Building a Self-Managing Dream Team With Jason Swenk

Many consulting agency CEOs find themselves in what I call the ‘Entrapment Cycle.’ On paper, they’ve built a successful business. Their expertise and personal touch brought them great clients and a solid reputation. But now that same expertise has become a golden handcuff. They’re trapped by their own success, stuck in a model where growth equals more hours and stress.

They look around and see competitors who seem to be growing effortlessly. Meanwhile, they’re working 60+ hour weeks, constantly putting out fires, and laying in bed at night, they think: “There has to be a better way.” Does this sound painfully familiar?

In my recent conversation on Agency Mastery Podcast, I shared how this pattern shows up and, more importantly, how you can break free from it.

12 years ago, I faced this reality myself when preparing for maternity leave – my business couldn’t run or grow without me. That crisis became the catalyst for developing the frameworks I now use to help agency owners build truly self-managing teams.

Here’s what you need to know to transform your agency from a job into a real asset:

Why Most Hiring Processes Fail

Many agency owners make the critical mistake of rushing their hiring process, then wonder why they can’t find the right talent. They write vague job descriptions, skip crucial screening steps, and hope for the best. But you can do better by:

• Creating compelling job ads that act as your first filter
• Adding strategic “mousetraps” to screen for attention to detail
• Testing candidates with real-world scenarios before hiring
• Looking for people who can match your pace and vision while bringing their own strengths

Building Self-Managing Teams From Day One

Want to know the secret to having a team that runs your business without you? It starts with how you onboard and develop your people. Here’s what works:

• Give clear outcomes instead of micromanaging processes
• Empower your team to create their own weekly action plans
• Structure check-ins around progress, not task management
• Create systems that encourage independence and critical thinking
• Let your team make mistakes and learn from them (within safe boundaries)

The Operations Manager Game-Changer

Most agencies struggle because they either don’t have an operations manager or they’ve hired the wrong person for this crucial role. Your ideal ops manager should have:

• Impeccable attention to detail and follow-through
• Natural structure and organization (they’ll likely be more methodical than you)
• Enough assertiveness to question decisions and push back when needed
• Proactive mindset about finding efficiencies and solving problems
• Ability to match your company’s pace while maintaining quality

Remember: You’re not looking for a mini-CEO. You need someone who compliments your visionary nature with strong execution skills.

The Path to Freedom

Here’s the exciting part – when you get these pieces right, everything changes. You’ll find yourself:

• Having more time to focus on strategic growth and big picture
• Building stronger client relationships without being stuck in delivery
• Creating predictable systems that scale sustainably
• Actually enjoying your business again instead of feeling trapped by it

The transformation doesn’t happen overnight, but it starts with a decision – your decision to build something bigger than yourself. To create a business that serves your lifestyle instead of consuming it.

Common Pitfalls to Avoid

Many agency owners make these critical mistakes:

• Hiring too quickly out of desperation
• Not having clear systems and processes in place
• Failing to properly train and develop their team
• Holding onto control too tightly
• Not giving their team enough autonomy to grow

Your Next Steps

Ready to transform your agency? Start by evaluating your current team structure and identifying where you’re still the bottleneck. Then, create a plan to systematically remove yourself from those areas through better hiring, training, and systems.

Want to dive deeper into building your dream team? Grab a copy of my new book “The Hands-Off CEO”!

Remember: The goal isn’t to work harder – it’s to build a team and develop leaders who work smarter. When you focus on hiring right and developing strong systems, you create a business that truly serves your lifestyle instead of draining it.

Hands-Off CEO – Executive Briefing