better company

What could you learn
from what 200 agency
CEOs have tried?

That’s where I come in.

You’re good at solving problems. You’ve proven that. But leading an agency is a lonely job, and the challenges you face and solutions available are greater than you might realize.

Let’s get started.

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A room full of agency leaders in conversation
On stage at the Ad Age Small Agency Conference In conversation at a conference Workshop wall of sticky notes Team working in the conference room
Jack Skeels

The question that started all of this was simple: Why is it so hard to make an agency run well? It turns out that if you can solve that, then pretty much everything gets better.

Every agency is unique. Its miseries are not.

Tolstoy said it the other way: happy families are all alike and every unhappy family is unhappy in its own way. But after working inside more than 200 agencies and talking to maybe three times that number, I’ve found the opposite is true.

When you dig into how an agency actually operates, they are all different. The cultures, the founders, the work, the clients; no two look alike. But the problems? The problems are almost always the same.

Every agency is trying to do something unreasonably close to perfect, inside an organization that is unreasonably difficult to manage. The multi-client, multi-project, multi-priority workplace that is also multi-managed and running on ad hoc processes despite having processes defined.

Agencies, almost all of them, have an exciting driving-on-the-edge-of-a-cliff nature, with deadlines and crises that rip the steering wheel out of your hands, and the elation and exhaustion of an IronMan’s finish line when the job is done. That tension and excitement is what drew me to this industry in the first place.

Often, an agency’s growth becomes its biggest challenge: the chaos grows faster than size. A pretty happy 25 person agency almost always becomes an unhappy one by the time it has 50 people. Sometimes the numbers are smaller.

Helping leaders find their way through these challenges is what I’ve done for over 15 years...and I love it.

What I learned: 166 Lessons from 200 Agencies

The cards are the content. Browse a few here, then follow the series.

Read the Series →

Minding the Culture Gap: Your Mission is on point, but your Monday is the problem.

Every agency mission, vision, or values statement I’ve ever read commits to the same three things: brilliant work and happy clients; passionate, engaged people who love the work and the company; and healthy growth and margin. The mission includes and defines the culture that you are hoping for.

But your culture is what Monday does.

It’s a safe bet, especially if you have grown much since you wrote it, that what’s driving your culture is not what you said, but what people really do to get the work done: their natural adaptation to the ill-fit structure you built three sizes ago, the new processes that were installed patchwork, and most of all, your tools, which shape behavior every hour of every day.

Most agencies talk about culture. The structure and tools — and especially their workarounds — produce the Monday.

Monday is the compilation of a thousand little changes: growth, new services, remote work, new tools — because every change realigns behavior a little, and the drift happens slowly and gradually.

Here’s a way to think about it, so you can start seeing it, from Chapter 20 in UNMANAGED. An agency is a stack of five layers: values and mission at the top, then culture and behavior, then roles and structure, then process and methods, then tools at the bottom. The stack works when the layers align, when what the wall (values) says matches what the meeting (process/tool) does.

Read: Culture Drift →
The Culture-Alignment Pyramid: Values at top, then Culture, Organization & Roles, Process, and Tools at the bottom
01

The talk versus the walk gap.

Pick your proudest value. What’s the most common behavior in your firm that quietly refutes it, and how will you change that?

02

Growth makes your agency lose focus.

Who in your firm hasn’t been asked for their thinking in a month, and how did a disempowering process find its way in?

03

How departments divide your culture.

What does someone in one of your departments believe about another department that they’d never say in a mixed room, and what’s your evidence it isn’t true?

04

When everyone wants to be a manager.

Where are your leaders spending their time: sorting out org charts and promotions, or elevating the conversation with clients, present and future?

05

How tools secretly shape your agency.

Count the tools your firm runs on. How many are bending your people to their way of working, and how many have dissolved into everyone doing their own thing?

Help No Longer Wanted

“They are on a mission to bring out all of the skeletons in our collective closets and help us address the real issues.”

Rebecca Flavin, CEO, Effective UI

“The focus on the cultural shifts versus just implementing tools has already shown more results than anything else we’ve done in the past.”

Amanda Ferber, 22squared

“It opened my eyes to how insufficient we may have been in the past.”

Michael Rykalsky, GTB

And now this.

AI and the Future of Your Agency

AI collapsed the cost of the assembly layer: drafting, structuring, producing. It did not touch the judgment layer: formulating the right question, interpreting ambiguous evidence, knowing what the data means for this client. Most agencies are using a restructuring technology as a productivity tool. That makes the structural problems worse, not better. Adding a motor to the hamster wheel.

jackskeels.com

How to Get Paid for Judgment

jackskeels.com

The New Economics of Client Distance

jackskeels.com

Twenty Things Every Agency Leader Needs to Hear About AI

jackskeels.com

What AI Actually Breaks When You Sell Thinking for a Living

The best change is what happens with your team, not to your team.

The changes that stick are the ones the team helped create. That’s not a philosophy; it’s the pattern from 200 engagements. When we change things we do it live: on real projects with your real teams, changing how the work flows: simpler structures, less hierarchy, rituals that put people back in deep engagement with each other and with clients. I use a wide range of models including: adult learning, pre-contemplative change, and cultural-linguistic framing.

How we work together →

Help No Longer Wanted

“In that first week, I literally saw our team members come alive in front of me.”

JaNette Connell, Insperit

“Everyone loved it. They say, ‘I don’t want to go back to the old way of working.’”

Ned Johnson, GTB

“It creates a forum where everyone is in the same room creating. I think it’s the future of working in our industry.”

Katie Reeves, Bloom Agency

15 years. 200+ agencies. The results are consistent.

200+

Agencies helped

53%

Paid back within 3 months

91%

Would recommend

30-50%

Faster delivery

Help No Longer Wanted

“In just a few days, you’ve done more work than we’d typically expect to get done in 2 months!”

Ron Merbler, Ford Motor Company

“All of our projects have come in on or under budget. That is a huge win for our small agency.”

Bryan Shavaner, Fifty&Fifty

“The week we spent in training was truly transformative. It unified our entire agency.”

Kim Manning, CEO, Cronin

“Cross-discipline collaboration is radically improved beyond our expectations.”

Dave Foster, COO, LaneTerralever

“We’re seeing large projects come in with fewer quality issues and at higher profitability rates.”

Deana Derocha, HelloWorld

I don’t know you (yet), but we would probably enjoy working with each other.

If you’re curious, let’s have a chat.

Book a time.

30 minutes. No pitch, no deck. You tell me what’s not working; I’ll tell you what I’d look at first.

Book a Conversation →

Drop me a note.

Prefer email? Tell me a bit about your agency and what’s on your mind. I’ll get back to you personally.

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