You know the type—talented, high-performing, but impossible to work with. In this episode of Dear Billionaire, we dive into how to coach the uncoachable—or cut ties with toxic staff for good.

Skipping straight to termination might feel tempting, but it’s lazy leadership. Real leadership means offering clear, documented opportunities for improvement.

Whether you're a house manager, estate manager, or high-net-worth homeowner, this episode will give you the tools to:

- Identify when to coach—and when to cut ties

- Document expectations and build accountability

- Reduce turnover and burnout among collaborative staff

- Protect your team culture from entitled behavior

Purchase Kelly’s Staff Success Plan Template Package: https://www.estatemanagementsystems.com/shop/p/staff-success-plan-template-package

Next Steps:

Get our "Master List of Lists for Managing a Mansion": https://www.estatemanagementsystems.com/email-signup

Talk 1:1 with Kelly: https://calendly.com/estate-management-systems/discovery-call

Shop: https://www.estatemanagementsystems.com/shop-three-offers

#Coaching #termination #leadership

If you think team building means dragging your household team to an escape room while Cindy the housekeeper solves every puzzle...think again. In luxury homes, siloed staff can quietly derail service and morale. To build a world-class household team, you must first break down the barriers that keep siloed staff from working collaboratively.

Whether you're an estate manager, house manager, or high-net-worth homeowner, this episode will give you the tools to:

- Improve communication and service consistency

- Reduce staff burnout and turnover

- Establish a culture of collaboration and cross-training

- Recognize and reward high-performing team behavior

Resources & Links:

Download Kelly’s new ebook: The Ultimate Guide for Creating a World-Class Team

https://www.estatemanagementsystems.com/shop/p/ebook-the-ultimate-guide-for-creating-a-world-class-team

Read more on our blog: https://www.estatemanagementsystems.com/blog/from-siloed-staff-to-a-world-class-team-team-building-for-domestic-staff

Household Staff PTO Series:

𝐇𝐨𝐰 𝐭𝐨 𝐏𝐥𝐚𝐧 𝐟𝐨𝐫 𝐇𝐨𝐮𝐬𝐞𝐡𝐨𝐥𝐝 𝐒𝐭𝐚𝐟𝐟 𝐏𝐓𝐎 𝐖𝐢𝐭𝐡𝐨𝐮𝐭 𝐃𝐢𝐬𝐫𝐮𝐩𝐭𝐢𝐧𝐠 𝐘𝐨𝐮𝐫 𝐄𝐬𝐭𝐚𝐭𝐞 https://youtu.be/SJKcSGwh_6A

𝐇𝐨𝐰 𝐭𝐨 𝐑𝐮𝐧 𝐘𝐨𝐮𝐫 𝐇𝐨𝐦𝐞 𝐋𝐢𝐤𝐞 𝐚 𝟓-𝐒𝐭𝐚𝐫 𝐇𝐨𝐭𝐞𝐥 (𝐄𝐯𝐞𝐧 𝐖𝐡𝐞𝐧 𝐒𝐭𝐚𝐟𝐟 𝐓𝐚𝐤𝐞 𝐏𝐓𝐎)

https://youtu.be/Iv7qxTmz-Pk

𝐍𝐞𝐱𝐭 𝐒𝐭𝐞𝐩𝐬?

Get our "Master List of Lists for Managing a Mansion": https://www.estatemanagementsystems.com/email-signup

Talk 1:1 with Kelly: https://calendly.com/estate-management-systems/discovery-call

Shop: https://www.estatemanagementsystems.com/shop-three-offers

#teambuilding #staff #teamwork

When staff take PTO, does your home fall apart? If the answer is yes—or almost—this episode is a must-watch. In world-class estates, operations stay seamless even when staff take PTO, thanks to cross-training, smart planning, and clearly defined systems. I’ll show you how to create the same results in your home.

