Let’s imagine a hypothetical scenario.

You assign your employee a task. They take time to prepare and present a plan. 30 minutes into the dialogue you respond “Sounds like a great plan! What happens if X, Y, or Z variable plays out differently than we think?”.

Now imagine your team member says - “Well….. I don’t know. You told me to come up with a plan. So I did. I didn’t make alternative plans.” You'd be frustrated and use the moment to coach them through thinking through Plan B, C, etc.

As we all know, Plan A doesn’t always work out. Plan B sometimes ends up being a better strategy because of any number of factors - market fluctuation, less friction, new connections, etc.

Your employee’s job is likely, hopefully, their Plan A. But should they have a Plan B? Probably. That’s just rational. Why should you be upset if you find out about their Plan B? As an entrepreneur, you’re always thinking about alternate scenarios, right?

I used to get super pissed when I learned about employees Plan B. Why aren’t they dedicated? It felt like I was being cheated on. Looking back over the last 15 years, I’ve realized I was totally wrong in my thinking. It’s not that dedication isn’t important. Rather, if your employee is performing well and can simultaneously dream up alternate plans, great! I now see that as a sign that someone is intelligent and resilient.

I believe you should strive to foster a culture that not only embraces employee’s side hustles, but also highlights them as a positive. In some cases, their side hustle should become their main hustle. If it’s adjacent to the core business they can support your business as an intrapreneur.

The key takeaway: Focus on making sure employees meet expectations without restricting their freedom to dream and do outside of their work duties. A healthy company empowers their team to do consistently great, profitable work, without controlling their entire lives!