Collaborative CEO Days: How to Structure Yours!

As entrepreneurs, we spend a lot of time working in our own businesses. The key to grow your business faster as an entrepreneur is to carve out quality time to work on your business too. 

We’ve all been there and felt it when things start to feel a little swirly, haven’t we? You have a lot of new ideas, or old ideas sitting in your notebook that are just waiting to be implemented. You get mired in the day-to-day tasks and haven’t had a chance to sit back and take a bird’s eye view of the big picture and path ahead. 

And, you can feel frustrated without a sense of clarity, not knowing the next step, or not being able to see the bird’s eye view of something that you’re just entirely too close to.

Enter the Collaborative CEO Day. 

If you haven’t already read my blog about the importance of CEO Days in your business, check it out HERE or the She Built This episode on CEO Day’s HERE.

This blog will help you answer what a Collaborative CEO Day is, what it can do for your business, how you can structure one for success, and how to choose WHO you will embark on one with.

Let’s start with what a Collaborative CEO Day is. 

A Collaborative CEO Day is when you get together with some fellow friends and colleagues and dedicate a day to making leaps and strides in your business in a particular direction. 

Some personal examples of what I’ve worked on and hashed out in a Collaborative CEO Day: 

• I gained the opportunity to lean into my own listening skills for others, get my finger on the pulse of what others were creating and struggling with, practice offering my skills, resources, and expertise to help others with creative solutions
• I created the framework, copy, and deliverables of my small group program the Marketing Momentum Lab
• I fine-tuned the messaging for my website copy by getting insights from those in my target market about what resonated and what didn’t
• I brainstormed every step (and micro step) of my Client Process as well as talked through pieces to be automated, client gifting, and what kind of experience it would deliver them
• I mapped out a big vision for the year while reflecting on celebrations and learnings of the past year in another.

The possibilities are endless! 

You can brainstorm problems, processes, struggles, get a clear plan and strategy in place, hear new ideas, access someone else’s expertise and brain power on YOUR business, and get an alternate perspective that can bring you to lands you never even DREAMED prior! 

The power of a collaborative CEO day is bringing in new savvy brains to your business and working together with the common goal of growth. 

You can dream up an op-tin, map out a program, figure out what offerings you should be providing, determine whether or not you want to keep doing the things you’re doing, or pivot. The strength lies in having the knowledge and perspective of other brains on your business – the thing you’re in every day and often too close to see what they see. 

How Do You Structure a Collaborative CEO Day? 

I think it’s helpful to start by thinking about WHERE you do one. 

We’ve rented out an Airbnb, a coworking space, gone to someone’s beach house, sat in a cafe, and been virtual on Zoom. 

When you decide to do one of these for yourself, I think that where you choose to go is important in helping you structure your day. For example, the one in the Airbnb, we all brought elements to contribute to lunch, added our own pieces to the coziness factor and it was a very casual retreat-like vibe which informed a bit on how we structured it. The coworking spaces have had a more down-to-business feel and were run a little more methodically because we were paying by the hour. 

Meeting virtually is a little different than in person because being in person is almost always naturally more energizing. It might need to be shorter for this reason. Holding it on Zoom also lends itself I think to much more regiment than the other ways.

There’s no WRONG choice – you just have to factor in what you want the day to feel like / be like, where people are coming from, and if you need lunch breaks, water, bathrooms, a stricter schedule, or an easier flow. 

Ideas for Structure: 

Upon arrival, make sure to allow for a little cushion time to ease in. Especially if people don’t know each other or aren’t familiar with one another, you’ll want some time at the beginning for getting comfortable with one another. In some cases, you might also need to do introductions and describe what your business really is all about. 

After the initial warm-up time, there are a lot of ways to potentially structure, here are a few ideas: 

• Each person goes around individually for about 45 minutes to an hour each. They describe their problem or struggle, get some concentrated brainstorming on it, and an opportunity for follow-up questions, and accountability. Then move on to the next person. This is a nice way to get a LOT of feedback on the bigger challenges and problems you might be facing. With 45 minutes to an hour, you can work through a lot of your own obstacles and things holding you back. 
• Everyone goes around and shares their challenge or struggle and then opens up a collective conversation to discuss them all in tandem with one another. The key here is to actively ensure each person gets seen and heard. You may need to establish a leader or discussion point person. In this format, you learn from each other as you go and you might even find that there’s a common thread between everything being shared that helps bring the conversation together with cohesion.
• If you’re working on something specific like a client process or content strategy or something you’re BOTH working on in your businesses. I think it helps to just sort of work through the pieces collaboratively and apply it to each business as you go. 

I’ve also done a CEO day where we each did a recap and shared for an hour each with feedback and focused attention, and then after that did an active work session for an hour and then came back with new revelations and insights to wrap up.

You could do a vision-setting activity together, a branding activity, and each take turns teaching and providing support for everyone else in a given area. 

You can structure it any way you like! 

The even more important part, aside from structure and where you’re meeting is WHO is part of this with you.

The WHO You Invite to Participate in Your CEO Day is Extremely Important. 

First of all, you absolutely need a level of trust with the others participating. 

If you don’t trust the person not to steal your ideas, you don’t trust they have your best interest in mind, you don’t trust them to see behind the curtain and know things about your business… you probably shouldn’t do a collaborative CEO day with them. You have to have a level of openness and a sense of safety. 

If you have no trust, the day just won’t be that effective for you, you will hold back, you won’t be able to express what you need to and you may walk away feeling like you gave and didn’t get anything in return. 

You’ll want to choose like-minded individuals, but people who are still able to offer different perspectives. 

It can be beneficial to do it with people at all different phases and stages of their business, and equally beneficial to focus only on people at the same (or about the same) level so you really get each other. 

I believe you should choose people you respect, would take advice or feedback from, have expertise you don’t, and admire in some way (bonus points if you make each other laugh, think, cry, and feel challenged). 

Who you choose to do a Collaborative CEO Day with you matters.

Collaborative CEO Days are extremely impactful and beneficial for your business and growth. They can propel you to places you can’t go alone -or at least not as fast. Surrounding yourself with others can help you dream bigger and see things in yourself you can’t.