
165: Working with Friends and Family
Hustle Humbly Podcast · Alissa Jenkins & Katy Caldwell
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Show Notes
Working with friends and family sounds like it should be easy… but it's often anything but.
In this episode, we're breaking down how to keep it professional with people you know—from getting them to choose you as their agent to navigating the transaction without damaging the relationship.
Because here's the truth: mixing business and personal life can get messy fast… unless you have clear systems, communication, and boundaries in place.
We're sharing real-life scenarios, mindset shifts, and practical strategies to help you avoid awkward situations, protect your time, and still deliver an incredible client experience.
If you've ever felt pressure to work with friends and family (or frustration when they didn't choose you), this episode will give you a healthier, more professional approach.
Here's what we cover:
-Why you can't expect friends and family to automatically use you -How to ask for their business without making it awkward -Why rejection from people you know isn't personal :contentReference[oaicite:0]{index=0} -How to handle it when someone chooses another agent -The two sides of this topic: getting the client + working the transaction -Why working with friends can feel more high-pressure than strangers -The importance of treating them like any other client -How your systems create consistency and professionalism -Why skipping your process leads to problems -How to set boundaries without damaging relationships -What to say when friends text or call outside business hours -Why not every friend or family member is a good client fit -When it's okay to refer them out (and why that protects your relationship) -How to avoid "looky-loo" situations with people wasting your time -Why you must communicate how and when you get paid -How to stay top of mind without being salesy -Ideas like CMAs, vendor lists, and asking for advice -Why some people will never refer you (and that's okay) -How to identify and appreciate your true advocates -The importance of not oversharing or complaining about your business -Why professionalism builds trust—even with people closest to you
Resources & Mentions:
-Episode: Be the Boss -Episode: What to Do When You're New or Slow -Email Templates 101
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Music: Straight A's by Connor Price The Good Life by Summer Kennedy Be The One by Matrika