Why I run towards drama

The best client relationships are born from the messiest briefs

Lmao this might end up being the newsletter I regret publishing. 

But in the spirit of riffing, I want to make the case for working with messy clients. 

In the agency world, there’s a set of best practices that are well understood. 

Work with nice people. 

On things that make the world a better place. 

With as little drama as possible. 

While I agree with the first two points, I’ve become more open-minded on the third. 😇

When I first started consulting in 2016, I didn’t have a framework for taking on new clients. 

It’s not like I had a million people knocking down my door. 

I was just getting started, jumping at every project I could get…no matter how messy. 

Looking back, it was a blessing in disguise. 

I wasn’t in a position to say “no.” 

And often had to deal with some really difficult challenges. 

But looking back one thing was clear.

Some of my best client relationships started from some of the messiest briefs. 

Misaligned teams. Tricky personalities. And the ultimate red flag— clients who churned through other agencies with very little success. 

These were the kinds of opportunities I would have turned down if I was looking for a “project positioned for success.” 

Over the years I’ve evolved my perspective on these types of clients. 

A lack of clarity is usually what’s holding them back. 

And without a clear sense of where they’re going, there’s no way an internal team or outside agency can help them get very far. 

That’s why at Off-Menu, we’re not afraid to run towards drama. 

In fact, sometimes the messiest clients make for the best relationships. 

We believe that if we can help a misaligned team come together around a shared North Star, they’ll trust us forever and recommend us to everyone they know. 

So before taking on new partners, here are the three guiding questions we ask ourselves.

01. Do we want to see this team win?

Instead of asking ourselves how “clean” a potential new project is, we re-frame the question to, “Do we want to see this team win?” 

Answering that question is equal parts mission & vibes, getting at the heart of their motivation.  

Why did they start the company? To get rich? To make an impact?

This is especially important in web3, and a huge determining factor if a company has the resilience to tough out a bear market. 

02. Do they have the ingredients to meaningfully stand out? 

As we get to know potential clients, we poke & prod to distinguish between founders with messy visions & those selling snake oil.  

While we are really good at helping teams articulate what makes them compelling, it’s extremely hard to do if a founder doesn’t have a unique insight or POV. 

Messy is good, but not if they don’t have the ingredients to be successful. 

03. If we help them win, is there an opportunity for a long-term relationship?

At Off-Menu, our goal is to be working with the same founders 10 years in the future. We’re in the business of life-long relationships and try to avoid transactional relationships at all costs. 

Seeing new business through this filter helps us avoid clients looking for a quick fix with unreasonable expectations. 

We can help fix messy clients who play long term games…but that’s a tougher ask for a two week turnaround. 

Closing thoughts

As I think about the case for messy, a few open questions are top-of-mind: 

• While this approach works well for me personally, does it make sense if I grow the team? I’m not sure a “messy wanted” sign is going to attract the best talent. 

• How do you price especially messy briefs? They often take more time, coaching, & persistence to get everyone on the same page before the work even starts. 

• One of the things I hear again & again is how Off-Menu wins where other agencies have failed due to the fact we are so good at storytelling & alignment. Who needs that? How do I market that? If you know anyone suffering from this, I’d love to meet them. Do we position ourselves as the Michael Clayton of agencies? Happy to play the role of George Clooney any day. 

If you're a freelancer, consultant, or agency lead, I’d be curious to learn what questions you ask yourself before taking on new clients—especially the messy ones.