If you’ve ever had that feeling about someone on your team—the subtle “something’s off” whisper in your gut—you’re not alone.

In this episode, Megan is joined by her longtime COO and teammate of 14 years, Gina Johnston, to unpack one of the trickiest leadership challenges: knowing when to coach…and when to cut ties.

Whether you’re leading a team of 10 or just thinking about hiring your first assistant, this is the honest, behind-the-scenes conversation every business owner needs to hear.

Because sometimes, leadership isn’t about waving pom-poms. It’s about setting clear expectations, having hard conversations, and asking yourself the uncomfortable but necessary question:

Is this a coaching opportunity…or is it time to let them go?

What You’ll Learn in This Episode:

✅ The 3 must-dos for onboarding a new team member
✅ What’s actually coachable—and what probably isn’t
✅ The leadership mistake Megan made that cost her time and energy (so you can avoid it)
✅ Why you shouldn’t hire in a moment of panic (and what to do if you already did)
✅ How to avoid getting stuck in the dreaded “gray zone” of mediocre team performance
✅ The one thing people pleasers need to hear when it’s time to let someone go
✅ A free resource to improve your team’s communication and event debriefs

Free Resource:
Post-Event Team Feedback Questionnaire
Get Megan & Gina’s go-to tool for checking in with your team after each event. It’s simple, practical, and a game-changer for team growth and accountability.
Download it here - https://learn.theplannersvault.com/teameventdebrief

Timestamps:

00:00 – The hiring gut check no one talks about
 02:27 – Meet Gina: 14 years, one unicorn hire
 04:11 – Why panic hiring is usually a mistake
 08:01 – The 3 non-negotiables for onboarding
 13:21 – How to give (and track) meaningful feedback
 16:10 – What you can coach (and how)
18:55 – What you can’t coach—no matter how nice they are
20:41 – People pleasing vs. leadership
24:24 – Boundaries when you’re also friends
28:15 – Using vendors as a feedback loop
29:21 – Let your team fail (seriously)
30:07 – How to navigate the gray zone with clarity
31:27 – Final takeaways + how to lead with intention

Weddings for Real on Social Media:

Instagram: @weddingsforreal

Facebook: @weddingsforreal

twitter: @weddingsforreal

Hosted by Megan Gillikin, Weddings for Real is presented by The Planner's Vault, and is produced by Walk West.