DesignOps Island Discs - S02E05: Tim Gilligan

Luke Murphy
Luke Murphy
  • Updated

The role of a Chief of Staff

One of the roles that's been gaining traction within DesignOps in the last couple of years is Chief of Staff. In saying that, a lot of folks still have no idea what it is that a Chief of Staff actually does! For this week's episode we sail to New York to talk to Tim Gilligan, Chief of Staff on commercial and small business design at Capital One. Tim tells us about his journey into DesignOps, what his job entails day-to-day, at what point a Chief of Staff makes sense for your design org, and what elements you can take as a design leader in smaller teams.

Show Notes


Luke: So I suppose a good place to start off with, as with anybody is, what was your path into being a Chief of Staff before we even get into what a Chief of Staff does?

Tim: I think for me, my career has been about a collection of stuff. I started my career in large-scale immersive theatre on the production side, so really helping mobilize designers, actors, producers, audience through really interesting space. I worked for this company called Punchdrunk that did shows at Sleep No More. And so from there, I was like, okay, how do I scale up? I got into UX strategy and creative program management and more of an agency space where I was learning this digital side and how do we create an experience at scale because theatre is very small. And then really found that my passion was helping creatives tell their story and do what they did best. So, put on my recruiting hat, joined a recruiting agency to build service designers. It was at this time where service design was a newer discipline in the US, there weren't a lot of college programs prepping folks to go into careers in service design. So I was like, okay, how do I take the disparate experiences of landscape architects of UX designers, of interaction designers and help them frame what they're doing in a more ecosystem sense. Dove really into service design as a discipline, helped co-organize the New York chapter of the global service design jam for several years and really got excited by the systems with which we work and how to enable creatives. And so that led me to Capital One in a design operations role, right at this moment where DesignOps was having surging popularity, was really starting to have strong foundations. And then the Chief of Staff role at Capital One, kind of evolved out of design operations, based on me chatting and understanding what a Chief of Staff was for the organization and what design operations was for design and finding ways to have harmony and the language in terms of the disciplines.

Luke: Ah, I see. Cause I think Chief of Staff is one of these roles that people have now heard of, but go back a few years and they probably wouldn't have. Do you want to just very quickly explain what it is that a Chief of Staff does within a design org?

Tim: I'll start with saying a Chief of Staff perhaps in its purest definition, is a role that enables their leader or principle, as it's called in the community, to be successful. So similar to DesignOps with it's wide ever-evolving scope and breath, Chief of Staff is really responsible for ensuring that the executives mission and vision can happen. We're fortunate enough at Capital One to have design operations as a function and Chief of Staff as a role. And so that means I'm focused a lot on creating the conditions for success for our team to thrive outside of delivery, outside of their agile pods or their integrated teams. So I spent a lot of time doing communications, events, strategy, and I am a Chief of Staff and I have about six peers who are also Design Chief of Staff, we spend a lot of time figuring out where there's arbitrary uniqueness, where can we work together, to really maximize our value as design to the organization. So it's a mixture of strategy, organizational design, all of that great finance and budgeting stuff and hopefully inspiring folks and really making sure we're showing up for the teams that really do the heavy lift to get products and solutions into market.

Luke: That's really interesting. And in terms of, so people can have context as well and understand, I am guessing that Capital One's design org is pretty behemoth. How many people are there?

Tim: So we have around 650 full-time designers today and we're growing to about 800 by the end of 2022.

Luke: So a lot of people know DesignOps through the lens of the different spheres, right? People talk about the workflow ops, people ops, business ops. So Chief of Staff it seems like has a bit of overlap between the people ops and the business ops. Is that pretty accurate to say?

Tim: That's fair. I would say it depends. And each Chief of Staff is a little different just like each design operator. But I think that's fair. I will say, there are times in which I do dive a little deeper, but absolutely I would say the people ops in biz ops is the core of the role.

Luke: Yeah, it's one of those things that you can understand when a company gets to that level of scale that you need those sort of specialist people to start helping, optimize is the wrong word, make it as good as it possibly can be.

