The Day Two Team Members Resigned: A Leadership Lesson

 Welcome to the first installment of my Leadership Lessons series! As a writing consultant and online business strategist with years of leadership experience, I'm excited to share valuable insights I've gained while building my business.

When you self-publish anything - whether it's a book, coaching program, or course - you're not just publishing content. You're growing into a new version of yourself that requires both self-leadership and the ability to lead others.

The Day Two Team Members Resigned

I recently experienced something many entrepreneurs face - team turnover. Inspired by reading about Gumroad's success with contractors, I decided to try building my business with an all-contractor team rather than employees, despite what my business coaches recommended.

After hiring what seemed like an amazing VA from Upwork, I later brought on her husband for a sales role, despite my reservations about hiring a couple. Initially things went well, but performance issues eventually emerged. When I began addressing accountability, they both submitted resignation letters on the same day, about an hour apart.

What happened behind the scenes? What were the red flags I noticed? And most importantly, what did I learn that can help you avoid similar situations?

Tune into the full podcast episode to hear the complete story.

What I Learned About Leadership

Here's what I learned from this experience:

1. Always Check Yourself First

The first thing I do when facing a team issue is never blame others. I ask myself: "What could I have done better as a leader? What did I miss? How did I show up?" Many people in the online education space are quick to point fingers, but in leadership, you have to look at yourself first.

After reflection, I concluded that I had been fair, extremely gracious, and clear in my communication. I don't think any party was at fault - their personal circumstances simply changed what they could deliver, and they chose to step away.

2. Don't Try to Make a Contractor an Employee

Unless they express interest in working full-time, don't try to turn contractors into employees. I went into these relationships wanting contractors to work full-time hours with flexibility, but I also needed dedicated people with ownership of responsibility.

What I learned is that contractors are contractors for a reason - they want to choose who they work with and when they work. Contractors are responsible for completing tasks, while employees are responsible for achieving outcomes.

Contractors will almost always choose themselves before you. You'll be loyal to them, bending over backwards, while they remain loyal to themselves. I've seen this time and time again.

3. Make Hard Decisions Sooner

When you start feeling dissension or disequilibrium about a team member, nine times out of ten they're feeling it too. Make the hard decisions as soon as possible - don't wait. When you delay, you cost yourself time, money, and unnecessary stress.

4. You Can Teach Skills, But Not Mindset

One of the most valuable lessons I learned from Adrian Dawson's "How to CEO" course is that you cannot teach attitude. Attitude is internal. You can teach skills by enrolling team members in courses or training them on processes, but you cannot teach mindset.

For example, there were red flags when my VA wouldn't complete new tasks because she felt "intimidated." When I asked her to upload coaching recordings to client boards, she simply didn't do it. When I followed up, she admitted she hadn't even watched the instructional video I'd provided.

The same thing happened with a Kajabi task - instead of seeking help from our tech team, looking on YouTube, or checking Kajabi's blog, she just didn't do the task at all.

This kind of behavior impacts customer experience. There's no space in my company for someone who not only doesn't complete tasks but also doesn't communicate about challenges or use available resources to find solutions.

How I Responded

When both team members resigned, I felt relieved since the decision was made for me within 24 hours of praying about it. I sent emails thanking them for their time and indicating we could work together on project-based assignments in the future.

I also learned that moving forward, I'll have someone else handle hiring and firing decisions since I don't enjoy that aspect of business. There are parts of business I love, and parts I don't - and what I don't enjoy, I outsource.

Interestingly, I discovered that the marketing agency I'd recently hired offered a package that covered everything my VAs were doing except sales prospecting. By upgrading my package with them, I saved money and got everything done more efficiently. Win-win!

Moving Forward

I've decided that moving forward, I'll hire contractors only for project-based work - one-time projects, one-time tasks, or short-term hourly assignments. For dedicated positions that require day-in, day-out commitment, I'll hire employees who believe in my mission and vision.

I want to work with people who want to see me win and who want to win with me - people who want to be part of the movement. Because ultimately, it's not about me personally; it's about my clients, my mission, and what I'm accomplishing in the world through my work.

Your Leadership Challenge

Leadership is a journey, and sometimes the biggest lessons come through hard decisions and unexpected shifts. This experience taught me that hiring isn't just about skill - it's about mindset, alignment, and commitment.

Contractors serve a purpose, but when you need true ownership in a role, employees are the way to go. Your business thrives when you have the right people in the right seats. If someone isn't fully invested, they will eventually check out, and it's up to you as a leader to recognize the signs and make necessary adjustments.

So here's my challenge to you: Evaluate your leadership and your team. Are you hiring people who are just checking a box, or are you bringing in those who truly align with your mission? Are you delaying hard decisions that are holding your business back?

Growth requires letting go, and when you release the wrong fit, you make space for the right ones.

If you're building or want to build a profitable online education coaching business and need help with developing curriculum-based offers, launch systems, hiring and training processes, and more, I invite you to apply to the Published and Paid Mastermind. It's a 12-month group coaching program designed to help you build your thought leadership empire. Visit JasmineWomack.com/mastermindapplication to apply.