The Moment I Realized This Founder Didn’t Need a Better Agency: He Needed Permission to Fire One

He had a spreadsheet ready before our call even started.

Three agencies, five years, and a column for each one: monthly retainer, what they promised, what they delivered, why it ended. He’d clearly done his homework. He was on a video call with me because he was shopping for agency number four, and he wanted to understand how Howl was different.

For the first twenty minutes, he mostly talked about his current agency. And here’s what caught my attention. He wasn’t complaining. He was defending them.

“They’re really responsive.” “The account manager is great, she always gets back to me the same day.” “The reports are really thorough.” “I think the market’s just been tough this year.”

Then, almost as an afterthought, he said, “But I don’t really know what we’re getting. Leads are flat. I’m writing most of the strategy myself in our monthly calls. And I feel like I’m managing them more than they’re managing the work.”

So I asked him one question.

“If you weren’t already working with them, would you hire them today?”

He was quiet for a long moment. Then he laughed a little and said, “No. No, I wouldn’t.”

That was the moment. He didn’t need a better agency. He already knew what to do. He needed permission to do it.

Why Smart Founders Stay Too Long

I love this stuff, and part of why I love it is that it’s so deeply human. On paper, this decision looks simple. The results aren’t there, so you make a change. In practice, founders stay in agency relationships months or even years past the point where they should have moved on. And it’s rarely because they aren’t paying attention.

Here’s what I see almost every week.

• Sunk cost feels like progress. You’ve spent eight months onboarding them, explaining your business, and walking them through your customers. Leaving feels like throwing all of that away. So you give it one more quarter, and then another.
• Kindness gets mistaken for performance. Responsive, friendly, organized people are easy to work with. But being pleasant and being effective are two different things. This founder genuinely liked his account manager, and that relationship was quietly keeping a contract alive that the results couldn’t justify.
• Admitting it isn’t working feels like admitting you chose wrong. Founders carry a lot of decisions. When one doesn’t work out, it can feel like a referendum on your judgment. It isn’t. Hiring the wrong partner is normal. Staying with the wrong partner once you know is the expensive part.
• Starting over feels risky. What if the next one is worse? What if you lose momentum? What if the ad accounts break during the transition? That fear is real, and it’s exactly why a lot of founders tolerate “fine” when they need “working.”

One of the biggest mistakes I’ve made in my own career was staying in a partnership far longer than I should have because I didn’t want to disappoint anyone. I told myself I was being loyal. What I was really doing was avoiding a hard conversation. It cost me time I didn’t get back, and I’ve never forgotten that lesson.

The Real Problem Usually Isn’t the Agency

This is the part that surprised him, and it might surprise you.

When I looked at his spreadsheet, the pattern wasn’t three bad agencies. It was three agencies hired to execute a strategy that didn’t exist yet.

Each one came in, looked for the fastest path to visible activity, and started running campaigns. Each one reported on what they controlled: impressions, clicks, cost per lead. None of them had been asked to own the harder questions. Who exactly is the buyer? What problem are we solving better than anyone else? How does a lead become a customer, and how will we know which dollars made that happen?

Without that go-to-market foundation, every agency was building on sand. And the founder kept filling the gap himself, which is why he felt like he was doing their job for them. In a real sense, he was.

I think too many businesses hire for execution before they’ve earned clarity. When that happens, you don’t have an agency problem. You have a strategy and ownership problem that no agency can fix from the outside.

Signs It’s Time to Move On

If you’re wondering whether you’re in the same situation, here are the patterns I’d pay attention to. None of these alone is a reason to leave, but when several show up together, it’s worth taking seriously.

• You can’t clearly explain what you’re getting for your retainer, even after reading the reports.
• The reports are full of activity metrics but never connect to pipeline or revenue.
• You’re bringing the strategy to the meetings and they’re bringing the updates.
• Conversations about results turn into explanations about the market, the algorithm, or timing, quarter after quarter.
• The one that concerns me most: you aren’t completely sure you own your own ad accounts, CRM, website, or data.
• That last one deserves its own section.

Before You Fire Anyone, Protect What’s Yours

This is where I get a little protective of founders, because I’ve seen this go badly.

Before you have the conversation, make sure every core go-to-market asset is in your name and under your control. Your ad accounts should belong to your business, with the agency granted access, not the other way around. Your CRM, your website hosting, your domain, your analytics, your email platform, and your social accounts should all have you or a trusted team member as the owner or primary admin.

Then take an inventory.

• Where do your landing pages live?
• Who has the logins?
• What automations are running in your CRM
• Does anyone on your side understand the reports being produced?

Tip: Export your reports and campaign history so you keep the learning, even if you’re ending the relationship.

This isn’t about distrust. Most agencies will hand everything over cleanly. It’s about good revenue operations hygiene. Your data is one of the most valuable assets in your business, and it should never be held by someone you’re about to stop paying.

How to Part Ways Well

Once your assets are secured, the conversation itself can be simple, respectful, and short and be sure you document your reasoning in an email.

Be honest without being harsh. Something like, “We’ve decided to go in a different direction. I appreciate the work your team has done, and I want to make this transition as smooth as possible for both of us.” You don’t owe a long justification, and you don’t need to relitigate every missed goal.

Important: Review your contract for notice periods and give the notice it requires. Ask for a transition document that covers active campaigns, logins, running automations, and anything in flight. Set a clear end date. And thank the people who worked hard for you, because most of them did.

The marketing world is smaller than you think. How you end a relationship says as much about your company as how you begin one.

What I Told Him (and What I Didn’t)

Now this might sound strange coming from someone who runs a marketing company.

I didn’t pitch him. Not on that call.

I told him that if he hired us, or anyone, before he had clarity on his buyer, his positioning, and how revenue actually moved through his business, he’d likely be filling in a fifth column on that spreadsheet in eighteen months. What he needed first was a clear go-to-market foundation that he owned, so whoever executed it would be building on something solid.

So we talked through what that would look like. Get clear on the customer. Define what a qualified lead means with his sales team. Make sure he owned every account and every piece of data. Then decide what kind of help he actually needed, whether that was an agency, a fractional leader, a strategist, or simply one strong hire.

He wrote me a message a few weeks later. He’d given notice, secured his accounts, and spent a few weekends with a notebook and a whiteboard working through his positioning. “First time in five years I feel like I’m driving,” he said.

A couple of months after that, he came back and we started working together. But this time, he walked in knowing exactly what he wanted us to own, and exactly how he’d measure it. That’s a very different kind of partnership, and it’s the kind I want for every founder.

You Already Know More Than You Think

If you’ve read this far and felt a little uncomfortable, that’s worth listening to.

Most founders I talk to already know when something isn’t working. The data has been telling them for a while. What they’re missing isn’t information. It’s permission to trust their own judgment and act on it.

So here’s your permission. If you wouldn’t hire them today, it’s okay to stop working with them. Protect what’s yours, part ways with respect, and take a breath before you hire the next partner. Use that space to get clear on your strategy, because clarity is what makes every future partner more effective.

This is the heart of what we wrote about in Startup Simple Marketing: strategy before tactics, clarity before spend, and a go-to-market system you own rather than rent. And if you’d like a second set of eyes on whether your current setup is working, that’s a conversation I’m always happy to have.

You’re probably closer than you think. Let’s figure it out.