This has been a good year at Article Group.

Creative ideas: flowing.

Revenue: up.

Staff count: up.

We’re lucky enough to work with companies like Google, GE, and NASA, just to name a few.

We have three offices in New York, San Francisco, and Rochester, New York. That’s a step up from two scrappy guys working out of coffee shops on opposite coasts. We thought it would take five years to get to where we are today. I’m proud that we did it in three, all while growing responsibly.

But it hasn’t all been smooth sailing.

We’ve had stumbles. We made some dumb mistakes. We made some obvious goofs. So this past week, in solemn observance of a certain day of atonement, we made a list of what we did wrong.

We made this list as an exercise during our annual leadership meeting, a time when we examine our strategy and make adjustments for the year ahead. We made this list for two big reasons

1. We’re trying to solve a hard problem
I come from outside the agency world. From the brand side. I’m accustomed to helping CEOs solve intractable problems at a very fast pace. To being a lone operator. And now, through Article Group — and in partnership with my co-founder, Andrew Kessler, who does come from the agency side — I’m trying to solve marketing problems at a larger scale. I wasn’t accustomed to the agency world’s workflows. We had work to merge two types of methodologies together. That’s hard. Getting there has its challenges. We want to recognize those challenges so we can improve.

2. We’re trying to grow responsibly
One thing I do know: Too many brands and service agencies sweep problems under the rug. That creates a toxic environment full of overworked and under-appreciated staff, which, ultimately, leads to poor client service. We want the opposite. We want to create a good culture, take care of our people, grow responsibly, and learn by synthesizing our goofs (also a strategy used by Devo!).

You’ll see our mistakes cover every possible function of an agency. Some mistakes concerned basics, i.e., the methods of building a responsible and sturdy business. Other mistakes concerned our offering, i.e., the methods of communicating our value to clients and executing on projects.

The full list is below. I bucketed them by business function, but they’re in no particular order. I hope this list is useful to other leaders and creatives out there, or gets business owners to chuckle knowingly with the memory that yes, building a client services business is hard … and you’re not the only one who’s slipped on the banana peel.

General Management

1. Crappy meeting culture 
At first, not enough meetings. Then, dear lord, too many meetings! Daily scrums are great for 1–10 people. Add more people and the scrum lasts for 30 minutes and staffers commit seppuku. So we stopped doing that. Implemented meetings by department and began holding a once-per-week all-hands. Nobody has ritualistically disemboweled themselves since.

2. Thought good tools would fix bad habits
Repeat after me: Slack will not fix your communication problems. You’ve heard that old saying, water flows where it’s easiest for water to go? Same with people. They’ll do what offers the least friction unless given an incentive not to. But sometimes less friction equals more crazy. You’ve gotta enforce cultural standards. And you’ve gotta realize nouns don’t solve verb problems. Working on this.

3. Didn’t keep everyone updated on wins
Figured everyone would just kinda know when good stuff happened. Incorrect. Fixed this with weekly updates. Don’t have a bell to ring but Robbie’s pretty good at keeping the mezcal stocked.

4. Didn’t have enough one-on-ones
Every management book in the world says to do this. I didn’t. I just thought people would speak up about challenges or about their feelings. Well, guess what? Every management book in the world is right (at least about this point). You’ve got to make time to check in. Otherwise assumptions creep in, which causes stress because people don’t know how they’re performing.

5. Hired jerks
Skills change. People who use the company card to ship their furniture to China don’t change.


6. Assumed everyone thought the same way
This was a super goof. I thought everybody thought like me. That they were all run-and-gun lone operators. That most good work was the product of a single actor. This, as you are doubtlessly aware, is super not true. I had to learn to delegate. To listen. To scale our processes. I probably had that old Emerson line in my head: “To believe your own thought, to believe that what is true for you in your private heart is true for all men — that is genius.”

Well, Emerson was a smart man. And I am terribly abusing this quotation. But that dude never ran a creative agency.

