What Makes a Great Fractional Product Leader with Drew Dillon

Intro: Welcome to the Daily Bolster. Each day we welcome transformational executives to share their real- world experiences and practical advice about scaling yourself, your team, and your business.

Matt Blumberg: Welcome to The Daily Bolster. I'm Matt Blumberg, co- founder and CEO of Bolster. And I'm here today with Drew Dylan. Drew is a Bolster member. He is a fractional chief product slash technology officer. Drew, fun fact, was one of our first, I think one of our first hundred members at Bolster.

Drew Dylan: Totally.

Matt Blumberg: Yeah, something like that. So Drew, welcome, happy to have you here.

Drew Dylan: Awesome, yeah. Thanks so much for having me, Matt.

Matt Blumberg: Yeah. The thing that I think is really kind of interesting about your career is you've gone back and forth a couple of times between being full- time and fractional. And the chief product officer, or chief technology officer role is one that a lot of CEOs don't quite understand. How could I have someone in that role that is not full- time, right? That is fractional. So I thought the question I would ask you is, what are the top one or two things that you can get done as a fractional head of product or technology? And then, what are the top one or two things that you can't? And I think that'll probably help a lot of our founders and CEOs who listen to this think about how to frame that role.

Drew Dylan: And for me, the way I think about it all comes down to trust at the end of the day. So much about product management is trust. It's a founder, a CEO, an exec team that have had this vision, they've been operating on this vision for months, days, years. And they need to bring in somebody who's actually going to take their baby and make sure that it can grow up and become a full- fledged adult. And I think the value of a fractional leader is, for me, that that trust happens really quickly. That I can come in, I can help facilitate the planning session with the exec team, I can use that planning to develop a roadmap. I can use that roadmap to go fix the development process, kind of jumpstart the whole scaling of the product development organization really, really fast with that kind of implicit trust, and that understanding that change needs to happen really, really quickly. That we want to accelerate, grow, and innovate a lot faster. So that to me is kind of the core of things that you can do as a fractional product leader, and the value that you can really quickly apply to the team.

Matt Blumberg: Probably a conversation for another one of these, of how you build trust so quickly. But it totally makes sense to me. Trust is the foundation of good, healthy executive relationships. And that orientation of, how can you jump in quickly and have an impact on either setting a scaling framework, or a roadmap is great. So what's the flip side of it? What's the thing that you really can't do if you're fractional, if you're a day or two a week, or even three?

Drew Dylan: And so to me, we come back to trust again. I think there's that immediate implicit trust of, I'm bringing on a consultant, they're here to do something. I'm going to let them do that thing. Long- term, the real value of having a product leader in your organization, is they trust that they build up over time. I worked with the CEO once who said, " I want my product leader to overrule me when it comes to product decisions." And that's a level of trust and a relationship you build with a CEO over a very long time span. Where they understand that you're an expert in the product, in the domain, and the exec is stepping a little bit back to actually operate the organization itself. And the way that you do that as a product leader, Amazon has this value of being right a lot. And I think you have to build up that track record over time. You have to have quick wins that customers like, that marketing likes. That make the support team happy and continue fixing bugs. And balance that with making sure everybody feels heard. As a product leader, you're not necessarily going to make decisions that are going to fit every need of every aspect of the organization, but you need the whole organization to be bought in on the idea. That didn't go, that's not the way I would've made that decision, but I was heard. My opinion was heard. It will come up when it comes up again. I know this person listens to me, and understands what we're trying to do. And that's just a kind of trust that takes much longer than what a fractional leader is going to put into the team. And fundamentally, that kind of work happens, it's little soft touches over a long period of time that ultimately is not worth paying a consultant for if they're even not going to be there in two years.

Matt Blumberg: That makes a lot of sense to me. Some things are easier to do in short bursts than others.

Drew Dylan: Yeah, absolutely. And yeah, I think there's, relating to those two points, a fractional leader will take the best intuitions of the company and help you operationalize them. And they'll, I will show you. If I disagree with you, I'll explain it to you. I'm not going to go and fight for that opinion. You're paying me as a consultant to help you understand it, not to go convince everybody. And where the flip side is that long- term leader should and has to go kind of fight for the right opinions.

Matt Blumberg: That's right. It's a great distinction between the two. Drew Dylan, thank you for being here. Anyone who's interested in connecting with Drew, he is a Bolster member. Thanks a lot.

Drew Dylan: Awesome. Thanks so much, Matt.