Moving from Execution to Strategy as a Designer

Catt Small at UXDX Community: Taking Action on Data, Career and Work Life. Video: https://youtu.be/XNNS-DwWvSU

Readable transcript: edited from the recording's captions for readability (fillers and false starts removed, punctuation and section headings added). Wording is the speaker's own. Timestamps are positions in the video. Names marked [?] could not be verified against the audio.

Why strategic design matters

[00:00:00] Hi there. Glad to be here, thank you for having me. As was said, I am going to be chatting about moving from execution to strategy as a designer, and thank you for the great introduction. As was said, I am a staff product designer at Dropbox. I am also a game developer, so I've made a variety of games over the past 10 years, happy to nerd out about that later. And I also co-organize the Game Devs of Color Expo, which is an annual conference that'll be in its eighth year this September, and we're looking for sponsors, so check out GDoC Expo for more information if you're curious.

[00:00:38] Today we are going to talk about strategic design, why it matters, how designers get sidelined and pressured to execute, which is something I have definitely experienced in my career, and tips and tactics for increasing design's contributions to product strategy. So let's dig into one of my favorite subjects.

[00:01:02] Let's start with the value proposition, just throwing out one of many buzzwords you'll hear. Just kidding. But why should we actually care? Why does strategic design matter, and why does it matter to have a design-led strategy?

[00:01:15] Firstly, we want to make sure that we are working on the right project, so direction. Having direction is really crucial, and designers are really good at illustrating, for example, North Stars, visions of the future, helping us to confirm that we are moving toward the right thing, especially in this growth-driven and experimentation-driven world.

[00:01:38] Secondly, innovation. Designers are amazing at looking outside of the box, thinking of inspiring solutions, looking at something that you wouldn't quite expect and drawing something from that, finding something amazing from it. And designers are also great at determining when it is better to stick to predictable solutions, so thinking about accessibility and things like recall versus finding totally new solutions out there. Sometimes it is actually good to have a predictable solution, and designers can really help to navigate that innovation and predictability paradigm.

[00:02:22] Next, confidence. Designers are also very good at helping people to validate that their solutions are going to have an impact. We have been trained to gather insights from everywhere, whether it be talking to individuals or figuring out competitive analyses, for example. Designers can really make sure that the work that we are putting into the world is actually going to reach the right people and send the right message, and that's really important for actually launching a product and then also finding product-market fit, for example.

How designers get sidelined

[00:02:54] But this drawing may look familiar to you: designers often aren't involved in product decisions. I've had this happen to me before, especially in this remote world, which I do love, but it is very easy for conversations to be siloed, especially when people don't understand what value a designer can bring to the conversation. So let's talk about that. Why is it that even though we bring all this amazing value to the table, we still get sidelined quite often?

[00:03:26] This has been said well by many people, so I'll just highlight one person who said it very well. A lot of companies wait until they think that they know the solution to a problem and then they actually engage designers. It's like they think that the job of design is making the solution look pretty instead of actually engaging with the problem itself and understanding how design thinking, systems design, all of these concepts can actually benefit validating the problem.

[00:03:56] A lot of people don't, as I alluded to, understand the value of design beyond aesthetics. Some of these phrases might be familiar to you, whether it's "oh, can you just add a little bit of spice to this," "can you mock this up for me," "I need this idea to pop a little bit more," "make it prettier." These are definitely things that I have heard in my experience as a designer, and I have done as much as I can to show people that there is more to being a designer than these.

[00:04:28] As I mentioned, designers often get pulled in after a solution or a direction has been determined, and then the designer often gets put in a very uncomfortable situation where you have to say, "hey, actually, are we solving the right thing?" Or, "I actually have talked to some customers and I don't know if this will resonate with them," things like that. Which means that you have to be the gatekeeper. You have to be the person who's pushing back on solutions, and that of course puts you at odds and increases that feeling of us versus them, which is really frustrating.