Tim: Yeah and help people. I mean, I think it's really about helping folks do what they want to do, right? It's a very humbling role because the role of a Chief of Staff is influence-first, right? We don't manage necessarily tons of things or tons of people, we manage tons of programs but our role is really to uplift. So there's a lot of things that I will get in stealth mode, like running, and then it's about moving it into a different team or a different leader or peer to take it over the finish line or to continue to scale or grow a program. I think I see my role as creating fertile ground for the work to happen, and then helping steward the team through process. But once those seeds have started to sprout, it's time for me to move to another space and cultivate that.

Luke: I mean, that makes a hundred percent sense as well. And I suppose I'm really interested, cause I think that with these roles, to be honest actually with roles even like a design program managers through to sort of Chief of Staff and a lot of the what are now the DesignOps roles, people assume that this is only a thing for huge organizations. And the more and more that I talk to people I'm like, oh no, we need to start filtering this down further. We need to get these into smaller orgs. I suppose, from your benefit with specifically looking at a Chief of Staff role, what would you say are some red flags that you may notice in an organization that may say that you would benefit from having a Chief of Staff?

Tim: I think, one of the biggest opportunity spaces is where there are silos, where teams are doing what they're supposed to do, right? They're delivering on their product plan, they're delivering value to market and perhaps design systems or the more nascent, how do we ensure that our commercial experience has talked to our consumer experiences so that we're not creating two platforms. I think those places where there can be cracks in efficiency because we optimize for the local, those are places where Chief of Staff can be really useful. I get the most play out of asking why, why are we doing it that way? Why are we creating something new? So I think for an organization of any scale that's really important because even if you have a small product team, a small tech team, a small design team, marketing over here, Chief of Staff can really run that red thread and stitch together those teams that are all running a mile a minute towards their individual goals and start to think about what connects it all.

Luke: And I suppose on that if somebody was listening to this and went, yeah, that makes sense, I think we need that in our org. I suppose a double question, have you heard of good ways to convince management this would be beneficial and I suppose similar to that, how are you measuring the success of the role of Chief of Staff at Capital One?

Tim: So, I was in a design operations role, a team of one and brought in my leader, was listening to what Chief of Staff was in other places and at Capital One I was fortunate that Chief of Staff is a thing across the org. We didn't have it in design, but I said, Hey, we need to optimize your communication strategy, we need to ensure you're showing up in the right ways for your team and we're leaving money on the table by not working smarter. So much of this is in my skill set, is in my wheelhouse, I've just been doing it locally, let me look across your portfolio to make you look good. And ultimately a Chief of Staff, my boss sometimes calls me her consiglieri, it's the second, right? We can be scrappy, we’re maybe a little bit closer to the team and the work that needs to get done. And I think there's a really strong story to say, Hey leader, I'm dedicated to your success, how can I enable you to be the best version of you and lead the most compelling organization possible to deliver value to the business. And that's how I did it. And I think always about incentives, right? Like what are the incentives of the folks who are going to give you a shot and frame it in that way. Around success, so I think there's softer successes, right? There's of course programs that I influence or participate in, but those are typically longer, year/two-year horizons. We do all associate scores and surveys, so a lot of how our executives are perceived and how our leaders are perceived as delivering. So I would say that is one of the strongest indicators that I look for. Also, we look at workforce data, right? Are people staying, are they leaving? Why are they staying, why are they going? And I would say the people metrics, so are people content happy, engaged at work? Do they feel like they know where the organization is heading are our big indicators for success for Chief of Staff?

Luke: Thinking from a brass tacks, staff retention and staff happiness is probably a really easy way to see whether you're successful at your job, right? Especially when, cause it almost sounds like part of the job is a really kind of people focused internal design advocate, right?

Tim: Yeah. It's this, transition translation layer, right? Like I think similar to DesignOps, it's really having a focus and an understanding of how the business succeeds and then being able to translate that into language, strategies and programs that can allow designers, researchers, service designers, business designers, analytics managers to find the way where they can feel fulfilled and powerful in that system and also be delivering value.

