10 Agency Questions Every Solopreneur Should Ask

Marketing agencies and freelancers aren’t the problem. Ambiguity is. And solopreneurs are the easiest target because you’re busy running delivery, sales, and admin—so marketing often becomes the first thing you “hand off and hope for the best.”

I’ve seen the same pattern play out across one-person businesses: you hire help, you get a flurry of activity, and three months later you’ve got a dashboard full of numbers… but no clearer sense of what’s working, what’s not, or what to do next. Worse, you find out your website, ad account, or analytics access is “owned” by someone else.

This post is part of the SMB Content Marketing United States series, where the focus is simple: practical content marketing strategies for small businesses in America—blogging, social media, and video on a budget. The checklist below reframes John Jantsch’s agency questions into a solopreneur-friendly filter so you can hire (or keep) marketing support without losing control of your business.

The solopreneur reality: you don’t need an agency—you need accountability

Answer first: If you’re a one-person business, the right marketing partner is the one who can tie work to outcomes and keep you in control of your assets.

Agencies love to sell outputs: posts, ads, emails, “SEO work,” a new website. Solopreneurs need outcomes: qualified leads, booked calls, purchases, and predictable pipeline.

The fastest way to spot the difference is to ask questions that force clarity. Not “What do you do?” but “What do I own, what will we measure, and what happens if this isn’t working?”

Here’s the checklist I’d use before paying another invoice.

Start with control: assets, access, and exit terms

Answer first: If you don’t own the accounts, you’re renting your marketing—and that’s how solopreneurs get trapped.

1) “Who owns my marketing assets and accounts?”

Your answer should be boring and immediate: you do.

That includes:

• Domain registrar and DNS access
• Website hosting and CMS admin access
• Google Analytics (GA4), Google Tag Manager
• Google Business Profile
• Google Ads and Meta Ads accounts
• Email marketing platform (list + automations)
• CRM (HubSpot, Pipedrive, HighLevel, etc.)

A legitimate partner can still manage everything with shared access. Ownership is non-negotiable.

Practical move: Create a simple “Marketing Asset Inventory” in a Google Sheet with the login email, admin users, recovery methods, and who has access. Update it quarterly.

2) “What happens if I want to end the contract?”

Most companies get this wrong: they negotiate price before they negotiate exit.

You’re looking for:

• Clear offboarding timeline (e.g., 14–30 days)
• Explicit handoff of files, creatives, landing pages, and reporting
• No hostage clauses (“we keep the site,” “we keep the ad data,” “pay a fee to transfer”)
• Reasonable terms (month-to-month is often a good sign for ongoing services)

Solopreneur lens: Your business can’t absorb long “dead months.” If performance isn’t there, you need a clean pivot.

3) “Who will I actually work with day to day?”

You don’t want to be sold by the senior strategist and then assigned to an inbox.

Ask:

• Who is my primary contact?
• Who writes, designs, builds, and optimizes?
• What’s the expected response time?
• How many clients does my account manager handle?

Green flag: You meet the people who do the work before you sign.

Define success like a business owner, not like a dashboard

Answer first: If success isn’t defined in leads, conversions, and revenue, you’ll get vanity metrics and vibes.

4) “How do you define success—and how often will we review it?”

A good answer includes:

• One primary goal (example: 10 qualified discovery calls/month)
• Supporting metrics (conversion rate, cost per lead, email reply rate)
• Review cadence (weekly quick check + monthly strategy review)
• A plan for what changes if targets aren’t met

Useful benchmark for content marketing: In 2026, a lot of solopreneurs win by building a content engine that produces 1–3 high-intent leads per week consistently, then improving conversion with better offers and follow-up.

5) “How do you report on results, and can I see a sample?”

If the “report” is a screenshot dump from tools, you’re paying for busywork.

A report worth reading has:

• What happened (the numbers)
• Why it happened (the story)
• What we’ll do next (specific actions)

My rule: If a report can’t fit on one screen with a clear narrative, it’s not a management tool—it’s a distraction.

6) “How do you connect tactics to strategy?”

Tactics aren’t strategy. Posting three times a week isn’t a strategy. Running search ads isn’t a strategy.

