AI Enters the Pitch & Asking Good Questions

Borrowed

"Ask the question that will get at the core of the issue and the decision. Ask the question that will confront underlying assumptions. Pose the question to your team and then stop. Instead of following up with your views, ask for theirs."

From "Multipliers" by Liz Wiseman [Book]

Learned

Changing it up today with some thoughts on my mind as we closed out the week last week.

AI Enters the Pitch

Last Friday morning, we got word we lost an opportunity with a prospect. It was a unique project: an international DTC business that had recently entered a new (international) market and was not doing as well as they hoped. They were looking to optimize quickly, hoping to see some quick gains. There are always flags in situations like this, so we were on the fence about pursuing, but after talking with their leadership team, decided to give it a go.

The reason I'm sharing this here is that it's the first time I can recall us losing to an agency that cited AI in their approach. In the client's words, the other agency is offering "agentic, autonomous website development, with real-time data and updates, that matched the pace we want to move at right now." I hope to get more clarity on what that actually means in practice. But more than anything, it's a signal of where AI is starting to show up in how clients think about the work and who they choose to do it with. Not a new signal, but one nonetheless.

On the Barrel front, I’m energized about AI. Earlier this year, I kicked off an internal initiative called Project AI and have loved exploring how the team is leveraging AI to fundamentally change how we work. There's an experimental energy buzzing across disciplines, and while we've made good progress, I know we're just scratching the surface. It's easy to let that feeling get overwhelming, but I find it all very exciting.

All said, Friday has me thinking more about when and where it makes sense to share (or emphasize) with clients how we're using AI in our work. For now, I think when its use is directly tied to achieving their outcome, that's probably where we'll land. We'll see.

Also worth mentioning: alongside the loss, we've got verbal wins from a couple of CPG brands I'll be proud to add to our portfolio. They’ve been on my Costco shopping list for years now. Getting to go behind the scenes with the teams of the brands I’m experiencing every day never gets old.

Making Space for Good Questions

This past week, I led my sixth monthly men's group, called Denwork. It feels great to say that, knowing how long I put it off. I don’t have much precedent for these sessions, so my approach has been to keep it open and bring new prompts each time. So far, it’s worked well. More recently, we’ve spent time reflecting on where we’re at, what we’re striving for, and what we need to do to get on track. This time, I thought I’d change it up: In the last month, when have you felt most happy or most like yourself?

It was cool to hear the guys highlight weekly rituals with their kids or specific moments in time. For me, it was a recent Saturday out riding my bike with Mylo on the back, and my first real one-on-one dinner with him the week prior, where he looked at me and said, “I’m happy.” Life is moving so fast, especially as a working parent. Even when we recognize these moments, they’re fleeting. It felt nice to spend some time sharing them.

I’m not sure if Denwork inspired me or not, but lately I’ve been drawn to throw out the agenda for the weekly meetings I lead with our leadership and growth teams. There's something to be said about a tight agenda that surfaces the right things, but with so much happening at Barrel, there have been topics I've felt need the time and space to dig into. In most cases, I've come up with specific questions for the group, which have led to productive discussions or, in some cases, difficult conversations that I’m not sure would have happened otherwise. I keep thinking about what we'd miss if I didn't do this, and how critical it is to my role.

& Thought

What's a question I should be bringing to my team this week that no agenda is going to surface?