Luke: And actually, I suppose, I'm curious whether you've seen if somebody was listening to this and again thinking, oh, maybe my design org could benefit from this, have you seen any data around tipping point of what size is the design org actually need to be before this does make sense? Or do you think it is just open for everybody?

Tim: Perhaps controversially, I'll say that titles are access, right? So, I think it's contextually specific. I think when you recognize that a leadership team is tapped out and that there are things that are falling through the cracks. This is a very similar story to when do we decide where at a scale where DesignOps needs to be part of the equation? I think it's similar with Chief of Staff. What I have seen is once you get to middle management, once you have an executive layer, a middle management layer, and then an IC layer, that's where Chief of Staff can really move the needle because there's a bit of distance between that leadership suite and the folks on the ground and really where I see the value and power of a Chief of Staff and how it shaped my entire DesignOps career is, how do I enable the leaders to be the best leaders they can be? And so I think, if it's a team of 10 and you have a head of design and then everyone rolls up to that head of design, maybe a Chief of Staff isn't needed because those folks are doing that work, are telling that leader or do it in the one-on-ones. When you get to a point where maybe you're talking to your executive every quarter or every couple of months, having someone who's able to do more interference in between, helps to ensure there's more consistency of the delivery of the team’s vision and strategies

Luke: Yeah, that makes me wish that I could go back in time, maybe tell that to some previous executives that I've worked with. I suppose one of the things that I'm curious about as well, in terms of your day to day work and the kinds of things that you would do as part of your day to day. Is there anything that you think that you could tool up, especially smaller orgs when it is that kind of, as you're saying, that it's maybe 10 designers to a Head of Design, that you could tool up a Head of Design and say, Hey, just to make your life easier in the future, maybe focus a little bit more on this.

Tim: Oh. Like advice to senior leaders. I think something that we would all do well to remember,  is the connection point of the business and design and telling that story. Because I think it's really easy to tell the business story. It's really easy to tell the design story, but to weave together as a design organization, as our executives are climbing and climbing, climbing, and getting those seats at those business tables, it's incumbent on us to actually think about and expand what design means and how design can be practised. I consider myself a designer, my palette is organization and executive. And so I think of course if you're a small team and you're working on an early-stage product and you're delivering product out the door, that's number one, but ensuring that you're connecting the dots and telling the stories to help the team also understand the abundant future at scale that design can have, and that impact is really powerful because I think it can be easy to think you're in your box in an organization. And in order to expand your scope, expand your breath, you have to look outside and that may be the case.  But more often than not, I think there's abundant opportunity for design to influence business, to influence the direction and way of thinking and looking and grounding in business, I think is a powerful tool for design leaders to think about that.

Tim: Yeah. I think it's funny actually because I think that in my first real design leadership position I had the exact same. I didn't realize how important communication was and communicating the value of what you were doing, because there is that understanding, as long as I get the work done, as long as I get the product out the door, everybody will understand why and everybody will understand the value for it and everybody will trust me going forward. I dunno, I think people definitely underestimate the time that it takes to actually communicate that story and to sit down and actually think about that story as well. Again, why didn't I talk to you about five years ago it would have been very handy.

I also think, message discipline is important. I think, sometimes leadership is incented to have another voice and another idea bringing to the table. Of course, right, we want that abundance. But how powerful is it when product leadership, tech leadership, design leadership, sales leadership are singing the same song? And in those meetings, maybe we're finagling, we're influencing, we're figuring out how to steer the ship. But I think ensuring that you're dedicating time in your schedule to think about how you're communicating and also spending time with the cross-functional leadership teams that you're on to ensure that there's harmony because although we're all running our own orgs right, designers work with engineers, work with product, and they're delivering product, but they're also talking to each other. So if there's message dissonance that can be a leadership challenge to overcome.

Luke: It can basically be a way to make your department fail very easily. All right, so I'm curious from your perspective, where do you see the future of design ops going? Or what is it that is exciting you or you want to see happen?

