5 Questions to Ask On Your Next CEO Date

What is it about the energy of Fall that has us entrepreneurs ready to go-go-go?

It’s an exciting time for sure. We’re all excited to blaze ahead, launch new offerings, and take our businesses to the next level.

But if we don’t take some time to reflect and integrate what we’ve accomplished and what we’ve learned over the year so far, chances are you’ll find yourself half-way through October, feeling burned out and not quite sure where you spent your time.

Scheduling regular times to reflect on the progress of your business is essential – not only to your business success – but for your own happiness and fulfillment.

My Fired Up & Focused Challengers know that I call this my CEO Date.

It’s the most important appointment in my calendar each week, each month, each quarter, and each year.

It’s how I make sure that I’m not only on track with my business goals, but I also make sure that those goals are still in alignment with my core desired feelings + my lifestyle design plan.

So if I realize a business goal isn’t helping me feel ease and freedom (two of my core desired feelings) and is actually taking me away from my family time or self-care time, I know it’s time to re-evaluate. And without these check-ins, it would be so easy to lose track of what’s really important.

Admittedly, it can be hard to keep my ambition in check! I’m for sure an overachiever who LOVES the work that I do. And this business practice of regular CEO Dates helps me ensure that I’m really living in my sweet spot and not over-extending myself.

So what do I do for my CEO Date?

Yearly CEO Retreat:

I take myself on retreat. Seriously, I’ll find a little hidden away place on AirBnB for a weekend. I’ll dream BIG. I put every possible thing out there that I want to create in the next year. Only after I’ve gotten all the ideas out on paper, then I start narrowing them down to what I’ll focus on this year and especially the next 90 Days.

Seasonal CEO Date:

This is when I take my ideas for that quarter and map them out. Every single step gets listed. Only then can I really see if it’s possible to actually make that idea happen! Once I can see the real scope of the idea, then I can figure out if I need additional help, where I might need to hire someone, or if there is a skill set I need to upgrade to make it happen.

Monthly CEO Date:

Now that I have my 90 Day plan broken down into steps, my monthly CEO dates are there to help me make sure I’m on track! Are we ahead of schedule? Do I need to replace a team member? Are there steps we didn’t expect? And most importantly, do I actually have the time available to implement or do I need to loosen up the timeline?

Weekly CEO Date:

My weekly CEO Date ALWAYS happens Monday at 9AM, right before we have our team meetings at 10AM. This lets me review what everyone completed the week before (my team sends me updates on Fridays), look at what else we need to work on, and map out my most important tasks for that week.

I should also add that I’m super aware of my work-a-holic tendencies! So another part of ALL of my CEO dates is putting time in my calendar for vacations, family time, self-care, yoga, and anything else that I really need to treat like an appointment (or else I’ll seriously work right through it)!

So today, I’m inviting you to make a CEO Date with yourself before you dive into Fall!

Set aside 30 minutes to reflect on the following questions:

How are you progressing towards your goals?

Are you on track? Are you behind? If you’re on track – yay! If you’re feeling behind – do you need to readjust your timeframes or expectations? Or do you need a better strategy?

Are you still excited about your goals for this year?

This is crucial – if it doesn’t absolutely light you up, it’s probably time to put that project on the backburner. I ONLY take on projects that I get excited about (what’s the point of being an entrepreneur if you can’t LOVE what you’re working on?).

If you’re not feeling the love, is there something else that excites you?

How does this fit in with your big picture for the year and going into next year (make sure it’s not just a distraction!)

What can you SIMPLIFY?

We tend to come up with these grand plans at the beginning of the year, then realize a few months in that maybe we bit off more than we can chew. Then we repeat the entire self-defeating process as we look at Fall.

In fact, I just had a strategy session with my business BFFs to simplify what I’m up to this Fall so that I can better balance my business with what I want to experience with my family. AND IT FELT GREAT!

Bottom line… take some of the pressure off.

What can you CELEBRATE?

It’s so easy to keep pushing ahead that we never take time to really celebrate what we’ve accomplished and learned! This weekend – celebrate a big win, a big lesson, a fab blog post. Personally, we’re celebrating that my husband Jameson is officially “retiring” from 8 years as a public school teacher so he can work with me!

Being an entrepreneur is not always easy, so it’s essential that you really honor yourself for the amazing work that you do. You deserve it!