01
Goals and growth targets
What does success look like for this business 12 months from now?
VisionAsk them to be specific — revenue targets, new markets, customer growth, product launches. If they are vague, probe: what would have to be true for you to say this year was a success?
Clarity of vision:
What is the primary growth driver the business is counting on — new customers, retention, expansion into new markets, or something else?
Growth modelIs the growth strategy clearly defined or implied? Does leadership agree on it? Ask: if you had to double down on one thing to grow, what would it be?
Gap:
Are marketing goals tied to business goals, or are they running on a separate track?
AlignmentAsk to see a recent marketing report or dashboard. Does it connect to revenue outcomes or does it report impressions, followers, and traffic in isolation?
Gap:
02
Current marketing efforts and channels
What marketing activities is the business currently running? Walk through every channel — paid, organic, email, events, partnerships, content, social.
Channel auditDo not let them summarize. Go channel by channel. For each one: how long have you been doing this, who manages it, what is the monthly spend or time investment, and what are you getting back?
Channel strategy:
Which channels are they most confident in and which ones feel like they are just going through the motions?
Confidence checkThis question surfaces honesty. Channels they are not confident in are almost always candidates for reallocation. Listen for "we feel like we should be doing this" versus "this is actually working."
Gap:
How did their last 10 customers find them? Can they answer this with data or is it a guess?
AttributionIf they cannot answer this with confidence, attribution is broken. Note it as a critical gap. This question alone often changes the entire conversation about where to invest.
Gap:
03
ROI and budget analysis
What is the total monthly or annual marketing spend, including all channels, agencies, tools, and internal time?
Total spendMost businesses significantly undercount their real marketing spend because they do not include internal time or tool subscriptions. Walk through each line item. What is the actual number?
Budget clarity:
Do they know their cost per lead, cost per acquisition, and customer lifetime value?
Unit economicsIf they cannot answer, that is the answer. Note it clearly. Without these numbers, there is no way to evaluate whether any marketing investment is working. This gap almost always belongs in the roadmap.
Gap:
Is budget allocation based on performance data or historical habit? When was it last reviewed?
Budget logicAsk: if you had to cut 30% of your marketing spend today, where would you cut first and why? The answer reveals whether decisions are data-driven or comfort-driven.
Gap:
04
Brand and positioning strength
Can leadership articulate the company's value proposition in one or two plain sentences that a prospect would immediately understand?
Value propAsk them to say it out loud right now. Then ask two other people in the room. Do the answers match? Is it customer-focused or internally focused? Does it describe an outcome or just a product?
Gap:
Is there a defined ideal customer profile? Is it documented and based on real data or built on assumptions?
ICPAsk to see it. If it exists, review it together. When was it last updated? Do sales and marketing agree on it? Does it include behavioral and psychographic attributes or just demographics?
Gap:
How does the business differentiate from its top three competitors and is that differentiation meaningful to the customer?
DifferentiationAsk them to name their top three competitors. Do they know how those competitors position themselves? Is the differentiation something a customer would actually pay more for, or is it internal pride?
Gap:
05
Market share and competitive position
What is the estimated size of their addressable market and what share do they believe they currently hold?
Market sizingDo not expect a precise number. Listen for whether they have thought about this at all. A founder who has never considered TAM or market share will approach marketing very differently from one who has a clear view.
Gap:
Are competitors gaining ground, losing ground, or holding steady relative to this business? What evidence do they have?
Competitive movementAsk: in the last 12 months, have you lost any deals to a specific competitor? Have you won business away from anyone? What are prospects saying when they compare you to alternatives?
Gap:
How does their pricing compare to the market and does their marketing reflect that positioning?
Pricing positionAre they a premium, mid-market, or value player? Does their website, messaging, and brand feel consistent with that price point? Misalignment here is extremely common and very fixable.
Gap:
06
Digital presence and SEO
Does the website clearly communicate what the business does, who it is for, and what to do next within the first few seconds?
Website clarityPull up the homepage together during the session. Ask them: if a stranger landed here, what would they understand in the first five seconds? Look at the headline, subhead, and primary CTA. Are they doing their job?
Gap:
Is Google Analytics or equivalent tracking installed and actively monitored? Are conversion goals set up?
AnalyticsWho looks at the data? How often? What decisions have been made because of it? If they say nobody looks at it regularly, tracking is essentially nonexistent for practical purposes.
Gap:
Do they know what keywords they rank for, where their organic traffic comes from, and whether SEO is part of their strategy?
SEOAsk if they use Google Search Console. If not, ask how they think about organic discovery. A business with no SEO awareness has a visibility ceiling they may not even know exists.
Gap:
07
Team and vendor assessment
Who is currently responsible for marketing inside the business and how much of their time is dedicated to it?
Internal ownershipIs there a dedicated marketing person, or is it split across the founder and others who have other primary jobs? Shared ownership with no single accountable person is one of the most common reasons marketing stalls.
Gap:
Are they working with any outside agencies or vendors? How is that relationship performing and does the business own all its accounts and assets?
Vendor auditAsk specifically: do you own your website, your ad accounts, your analytics accounts, and your email list? If any of these are owned by a vendor, flag it immediately. This is a critical risk.
Gap:
What marketing decision are they trying to make and who will ultimately own it?
Decision ownershipThis is the question that ties everything together. Is the decision maker in the room? Do they have the authority and budget to act on the roadmap? If not, the engagement may need to include a different stakeholder.
Readiness:
08
Customer journey and funnel health
Walk through the typical path a customer takes from first hearing about the business to becoming a paying client. How long does it take and where do most prospects drop off?
Journey mapAsk them to walk through it step by step out loud. Where do leads come from? What happens next? Where do things slow down or stall? This narrative often reveals the biggest gaps faster than any data point.
Gap:
Is lead follow-up fast, consistent, and tracked? What happens to leads that do not convert immediately?
Lead handlingHow quickly does sales follow up after a lead comes in? Is there a nurture sequence for unconverted leads or do they just go cold? Speed and persistence in follow-up are often the highest-ROI fix available.
Gap:
Is there a retention and referral strategy in place for existing customers?
RetentionWhat is their customer retention rate? Do they actively ask for referrals or reviews? Is there a structured program or does it happen organically when it happens at all? Existing customers are almost always the cheapest source of new revenue.
Gap:
09
Overall observations