[00:05:04] It results in a focus on production. It generates worse outcomes for customers. And of course, when it comes to teams, it makes people not want to work together, so it will just intensify the challenges that you have with getting things done in the future.

[00:05:21] I have experienced these kinds of things personally. For example, with my experience on the SoundCloud Go launch in 2016. I absolutely love SoundCloud, and I was very excited to get to work on helping them figure out how to monetize their product experience. They already had a product that existed for creators, so people who would upload sounds to the platform were actually paying for storage, but they also needed to figure out a way to pay the music industry and the music labels for the tracks that people were listening to, especially when those were copyrighted content.

[00:06:00] And so they wanted to release a subscription service, but the subscription service that they had put together had mostly been done without user research or talking to designers. And so when they had figured out the package, they then pulled in designers to actually figure out how to sell it to customers. From research and from doing lots of design work, we recognized that a subscription service of the kind that they had put together was not going to be compelling. So then we had to figure out how to say "no, no, wait," but it was too late to do that. And so subscription numbers were super low, and SoundCloud is still one of my favorite platforms, but it's definitely been in recovery mode since then. For me, this really underscored the importance of designers being involved earlier.

Tactic one: focus on goals

[00:06:50] So let's talk about how we can do that. How the heck do you do that? I'm going to share several different tactics for increasing design-led strategy, and I'm going to be talking to people who are ICs as well as people who are in management roles. So whether you are somebody who is on the ground who is often being asked to ship design, or you are a leader in the management sense who is hearing constantly, "I need to be involved sooner in the process," or "these PMs never involve me," those kinds of things, I'm going to share some opportunities for both groups.

[00:07:26] Tactic number one is to focus on goals. Again, a lot of people have said this very well, and I think that it's very important to share your goals with your team and to get them involved and to learn what matters to the business.

[00:07:42] Here's an example of what happens when you don't do this. A lot of newer designers will forget that design occurs within the context of an organization. They've gone to design school, and a lot of times, as a person who went to graphic design school, I definitely was guilty of this. I thought about design in terms of the creative, artistic sense and not really about how it connects to the broader strategy and the potential that it has in terms of helping businesses connect with their customers and finding products that really match both with the business needs and the customer needs.

[00:08:20] That was the thing that I learned over time. I learned through a process of just making mistakes, and also through taking some courses, that design in real life is much more messy. It's complicated. Everybody is contributing to the experience that's actually going to get released. We don't have a lot of control, and so the more that we can learn to speak the language of other people and to understand how we fit into a business, we can actually operate in a way that is more likely to create better experiences.

[00:08:51] What I would start with is to actually go speak to people. I talk to my PMs and the people that I work with quite often, and I work to learn what their goals are. Everybody has goals around you and you just have to ask them what those are. A lot of people are very, very open to chatting with you for 30 minutes, for example, and just answering questions. People absolutely love to talk about themselves.

[00:09:18] More specifically, if you are working with a product manager and a data analyst, engineering leads, people like that, definitely reach out to those folks and start to ask them, how did you get into this? What really excites you about product management or engineering or whatever their role is? What are the things that you're focused on for the next one to three months? Those kinds of questions will really help you understand how you might be able to pitch them on something or to collaborate with them better.

[00:09:48] And when you focus on this, you're going to start to unlock a shared language. That's really important because you want to make sure that you are framing your conversations from their lens. One thing I used to do as a designer is I would say, "oh, here's this design problem that is really hurting design or our customer experience." But when you actually start to speak the language of other people, you might say, "hey, we are actually affecting user churn," or "we are creating an experience that leads to this amount of revenue loss because of the way that this experience is not functioning properly." And when you do that, it's actually more likely that people will listen to you. That kind of is frustrating, but it is real.

