Tent Talks Featuring Jesse James Garrett: Leadership is Torn

Tent Talks Featuring Jesse James Garrett: Leadership is Torn
Jesse James Garrett
Author & Executive Coach
Jesse James Garrett has been one of the most prominent voices in digital product design for more than 20 years.

On Monday, October 24th at 5:00pm Central, Jesse James Garrett joins us for a live Q&A session: “Leadership is Torn.”

Session Notes

In this insightful session, Jesse James Garrett, a visionary in the field, delves into the intricacies of design leadership amidst the dynamic interplay between executive expectations and team aspirations. He reflects on the evolution of design leadership, the spectrum of design maturity, and provides a nuanced understanding of navigating leadership responsibilities.

Balancing Needs and Expectations:

  • Acknowledgment of design leaders as a unique bunch, learning on the job due to a lack of formal education in design leadership.
  • The “design leadership playbook” is an amalgamation of trials, errors, successes, and failures over the last two decades.
  • Importance of translating the value proposition of design not only to the design team but to the larger organization.

Reconciling Product Success with Design Maturity:

  • Questioning the long-term goal of design maturity and emphasizing that it should lead to greater product success visible to people outside design.
  • Design maturity described as an asymptotic approach towards perfection that can never be reached, thus requiring realistic goal-setting.

Misunderstood Executive Motivations:

  • Highlighting designers’ potential misinterpretations of executive motivations, especially regarding financial and quantitative aspects.
  • Advocating for more empathy and attunement towards those who do not share the designerly way of seeing things.

Navigating Tough Decisions:

  • Discussing the delicate balance between being responsible and being compassionate when making tough decisions.
  • Encouraging design leaders to clarify their mandates and align their change-making goals with organizational expectations.

Notable Quotes:

  • “Leadership is the art of disappointing people at a rate they can handle.” – quoted by Chicago Camps from Carmen Medina’s Tent Talk session.
  • “Design maturity is not an end in itself… It has to add up to something more that is visible to people outside design.”
  • “If your boss is like, I thought I hired you to build me a function to keep this dev engine fed with front end assets. And you’re all, I came here to create systemic organizational and cultural change to drive a revolution of human-centered thinking across the company. Yeah, you’re going to have a disconnect.”

Session Transcript

[00:00:37] Chicago Camps: What can design leaders do to balance the needs and expectations of executives with the aspirations and growth of the design team?

[00:00:51] Jesse James Garrett: We’re starting at the top, so to speak, which is how do you contend with the tension between your team and your boss, basically, and so much of it comes back to how you see what you have to offer as a leader, because I think that a lot of leaders, so first of all, we have to acknowledge that design leaders at this point in history are a really weird bunch.

[00:01:13] Most people who are in leadership roles in digital product organizations. They learned this on the job. They learned it on the fly. There were no graduate programs that they could go to for design leadership. There were barely any that they could do for digital product design to begin with. So the design leadership playbook, so to speak, is one that has been pieced together over the course of the last 20 odd years from a lot of trial and error and a lot of successes and failures.

[00:01:43] And what that has led to is really a diverse range of ways of seeing and thinking about and understanding the value proposition of design as a function. But even beyond that, the value proposition of a design leader. Why do you have a design leader? And for a lot of design leaders, because they came up as designers, they came up in design team environments.

[00:02:09] They’ve got a lot of ideas about how to better serve design as a practice. And how to better serve designers as resources. But when it comes to figuring out how to translate all of that into a value proposition just to your design team, but to the larger organization that you’re a part of, that’s often where it starts to break down for people because they’re not really sure what they are there to do other than keep the design machine oiled and keep the designers happy. Right? Keep the designers from leaving.

[00:02:45] A lot of the stuff I came up with the Elements of User Experience 20 odd years ago as a way of describing user experience, design work to people who had never attempted to create a digital product before the web was exploding. It was 2000. There were all of these people getting involved in making software products who’d never done it, had no idea what was involved and.

[00:03:10] Elements was an attempt to hear all the things that are involved in this to people who’d never seen an app, had never built a website or any of this kind of stuff. Fast forward 20 plus years, everybody in the room has literally thousands and thousands of hours of experience with digital products.

[00:03:29] Everybody in the room is coming into the room with their own expectations of Design is good for in a digital product and what it’s not. Moreover, if they have been working as technology professionals for any length of time, they have their own experiences that inform those expectations of design. One of the biggest ways in which design leaders are torn between their executives and their teams has to do with the expectations that those executives and the value proposition that you have as a leader to fulfill those expectations.

[00:04:04] Chicago Camps: Do you have any advice for design leaders on how to reconcile that immediate demand of product success with a long term goal of achieving design maturity?

[00:04:15] Jesse James Garrett: I have to question that long term goal because product success. It’s clear on the face of it what the value of that is. I would say design maturity toward what end?

[00:04:27] What greater product success does your investment in and advocacy for design maturity create? Design maturity is not an end in itself. No matter how much your stories of creating design maturity for your organization are going to impress your fellow designers, your fellow design leaders. It’s not an end in itself.

[00:04:52] It has to add up to something more. It has to add up to something more that is visible to people outside design. So it feels like a tension for people because they feel like if they give too much ground on the short term, they’re never going to get to that longer term goal. I think what it is that design maturity is a level of perfection that can never be reached.

[00:05:15] And what you describe as a plateau would see as being, you know, design as a discipline, asymptotically approaching that perfection without ever quite reaching it. And so that’s why it looks like just a long flat plane out into infinity. I think that there have been design maturity models for a long time, by the way, we did our first design maturity model Adaptive Path back in, I want to say 2002, 2003, something like that.

