In this episode of Inside the 90, Andrew talks with Jenna Spencer, founder of AssistPro and a newly licensed EOS partner focused on delegation and elevation. Jenna traces her path from corporate banking to building a company that matches business leaders with the right assistant, a journey that started when she worked directly for two EOS implementers.

The conversation dives deep into why delegation fails, the difference between delegating tasks and delegating true ownership, and how to build trust with a new team member over time. Jenna shares practical frameworks, including the delegate and elevate tool, the relay race analogy, and the power of defining ideal outcomes instead of micromanaging the mechanics of a task.

Key Topics

– Jenna Spencer's path from corporate banking to founding AssistPro.

– Why most leaders struggle with delegation and end up doing task delegation instead of ownership delegation.

– The mail-checking analogy for understanding true delegated ownership.

– Where to start delegating, including knowing yourself and picking just a few things first.

– The real cost and return on investment of delegating a leader's time.

– Building trust with a new assistant or team member over time.

– Why protected weekly meetings matter for a healthy delegation relationship.

– The delegate and elevate tool and defining roles by quarter.

– Using DISC, Kolbe, and Working Genius to build well-matched teams.

Chapters

0:00 – Welcome to Jenna Spencer and introduction to AssistPro.

1:30 – Jenna's journey from corporate banking to founding AssistPro.

3:30 – Working as an assistant to two EOS implementers.

5:00 – Why delegation is one of the hardest leadership skills.

7:00 – Task delegation versus true ownership delegation.

9:30 – The mail-checking analogy for delegating ownership.

11:30 – Where to start delegating as a maxed-out visionary.

14:00 – Knowing yourself and picking a few things to delegate first.

16:30 – The real cost and ROI of delegating your time.

18:30 – Learning to slow down and build trust over time.

21:30 – Navigating trust and communication with an assistant.

24:00 – The importance of protected weekly meetings.

26:30 – Focusing on the issue, not the person.

28:00 – Tactical first steps to hiring an assistant.

30:30 – Using DISC and Kolbe to find the right match.

32:30 – The all-or-nothing rule for calendar and email delegation.

35:00 – The relay race analogy for handing off responsibilities.

37:00 – The delegate and elevate tool and defining roles by quarter.

39:00 – The Responsibility Clarifier and outcome-based delegation.

42:00 – Why unclear outcomes cause delegation to break down.

44:00 – Applying delegation lessons beyond assistants to any role.

46:00 – Using Kolbe, DISC, and Working Genius to build balanced teams.

49:00 – Where to find Jenna Spencer and closing thoughts.

Mentions & Credits

EOS Worldwide – https://www.eosworldwide.com

Wonder – https://workwithwonder.com

AssistPro – https://assistpro.com

Alex Freytag – https://implementer.eosworldwide.com/alex-freytag

Delegate and Elevate Tool – https://www.eosworldwide.com/delegate-and-elevate

Gino Wickman – https://www.ginowickman.com

The 6 Types of Working Genius – https://www.workinggenius.com

Kolbe – https://www.kolbe.com

DISC – https://www.discprofile.com

Strategic Coach – https://www.strategiccoach.com