(Not Just Management)

What actually makes a good boss in an agency setting? It is not just being the hardest worker or the person with the biggest title. Leadership in your agency shows up in how you treat people, how you set standards, and how you handle the messy parts of growth like hiring, feedback, and sales.

In this post, we will walk through real stories from agency owners Kurt von Ahnen and Toby Cryns. They talk about bad leadership habits, hard lessons, better systems, and the mindset shift from “high performer” to actual leader. If you run a small agency or studio, this will feel very familiar.

From Hard-Nosed Manager to Actual Leader

Kurt did not start out as a good boss. By his own words, he was a “hard-nosed jerk.”

As an employee, he was a high producer with workaholic habits. Every time someone promoted him, he treated management as a chance to push harder and faster.

His style was simple and harsh:

• Work harder because he said so.
• Hit goals at all costs.
• If you do not like it, someone else will take your job.

The results were mixed. The teams hit numbers. The organization got results. But, as Kurt says, “People enjoyed the successes, but they did not enjoy working with me.”

He had embraced management, not leadership.

Management for him meant pressure, threats, and rigid goals. Leadership came later, after he realized something was broken. People did not want to work with him, and that was not a “them” problem.

He went deep into John Maxwell’s work, read the books, and even got John Maxwell certified. That process forced him to rethink what a leader is supposed to do.

Here are a few key lessons that changed his approach:

• Extend grace to people instead of assuming bad intent every time there is a miss.
• Accept that if someone can do a task 80% as well as you, that is usually enough.
• Stop expecting employees to “take ownership” like founders do, because the project is not theirs to own.

As Kurt puts it, as an entrepreneur, our buy-in is much higher than the average person’s. Expecting the same emotional stake from a salaried developer or a contractor sets everyone up to fail.

Leadership starts when you accept that reality and lead people where they are, not where you wish they were.

Turning “Ownership” Into Clear Processes

Agency owners love to say, “I want my team to take ownership.” It sounds great, but in practice, it often hides a process problem.

Toby shares a real example from his web development team. His biggest pain point is quality assurance. Developers were shipping work that they claimed was client-ready, but basic issues were still present. Menus broken, headers not matching designs, and mobile layouts off.

You could call that a “lack of ownership,” but that label does not solve anything. The better question is, what process is missing?

How Kurt Uses Training Instead of Nagging

Kurt takes a very structured approach. Since he is an e-learning nerd (his words), his team records video screen shares of their processes. They turn those into lessons inside a private course on their site.

When they hire someone new, they do light onboarding as humans, then let the training do the heavy lifting:

1. Introduce the new person to the team.
2. Point them to the course sections that match their role.
3. Have them complete those lessons so they learn the exact process.

This equips them without one-on-one training every time. It also acts like a checklist with context, since people see real examples, not just a bullet list in a doc.

This kind of structure also guards against enabling bad performance. With clear training and standards in place, the conversation shifts from “You should know this” to “You had access to this, what is blocking you?”

You encourage people to get better, and you keep responsibility where it belongs: on leadership to define and teach the standards.

Leadership vs Management: Filling Gaps Without Blame

There is a simple line that helps separate management from leadership:

• Management says, “You just need to do better.”
• Leadership asks, “How can I help you do this better?”

That one shift is huge. Great leaders shift responsibility to themselves to keep standards clear and give people what they need to succeed.

Of course, not every problem is a training issue. Sometimes people are just lazy or not a fit. The hard part is knowing which is which.

A Powersports Example: “Advanced” Managers Who Are Not

Kurt also runs training for service departments in motorcycle dealerships. Owners often tell him, “My service manager has been doing this for 20 or 30 years. He needs an advanced course, not beginner stuff.”

Then Kurt gets those managers on a call, sometimes 6 to 10 dealers at a time, and asks simple questions:

• “How many motorcycles did you work on last month?”
• “How many hours did your technicians turn?”

No hands go up.

These are the supposed experts, but they do not know the basics of their own numbers. That shows a core truth:

Time in a role does not equal skill without formal training.

We do this in agencies too. Someone has been a “project manager” or “lead developer” for years, so we assume they are advanced. Then we are shocked when they break under real standards.

Leadership in your agency means you stop assuming and start checking for gaps in understanding.

When You Are Mad at Your Team

Even with the best mindset, leading people is emotional work.

Toby talks about how he still gets angry when developers do not meet his expectations. His own background as a developer means he expects them to code and QA like he does, idiosyncrasies and all. When they do not, he sometimes has to close the laptop and walk away.

His frustration is not really about new vs seasoned team members. It is about whether people seem to care and take responsibility for what they ship.

A Consulting Story That Shows Why This Is Hard

Toby is also consulting with a 40-year-old company that wants to “modernize” because AI is changing their industry. His job is to push them forward.

They finally agree on one innovative project. They plan it, decide it is a good idea, and then schedule it to start the following June.

It is October.

Toby says, “Great, we have that locked in. Let us meet next week and plan the next thing.” They shut him down. They want to stop until the following October.