[00:05:43] There’ve been a lot of folks over the years who have come up with other ways of framing it. But this is the thing again, there was barely. One correct way to do it, at the start, when it was a very small group of people working on a very small, relatively focused set of problems as we were wrestling with web technology and so forth, the growth of the field has just been so explosive that people find their way into this work by many different paths, by many different experiences.

[00:06:15] I actually have a hard time coming up with a model for design maturity that I can say is broadly applicable. I think it’s very industry and category dependent and geographically dependent too. What looks like maturity in some parts of the world is completely different from what looks like maturity in other parts.

[00:06:36] I think that capital D design is something that every design leader has to define for themselves their relationship to. This notion of, this grand notion of, design that has been promulgated by designers for at least the last couple of decades and in other areas for a few more beyond that.

[00:06:56] But certainly in this space, the idea of design as a cultural force as a change maker in the world is great. It is noble, it is valid. And what looks like is going to be very different for different people in different contexts. I think that if you find yourself as a leader feeling frustrated by the progress you’ve been able to make against the goals that you had for this organization, I might ask you how realistic were those goals to begin with?

[00:07:36] And to what extent are you here to make this organization successful and to what extent are you here to make the project of design in the world successful because that’s the trade off that you ultimately have to balance there.

[00:07:50] Chicago Camps: And now a question from our live studio audience. Sean asks, what do you think are some of the motivations and goals of business executives that are most commonly misunderstood by UX leaders and team members.

[00:08:04] Jesse James Garrett: Thanks, Sean. That’s a really good question. So it’s designers allergy to financials and all things quantitative is of course well documented and understood. But I, that’s the quantitative is to my mind is rarely where it starts.

[00:08:23] The numbers are usually there to justify a course of action and a set of perceptions on the part of the executives about what really matters. And when it comes to their motivations that might not be as visible to UX folks, I think a lot of it has to do with the fact that They often don’t experience products the way that we do, honestly, it is the designer’s lens that I think is something that we assume that other people carry around with them.

[00:09:00] We assume that they can see things the way that we can, or that with just a little nudge, with just a little education, they would be able to see things the way that we would. When you’re dealing with people who come out of, they are CFOs, they are people who are marketing executives who are used to wielding multi-million dollar brand campaigns, when they are engineering people who are used to managing massive networks of data centers with incredible complexity to them, these people, people who are used to running three floors and stuff like that, these people are going to have a pragmatic edge that makes it challenging to have these conversations about intangibles with folks.

[00:09:44] And so I think that a little more empathy and a little more attunement to folks who don’t see things in the designerly way is often what is required in these executive engagements. You’ve used evangelism as a frame for that alliance seeking for so many years. And I don’t think it really serves us anymore.

[00:10:04] I think it was valuable at one time, but where we are right now, I think with the development of the field is that that kind of, I’m going to beat messages into your brain until you get religion, it’s just not a winning strategy and in the current environment, it is at least as much about listening as it is about talking.

[00:10:23] It is at least as much about using their language as getting them to adopt yours.

[00:10:30] Chicago Camps: Carmen Medina shared a great quote in her Tent Talk session, and it’s by John Ortberg. “Leadership is the art of disappointing people at a rate they can handle.” Which is a really interesting take, and it leads me to the final question.

[00:10:44] How can design leaders navigate the fine line between making tough decisions without being perceived as overly harsh or unreasonable? Or, in the terms of Russ and Jesse back and forth in email, how can design leaders navigate wielding their power versus being an asshole?

[00:11:01] Jesse James Garrett: Wow, I actually feel like those are two questions, and both entirely valid, first of all.

[00:11:08] To your point that you were just making a minute ago, any kind of leadership position at all involves navigating trade offs in a lot of ways. This is something that product managers are very familiar with. That doesn’t come up as much, I think on the design side, we’re used to making trade offs in the context of a design solution where we have criteria, where we can analyze the trade offs and we can analyze the, whether it’s through A B testing or other kinds of explorations, we can validate a direction, the trade offs that are involved when you get into these kinds of leadership decisions, very different kinds of trade offs, they’re much squishier, they’re much more human and messy and nuanced.

[00:11:48] It is about, I think, knowing the balance to be able to strike between Being, being responsible and being compassionate as with a design trade off, it’s usually not an all or nothing thing. We as designers throughout our careers, we see ourselves as, and we try to be, I think champions of compassion in our work.

[00:12:13] One last comment on that last quote from Carmen, because I think it really is apt. If you listen to my podcast, Finding Our Way, if you listen to other podcasts about design leadership, the pattern that I’ve heard, the pattern that I think that you will hear is. That the leaders who have the most to show for their work, leaders who have been able to get the big wins and to gain the authority and the headcount and who are have been able to drive these organizations to these higher levels of design maturity, however you define it, almost none of them are doing that.

[00:12:46] Through some sort of ideological campaign, they are finding ways to, to deliver value and to make that value visible. And that’s actually how the work gets done. I think that for every leader, it’s just a matter of getting clear on how much is change making actually a part of your mandate? How much was that actually the job that you were hired to do?

[00:13:11] Because… If your boss is like, I thought I hired you to build me a function to keep this dev engine fed with front end assets. And you’re all, I came here to create systemic organizational and cultural change to drive a revolution of human centered thinking across the company. Yeah, you’re going to have a disconnect.

[00:13:31] You’re going to have some breakdowns for sure.


Event Details
October 24, 2023
5:00 pm
October 24, 2023
6:00 pm
Tent Talks Featuring Jesse James Garrett: Design Leadership is Torn On Tuesday, October 24th at 5:00pm Central, Jesse James Garrett joins us for a live Q&A session: “Design Leadership is Torn.” Jesse James Garrett Jesse James Garrett has been one...
May 2024