In this episode, we cover:

- Why most private homes are one vacation away from chaos

- The must-have Cross-Training & PTO Coverage Plan used in elite households

- The real cost of staff burnout—and how to prevent it

- 4 simple steps to maintain five-star service

- How to stop turnover and keep your best people long term

Household Staff PTO Series:

𝐇𝐨𝐰 𝐭𝐨 𝐏𝐥𝐚𝐧 𝐟𝐨𝐫 𝐇𝐨𝐮𝐬𝐞𝐡𝐨𝐥𝐝 𝐒𝐭𝐚𝐟𝐟 𝐏𝐓𝐎 𝐖𝐢𝐭𝐡𝐨𝐮𝐭 𝐃𝐢𝐬𝐫𝐮𝐩𝐭𝐢𝐧𝐠 𝐘𝐨𝐮𝐫 𝐄𝐬𝐭𝐚𝐭𝐞 https://youtu.be/SJKcSGwh_6A

Read More On Our Blog

https://www.estatemanagementsystems.com/blog/how-to-run-your-home-like-a-5-star-hotel-even-when-staff-take-pto

𝐃𝐨𝐰𝐧𝐥𝐨𝐚𝐝 𝐭𝐡𝐞 𝐅𝐫𝐞𝐞 𝐂𝐫𝐨𝐬𝐬-𝐓𝐫𝐚𝐢𝐧𝐢𝐧𝐠 𝐏𝐥𝐚𝐧 𝐓𝐞𝐦𝐩𝐥𝐚𝐭𝐞

Use the exact system I’ve implemented in dozens of high-net-worth homes:

https://www.estatemanagementsystems.com/cross-training-program-optin

𝐖𝐚𝐧𝐭 𝐦𝐨𝐫𝐞? 𝐆𝐞𝐭 𝐭𝐡𝐞 “𝐌𝐚𝐬𝐭𝐞𝐫 𝐋𝐢𝐬𝐭 𝐨𝐟 𝐋𝐢𝐬𝐭𝐬 𝐟𝐨𝐫 𝐌𝐚𝐧𝐚𝐠𝐢𝐧𝐠 𝐚 𝐌𝐚𝐧𝐬𝐢𝐨𝐧”:

https://www.estatemanagementsystems.com/email-signup

𝐁𝐨𝐨𝐤 𝐚 𝟏:𝟏 𝐜𝐚𝐥𝐥 𝐰𝐢𝐭𝐡 𝐊𝐞𝐥𝐥𝐲:

https://calendly.com/estate-management-systems/discovery-call

𝐄𝐱𝐩𝐥𝐨𝐫𝐞 𝐨𝐮𝐫 𝐭𝐞𝐦𝐩𝐥𝐚𝐭𝐞𝐬 & 𝐭𝐨𝐨𝐥𝐬:

https://www.estatemanagementsystems.com/shop-three-offers

What’s working in your household when someone takes PTO? Share your wins or challenges below—I’d love to hear your story.

#StaffPTO #EstateManagement #LuxuryHomeLife #HouseholdStaff #PrivateService

Your staff deserves time off, but your house and family keep running full steam.

How do you balance both without chaos?

In this episode, we’re exploring smart, seamless strategies for managing household staff personal time off (PTO) so your home runs smoothly even when key team members are away. From proactive scheduling to cross-training tips, I’ll show you how to maintain consistency, reduce stress, and keep everything on track — no scrambling required. By the end of this episode, you’ll have a game plan you can actually rely on.

Read more on our blog: https://www.estatemanagementsystems.com/blog/how-to-plan-for-household-staffs-pto-without-disrupting-service

Get our FREE Personnel Time Off Plan template: https://www.estatemanagementsystems.com/personnel-time-off-plan-optin

𝐆𝐞𝐭 𝐘𝐨𝐮𝐫 𝐅𝐫𝐞𝐞 𝐓𝐨𝐨𝐥𝐤𝐢𝐭!

