Episode 047. The Delegation Mistakes That Keep Founders in the Weeds

17 Feb

Leadership is hard. Leading while running a business, managing a team of freelancers, and trying not to burn yourself out in the process? Even harder.

In this episode, Melissa and Meredith sit down with Steve Guberman, founder of Agency Outsight, former agency owner who scaled to 12 people before selling, and now an agency coach who's helped hundreds of founders navigate the messy middle of growth.

They get into the real stuff: How do you delegate without feeling like you're losing control? What does it actually look like to shift from doer to CEO? And what happens when your ego leads you to chase a "dream client" that nearly breaks your business?

Most Agency Founders Never Set Out to Be Leaders

They set out to be designers, strategists, writers. People who were really good at a thing and wanted to do more of it. Then clients came. Then a team became necessary. And suddenly you're managing people, processes, and payroll while trying to remember why you started this in the first place.

Steve Guberman knows this journey intimately. He started as a designer at Panasonic, moved through agencies, and eventually launched his own shop with a simple (ego-driven, he now admits) belief: I can do it better. But designing and running a design business are two very different things.

Learning to work on the business instead of in it (building systems, managing cash flow, leading a team) requires a complete mindset shift. The visual Steve uses: working on the business is like maintaining the jet's engine. Working in the business is flying it. You can't do both forever.

Empathy Doesn't Mean Doormat

One of the biggest misconceptions among agency founders? That being empathetic makes you a bad boss. Steve sees it constantly: founders pulling all-nighters because they didn't want to "bother" their team during business hours. Taking on work themselves because asking someone else felt demanding.

Absorbing everyone else's problems isn't empathy. It's actually working against yourself.

Real empathetic leadership looks like asking your team: "What do you need from me to be successful?" It looks like clearing obstacles and creating conditions for people to do great work, while still holding them accountable to commitments they've made.

The key word is commitments. When working with freelancers, you can't dictate hours or methods (legally speaking). But you can ask them to commit to a deadline and expect them to honor it. The framing matters: "Can you get this done by Monday so I have time to review before the client deadline Tuesday?"

If they say yes, you're expecting them to fulfill that commitment. If they consistently don't? That's not a scheduling problem. That's an integrity problem. And you need different people on your team.

The Founder-to-CEO Identity Crisis

The transition from founder to CEO isn't just tactical (delegating tasks, building systems). It's deeply personal. Many founders struggle with imposter syndrome in the leadership role because their identity has been wrapped up in doing the work, not managing it.

Steve sees this at every revenue level, from $500K agencies with a handful of freelancers to $20 million companies. The question is always the same: "What does it mean to show up as a CEO when I've always been the doer?"

The shift takes at least a year. Often longer. And it requires something most founders aren't prepared for: grief. Letting go of being the best designer in the room. Trusting someone else to have the client relationship. Accepting that your job now is vision and systems, not execution.

Not everyone wants to make that shift. And that's okay. Some founders realize they were happiest at three people, not thirty. The courage isn't just in scaling. It's in being honest about what you actually want and building intentionally toward that, even if it means contracting.

The Story That Changes How You See "Dream Clients"

Steve shared his own experience chasing a major AOR that everyone warned him was toxic. He went for it anyway. Won the pitch by underbidding.

They won. They underbid. They doubled overnight.

And nine months later, the client put them on notice. Steve had to lay people off for the first time. The thing his ego chased became the thing that forced him to contract. He sold the agency the following year, partly because (between layoffs, losing the account, and his divorce finalizing in the same months) he'd lost the confidence to close new business.

In hindsight, he believes they could have rebounded into a healthier, leaner agency. But that hindsight became the foundation for the coaching work he does now.

The Time-Tracking Exercise That Changes Everything

For founders struggling with delegation, Steve recommends a simple exercise: track everything you do for one week. Then grab four highlighters and categorize: project management, design, production, admin. Look at how you actually spent your time versus how you should be spending it.

Most founders are shocked. Hours of admin tasks that could go to a VA. Design work their designer should be doing. The low-hanging fruit becomes obvious.

The mindset shift underneath: your time as a founder should be spent on the thousand-dollar-an-hour activities (new business, strategy, vision), not fifty-dollar-an-hour tasks you could delegate or automate.

The Thread Through Everything

Intentionality and courage. They're not one-and-done mindset shifts. They're daily practices. Every founder wakes up some days without confidence, without clarity, without certainty. The work is showing up anyway: setting the vision, leading with empathy, and having the courage to resize, redirect, or reinvent when the business you built isn't the business you want.

Life's too short to work for shitty clients and spend 100 hours a week on a business you don't believe in. The thing you're most afraid to change? That's probably exactly what needs to change.

(00:00:00) Intro & Meet Steve Guberman

From agency owner to coach helping hundreds of founders navigate the messy middle
The ego-driven belief that launches most agencies: "I can do it better"
Why designing and running a design business are two very different things

(00:05:11) Setting Expectations with Freelancers: The Lawful Way

The commitment-based approach to holding people accountable (without crossing legal lines)
Why clear expectations must come before accountability
The difference between empathy and being a doormat

(00:10:31) The Inner Conflict: Empathy vs. Running a Business

When "leading with empathy" turns into self-sabotage
Absorbing everyone else's failures because holding them accountable feels mean
The Brené Brown moment: "You can lead with empathy and still be a good boss"

(00:13:05) The Emotional Burden of Being Responsible for Others

"People are depending on me to eat. That's a heavy burden to carry."
The weight of being responsible for your team's rent, their kids' activities, their mental health
Why this pressure can feel crushing even when you're doing well

(00:19:21) CEO Is a Mindset, Not a Headcount

The founder-to-CEO identity shift (it takes at least a year, often longer)
Why you can be a CEO of a two-person agency
Being honest with yourself about what you actually want to build

(00:24:06) Steve's Agency Story: Winning the AOR That Changed Everything

The massive AOR that doubled his agency overnight
The ego that drove him to chase that client
The painful layoffs when it fell apart a year later

(00:36:11) The Delegation Chicken-and-Egg Problem

When you can't afford to delegate but can't afford not to
The thousand-dollar-an-hour rule for founder time
Getting out of a toxic client relationship without blowing everything up

(00:39:21) The Time-Tracking Exercise That Opens Founders' Eyes

Four highlighters: what to stop, start, delegate, and keep
Making delegation obvious instead of theoretical
Focus on the thousand-dollar-an-hour activities

(00:44:52) Final Thoughts: Intentionality and Courage in Leadership

The courage it takes to build the business you actually want
Why the hardest work isn't in scaling, it's in being honest with yourself
Real empathetic leadership: ask what they need, clear obstacles, hold them accountable

This episode is brought to you by:

Copilot Money is the personal finance app that helps you navigate your finances with confidence. Copilot Money was built for the Darlings. It's a beautifully designed app that lets you track every card, account, budget, investment, and net worth trend in one place. Use our code DARLINGS for a 2 month free trial and get yourself set up for your next level of personal growth today. Get two months free with promo code DARLINGS at copilot.money/darlings

Want To Dive Deeper On These Topics?