7. Didn’t unify our creative functions
Who we are is where we come from. I come from brand marketing. My specialty is helping CEOs write their vision for the future. My partner comes from the agency world. His specialty is big creative marketing and advertising ideas. He makes a lot of campaigns (and once opened a bookstore that, uh, only sold his own book). Both practices are valuable. But both use internal resources differently. As we grew, the business would be lopsided at times. That created internal tension. The advertising creatives didn’t know what my team (the brand creatives) did or how to help. So we integrated the two disciplines. Realized they weren’t that different after all. Their value lies in connecting their systems and concepts. They provide different paths to client work, but common destinations.

8. Didn’t invest enough in project management at the beginning
I know, I know, I know! As a lone operator, I didn’t understand that creative teams thrived with capable PMs. Fixed that years ago. Still embarrassing to admit! 😬 😬 😬

9. Didn’t let go of old ideas quickly enough
Turns out, you can find strategists who are also good designers, and you can find brand designers who are also A+ at designing decks. I didn’t think this was possible, and so we got stuck in an old hiring paradigm. We’ve since learned to invest in leaders and creatives who can teach systems to other employees, which creates the conditions for scalable growth. There’s a certain symmetry there: we specialize in creating systems that do exponential work for our clients, too.

10. Thought a wonderful culture would just magically manifest itself
This was just silly. I thought that a great culture would just, you know, “happen.” Well, we got a culture, but it was disjointed and out of touch. We realized that we needed to actively work toward the culture we wanted. More off-sites. More team lunches. The occasional go-kart race.

But more than that, our creative team has begun working on a Digital Living code. It’s a handbook that sets expectations and standards for how we work together across this funky thing called the internet. It’s very simple: don’t take video calls in inappropriate environments, communicate your travel plans at least two weeks in advance, be inclusive and sensitive to everybody’s needs, stuff like that. Like a creative brief for our clients, it guides our operations across all departments and hires. Keeps everybody happy because it provides the right amount of structure without being overbearing. That scales.

11. No after-action reports
We’d have a great project or a project that didn’t go so well. But either way, we didn’t socialize the learnings with an after-action report, so it was hard to distribute knowledge. That was dumb.

Business Development

12. Didn’t clarify what we were selling
We confused some of our clients and potential clients by using mealy-mouth language to describe our offering. And so we’d end up in a conference room and an executive would say, “Article Group — you’re the guys who do content, right?” That was never a good sign. We do so much more than content, but we hadn’t done the hard work of being explicit about what we sell.

13. Made it too hard to buy our offering
Our core expertise is creating systems and solving big business problems with creative solutions. But when it comes to making a purchase, brands don’t have line items for “creative systems” or “audience touchpoint map.” Too often we would sell the “why” without selling the “what.” Clients would say, “You guys sound really smart, and a few of you have cool beards, but can you just tell me what exactly you’re going to create for us?”

14. Thought a consultant would fix our BD process
Nope. Nyet. Nein. We invited a consultant to come in and help us develop our BD process and even some of our work product. He was experienced and accomplished. Smart guy. But we should have pushed back on some of his assumptions and ideas more than we did. The lesson here is that we needed to put in the hard work, rather than thinking a single person would magically fix everything. There are no magical unicorn hires.

15. Didn’t sell strategically
As a young agency, a lot of our selling has been through the virtue of our good relationships. As my co-founder Andrew (still looking over my shoulder) says, our business has endured because everyone is in sales. And this can be a good thing! There are low-opportunity costs to staying in touch with contacts. But it wasn’t a good thing when we didn’t also have a strategic approach to the market, i.e., targeting the types of companies we wanted to work with and the type of work we were best at and wanted to do. You can and should rely on your personal network, but not to the exclusion of a strategic development plan. The opportunity costs for misspending time only get bigger as your agency grows.

16. Competed for the wrong work
We do our best work when we’re creating innovative and useful marketing systems for our clients. But sometimes we’d end up competing for work that was more tactical — X number of white papers, Y number of banner ads, Z number of articles. We prefer to first work more strategically (“Why do you need XYZ?”) instead of assuming the usefulness of XYZ is a given.

