The problem isn’t just bad agencies (though they’re plentiful) — it’s our unwillingness to ask questions that make everyone uncomfortable.
“In the marketplace of marketing ideas, most agencies survive by selling the illusion of competence rather than delivering the reality of results.”
Every agency meeting follows the same script: they show you beautiful graphs pointing upward, smile through rehearsed presentations, and carefully manage your expectations while exceeding their billable hours. It’s a dance as old as advertising itself.
But what if we stopped the music?
I’ve spent two decades watching businesses get seduced by agency theatrics while their ROI quietly flatlines.
Press enter or click to view image in full size
The Truth-Extraction Protocol
“The most dangerous relationship is one where performance claims go unchallenged and measurement exists to justify fees rather than improve outcomes.”
These questions aren’t designed to be friendly. They’re engineered to crack open the glossy veneer agencies spend thousands perfecting. Use them strategically and watch closely — the real answers hide in the micro-expressions between their words.
1. “What’s the single biggest mistake you’ve made working with us, and how did you fix it?”
Great agencies have relationship memory. They track their failures with the same precision as their successes. When I implemented this question with a major retail client, their agency stammered for three painful minutes before admitting they had never systematically tracked their missteps.
A competent agency doesn’t just acknowledge failures — they’ve built systematic approaches to prevent similar mistakes. Their answer should reveal both vulnerability and methodology.
According to research from the Society of Digital Agencies, only 28% of agencies have formal systems for tracking and analyzing their strategic errors (SoDA Digital Outlook Report, 2023).
2. “Show me the data that proves your work directly impacted our customer acquisition cost (CAC) and lifetime value (LTV).”
“The agency that measures only what makes them look successful is not your partner but your parasite.”
Here’s the dirty secret of digital marketing: most agencies design measurement frameworks that make themselves look good rather than accurately tracking business impact. They’ll show you engagement rates rising while your acquisition costs quietly balloon.
During a recent audit, I discovered a fashion brand’s agency touting a 43% increase in social engagement while their CAC had silently climbed 37%. The agency had created a measurement mirage — impressive from a distance, empty upon inspection.
Forrester’s Marketing Measurement and Optimization Survey revealed that 67% of marketing leaders cannot quantify their agency’s direct contribution to revenue growth (Forrester Research, 2024).
3. “What’s one thing our competitors are doing better than us, and why haven’t you recommended we do the same?”
“An agency that won’t acknowledge your competitors’ strengths is either strategically blind or ethically compromised. Neither serves your interests.”
Agencies exist in a strange paradox where they simultaneously work with your competitors while pretending they don’t. This question forces them to acknowledge the competitive landscape they navigate daily.
A luxury hospitality brand’s agency once responded to this question with such detailed competitor intelligence that it raised serious ethical questions — yet they’d never volunteered these insights during regular reporting.
The Digital Marketing Institute’s 2024 Agency Transparency Report found that only 34% of agencies proactively share competitive intelligence with their clients (DMI, 2024).
Press enter or click to view image in full size
4. “If we fired you tomorrow, what would your replacement need to know to avoid repeating your mistakes?”
“The strength of an agency relationship can be measured precisely by how well it would survive its own termination.”
This question creates a simulated crisis that reveals their knowledge management practices. Do they have systems for preserving strategic insights, or does critical intelligence live exclusively in their account director’s brain?
When an e-commerce company posed this question, their agency produced a comprehensive transition document within 48 hours — revealing they had been preparing for termination for months. The question exposed not just their processes but their relationship perspective.
The Association of National Advertisers found that 71% of marketers cite “loss of institutional knowledge” as a primary concern when changing agencies (ANA Agency Selection Report, 2023).
5. “What’s the most controversial or unpopular recommendation you’ve made to us, and why did we reject it?”
“The quality of strategic advice is inversely proportional to how comfortable it makes you feel upon first hearing it.”
This question tests whether your agency pushes boundaries or simply executes requests. Strategic partners should occasionally make you uncomfortable — that’s where growth happens.
A financial services client discovered their agency had never made a single recommendation their internal team hadn’t pre-approved. They weren’t getting strategic guidance; they were renting execution capacity with a premium markup.
McKinsey’s Digital Marketing Excellence study showed that agencies rated highly for “strategic partnership” were 3.4x more likely to regularly make recommendations that clients initially resisted (McKinsey & Company, 2023).
6. “What’s the one thing you wish we’d stop doing that’s holding back our success?”