Download our 𝐇𝐨𝐰 𝐓𝐨 𝐌𝐚𝐧𝐚𝐠𝐞 𝐀 𝐌𝐚𝐧𝐬𝐢𝐨𝐧™ 𝐖𝐨𝐫𝐤𝐛𝐨𝐨𝐤 & 𝐂𝐡𝐞𝐜𝐤𝐥𝐢𝐬𝐭 to manage your property and staff with clarity and confidence.

https://www.estatemanagementsystems.com/how-to-manage-a-mansion

𝐍𝐞𝐱𝐭 𝐒𝐭𝐞𝐩𝐬?

Get our "Master List of Lists for Managing a Mansion": https://www.estatemanagementsystems.com/email-signup

Talk 1:1 with Kelly: https://calendly.com/estate-management-systems/discovery-call

Shop: https://www.estatemanagementsystems.com/shop-three-offers

#luxurylifestyle #employeeengagement #highnetworth

"You’re Not A Good Fit."

Homeowners use this phrase to dismiss staff when they want to take a chance and see what happens next. It’s their right and privilege to choose who they want in their home and to relieve staff of their duties, even those who are competent, for reasons that may seem irrational or unfounded from an outsider’s (or even an insider’s) perspective. These decisions, whether logical or not, often reflect underlying dynamics that may not be immediately apparent from an employment standpoint.

Let’s dive into 10 reasons WHY homeowners use this tactic to dismiss domestic staff.

Thanks for listening!

Read the blog post: https://www.estatemanagementsystems.com/blog/private-services-worst-trait-youre-not-a-good-fit

For more information, visit our Linktree: https://linktr.ee/estatemanagementsystems

#estatemanagementsystems

#Estatemanagerhousemanual

#Estatemanual

#digitalhousemanual

#estatemanagement

#privateestatemanagement

#estatemanagementsoftware

#housemanuals

#housemanualtemplate

#housemanagersoftware

#householdmanagement

#howtomanageamansion

#uhnw

#ultrahighnetworth

#Luxurylifestyle

In the world of the ultra-wealthy, few purchases are as significant as acquiring a mega-mansion (10,000+ square feet). This is the ultimate status symbol — of wealth, success, security, and, often, a new phase in life.

However, life in such a home involves significant adjustments beyond the luxury. In this episode, I explore 7 related considerations.

Thanks for listening!

Read the blog post: https://www.estatemanagementsystems.com/blog/mega-mansion-equals-mega-changes

For more information, visit our Linktree: https://linktr.ee/estatemanagementsystems

#estatemanagementsystems

#Estatemanagerhousemanual

#Estatemanual

#digitalhousemanual

#estatemanagement

#privateestatemanagement

#estatemanagementsoftware

#housemanuals

#housemanualtemplate

#housemanagersoftware

#householdmanagement

#howtomanageamansion

#uhnw

#ultrahighnetworth

#Luxurylifestyle

As a homeowner, your staff is your most important asset when building a residential real estate portfolio.

With them, your property values will stay high, and the enjoyment of owning these homes can feel manageable. Ensuring your staff feel heard, supported, and appreciated goes a long way toward fostering a productive and loyal team and protecting one of your most valuable personal assets.

This small gesture requires no massive time commitment — just a one-hour appointment with each staff member.

Spending this dedicated time with your staff offers multiple rewards:

1. Proactively troubleshoot issues: Address staff concerns and operational challenges before they escalate.

2. Receive direct feedback, without relying on intermediaries.

3. Receive enhanced service: Discover ways to improve household operations and provide better service to your family.

4. Strengthen staff relationships: Build rapport and trust with your team, creating a more cohesive working environment.

5. Understand whether their goals and objectives align with your family’s needs and desires.

6. Identify who is truly happy and fulfilled in their role.

7. Evaluate whether staff members are in the correct positions or if employment shifts are necessary.

8. Determine areas where additional training or classes could benefit your team.

Thanks for listening!

