A business owner I know spent $60,000 with a marketing agency last year. The agency came in with a playbook: run Google Ads, post on social three times a week, build an email drip sequence. Standard stuff. Twelve months later he couldn’t point to a single new customer that came from the work.
The agency wasn’t incompetent. They executed the playbook. The problem was the playbook.
Two kinds of problems
In the 1970s, researchers Horst Rittel and Melvin Webber drew a distinction that’s been rattling around policy circles ever since but hasn’t made it far enough into business. They separated problems into two categories: kind and wicked.
Kind problems have clear rules. The boundaries are defined, the feedback is immediate, and what worked last time will probably work next time. Chess is a kind problem. So is filing your taxes, assembling furniture from instructions, or optimizing a Google Ads campaign for a known keyword with a known conversion rate. You can hand kind problems to someone with a checklist and expect decent results.
Wicked problems resist that approach. They’re contextual. The variables interact in ways you can’t fully map in advance. The act of trying to solve them changes them. And two wicked problems that look similar on the surface can require completely different solutions.
Growing a business is a wicked problem. So is fixing a marketing operation that’s been underperforming for years, or figuring out why a company with a great product can’t seem to get traction. These situations don’t have instruction manuals. They have histories, politics, assumptions, blind spots, and constraints that are invisible until someone gets close enough to see them.
The mismatch
Here’s where it gets expensive. The marketing industry is built to sell kind solutions. Packages. Retainers with predetermined deliverables. “We’ll post X times per week, run Y campaigns, and send Z emails.” These are productized services, and they exist because they’re easy to scope, easy to price, and easy to staff with junior people.
None of that is inherently wrong. If you have a kind problem, a kind solution is exactly right. You know your audience, you know your channels, you have a conversion funnel that works, and you just need someone to run it. Great. Hire the agency with the checklist.
But most of the businesses I work with don’t have kind problems. They have wicked ones. They come to me after spending money with agencies and consultants and having nothing to show for it, or worse, having built a dependency where results evaporate the moment they stop paying. The pattern is remarkably consistent.
Three failure modes
The businesses that land in my office tend to describe one of three experiences.
The first: they hired a strategist who had ideas but didn’t do anything. Someone smart showed up, assessed their situation, produced a deck full of recommendations, and left. The client was supposed to execute. They didn’t, because they didn’t have the team, the time, or the expertise. Nobody needs another smart person telling them what they should do. They need someone who will actually do it.
The second: the work got handed off. They hired the senior person but ended up working with the junior one. The pitch was expertise and experience. The reality was a $45/hour contractor in another time zone who’d never heard of the client’s industry before Tuesday. The senior person showed up for the quarterly review. The contractor did the actual work. And the client could feel the difference.
The third: dependency by design. The marketing “worked” as long as they kept paying. The moment they paused, everything stopped. No systems were built. No knowledge was transferred. No capability was developed inside the organization. The agency had every incentive to stay essential and no incentive to make the client self-sufficient.
All three of these are kind solutions applied to wicked problems. A predetermined playbook. A delegated execution model. A vendor relationship optimized for recurring revenue. They work when the problem is straightforward. They fail when it isn’t.
Why the distinction matters
When you treat a wicked problem as a kind one, you don’t just waste money. You lose time and, often, confidence. Business owners start to believe that marketing “doesn’t work for us” or that they’ve just had bad luck with agencies. They haven’t. They’ve had a category error. The solution type didn’t match the problem type.
A manufacturing company that needs to rethink its pricing transparency because Google Shopping won’t index products without prices doesn’t need a social media calendar. It needs someone who can see the upstream business decision that’s constraining the marketing, have that conversation with ownership, and then execute the downstream changes. That’s not a marketing tactic. It’s a diagnostic process that happens to involve marketing.
A property management company that’s been conditioned by its previous agency to measure generic keyword rankings instead of actual leads and conversions doesn’t need more SEO. It needs someone to reset the definition of success before any work begins. Otherwise you’re optimizing a metric that doesn’t connect to revenue, and everyone feels productive while nothing changes.
What wicked problems actually require
Wicked problems need a different operating model. Not a bigger budget or a better agency. A fundamentally different approach.
They need diagnosis before prescription. Not a discovery call where someone fills in a template, but genuine investigation into what’s actually happening: the marketing, the systems, the team dynamics, the real constraints. I’ve walked into engagements where the marketing problem turned out to be a leadership alignment problem. I’ve seen cases where the CRM was so broken that no amount of lead generation would have mattered because leads were disappearing into a black hole. You can’t know this from a pitch meeting.
They need the strategist and the executor to be the same person. When the person who diagnoses the problem is also the person who implements the solution, there’s no translation loss. No game of telephone between the thinker and the doer. Adjustments happen in real time because the person doing the work understands why it’s being done that way.
They need someone willing to say the uncomfortable thing. Not every client wants to hear that their website isn’t the problem, their business model is. Or that the reason their marketing isn’t working is that they haven’t decided who they actually are yet. A vendor who depends on your monthly check has a structural disincentive to tell you that. An advisor who’s measured by your outcomes doesn’t.
And they need an exit strategy. The goal should be to make the organization more capable, not more dependent. Build the systems, transfer the knowledge, develop the internal capacity. If the engagement ends and everything falls apart, the engagement failed, no matter how good the monthly reports looked.
The real question
Before you hire anyone for marketing help, ask yourself one question: Is this a kind problem or a wicked one?
If you know what you need and you just need someone to execute it, find someone who executes well and pay them fairly. That’s a perfectly valid path.
If you’re not sure what’s wrong, if you’ve tried things that should have worked and didn’t, if you suspect the problem is deeper than the marketing itself, then you need a different kind of engagement. You need someone who will look at the whole system, not just the marketing. Someone who does the work, not just the thinking. Someone whose success is measured by your capability, not your dependency.
That distinction is the one most businesses never make. It’s also the one that determines whether the next check you write will be an investment or an expense.