“In the delusion of perfect client behavior lives the alibi for agency underperformance.”
The client-agency relationship isn’t one-sided. This question acknowledges that your organization might be the performance bottleneck.
When a technology company asked this question, their agency’s response exposed a dysfunctional approval process adding 27 days to campaign implementation timelines. The agency had never mentioned this because they feared losing the account.
The 4A’s Client-Agency Relationship Survey revealed that 82% of agencies withhold critical feedback about client-side inefficiencies due to fear of damaging relationships (American Association of Advertising Agencies, 2024).
Press enter or click to view image in full size
7. “How much of our budget are you wasting on activities that don’t drive results, and why are you still doing them?”
“Budget waste isn’t accidental; it’s the structural byproduct of misaligned incentives and unchallenged assumptions.”
Agencies perpetuate ineffective activities because change requires effort. This question demands fiscal accountability and exposes resource misallocation.
A retail brand discovered their agency was continuing to invest 22% of the social budget in a platform where customer acquisition costs were 3.7x higher than other channels. The reason? The platform’s aesthetic aligned better with their case studies.
PwC’s Digital Marketing Efficiency Study found that the average marketing department wastes 26% of its budget on ineffective activities that continue due to inertia rather than results (PwC, 2024).
Press enter or click to view image in full size
8. “What’s the most uncomfortable truth about our business that you’ve been avoiding telling us?”
“The value of an agency is not measured in comfort but in their willingness to speak truths that internal teams have collectively agreed to ignore.
Agencies accumulate insights about your brand that internal teams miss. This question extracts those hidden perceptions.
A consumer electronics company learned their agency believed their product design was fundamentally flawed but continued creating campaigns emphasizing the very features consumers found confusing. The agency had been constructing marketing band-aids rather than addressing core product issues.
Gartner’s CMO Survey found that 76% of agencies report regularly withholding potentially valuable but negative feedback from clients (Gartner, 2023).
9. “If you had to cut your own fee by 30% to stay on our account, what would you stop doing to make it work?”
“In the list of services an agency would immediately sacrifice lies the true inventory of what they know doesn’t create value.”
This question reveals what your agency actually believes creates value versus what they include to inflate retainers. It distinguishes their core value proposition from the superfluous services packaged to justify higher fees.
A healthcare organization discovered 40% of their monthly deliverables were essentially performative — activities their agency would immediately eliminate under budget pressure while still delivering core results.
Deloitte’s Marketing Efficiency Index showed that organizations implementing zero-based budgeting exercises with their agencies identified an average of 23% in non-value-adding activities (Deloitte Digital, 2023).
10. “What’s the one thing you’d do differently if you could start over with us today?”
“The greatest waste in business is not money but the perpetuation of approaches that historical evidence has thoroughly discredited.”
This question examines their capacity for strategic evolution. Digital marketing changes weekly, yet many agencies follow playbooks established years ago.
A B2B software company learned their agency would completely restructure their attribution model if starting fresh — essentially admitting their current performance reporting framework was fundamentally flawed.
8The Harvard Business Review’s Agency Effectiveness Study found that 61% of agency leaders admit to continuing suboptimal strategies due to the difficulty of pivoting established programs (HBR, 2024).
More to explore
The Digital Accountability Revolution
These questions aren’t just interrogation tactics — they’re the foundation of a performance-based partnership. Organizations implementing this framework discover a startling truth: many agencies welcome this directness once they realize it replaces the exhausting performance theater with genuine strategic collaboration.
The best agency relationships aren’t built on pleasant meetings and holiday gift baskets. They’re built on uncomfortable truths, radical transparency, and mutual accountability.
Your business deserves nothing less.
Digital Transformation Architect & SEO Strategist — rite.io/ai/
Simon Dodson operates at the intersection of technical SEO mastery and strategic business growth. Known for dismantling digital dogma, he transforms underperforming channels into revenue-generating machines.
While others chase algorithm updates, Simon engineers scalable systems.
By day, he crafts data-driven strategies that boost traffic by 40%+. By night, he toggles between Bangkok street food hunts and Brisbane strategy sessions, maintaining dual home bases with the same efficiency he applies to omni-channel campaigns.
His approach? Question every SEO assumption. Test relentlessly. Document obsessively. And never confuse correlation with causation.
Simon doesn’t just navigate the digital landscape — he reconstructs it, leaving conventional wisdom in the dust while delivering measurable results that matter.