Tools of the Trade: Patrick Holly from Upwork

By Kyle O'Brien 

Tools of the Trade is an AgencySpy feature to help highlight the many tools that help make advertising and marketing folks successful. The tools can be anything that helps you perform at your top form, from your favorite drafting table to your best software program to a lucky pen, a vintage typewriter or a pair of headphones.

Next up is Patrick Holly, executive creative director at talent platform Upwork.

Upwork Zoom

Upwork’s team meeting with the crew as the character from its latest ad campaign.


What is the name of the one tool you use all the time at work, and how does it inspire your work? 

This pick might break the rules, but my tool is the kickoff meeting I have with my team every Monday. While merely having this kind of meeting is not special nor unique to me or my team, it’s what we do with that time that makes it our secret weapon.

While most teams spend their weekly sync talking about the tasks at hand for the next five days, we spend the vast majority of our hour together talking about anything but work. It includes multiple show-and-tell sections, a Trader Joe’s snack review and a full 15 minutes dedicated to giving thanks for others on the team.

Why is it your favorite?

When you run a remote team, especially one 50 people deep, a strong culture becomes especially important to ensure the success of your team. So, when it comes to building and maintaining that culture, step one is to recognize your teammates as fellow humans, not just rectangles on a screen. Those 60 minutes we spend together every week are designed specifically to familiarize our team members by focusing on the people doing the work, not the work itself. We realized quickly that, in this remote world, you only spend time together when you schedule time together, and you only schedule time together when you have to talk about work. Thus, we wanted to schedule time to talk about who we are outside of work.

How did you acquire your tool or hear about it for the first time?

Honestly, we stumbled through developing it throughout the past two-plus years of being remote. It was a long period of stumbling and learning and refining to get to what we have today. Most of my career was spent having a run of the mill weekly check in, but when we all went remote, we knew we had to find a better way to replace the old ways of connecting with our fellow teammates.

How does it help you be successful?

A happy team makes for a happy leader.

Does it have sentimental value?

Of course. I’ll bring this tool with me throughout my career from this point forward, and I hope it inspires my team members to do the same.

Do you think your tool could go TikTok viral?

Totally. A TikTok compiling our team’s favorite Trader Joe’s snack picks? I love it. Plus, there is nothing more viral than kindness. Now that the world’s talking about the new ways of working, I think it would have a fair shot at getting traction in culture.

We want to know what tools you use to make you successful. If you’d like to contribute or know someone who would want to be featured in Tools of the Trade, contact and fill out our survey.