EP 139: Getting The Best From The People Who Work For You With Eventual Millionaire Founder Jaime Masters

The Nitty Gritty

  • Jaime’s lessons from hiring virtual assistants in the Philippines — and why she eventually hired an employee local to her
  • How Jaime and her team use Asana to manage projects and assign tasks
  • What books and tools Jaime uses to track employee time — and how she uses that as a tool to ensure employees are doing what they love with their time
  • Hear more about Jaime’s approach to the not-so-fun aspect of running a business: firing employees
  • The difference between an owner and an operator — yet how crucial they are to each other’s success

Jaime Masters is a business coach and host of the Eventual Millionaire blog and the going-on-seven-years podcast series. In this episode of What Works, Jaime walks us through her process for hiring and keeping employees happy. She also shares her tactics for firing underperforming employees in a fair and diplomatic way.

Curious about the resources that Jaime mentions on this episode? You can find them all at this link!

We release new episodes of What Works every week. Subscribe on iTunes so you never miss an episode.

When hiring an employee is good for business

“Before I was trying to hide from the responsibility [of having employees] because I had a bad experience. But it made me understand how important it is to not do everything yourself. I thought I was good at everything but my executive assistant was good at so many other things than me. Letting go made a huge different in my sanity. I could double myself.” — Jaime Masters

Before Jaime hired her first employee, she tried working with virtual assistants from the Philippines. Jaime was afraid to hire an employee because of negative experiences in the past — and she thought that a V.A. would meet her business needs.

But a coach she worked with told her an employee is a good thing. “You’ll be a better business owner because you have that responsibility,” they said. Jaime took that to heart and hired her first employee: an executive assistant. It turns out Jaime’s coach was right: not only did hiring an employee force Jaime to show up on time — it also made her more dedicated to her work. “It made me put roots down and say: okay, we’re doing this!” she says.

Today, Jaime employs four full-time employees: an operator, a full-time virtual assistant, a technician who specializes in Infusionsoft, and a personal assistant. She also works with many contractors, including ghost writers, copywriters, and podcast editors.

An overlooked reason why tracking employee time is a good thing

“The goal is to level up the things that they do best so that they can feel in flow and love their job.” — Jaime Masters

In most jobs, tracking time and tasks is a way to keep employees accountable. But in Jaime’s world, she uses time tracking not only to see what employees are spending their time on — but also to ensure they’re spending time on the things that they love.

If employees spend more time on things they’re naturally good at, they’re happier and more productive. That’s what Jaime’s seen with her team by putting this practice into place. And it’s super simple: they use the RescueTime time management software.

Taking the emotion out of firing underperforming employees

“I had to put something in place on the firing side so that I could separate it from my emotions because I want to help everybody and I hate firing people. Everybody’s probably heard that you want to be slow to hire and quick to fire. And I can tell other people to do that — but it’s hard because you’re dealing with humans.” — Jaime Masters

Anyone who’s had to fire an employee knows that it doesn’t feel great to do it. You want your employee to succeed in their role. And sometimes… it just doesn’t happen. But before you fire someone out of nowhere, Jaime emphasizes the importance of process.

It’s crucial, Jaime says, to set up your process and inform your employees in advance. For example, if your employee is inconsistently fulfilling their daily duties — like answering customer service emails within your promised time frame of one business day — there needs to be a clear process to improve the desired behavior.

Will there be a warning, verbal or written? How many do employees get? And what happens when their work doesn’t improve after a warning? Having your process outlined makes it that much easier to take your emotions out of firing someone.

You can find all of the resources that Jaime mentioned at this link.

Hear more from Jaime Masters on hiring and firing employees, how she and her team use Asana to manage projects, and more about her experience with running her business in this episode of What Works.

By Tara McMullin

Writer, Podcaster, Producer. Founder of What Works.

Jun 26, 2018

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EP 299: How To Design Your Own Sales System

This week, I’ve got 4 more stories to share with you from small business owners who have intentionally done things their own way when it comes to sales and selling. They’ve found what truly works for them–even if it bucks the prevailing wisdom or would make a bro marketing expert role his or her eyes.

These stories come from business coach Ashley Gartland, marketing expert Amy Lippmann, designer Mel Richards, and work reinvention coach Lydia Lee.

Listen for how they incorporated these same considerations into finding their own unique sales systems. They designed their systems with personal values, strong relationships, reduced anxiety, and agency in mind.

EP 298: Creating A Less Harmful Sales System with Wanderwell Founder Kate Strathmann

This show is called What Works for a reason.

Sometimes it’s a declaration: this is what worked for this small business. And often, it’s a question, “What works?”

Today’s episode is very much a question, many questions, really:

What works when it comes to selling when you want to avoid manipulative or exploitative practices?

What works when your values conflict with many of the best practices of selling online but you still want people to buy your stuff?

What works when it comes to sales in a business that is actively anti-racist and anti-capitalist?

And even more bluntly: Can you even sell things without causing harm or perpetuating harmful systems?

My friend Kate Strathmann is the founder of Wanderwell, a bookkeeping and consulting firm that grows thriving businesses while investigating new models for being in business.

Recently, Kate took a bit of a detour from how she’s used to building her business, which is 90% referral based and fueled by deep relationship- and community-building. She decided to offer a small group program called the Equitable Business Incubator as a way of exploring anti-capitalist business practices and how they apply to the small businesses we’re building.

To fill the program, Kate need to sell differently.

Which led her to asking the question: Can you even sell things as a anti-capitalist?

While that might not be your specific question, I have a feeling that you too have wondering how you can effectively sell your offers without causing harm, perpetuating harmful systems, or damaging relationships. And that’s why I knew Kate and I needed to explore this topic on the show.

This is a conversation about what a kinder, less harmful sales process could look like—and it probably contains more questions than answers. But I’m confident those questions can help you find the answers that are right for you and the sales system that you want to build to make your business stronger.

We start out by defining what we’re really talking about when we talk about capitalism and anti-capitalism. Then, Kate shares how the Equitable Business Incubator came to be and how she ended up selling it. And then we dig into what makes many of the sales formulas and best practices being taught today problematic—and how to think differently to create your own alternative practices.

Now, let’s take a look at what works for creating less harmful sales systems!

What Works offers in-depth, well-researched content that strips away the hype of the 21st-century economy. Whether you love the podcast, the articles, or the Instagram content, we’d love your support