[00:10:31] Something else that you can do is you can take a class to build more of a vocabulary. I took a class with Designer Fund. There are a lot of courses out there, especially right now we're having a huge boom of people talking about things of this nature, so you can definitely look into different classes. I'm sure UXDX will have more things as well talking about topics of this nature. But it's really important to dig into the language of business and understand things like what business model the company that you're working for has. Or maybe you're working as a freelancer: what is the business model of the client that you have? How do they make decisions around what projects or initiatives to support, fund, defund, things like that? Super important for actually figuring out how to move forward and to get people to actually stand behind your ideas.

Tactic two: show up and make design visible

[00:11:23] Next, it's important to show up, to be present. What I mean by this is that you need to show people the value of design, not just say it. People often at the beginning think of design as an output, but something that you can do is you can help everybody, yourself included, achieve their goals through design. So you can insert yourself into conversations where design can help, in the least creepy ways possible, and you can do things like what my coach calls starting a campaign: figuring out what your thesis is, what your goal is, and then thinking about the methods through which you will actually nudge people and influence toward your goal.

[00:12:05] Something that you can do that's really tangible, for example, is say that you have learned something about the total addressable market, or TAM. You can then start to ask questions about that. Or say that you have learned about targeting in terms of an audience, or how a persona actually might benefit the work that's being done on market research, for example. Those are things that you can start to ask people about. Hey, when are we planning to launch this experience? Why do we believe this change needs to be made now? Where else in the product might this experience provide value? What are open questions that research could help us answer? Is there anything that we are feeling less confident in that might be helpful to actually visualize? What about maybe doing an end-to-end analysis, or an audit, or something like that? There are great ways to help people to just think a little bit more deeply, and design is really great at that.

[00:12:58] Something I just want to note is that tone is incredibly important here. The goal is not to be indignant, which I am guilty of. I definitely used to say, "ugh, we didn't even do X, we're not doing the process right," things of that nature. People are going to feel attacked and defensive, and if you put people on the defensive they are not going to be incentivized to include you. I don't like being that person to say that tone matters, but in this case it is quite important if you want to maintain these relationships, which I think you do, because we're trying to eat, we're trying to pay rent, we're trying to make cool work and release things that we're proud of. So it is really important to think about the way that people are perceiving your message.

[00:13:43] You can facilitate quick alignment with design. Something that I have done is actually volunteer to illustrate concepts that people are debating, and you can see an example of this here. There was a conversation at Asana where it was all about how we're going to build out this data model, and one of the things that I did to help move people forward with this conversation was actually sketch out all the different options that were being discussed in Dropbox Paper or something like that. They just had a huge doc where they were talking about this, and I was like, no, no, this is what design is for, so we can actually show how decisions that you make on the back end are going to affect the experience on the front end. I think from that people really started to understand, oh my gosh, design actually has something to say. It's really useful, and it's not just about things that are ready to launch or execution. It's actually more conceptual than that. So I'm really proud of that.

[00:14:41] I've also run workshops to encourage discussions and generate ideas, and you can see some examples that come from both Etsy and Asana here. These kinds of conversations can be great for involving lots of people and showing that design can actually also be a facilitator of conversations that can move decisions forward. I think without doing these kinds of workshops, it would have taken a lot longer to make these decisions, because I would have had to — I don't even know if I would have been involved, but my PM might have had to go around to a lot of these groups of people that we were talking to individually and actually try to influence them in more silos. And by doing this in a workshop format or in a communal format, you can actually have those conversations out in the open, get through all the conflict as quickly as possible, and move on to the point, which is again making good customer experiences. I actually know a friend of mine, Aaron Nolan, is running a workshop about facilitating good workshops, if you're curious, so I can definitely share a link to that later.