He is frustrated, but the free Zoom meeting ends at 45 minutes and cuts him off. He is relieved, because he was about to lose his cool.

In both his agency and his consulting, the pattern is the same. Leadership means managing your own reactions when people do not match your pace or urgency.

The Origin of “Mañana No Mas”

This tension even helped name Kurt’s business.

Years ago, he had a room full of clients who had not done their homework for their websites. No content, no prep, nothing. He snapped and said, “Mañana, there is no easy button. If you are not vested in your own success, I cannot make you successful. You cannot put off till tomorrow what you should be doing today.”

“Mañana, there is no easy button. If you are not vested, I cannot make you successful.”

Someone in the room said, “That would be a good name for your business.” Mañana No Mas was born.

Frustration can be a warning light. It tells you there is a system problem, a people problem, or an expectations problem. Good leaders go looking for which one it is.

Giving Honest Feedback Without Burning Bridges

Honesty matters, but so does how you say it.

Toby shares how his feedback style has changed. In the past, he might say, “You promised to deliver this today, and you did not. What is going on?”

Now he tries to keep the same honesty, with more care for the other person’s dignity.

More Helpful Phrases You Can Use

Kurt gives some useful wording that keeps things firm but fair:

• “I understand that life happens, but we also have firm deadlines for our clients.”
• “I was expecting this deliverable by [date] and have not seen it. If I missed it, please point me to it.”
• “If you have not delivered it yet, I need to understand why, because this affects what we promised the client.”

He also likes to ask, “Are you overcommitting and underdelivering?” If someone says they will hit October 24 but secretly thinks November 1 is fine, they would rather they just say November 1.

Computers update, internet fails, platforms go down, but the client still expects what you promised. Mature feedback makes that context clear without turning it into a personal attack.

Over time, honest but diplomatic feedback builds more trust than either silence or anger.

Growth, Roles, and Misaligned Ambitions

During a recent interview, a candidate asked Toby a good question: “What are the growth opportunities at Mighty Mo?”

The honest answer is tricky for a small agency. There are not many roles to move into, and ideally, no one is leaving.

His reply was simple. If you are enterprising and spot opportunities, there will be room to grow, because the company itself is growing. If you expect a corporate-style ladder, you will be disappointed.

Kurt looks at it in a similar way. If someone brings in referrals, helps with proposals, and pushes projects forward, the “upside” is there. But:

There is no “mama bird feeding baby bird.” You have to help build the thing if you want to grow with it.

He learned that the hard way with a CEO he once hired. At first, that CEO was helpful. After a year and a half, he wanted to scale the business back so he could take more vacations. He tried to work during vacation with bad internet, and it embarrassed the company in front of clients.

Kurt had to fire him. Even at the top, people can be out of sync with the actual growth goals.

Leadership in your agency includes being honest about where the company is going and who fits that journey.

Hiring for Skills, Communication, and Work Style

Toby is clear that he does not hire for “vibes” or feelings. He looks for skills, some talent, and especially strong communication.

Most of his team speaks English as a second language. That is not the problem. Disorganized communication is.

He shares an example of a teammate who called a meeting and was supposed to lead it. When Toby joined, there was no agenda. They talked for 20 to 30 minutes, and he still did not know what the meeting was for.

He stopped the call and said, “Let us reschedule. Next time, show up with an agenda. Otherwise, what are we doing here?”

If that pattern continues, it might be a deal breaker. You cannot lead projects if you cannot structure a conversation.

The REAL Model: Hiring for Work Style

Kurt looks at “work styles” more than old-school personality types. He uses a simple REAL model:

Letter	Type	Short Description
R	Rulers	Take charge, drive decisions
E	Entertainers	Detail-oriented, love structure and data
A	Analysts	Emotional, relationship and support-driven
L	Loyalists	Emotional, relationship and support driven

He knows he is a mix of Ruler and Entertainer. If he hires too many people like himself, meetings turn into conflicts. So he looks for more Analysts and Loyalists to balance the team.

For example:

1. Rulers and Entertainers push, present, and lead.
2. Analysts build agendas, process, and structure.
3. Loyalists bring heart, support, and often creativity.

He has an artistic team member who is a strong Loyalist. Her design work is outstanding, but her communication style can be messy and emotional. Because her core skill is so strong, Kurt works around the style and pulls her back in as needed.

Skills matter, but often you can train skills if there is a base. Work style and communication are harder to teach.

Mission, Vision, and Saying No to the Wrong Clients

A friend of Toby’s runs a larger agency with 60 to 70 employees. They talked about mission and vision, and his friend said something interesting.

Mission and vision did not feel important until he stepped out of daily operations. Once he was not there every day, people started asking, “Why are we here? What are we aiming at?”

When the “captain” is on the boat, people just follow. When he leaves in a smaller boat, the crew needs a chart.

