The Kind vs Wicked Agency

In partnership with

Before We Get Into Today’s Topic…Let Me Ask You A Question…

What Are You Doing On Thursday Jan 8?

Stop Shining Yourself On With BS New Year’s "Resolutions"

On January 8th at 2pm Eastern, I'm running a live 90-minute workshop where we build your actual sales, content, team, and agency finances…not theoretical frameworks you'll never use, but documents you can use that same day. You'll also get the recording, slide deck, and a 2-month free trial to Call Lab Pro & Discovery Lab Pro ($120 value). If your 2025 plan didn't survive February, this is your shot to fix that.

→ Register HERE

I Listened To A Snippet of an Interview…on TikTok…WOW

I never thought that TikTok would lead me to anywhere other than brainrot headquarters, but there was a clip about Kind vs Wicked learning. David Epstein, the author of Range, was being interview and he kinda blew me away by articulating so much stuff that I’ve known and felt throughout the years as an entrepreneur, a CEO & a coach. (I am in the middle of Range & it’s pretty freakin’ fabulous so far.)

The basic idea is that there are two different ways of learning → specialist & generalist, or kind & wicked.

Kind learning is basically the way most agencies train their staff:

1. Here are the tools we use.

2. Here is a step by step SOP (Standard Operating Procedure).

3. We will give you structured, regular feedback.

4. If there are issues, we will adjust the tools & SOP.

5. Go back to #1.

The end result is that you get someone who is REALLY freakin’ good at doing that SOP & really freakin’ good at using the assigned tools & really freakin’ good at that workflow. This is process-based, muscle memory, nearly rote performance.

Wicked learning is how “A players” learn:

1. I know a lot of stuff about a lot of stuff.

2. I have an outcome to achieve but few guidelines.

3. I see patterns based on my past experiences.

4. I use those patterns to plan a novel course of action.

5. I evaluate progress and adjust.

6. Changing priorities & inconsistent feedback are accounted for in my plans.

The end result of a wicked learner is that you have a resource that can take ownership of pathways and outcomes. You have a resource that can grow and change w/o being told how…

The Future of AI in Marketing. Your Shortcut to Smarter, Faster Marketing.

Unlock a focused set of AI strategies built to streamline your work and maximize impact. This guide delivers the practical tactics and tools marketers need to start seeing results right away:

• 7 high-impact AI strategies to accelerate your marketing performance

• Practical use cases for content creation, lead gen, and personalization

• Expert insights into how top marketers are using AI today

• A framework to evaluate and implement AI tools efficiently

Stay ahead of the curve with these top strategies AI helped develop for marketers, built for real-world results.

Download the Free Report

Agency Leaders Get Stuck In Kind Learning Environment Hell

It sounds funny, doesn't it? Stuck in a kind hell. In the early stages, agency leaders often hire people who can only work in kind learning environment. These team members don't have the breadth of skills, a sense of personal agency, or even a bias towards action. In a kind of learning environment, feedback is regular, frequent, and immediate.

That dynamic provides safety to the teacher and the learner…just like school did. The teacher tells you what to create (an essay, presentation or even a goddamn “diorama” - I hated when my kids had to make those), and your grade was measured by how well you adhered to directions. Fidelity to the model is the most well-rewarded trait.

If you stock your agency full of kind learners (which is VERY common), you might develop a team of folks who are AMAZING at running DTC Facebook ads. If you land a client who also wants to advertise on Pinterest & Reddit, your team of crack Meta Ads experts likely do not have the aptitude to expand. The deeper one invests in a particular skill, the less likely they are to be able to easily see familiar circumstances, patterns & thinking in new places.

Your team can’t grow in the way you need because they might just be too damn good at what they do. Or, more likely, they can’t grow in the way that you need because they have no experience following a path that someone else hasn’t already marked.

Six resources. One skill you'll use forever

Smart Brevity is the methodology behind Axios — designed to make every message memorable, clear, and impossible to ignore. Our free toolkit includes the checklist, workbooks, and frameworks to start using it today.

Access the free resources

Specific Expertise Is REALLY Valuable (Until It Isn’t)

The kind learning environment thrives on models and feedback. Do the task, get feedback, apply the feedback & get better at the task. Repeat until you are world class. That’s the basis of doing something for 10,000 hours makes you elite - this idea is at the heart of Malcolm Gladwell’s great book, Outsiders.

Kind learning environments ABSOLUTELY speed the development of expertise in early career workers. In 30-60 days, with good training and feedback, can get pretty good at some basic agency-type marketing skills.

But here is the scary thing…you know what else really thrives on clear direction and regular feedback?

You guessed it - AI.

Early stage folks and some truly experienced experts run the risk of being disintermediated by lower cost remote workers or the very low cost AI worker.

Wicked Learners Are Less Susceptible to AI Disintermediation

It’s not that wicked learners are more valuable or better in any way. Kind learning environments create virtuoso violin players, surgeons & pro golfers - all really amazing skill sets that I will never approach.

But the wicked learner is more diverse, more broad & less “contained”. As AI & tech platforms handle more and more of the kind tasks, you are going to need to retool your staff.

You can’t take someone who has only operated in a kind learning environment and throw them into a wicked learning environment and expect them to thrive. But you need to build a pathway to wicked…

Wicked & Wonderful

Most educational & professional experiences lean kind. But you need to create wonderfully wicked learners to explore what is happening next while the kind tasks get disbursed to experts who never get tired as long as the data center is getting all the juice it needs.

Here is a wonderfully wicked development plan that your kind learner team mates might actually LOVE:

1. Teach Them Kindly - For A While: Help them develop skills and learn to apply feedback. When they are ready (which will be obvious because you will trust that they can do their job), you will pull back on giving feedback.

2. Start Asking For Self-Assessment: Instead of feedback, you ask them to give themselves feedback… Example: “Hey Susan, how did things go with {big client} last week? Give me 3 things we did really well and 3 things we need to improve on.” The first few times you make this ask, the answers will be terrible. Gently push and the actual self-assessments will become insightful.

3. Start Asking For Improvement Plans: After you start noticing some feedback patterns, you switch it up and say “Hey Susan, over the last month, we’ve had these issues a couple of times - how do you think we ought to fix it.” They will offer up a terrible solution, and you will gently prod until they get something good. It will take a while…

4. Start Asking For Plans That Aren’t Right Up Their Alley: After their self-diagnosis and remediation skills are working well, ask them to opine on something a little bit outside their expertise, like “Hey Susan, thanks for your help in getting monthly reporting in a better spot. Maybe you can gather some thoughts around onboarding?” At the beginning, theyu won’t be terrific thoughts, but just exercising those muscles is developing their wicked sensibilities.

5. Ask Them What Project They Want To Work On: Ask them where they REALLY want to contribute - and let them. Let them stumble, fall & catch them before it gets messy.

Then you’ve got a full-fledged wicked thinker, learner & doer who will drive value for your business regardless of low-cost labor or the latest agentic magician conjured up by Sam Altman.

Easy setup, easy money

Your time is better spent creating content, not managing ad campaigns. Google AdSense's automatic ad placement and optimization handles the heavy lifting for you, ensuring the highest-paying, most relevant ads appear on your site.

Earn with Google AdSense

Our sponsorships are ads (obviously - duh). But some of the companies or services linked in our content may pay us a minimal commission if you buy something from them. Potential payment is never a factor in what we link to, and we have direct experience with every company or service where you can buy something that we mention in our content.