[00:15:43] Design can also help people make decisions through illustrating the future. I showed a little bit of an example of that in sketch format, but you can also actually visualize other things like plans. You can visualize roadmaps, you can visualize the prioritization of different features, monetization for example. These are different diagrams that I've created at different points in time that helped to actually move conversation forward. What I would do is I would create these diagrams and then I would walk to the different people, or in the digital world I would send these folks these different artifacts, and then ask them questions like: does this look right? Is this what would happen for this particular user group? Is there anything that we need to change? Are there any red flags based on what I've outlined here? Those are conversations and questions that move things forward again. This is something that I think some designers might scoff at, in terms of "oh, I'm being asked to illustrate things," but these are actually really crucial parts of the conversation, and I believe that the more that we can be involved in the decision-making process, the more that people are going to look at design as a value add.

[00:16:52] And then of course, product visions. Love product visions. Making sure that they're done at the right time and that they're actually referenced is something that's really important here. A trap that designers often get themselves into is that they create a vision for the sake of making a vision, but I think that it's really important to actually confirm that if you're going to create a vision that is looking one to two years in the future, for example, that it's something that your team is actually going to reference on a regular basis.

[00:17:21] And all of this is going to help again to show the value of design. It's going to speed up the process, it's going to create clarity. And as a note, if there's a chance to include design in something that you missed — say that you weren't included in a conversation that has already happened — you can always reach out to those folks and suggest ways that design can contribute in the future.

Tactic three: incentivize strategic design

[00:17:42] Finally, tactic number three is to incentivize. This one is more centered around leaders. The previous one, for example, was much more of an IC focus, or the first one especially, if you don't know the language then that's probably more of an IC. The middle one, the second one, could be ICs and managers, but this is definitely focused on managers.

[00:18:07] Leadership needs to change the incentive structure to reward strategic design, because if there are not incentives to improve, nothing is actually going to get better. What I mean by this is, say that your priorities at the company in terms of user experience are mostly visual design focused and not really rewarding people who are more strategic, people who are facilitating conversations, things of that nature. Those people are going to either stop doing that work or they are going to leave. And it is really important that you reward those folks if you want to see better products.

[00:18:43] Just underscoring this here: it's important that this is not just a bottoms-up effort. If there are not leaders in design — managers, directors, VPs, whomever you have who's in a leadership position — if those people are not pushing priorities, then your efforts are going to be ignored. And that can be really frustrating, but it is the unfortunate truth. If you are doing things that people do not value, you will not be rewarded for it, as hard as that is to say.

[00:19:15] As a leader, what I would suggest, if you manage people for example, I would ask you: how can we reflect the need for strategic design thinking in our work systems? If you're an IC you can ask your manager that question.

[00:19:29] Just to underscore with an example: one time when I was a manager, I asked a report if they wanted to try mentoring a more junior designer, because people learn by hearing from other people. Mentorship is super valuable and it was something that I really wanted people to think about doing. This person asked if the company actually valued mentorship, and so I went and looked in the career ladder and it was not there. So the answer was no.

[00:20:00] That's just one example. This happens for all kinds of situations, and that includes the incentivization of aesthetics over strategy. This is something that's very important for you to do as a manager: think about ways that you can actually incentivize quality of the experience, for example, which should mean both how it looks and what it's actually like to move through the different parts of the experience. This is something I've experienced myself as an IC, so I've definitely had to have conversations about how we can make sure that, for example, the word "craft" — which can be really buzzwordy or triggering for designers depending on if you have been in certain companies — craft can mean a lot of different things. Sometimes it can mean aesthetics, sometimes it can mean that shared experience, the full experience. And so it's really important to make sure that you clarify what that means, and if there's a lot of focus on aesthetics and less about whether it actually helps people get their tasks done, then how can things be more balanced?

Aligning design's goals with other functions

[00:21:04] Something else that's really important, as I've mentioned, is making sure that design is not doing this as a silo. So how can design's goals and career ladders complement other functions? Some of the questions that you might be able to ask are: can we stop pressuring PMs to ship quickly? Can we require projects of a certain size to be tested at least once with users? Can we build out our design systems so the designers can actually move faster and concentrate more on information than thinking about which color button to use, or which pixel size or spacing, and things of that nature?