A real strategy sounds like:

• “We’re positioning you as the go-to for X problem in Y niche.”
• “We’ll publish two comparison posts and one case study monthly because they convert for high-intent searches.”
• “We’ll retarget site visitors with a webinar because your sales cycle is 21–45 days.”

Solopreneur shortcut: If they can’t explain the plan in plain English, they don’t have one.

Make sure their process starts before the posts and ads

Answer first: The best marketing partners do discovery first, because content marketing only works when your message is sharp.

7) “What is your process for creating strategy before you execute?”

Before anyone touches your website or content calendar, you need alignment on:

• Ideal customer (who you’re for—and who you’re not for)
• Core message and point of view
• Differentiation (why you instead of another freelancer/consultant)
• Customer journey (first touch → lead magnet → call → sale)
• Offer structure (what you sell and how people buy it)

If a partner jumps straight to “We’ll do SEO + social + ads,” you’re watching a buffet approach. Solopreneurs don’t need more channels. You need a tighter path.

8) “How will you collaborate with my team (and other partners)?”

Even as a solopreneur, you have a “team”:

• your web developer (even if it’s part-time)
• your VA
• your podcast editor
• your CRM/setup freelancer

The right marketing partner integrates with those people. The wrong one insists on being a black box.

Operational tip: Ask them to describe their collaboration process in one sentence—Slack? Asana? Weekly standups? Loom walkthroughs? You’re checking for friction.

Ask the modern questions: AI usage and client education

Answer first: AI is fine. Hidden AI is not. You’re paying for judgment, not just output.

9) “How are you using AI, and what is still human-led?”

In 2026, every serious marketer uses AI somewhere. The question is whether they use it to:

• speed up research and outline creation
• generate variations for ad testing
• summarize call transcripts into insights
• spot patterns in performance data

…while keeping these human-led:

• positioning and messaging decisions
• brand voice and tone
• offer strategy
• final editorial standards
• ethics and compliance (especially in health, finance, legal)

Direct stance: If a provider is charging premium rates and delivering unedited AI drafts, you’re funding their margin—not your growth.

10) “What will you teach me along the way?”

You don’t need to become a marketer. But you do need to become a better buyer of marketing.

The best partners:

• explain tradeoffs (speed vs. quality, SEO vs. ads, volume vs. focus)
• show you what they’re doing and why
• help you make decisions faster next month than you did this month

A good marketing relationship reduces dependency over time. If you feel more confused every month, that’s a signal.

A simple scorecard: how to evaluate answers fast

Answer first: If you want a quick decision tool, score each answer on clarity and ownership.

Use a 0–2 score for each question:

• 0 = vague, defensive, or confusing
• 1 = partially clear, some gaps
• 2 = clear, specific, documented

Add up the points:

• 16–20: strong partner potential
• 11–15: proceed only with tight scope + short commitment
• 0–10: you’re buying risk

Solopreneur-friendly rule: If they can’t give clear answers before they have your credit card, they won’t become clearer after.

People also ask: quick answers solopreneurs need

Answer first: These are the three most common follow-ups that matter for hiring marketing help.

Should a solopreneur hire an agency or a freelancer?

If you need one primary skill (SEO writing, ads management, email automation), start with a specialist freelancer. If you need coordination across channels and you’re willing to pay for leadership, an agency or fractional marketing lead can make sense.

What’s a reasonable reporting cadence?

Weekly lightweight updates (1–2 bullets) plus a monthly performance review is a practical cadence for most small businesses. Quarterly, you revisit strategy and offers.

What should I own if someone builds my website?

You should own the domain, hosting account, CMS admin access, and all creative files. Contractors can have access, not ownership.

The point of these 10 questions

The reality? A solopreneur doesn’t “need marketing.” You need a reliable system that turns attention into leads—and a partner who can prove they’re building that system with you, not around you.

If you’re working through the SMB Content Marketing United States playbook—publishing consistent content, reusing it across social, and building simple funnels—these questions protect the foundation. They also make your marketing measurably better because they force strategy, ownership, and real accountability.

Which question would you be most nervous to ask your current marketing partner—and what would it mean if they couldn’t answer it clearly?