17. Sold the right thing at the wrong altitude
CMOs, CTOs, C-whatever-Os … they tend to understand and enjoy systems thinking. They get the power of exponential marketing, i.e., do the hard work up front in order to get long term benefits. That’s strategy. Marketing managers get strategy, too; they just don’t need it right now. They need tactical solutions. They need X white papers or Y banner ads or Z articles. Sometimes we would find ourselves selling strategy to somebody who needs tactics. Sometimes this would work. But other times it wastes our time and the client’s time, too. Stopped doing this.

18. Didn’t ask enough questions about the client’s business
Article Group prides itself on doing useful work. That is, work that takes into account the client’s business, how their incentives are aligned, and what their feedback loops are — and then we execute within that system to make a thing of value (or, when necessary and advisable, change that system). We’re really good at that. But in the beginning, we didn’t ask enough questions about our clients’ businesses. We made too many assumptions. That lengthens project times and makes it harder to “get to useful” faster.

19. Didn’t raise our hand
We have great relationships with our clients. We’re super proud of how closely we work together. And so we have seats at various tables waiting for us … but we didn’t ask to sit down. It took us so long to raise our hands with various senior execs we know, and say, “Hey, include us on stuff, yeah?”

20. Undercut our own creatives
Sometimes we had clients come to us with big ambitions to solve important and existential business problems. But then they didn’t want to pay for us to take the necessary steps to fully solve them. They wanted the work done really quickly. So we agreed to take some shortcuts. The net result was we did our best, but we didn’t always have the level of insight we needed to get to the heart of the matter. Look, this is going to happen. We have to be flexible. But we also learned we have to speak up when this challenge arises. That way, we’re prepared internally, and the client understands the limits of what they might receive.


21. Used too much jargon
Our habit was to hire super talented people from different types of places (brands, agencies, publishers) and drop them into projects to let them do their thing. Effective! But it prevented us from standardizing our language. We’d have three different staffers using a different word to describe the same thing. I mean … this was just … dogs and cats. Living together. Mass hysteria. Fixed that.

22. Didn’t define “insight” to our clients
One of the things we sell is insight. Sounds oracular. A lot of folks think insight is simply data: a particularly juicy tidbit of information. We think insight is interpretation. It’s about considering a pattern of facts, revealing the deeper truth behind them, and translating that truth into a powerful opportunity for our clients. The process of doing that is as much about creativity as it is about critical thinking. It’s subjective, and it can be messy. And that’s where we slipped. By not telling the full story of what insights are and how we get them, we led our clients to think that great insights come in neat little packages, without much time or effort.

23. Didn’t include strategists early enough
Strategists are trained to examine client challenges, do the appropriate research, and recommend action. They thrive on context. When you include strategists after the engagement begins they can’t do their best work. Lesson: include them early and often.


24. Hired smart people thinking that we’d figure out their role later
This. Doesn’t. Work. At least, it didn’t work the way we did it, or at our scale and with our business model and our management. We hired against needs and processes that we hadn’t really defined, so we ended up hiring the wrong people. We had to let some people — good people — go because they didn’t fit with our business. It would have been smarter to freelance archetypes of the people we needed, so we didn’t have to put people on an employment roller coaster. Lesson learned. Know thyself.

25. Didn’t create a predictable hiring pipeline
We didn’t make clear enough guidelines for who to hire and when. Had a vague idea and did some research, but we weren’t proactive in implementing. Fixed this.

26. Didn’t hire quickly enough
We were chronically understaffed, but the team we did have was so productive that we didn’t realize how worn down they were. Then everybody crashed and a client noticed. Ouch. We restructured a department, defined projects more thoughtfully, and got a key exec some help.

27. Should have made employees into owners sooner
It took us almost a year to implement an Employee Stock Option Program (ESOP). We said it was coming, but it took longer than we thought and employees noticed. That didn’t help morale. Good news is we’re rolling it out as we speak.