Read the blog post: https://www.estatemanagementsystems.com/blog/8-reasons-staff-evaluations-benefit-your-home

For more information, visit our Linktree: https://linktr.ee/estatemanagementsystems

#estatemanagementsystems

#Estatemanagerhousemanual

#Estatemanual

#digitalhousemanual

#estatemanagement

#privateestatemanagement

#estatemanagementsoftware

#housemanuals

#housemanualtemplate

#housemanagersoftware

#householdmanagement

#howtomanageamansion

#uhnw

#ultrahighnetworth

#Luxurylifestyle

Managing a large household with full-time staff is as complex as running a not-so-small business. Estate Managers who run that business make daily decisions that could impact their employment.

For an estate manager, fear of losing their job may cause them to hesitate on both big and small decisions that impact progress at your property. Incorrect assumptions can cause a homeowner to deem them "not the right fit."

What’s my secret sauce for getting things done?

Implementing a PROPOSAL SYSTEM. This ensures that staff work without assumptions while implementing homeowners' preferences.

In this video I share guidance on:

- When a proposal is needed

- When you don't need a proposal

- What should be in a proposal

- How to submit your proposal

- Results that come from this process

Thanks for listening!

Read the blog post: https://www.estatemanagementsystems.com/blog/my-number-one-secret-for-getting-things-done

For more information, visit our Linktree: https://linktr.ee/estatemanagementsystems

#estatemanagementsystems

#Estatemanagerhousemanual

#Estatemanual

#digitalhousemanual

#estatemanagement

#privateestatemanagement

#estatemanagementsoftware

#housemanuals

#housemanualtemplate

#housemanagersoftware

#householdmanagement

#howtomanageamansion

#uhnw

#ultrahighnetworth

#Luxurylifestyle

Why is it important to understand and identify toxic people inside your organization?

- You won’t get the service you are paying for.

- Your revolving door of entering and exiting staff will require additional resources and patience during these transitions.

- Your family will continue to feel disrupted in their daily lives.

- Your household staff will feel insecure and seek more secure opportunities. Or worse, they’ll stay but burn out trying to navigate endless no-win situations.

- Your risk of legal action by disgruntled employees increases.

And you’ll be the last to know.

Before you designate your new hires as “not a good fit,” determine if your executive team is the problem.

Thanks for listening!

Read the blog post: https://www.estatemanagementsystems.com/blog/toxic-staff

For more information, visit our Linktree: https://linktr.ee/estatemanagementsystems

#estatemanagementsystems

#Estatemanagerhousemanual

#Estatemanual

#digitalhousemanual

#estatemanagement

#privateestatemanagement

#estatemanagementsoftware

#housemanuals

#housemanualtemplate

#housemanagersoftware

#householdmanagement

#howtomanageamansion

#uhnw

#ultrahighnetworth

#Luxurylifestyle

When I think of a successful, live-in staffing scenario, I can only come up with Alice from The Brady Bunch.

Fast forward to today and real-life situations…I’m not sure live-in situations are a good idea. I’ve seen many bad examples lately of House Managers losing their livelihood and housing – and not being prepared with a Plan B.

If you think about the most stressful situations in life, aside from death and divorce, a new job and moving are at the top.

In this episode I share:

- How the employer and employee/tenant relationship can be tested

- The upsides for homeowners

- Real talk when it comes to the selling point of "free housing"

- My best suggestions for live-in employment

- An alternative arrangement for homeowners whose focus is rental income

PLUS: When it comes to private service professionals, I also share things to look out for in these employment + housing arrangements.

Thanks for listening!

Here's the blog post Kelly mentions in this episode, on setting healthy boundaries with household staff: https://www.estatemanagementsystems.com/blog/when-staff-become-family-here-is-how-to-set-boundaries

For more information, visit our Linktrees:

https://linktr.ee/dearbillionairepodcast

https://linktr.ee/estatemanagementsystems

#luxurylifestyle #luxuryhomes #uhnwi #domesticstaff #estatemanager #billionaire #millionaire #mansion #householdstaff #housemanager