What Baking 500 Cookies Taught Me About Leadership

For the past decade, I’ve been baking holiday cookies and giving them to my loved ones. It’s become kind of a big production. Just this week, I shipped out about 200 cookies to friends, family, colleagues, and clients all over the country, plus all the boxes I have at home to hand-deliver. 

I research different types. I bake new recipes. I get them out to the people who I know will enjoy them. 

And you might be thinking, “That’s really cute, Christina, but what do cookies have to do with coaching?”

When I look at what it took to make this project happen - getting out all of these delicious treats, despite everything else going on in my life, including having a 5-month-old baby and going back to work full-time - I realized that three things made this possible. And it beautifully aligns with leadership. 

So here are the three things I put into place to bake cookies that you can also bake into your leadership. 

Manage Expectations

The first thing I took a look at is what expectations needed to be managed. This is a bit of a slippery topic. More often in coaching, we don't talk about managing expectations. Instead, we talk about “declaring” and “fulfilling” and “shooting for the stars” and all of that. 

And yes, those practices are super important. 

But when I say managing expectations, what I really looked at was: “How could I still fulfill the vision of this experience that has mattered to me for the last decade, even if it means reinventing what it looks like?”

Part of what managing expectations looked like, for me, was acknowledging that to go about this, the way that I usually do (which is five different types of cookies and therefore about 500 of them baked in a week or two) I'd have to give something up. I'd either have to give up time with my daughter or work or sleep - which is a precious commodity these days!

So instead I set myself up to win. I told myself, “People just care about the thought and they don’t care how many cookies there are.” So I narrowed it from my five unique types to three unique types because it's the thought that counts. People still get cookies!

I set a goal that was ambitious, given everything that's going on right now, yet still achievable.

Set-Up Support Structures

I set up structures to support me with this project. I looked at my schedule, figured out when I could work on this, and then made sure that the other people in my life knew how to support me.

I let my husband, Paul, know about my plans. I let my mother, who was watching the baby that day, know what I was going to be doing. I didn't just create this plan in a vacuum and hope that I could fulfill it by myself. 

This is really important, especially as we're looking at leadership and career goals for the coming year, because we should be setting goals for ourselves while still making sure that other people around us can provide support. 

Get Clear on the “Why”

To make this cookie project happen, I had to get really clear on WHY. What was I doing this for? 

To be candid, parenthood has reminded me over and over again to stop taking on shit that doesn't actually matter to me. I'm no longer into impressing people, proving that I’m worth it, or looking cool. 

I'm really only interested in taking on projects that are really, really meaningful for me. The same could apply to anyone about anything that is important to them. 

For me, cookie baking for a decade was a legacy that mattered to me. But even more importantly, I enjoy helping people feel seen and celebrated with yummy treats. That vision was sufficient to me. 

So figuring out the rest of it - managing the expectations, creating the game plan, getting people on board to help me with it - followed only after I established my “why.” 

If I didn't have a crystal clear vision, then likely I'd be sitting there on December 22nd thinking, “That sucks. I didn’t get any baking done.”

But I did. And it was awesome. 

See you next year!