Kurt adds another angle. He used to say yes to everything when he lived in a tougher economy. After moving to a region with a stronger economy, he gained the freedom to say, “That is not a great fit for us right now.”

That shift changed everything:

• Better fit clients.
• Better work quality.
• Better project revenue.
• Less stress.

Companies can look identical from the outside but be very different inside. Values, pace, and mission matter more than a logo and a website.

Part of leadership in your agency is choosing clients who fit what you are building.

Marketing vs Sales: Why Growth Needs Both

A common trap for agency owners is confusing marketing with sales.

Kurt talked with someone who was proud of their “plenty of clicks” and traffic, but had very few new customers. Everything they described was marketing: branding, content, website visits.

None of it was sales.

Sales is picking up the phone, sending personal emails, and asking people to work with you. It is follow up, not just impressions.

Kurt admits he probably needs a salesperson himself. He is on several podcasts a week and makes a lot of content, but the plays on shorts and videos are small. Exposure alone does not pay the bills.

Toby is attacking the problem by hiring a full-time LinkedIn lead generation specialist. His goal is to roughly double revenue. They are already at about 180% of last year and may hit the target.

You Do Not Need a Million Customers

Most marketing books are written for products that need huge audiences. Agencies do not. You might only need ten great clients a year.

Toby uses an example from music. A friend wanted to get her songs in front of Billy Corgan, Radiohead, and Eminem. She saw it as a marketing problem.

He reframed it as a sales problem.

You do not need one viral post. You need to map the network around that person:

• Who is the assistant?
• Who knows the assistant?
• Who can introduce you to that person?

Then you take people out for coffee, ask for small intros, and work your way in. In six months, you might get a five-minute meeting where they are actually ready to listen.

It might be harder to get in front of a CEO at Best Buy or Walmart than a rock star, but the process is the same. Sales is targeted relationship building, not shouting into the void.

Networking and Lead Generation That Actually Creates Work

Kurt treats LinkedIn like a deliberate networking tool.

He grew from about 1,200 connections to 10,000 in two and a half years. During that time, he invited new connections to short “icebreaker” calls and ended up speaking with roughly 7,000 of them.

How His Icebreaker Calls Work

He does not pitch in the DMs. Instead, he sends a simple invite: “Thanks for connecting. Want to have an icebreaker conversation?”

On the call, usually 15 minutes, he asks:

• Who are you and what do you do?
• What do you like to do when you are not working?
• If you were not doing this for a living, what would you do instead?

That last question often uncovers people who secretly want to write a book, start a business, or become a coach.

Once the ice is broken, he usually says something like, “You are probably not ready for my services right now. I just want to stay in your mind for the future. But who do you know that I should know?”

They agree to play “referral ping pong,” sending each other introductions over time. The result:

• New contacts in the same city or niche.
• Podcast invitations.
• Real revenue.

He met people like serial entrepreneur David Valentine and podcast host Eric Allen this way.

Some people say, “I do not have time for coffee with everyone.” Kurt’s answer is simple. He is not having coffee with everyone, only with people he targets through search.

And in his view, coffee with a “nobody” is still better than sitting alone waiting for work.

Building More Than a Job: Diversification and Exit Strategy

Agencies often see behind the scenes of many different business ideas. That is a gift if you pay attention.

Kurt built e-learning sites for brands like Ducati and Suzuki. After seeing what worked for them, he asked, “Why not launch my own version?”

He started Powersport Academy. For years, it did almost nothing. Now it is on track to bring in about $60,000 a year.

That extra vertical means he does not have to rely on the next e-learning client to pay the mortgage. When website leads slow down, training revenue keeps flowing.

Some experts say “the riches are in the niches” and warn against spreading out. But dry months are real. Multiple revenue lines make those less scary.

From Job to Business With an Exit

Kurt draws a line between a job and a business:

• A job is when you only support yourself.
• A business is when you also support other people.

He moved from solo work to leading a team of contractors across the globe. That feels like a real business to him.

The next question is, what happens when you want to step away?

If your agency is just:

• A handful of clients,
• A few contractors,
• Some random habits in your head,

There is nothing to sell.

If you build:

• Documented processes,
• Training paths,
• Onboarding systems,
• A clear strategy,

you create something that someone else can buy and run.

Employing others and building those systems is a rich life experience on its own. But it also sets up a future where you have options, not just a never-ending list of tasks.

Conclusion: Leadership Is Your Real Growth Engine

Leadership in your agency is not a slogan or a book on your shelf. It shows up in the way you:

• Treat people when they miss.
• Turn “ownership” into clear processes.
• Give honest feedback without shaming.
• Hire for work style and communication, not just skills.
• Invest in both marketing and real sales activity.
• Build networks that actually feed your pipeline.
• Create systems that outlive you.

If you run an agency, pick one area from this post and improve it this month. Maybe you record a training video, rewrite your feedback scripts, or schedule ten real LinkedIn conversations.

Over time, those small leadership moves add up to something that looks a lot like freedom: better clients, better work, and a business that can keep going even when you are not in the room.