I’m enjoying the refreshing breeze of crisp airplane air as I fly back to Indianapolis from Boston. It’s the second week in a row spending time with the team, and I couldn’t be more energized for what we are building at Jellyfish. 

Shoutout to the 2025 marketing team at Jellyfish, who taught me the value of karaoke at the Hong Kong bar as a crucial team-building exercise and the importance of team values.

Every leader should have a quick hit list of words to remember to help guide day-to-day work. The only rule? Write them in sentence form. Easier to remember! Here’s what we talked about on Thursday: 

1. We share before ready. 

2. We celebrate outcomes, not projects.

3. We have difficult conversations. 

4. We surprise and delight. 

It’s how we focus, drive change, and launch our ideas. It’s how we elevate marketing to an influencer, not an order-taker. 

Nobody wants to be an order-taker.

❤️ Kyle

On Asking Questions vs Having Answers

In the first edition of this newsletter, I wrote about "sharing before ready." It’s an easy way to remember the importance of sharing your work before it’s ready to encourage collaboration on an idea. It’s also about asking the right questions.

Asking questions builds trust between your team and peers. 

Asking questions helps identify the RIGHT problems to solve. 

Asking questions forces (in a good way) collaboration. 

We often feel we must have the answer, but true leadership is about gaining understanding. As a marketer, I naturally want to solution: I hear a problem and want to fix it immediately.

But here’s the thing, launching quick fixes without fully understanding a problem leads to managing a bunch of projects, not driving outcomes. 

And managing projects will forever relegate marketing to the “order-taker” designation. Ah yes, just check-the-box-and-use-this-one-pager life.  

Let’s look at an example.

Sales Leader: “We keep losing to competitor X! We need to do something! This is CRAZY!” 

Marketing Leader: “PRODUCT MARKETING. INBOUND. DEMAND GEN, DESIGN. WITH OUR POWERS COMBINED WE WILL DEFEAT THIS SCOURGE!” 

CEO: “That’s great. What’s team marketing going to do!?”

Marketing Leader: “We already have battle cards written. Let’s put a team in place to run at the problem. They will join calls and support every single deal. We will win through BRUTE FORCE! COMPETITIVE SWAT TEAM UNITE!”

Might be a good idea. But it’s a quick-fix project and doesn’t dig deep into the challenge. Quick fixes are based on assumptions, outcomes come from asking questions. 

Instead, step back and dig deeper. Assess the problem by asking questions across departments, review the competitive win/loss data, and ask the leadership team their take:

How is competitor X winning?

• Are we missing a market segment, persona, or product?

• Is our sales team’s timing off in demos creating a disadvantage?

• Is the market evolving in a way that requires a messaging or roadmap update?

• Should our roadmap be adjusted to support other features?

• What are our customers saying?

Asking the right questions will lead to a better understanding of the problem. The answer might still be a “competitive SWAT team to help increase competitive win rates,” or you might have to invent something completely new. 

Resist the need to have the answer and be the fixer. Dig deep and collaborate. Asking questions might take longer, but it leads to true outcomes, not quick fixes. 

Quick fixes do not scale companies. 

On Delegation

Once you ask the right questions and form an answer, you must point the team in the right direction. 

I thank the X gods for Michael Girdley and his decision to start posting content. I love his style (and his weird affection for Chilis). He recently shared reflections on the five steps to effective delegation, which I have found myself referring to over the last few weeks.

You need to follow the five steps in order to effectively delegate, but I spend the most time on the output and constraints. They aren’t the MOST important, but I believe they get the job done.