28. Didn’t have an onboarding process
We’d hire people and just throw them off the high dive. Just an email or two about benefits and a Slack login. ¯\_(ツ)_/¯ I didn’t listen to our engagement lead, who was (and continues to be) a strong advocate for onboarding (thanks for pushing us to be better, Matthew!). Getting better here.

Engagement / Project Management

29. Didn’t productize processes for staff
We thought we could PM ourselves. Guess what? We could not PM ourselves. That led to a lot of long nights and tired mornings. And, since we invested in PM late, we didn’t create repeatable processes internally for this function. That led to confusion between engagement and the creatives who staff projects. Fixed this. Live and die by our engagement team now.

30. Didn’t transition elegantly between BD and Engagement
The person who has the best relationship with the prospective client isn’t going to be the person who manages the project day-by-day. We knew this, but we didn’t create an elegant hand-off process. Sometimes that created tension with our clients. We’ve since solved.

31. Didn’t always have the hard conversations with clients
Projects are relationships. The more you communicate in a relationship, the more likely your expectations are aligned with reality. This is important because things like timing and scope are living, breathing things. Sometimes scope changes because the client decides they want more of X or less of Y. That scope change can affect timing. That timing change can affect cost. Along the way, we should continually be having open and honest conversations with our client: “Hey, these changes are going to affect deliverability. Here are options of how we can proceed.” If you don’t have these conversations, you’ll end up a) straining your creatives; b) misaligning your internal projects and estimates; and c) setting a client expectation that you eventually won’t be able to meet. This is a constant area of focus for us. We’ve gotten so much better.

32. Didn’t “get to useful” quickly enough
One of our guiding mantras is “get to useful quickly.” Useful is the point where our client can put our work into market. Where they see positive change, and quickly. Where we see market feedback and iterate accordingly. In the early years, we didn’t structure our engagements to get to useful quickly enough. These days, we always keep the mantra in mind and act accordingly.

33. Didn’t maintain the right relationship throughout the engagement
A while back, we began a project with the full support of the CEO. I had a good relationship with her. But when the work began, the CEO just … disappeared. We were left to work with mid-level management, which had no influence within the organization. So when we delivered our work, it landed with a thud. Since the CEO wasn’t part of the process, she didn’t have any buy-in. I should have spoken up along the way or asked for her continued involvement. Good news: now I can recognize when this process unfolds within an engagement and, if necessary, raise my hand.


34. Took too long to define a cohesive message
This is a direct result of our two different creative approaches. Caused problems when growing business; if a client wanted to suggest us to another group within the same organization, the client would have difficulty telling that other group what we could do for them! We’ve addressed, and recognize this as an area that will require constant vigilance.

35. Kept an ugly website
The first iteration of our website fell off the ugly tree and hit every branch on the way down. Wasn’t a big deal when business relied on word of mouth. But it succcckkkked once we tried to market ourselves. Fixed this. Better reflection of who we are now. Also realize it will continue to change as we evolve and grow.

36. Didn’t tell people about ourselves in the right way
There is a time and a place to do the hard sell. But there are also times and places to sell softly. One of the things our content team is always telling me, and a practice we try to communicate to clients, is “help people be themselves.” That means that the best content doesn’t try sell the reader on your value. The best content gives value to the reader. It gives them access to information they need to solve their problems or to access feelings they enjoy. The best content helps the reader to be a better version of themselves. We understand this now, and that’s why our newsletter is growing so quickly. People love it because it’s informative and delightful.

37. Didn’t create fun side projects
What were we thinking! A big part of the fun at an agency is being surrounded by creative people who love to work on creative projects. This year we institutionalized making the types of fun projects and ideas that got us here in the first place. That includes an annual project for creating holiday gifts for clients. We’ve got a good one on tap. Can’t wait to roll it out. Maybe you’d like to help?

If you’ve read this far, you’re clearly a student of building responsible, sustainable, and creative businesses. We’re hiring in San Francisco, New York, and Rochester. Creativity loves company. Thanks for reading.