How To Lose Most Of Your Employees In One Year w/ Benji Carlson

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Sep 9, 2025

Discover how an effective people plan can save your team from chaos. Benji Carlson shares insights from a challenging year in leadership, highlighting the importance of clear communication and trust. Learn about the common pitfalls contractors face and how to break the blame cycle within teams. Hear real-world reflections from business owners and practical strategies to empower your employees and enhance accountability. Tune in for actionable takeaways that can transform your organization!

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INSIGHT

Strategy Fails At The People Layer

Strategy is exciting until it must be executed through people, which is the hard part.
Execution fails when plans meet human behavior and communication gaps.

ANECDOTE

A $250k Business That Blew Up

Benji recounts his 2012 dumpster-fire year running a student painting franchise with poor hires and safety incidents.
The season collapsed, revenue fell short, and he learned the hard costs of no people plan.

ADVICE

Vision First, Structure Then People

Put vision first, design structure second, then hire people to fit the structure.
Write the org X's and O's before filling seats so hires match the plan.

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In this special episode of The LeanScaper Podcast, Benji Carlson takes the stage to deliver one of his most impactful talks yet: how to build a one-year people plan that actually works.

Most contractors love strategy - it’s fun, exciting, and creative. But sooner or later, every great plan must run through people… and that’s where the real challenges begin. In this live session, Benji shares the painful lessons a particularly bad year in business taught him about leadership, and the simple but powerful framework any entrepreneur can use to align their team, prevent chaos, and drive results.

You’ll hear from a bunch of the business owners in the room too, raw reflections on leadership mistakes, and practical takeaways you can implement immediately in your own company. If you’ve ever wondered how to get your people to care as much as you do, this is the episode for you.

In This Episode:
• Why strategy always breaks down at the people level
• The lessons Benji learned from his “dumpster fire year” in business
• How to design your org chart around vision, not chaos
The three most common hiring and leadership mistakes contractors make
• Practical tools to build trust, accountability, and performance across your team
• Audience Q&A: real-world people challenges and how to solve them If you’re interested in coming to a LeanScaper event like the one this talk was taken from go to LeanScaper.com/events to see our event calendar. We’d love to see you at our next one!

Timestamps
0:00 – Welcome to The LeanScaper Podcast
2:15 – Why strategy fails without people
6:30 – Benji’s “dumpster fire year” story
12:50 – Vision first, structure second, people third
17:45 – Clear deliverables and written agreements
22:40 – Chaos addiction vs. structure
25:00 – Why management systems matter
29:10 – Real-world people challenges shared from the audience
34:05 – Nervousness around delegation and leadership growth
38:50 – How to earn respect and inspire your team
40:55 – Every pair of hands comes with a free brain
46:30 – Hiring, firing, and culture fit lessons
49:00 – Closing reflections and takeaways