

  • Where do you want the business to be 12 months from now, and what needs to happen to get there?
  • What’s your ideal mix of ecommerce, in-store, and wholesale revenue?
  • Are you building to scale, sustain, or exit?
  • What does “success” look like to you this year (besides just revenue)?

📈 Revenue & Growth Targets

  • Do you have a monthly revenue or order volume goal you’re aiming for?
  • What’s been driving the most growth—product launches, promotions, organic demand, etc.?
  • Are there specific launches, collaborations, or sales moments that you want ops to be ready for?

đŸ§© Operational Pressure Points

  • What’s currently causing the most stress or confusion operationally?
  • What are you spending time on that you wish you didn’t have to?
  • Are there parts of the business you want to delegate—but haven’t figured out how yet?
  • What would need to change for you to feel like the backend is “under control”?

💾 Cash, Margin & Inventory Strategy

  • Do you feel confident in your current inventory planning—or is it more reactive?
  • How much of your margin is getting eaten by fulfillment, shipping, or returns?
  • Are you trying to free up cash tied in inventory, or planning for larger buys?
  • Have you mapped how inventory and cash flow need to align with your growth goals?

📊 Accountability & Visibility

  • Do you have regular visibility into how things are performing operationally?
  • Are there metrics you care about but don’t have a clean way to track yet?
  • What decisions are you flying blind on today that you want more control over?

🧠 Founder Capacity & Delegation

  • What are you currently doing yourself that you’d ideally hand off?
  • Are you looking for someone to help you think strategically—or just execute?
  • Do you have a team you trust, or are you still doing most things solo?
  • If I could take three things off your plate tomorrow, what would they be?

🧠 Advanced Diagnostic & Discovery Questions

Fractional COO / Operational Audit Intake

🏗 Organizational Structure & Ownership

  • Who are the key decision-makers across operations, fulfillment, finance, and CX?
  • Are there any tasks or workflows currently dependent on one person?
  • Are team members clear on what they own vs. what they support?
  • Do you have defined roles for ecommerce vs. retail ops—or is it blended?

🛒 Ecommerce Operations (Shopify, Amazon, etc.)

  • What systems are currently in place for processing, picking, packing, and shipping online orders?
  • Who owns ecommerce fulfillment day-to-day?
  • How do you track order status and follow-up issues (delays, lost packages, returns)?
  • Are shipping rates and rules customized by product, region, or customer type?
  • Do you have pre-order or limited drop workflows? Are they manual or automated?

đŸ§Ÿ Inventory Management & Purchasing

  • How are SKUs categorized and tracked across platforms?
  • Do you have a centralized system or spreadsheet for real-time inventory?
  • How do you reconcile physical inventory with digital (Shopify, POS, FBA)?
  • What triggers reorders—forecasting, rules, or gut feel?
  • Are there dead SKUs tying up cash? Fast movers that run out too often?
  • Are you tracking inventory cost changes (landed cost, shipping, supplier changes)?

đŸ§± Brick-and-Mortar Operations

  • What POS system is in use and does it sync with ecommerce?
  • How are new products added to the system across both channels?
  • What’s the typical customer flow in-store—and how is it tracked or leveraged?
  • Do you run in-store events or fan activations? What’s the ops lift and ROI on those?
  • What inventory movement happens between store and warehouse, if any?

📩 Fulfillment & 3PL / Shipping

  • Are you using a 3PL or fulfilling in-house? If in-house, who owns each step?
  • How are returns handled logistically and operationally?
  • What are your average fulfillment costs per order—and do you track it by channel or region?
  • What packaging types are used and who manages that sourcing?
  • Are there any bottlenecks during Q4, drops, or pre-order launches?

🧰 Tools, Systems & Automations

  • What tools are being used for:
    • Project management
    • Order processing
    • Inventory tracking
    • Customer service
    • Staff communication
  • Are there tools the team isn’t fully using or finds cumbersome?
  • What’s currently being done manually that could be automated?

đŸ’” Financial Ops & Cost Visibility

  • Do you have a current view of margin per SKU or product category?
  • What are your largest operational costs outside of product?
  • Are you forecasting cash flow based on inventory, launches, or supplier timelines?
  • Are there recurring fees (subscriptions, platform tools, storage, etc.) that need review?
  • What’s your current cost per order, all-in (fulfillment, shipping, returns)?

🔁 SOPs & Process Maturity

  • Do you have documented processes for core ops (order fulfillment, returns, new hire onboarding, etc.)?
  • Are those SOPs used and followed—or just written and forgotten?
  • What tasks break down when someone’s out of office or unavailable?
  • How do you currently train new team members or cross-train roles?

📊 Reporting & Performance Tracking

  • What KPIs are being tracked consistently? (Delivery times, return rates, OOS % etc.)
  • Do you have visibility into daily/weekly/monthly ops performance?
  • Are there reports you wish you had but haven’t built yet?
  • Is any data being pulled manually that could be automated?

🌍 Growth & Strategy

  • Are you planning for more stores, product lines, or sales channels?
  • Are operations currently scalable, or do you know things will break?
  • What are the top 3 growth goals right now, and what’s blocking them?
  • Have you considered retail distribution (beyond DTC) or international shipping?
  • Do you feel the backend of the business is built to support growth—or just keeping up?