611: Driving Your Team Forward with a CEO Workcation

When we first decided to take a workcation, there was no way of knowing just how beneficial it would be. We have always added in times to do planning sessions and pin down what we want, but what we have learned is that creating a dedicated time to make sure it happens is so, so important. The only way for our business to move forward in the past was for us to hop on the phone with one another, and brainstorm ideas. But as our roles have shifted, this hasn’t happened as often. That’s why we’ve carved out CEO time on our to-do list, to help us have the correct focus. 

We’ve all spent so many years working for businesses that are not structured well, not managed well, and that took all the lessons we didn’t like and implemented them in the workplace. This is the extreme opposite of many of our efforts to create flexible environments that take into account all of our humanity. But what we’ve found is that the answer lies somewhere in the middle. Not having boundaries or expectations doesn’t help anyone either!

To us, knowing that we had the time to think and brainstorm without boundaries, but also adding boundaries to make the follow-through inevitable, was everything! It’s so important to add enough momentum to make sure that you achieve what you’re hoping to achieve. When you take incremental steps, it doesn’t feel like you’re eating the whole pie at once! Our main takeaways from the experience were that there’s a difference between the conversations that are had within leadership and team meetings, and within the room where it’s just you and your business partner. It’s so important that this happens periodically for the good of the business. That’s the high-level stuff that moves everything forward. If you’re not ahead of your people, they’re not going to know where to go. 

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