[00:21:39] This is something that is incredibly important, because if design is operating in a silo and decides that experience matters but doesn't go talk to PM or to engineering, they all have their own goals. This is also a very meta topic, but it is important to make sure that the goals are all working toward the same outcome, because if they are not, then you're just going to experience more of the same.

[00:22:04] At Dropbox we have staff and principal product designers who actually work with product and engineering directors, and this is something that's really helped to increase the value, the quality of the customer experience. That's something that took a lot of advocacy and a lot of effort, and I'm super excited to be a part of that team, but that is something that needed to be prioritized across the company. So you and your leaders are going to have to work with other people to make that happen. And when the incentives actually do align, you're going to start to see positive results.

[00:22:35] What I'm saying here is that if you're a manager, go out there and fight for your ICs. If you're an IC, you've got to find out which of your managers or skip levels or whomever is going to actually be willing to go to bat for this, because it is not otherwise probably going to happen. So something you can do again is to talk to your manager and your skip level and see what their goals are. How can you align your goals with theirs? How can you talk their language, and how can you share solutions and not just problems?

[00:23:07] And those are my tips. Something I just want to say is that this is really challenging and that this is probably going to be a long-term kind of change. It's a cultural adjustment, so make sure to give yourself some love, to be kind to yourself and to others along the way.

[00:23:23] So to wrap up: many people think that design is aesthetics. It's important that you help your team see how design is actually contributing to the business, or could contribute to the business. And it's important to get involved in an open, curious and goal-oriented way. If you like this talk, I'm actually running a design strategy intensive workshop that's going to be on June 26th, 28th and 30th of this year. Early bird tickets are available on Rosenfeld Media's website, so you can go to the link to reserve your spot. With that, thank you so much for taking the time to listen and nerd out with me about design strategy. I am excited to hear a couple of questions. Thank you.

Q&A

[00:24:07] Host: Excellent, thank you very much, Catt. That was really interesting. I actually haven't seen it being pitched before, the kind of the workflow model, but I think that's brilliant, because you catch so many of the edge cases when you do that that you don't normally think about.

[00:24:21] Catt: Yes.

[00:24:23] Host: If anybody has any questions, please do send them in. I'm going to ask one, because I worked at a company where — I love the idea of getting the business mentality. We're not getting involved, we're getting pulled in too late. So I said, okay, well let's go talk to them, why aren't you talking to them? And the answer was, "I didn't know we were allowed." Nobody had ever told them they couldn't, but they just assumed that they couldn't go talk to these other people who sat just one floor away in the building. So what kind of advice, or have you encountered something like that, and how do you get people to — I guess it's your "show up" point — so how do you get people to do that?

[00:25:11] Catt: Yeah, some things that I've done is to be more visible. If we're working remotely, or even if we're not, I will share things in Slack, I will invite people to have a conversation with me, I will point things out, ask questions. I think it's very important to show that you are open and very excited to communicate and collaborate with other people. I will also say that, again, the value of having one-to-ones with people who are in different functions is really, really important. Sometimes those people are afraid to reach out. Maybe they don't know how to work with designers yet. I've definitely had that happen to me before, so the more that you reach out to them, the better.

[00:25:56] Catt: I do think that figuring out ways to have that happen at the design org level is also important, so it doesn't just have to be you, although of course you'll look very good if you are proactively reaching out. Maybe that's also a question of, hey, how can we show more people at the company how design works and give them the opportunity to actually be involved? So I think there's also definitely some organizational work that could happen.

[00:26:21] Host: Yeah, I've talked to people on the business side of things and they're crying out for support. They just don't know that it's available or where to get that support. Brilliant. I think that brings us to time, but if anybody does have any questions, please post them in. We'll post them on the UXDX Community Slack group and we'll invite Catt to come and answer the questions there.

[00:26:42] Catt: Perfect, thanks y'all.

[00:26:45] Host: Thank you very much.