Agency evaluation is genuinely hard. Pitch decks are designed by professional marketers. Case studies are cherry-picked. References are pre-screened. Testimonials are curated. The agency that looks most impressive in a pitch meeting isn't necessarily the one that will deliver results for your specific business.
These 10 questions are designed to bypass the polish and get to the substance.
1. Who will actually be working on my account day-to-day?
Agencies pitch senior people and deliver junior people. Ask specifically: what is the name of the person who will be my day-to-day contact? What is their experience level? Will any of my work be outsourced? A good agency answers these questions directly. An agency that deflects or gives vague answers about 'our team' is warning you of something.
2. Can you show me a campaign you ran that didn't work, and what you learned?
Every agency has case studies of successful campaigns. No honest agency has a portfolio of 100% successes. Asking about a failure — and how they responded — tells you far more about their character, transparency, and learning culture than any success story. If they can't answer this question, they're either lying or incapable of honest self-assessment.
3. What will you need from us to be successful?
Agencies that overpromise autonomy often underdeliver. Effective marketing requires client input: brand guidelines, customer insights, campaign approvals, content contributions, access to analytics and CRM data. An agency that honestly describes what they'll need — and what happens if they don't get it — is setting realistic expectations from the start.
4. How do you measure and report on success?
Ask for a sample report. Look at: Are the metrics tied to business outcomes (revenue, leads, cost per acquisition) or vanity metrics (impressions, followers, clicks)? Is the data raw and transparent, or interpreted through proprietary dashboards that obscure the underlying numbers? How frequently do they report, and what happens when results are below target?
5. What's your process for the first 90 days?
The first 90 days tells you everything about how structured an agency's delivery process is. A good agency describes specific phases: discovery and onboarding, audit, strategy development, initial implementation, reporting review. Vague answers suggest improvised delivery.
6. Do you have experience in our industry?
Industry experience matters — but not as a strict gate. An agency without direct experience in your sector can still deliver excellent results if they're rigorous researchers and fast learners. What matters is whether they can demonstrate how they'd learn your category: customer research, competitor analysis, talking to your sales team, reviewing your best-performing historical content.
7. What are your contract terms?
Standard agency contracts range from month-to-month rolling to 12-month minimum terms. Longer minimums aren't inherently bad — SEO genuinely takes time — but they should be accompanied by performance milestones that give you recourse if delivery is poor. Be cautious of long lock-ins with no performance review clauses.
8. Can we speak to a client in a similar sector to ours?
Agencies select their reference clients carefully. Ask for a client in a similar business size and sector, and ask to speak with them directly — not via a pre-submitted testimonial. Ask the reference client: what was the agency's communication like when things went wrong? Did results match expectations? Would you rehire them?
9. How do you stay current as the landscape changes?
Digital marketing changes faster than almost any other profession. Algorithm updates, new ad formats, privacy changes, new platforms — agencies that aren't actively learning fall behind quickly. Ask: what changed in the last 6 months that changed how you work? What are you experimenting with right now? Thoughtful, specific answers signal an active learning culture.
10. What would you not change about what we're currently doing?
Most agencies in pitch mode focus on what they'll change and improve. Asking what they'd keep — if anything — tests whether they've genuinely understood your current situation or whether they're applying a standard pitch regardless of context. An agency that says 'nothing' without having done a proper audit hasn't done the work.
We're happy to answer all 10 of these questions for Omakaase — the good and the difficult ones. We believe the best client relationships start with honest expectations.
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