Tim: I think I've already talked about the intersection of business design and design operations. I think that's a powerful thing. I'm curious how data might inform our strategies, and how we might inform how data informs our strategies, right? We're collecting more and more and more data on the people who deliver value for us, right? Through HR systems, through monitoring, through all of these tools and systems and Chief of Staff design operations is situated working with a lot of those partners in HR and cyber and risk. And I think there's a lot of ways to find efficiency, there's a lot of ways to track effort and ensuring that we're doing that in virtuous ways, in ethical ways, in generative abundant ways, right? And celebrating the unique contours and dimensions of the folks that we bring in, regardless of discipline, I think is a huge opportunity space that we'll see, because people tech is huge, right? Everyone's investing in how they can retain their folks, how they can grow their folks and there's a data side of that for executives and those who are investing in those platforms. And so I think it's like now, what do we do with that data, now that we've invested in our folks, we're starting to collect this stuff, what are the programs, what are the strategies that we build to really think about design of the future and the directionality and hopes we have for what we hope to create. So I think that's the future I'm excited about.

Luke: Yeah. I feel like the more mature that all the different aspects that go into creating products or creating services, the more mature they get the more we start treating these things like an actual product itself, right? And I feel like that's the next stage for us, I feel like the next stage for DesignOps is actually figuring out the right ways to measure through getting that data. But then as you say, it's the what do we do with that? And how do we do that in an ethical way? Because I think it's definitely something that product didn't quite nail, the whole actually doing things ethically.

Tim: And I think it's, I mean, that's the value of service design and systems designers and ecosystem designers, right? Nothing that we create exists in a vacuum, look at shipping, right? One boat gets stuck in a canal is a very, very, very big, big boat, but it has all of these cascading impacts on our global world. And I think, as we move into more and more abstracted products and spaces, it's incumbent on design to at least bring those questions to the table. And I think design operations can help frame it because there is deep risk and there's deep costs to companies if we do not consider all of the downstream potential impacts of the design decisions we make.

Luke: Definitely. I think it's interesting too cause I think that there's also a lot of potential societal implications from an ethical point of view as well, especially with DesignOps. If what we do as professionals is try and find efficiencies in business, and we want to do that from a people-first point of view, but at the same time, automation is one of the best ways to screw up a workforce, right? So we're got to make sure that we're doing things in sustainable, ethical ways. I think that's at least needs to be balanced with business.

Tim: Yeah, I think it's a design constraint on the business, right? This is what design futurists do all the time, right? When will it be bad? And when will it be bad for the business? I think I am a hopeful person, I believe in abundance, I believe we can make protopia, we can make things incrementally better, I think it is having the bravery to tell the business, Hey, this is why I think this is not going to work out in the long run. So do the analysis, see what happens, right? Especially as we rely more and more on automation and self-learning, continuous learning models and machine learning and A.I. because they're imperfect tools and they can just work a lot faster than we can. So it takes longer for us to catch the mistakes than if it was something that we were doing ourselves.

Luke: Definitely. Now that we've veered off-topic enough, I think that it's time that we cast you off to your imaginary island so you can have a bit of a relax. So as part of that, you get to take as comfort, one piece of music, one piece of literature, and one luxury item with you. So I suppose let's start with the music. What music would you take with you?

Tim: I'm a musical theatre fan and also kind of a folksy fan. So I think I would take ‘Hundred Days’ by the Bengsons.

Luke: Ah, okay. I know nothing about this, but those two combinations sound amazing.

Tim: Yeah. It's a story of what would you do if you only had a hundred days left and how would you live your life? So pretty cool song cycle, check it out.

Luke: Fantastic, that will definitely be in the show notes, as for the piece of literature.

Tim: So thinking about going to like an island and it's like, oh, fantasy and magic, I think I would bring A Wrinkle In Time, by Madeleine L'Engle, just like go back to childhood and ethics. I mean there’s so much that we were talking about that I think shows up in A Wrinkle In Time.

Luke: Yeah, great choice. And then finally your luxury item.

Tim: Oat Milk, I can’t live without oat milk.

Luke: Just an endless supply of oat milk.

Tim: It feels luxurious to drink oat milk.

Luke: I think that's amazing. If you do get horribly summer on the island, you can even just make yourself a lovely bath of oat milk as well.

Tim: Absolutely, multipurpose.

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