Microsoft’s Jamie Young on Storytelling and the Need for Designers to Evolve

Jamie shares with us his thoughts on the evolution of the design role, the need to be a good storyteller, and about staying as an individual contributor vs. moving into management.

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Photo of Jamie Young

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Principal Design Manager @ Microsoft

Jamie Young

Connect with Jamie

LinkedIn, ADPlist

Full transcript

This transcript is provided by an automated transcription service and might not be entirely accurate.

Christian: Welcome to Design Meets Business, a show where design leaders talk about practical ways to quantify design, about making our work more transparent, and about how designers can make a bigger impact in their organizationI’m your host, Christian Vasile, and before we begin, I’d like to thank you for tuning in today..

On the last episode of season two, one of my favorite conversations with Jamie Young principal design manager of Microsoft. We’re talking about the need for designers to evolve. We’re talking about why storytelling is an important skill to have, and we’re talking a bit about being an individual contributor and staying an individual contributor versus moving into management.

We are ending season two on a high and I hope you liked this episode. Just as much as I do.

Jamie welcome to Design Meets Business you have got 20 years or so in the design world. And during that time you’ve been an interaction designer, visual designer, mobile web designer, graphic designer, brand designer. And that’s probably not all of it. So on top of that, you’ve worked at early stage startups agencies, and now we’re tied to any company like Microsoft.

So it would be interesting to hear a bit about that journey and a bit about why you’ve been in so many different roles. And what’s exciting about 

Jamie: exploring different roles. Of course. Thank you, Kristin. thanks for bringing me into this and asking me to talk about some of these things

 To introduce myself briefly, I’m currently a design manager on ML or Azure ML for Microsoft, but I’ve also spent time in Microsoft running the developer tools team. And before that, and worked in a software company called canonical, which made a, an open source operating system called open to which probably people have heard of you.

And as you described kind of the run-up to, that has been at a whole mishmash of different things from marketing, websites through to mobile apps and way back in the midst of time 20 years ago, or so I was, I kind of, you know, branded communication and campaign designer as well.

Um, and I think, yeah, I think that’s, it’s, it’s, it’s an interesting, 

Christian: it’s an interesting 

Jamie: one is in the front door. So, uh, it has been an interesting journey. I think we can leave them to be at the front door. Um, it’s been a, yeah, it’s been a really interesting journey. And I think that. One of the things that has, does, I guess connect, I suppose, all of the experiences that I have, is a strong belief that I have that kind of like design principles and design values that are arguably, consistently useful through, out all of those kind of form factors in which we design within.

The importance of, and the value of design, um, was important when I was a brand designer. it’s important to in your mobile, I think good design is good design. And although I work in what this, what I sort of sometimes pinch myself as a very slightly weird, very technical area of design right now, you know, working on kind of machine learning tools for Microsoft the importance of good design and good user experience is still, yeah.

 Top of everything that we do. And that the thing that I think about it and think I talk about all the time, the user is still the user and they still need a good user experience. Yeah. 

Christian: How have you seen design change over these years? I assume the value of design was no different 20 years ago than it is now, at least two different how, at least how to help businesses, we’re thinking about it.


Jamie: I think that’s it. I guess the, you know, 20 years ago to now the, my involvement in those conversations about the value of design was very different as well. When you were a kind of, you know, uh, a graphic and a brand designer, um, it was it’s, it’s weird. It was almost when the clients I worked for back then, it was almost a given.

Th that you needed a designer to do some of the work that you did like, and that’s, what’s quite interesting actually. You know, when I, when I started working, I worked in things like express. I worked on print, I worked, you know, I did really, really kind of arcane things that a lot of your listeners may never even heard of, hopefully somehow.

 and, but the portions of design or rather the importance of the involvement of designers was unquestioned in some ways in as much as like you needed a designer to deliver on a, on a brochure or a book or a piece of brand work was kind of a piece of communication, a campaign that was a sort of an essential component of doing any of those bits of work.

I think what’s really interesting. Now as we evolve the design discipline. And I, you know, I was having conversations with designers in my team just this week about like the kind of idea of a full stack designer or a generalist designer. And I think we’ll get into that a little bit, cause that’s a really interesting topic.

 The essential need of the design capability. As a kind of discipline is, is, gets blurrier. these days in software design, because of, and because of tooling, I think because of like the, there are, um, what’s the word for it, our access to the tools now, whereas before it was incredibly expensive and you needed a lot of training to do a lot of the work, you know, these days, arguably that’s not the case anymore.

And what’s interesting with it, you know, we, yeah. So it’s interesting. I think that’s the big change, which is, I don’t know. Some people might see as a fearful thing. Some people might see as a worrisome kind of like, well, we’ve got cheap access to design tools. Therefore everybody’s a designer does it democratize design?

I think it challenges that design, uh, discipline to. Look hard at themselves and figure out what it is that makes design important component in the process. Again, I think that’s an interesting time. 

Christian: Yeah. So you said a bit earlier in the beginning, it was very much around delivery, right? The value of design was, was you had to deliver a poster or whatever it was, but in the present, it’s not so much about delivery anymore.

Eh, It’s much more about how can you as a designer provide any business value or how can you help the business grow? Because the way I see it then, and very much to the point that you’ve made is tooling is not as complex as it used to be in the past. Access and tutorials are free on the internet. Anyone can really anyone with enough time on their hands, anyone can design a wireframe where anyone can put together a flow in Figma today, or in sketch, whatever people are using, however, the skills that are necessary.

And if anything really valued, have changed over time from delivery to more strategic, if you will, would you say that’s accurate, you know? 

Jamie: Yeah. Honestly, that taps right into what I, I’m pretty passionate about talking with people I work with kind of day to day about and have done over kind of my time at Microsoft.

And I think it was Almost certainly the realization when I started managing a team and having to figure out how to make a team of 30 people that were suddenly looking to me for kind of guidance and strategy, how do you make them, how do you make them have the most impact of that you can with a team that size.

And it’s when I really started to dig into just what you described, Christian, where honestly speaking, when your design team of 30, back in the day, science quite big when you’re sitting inside Microsoft and your closest partner is PM who are probably in the hundreds and then engineering or almost in the thousands, you need to start to really think about like, okay, how do I make impact and how do I bring value out of every single one of those people?

And We talked about this thing when you’re in dev tools, the idea of shifting left the idea of, tackling problems that may become kind of bigger gnarlier things later on in the process tackling them earlier. And I started to think about design in that kind of capacity.

So I started to really think about, okay, if we have 30 people really making everybody a Uses Figma and turns out screens is not a good use of everyone’s time. And so how do we in fact engage design as a discipline much earlier in the problem-solving in the concept creation in the strategic thinking in the process to have ultimately more impact it’s that early point that you can engage.

Um, and it’s what I’ve been pushing where I am right now for the last kind of 18 months in Azure ML as well, and trying to get the team thinking that, and, you know, I think the other thing that I have experienced and been quite interesting in my time, kind of working in two teams now in, in Microsoft and spending most of my time in developer tools, where we actually had that arguably centralized design organization and challenged by.

 The fact that on the whole, how getting that early involvement was a kind of, you know, it was something that we had to push for and ask for and try and drive towards. More recently I’ve spent the last we’ve had about six can’t. Remember how many months exactly was five or six months ago where I am in Azure ML.

 We actually did a mini reorg and we work as, as much more cross-functional group. And I’ve noticed one of the, one of the interesting things my goal of always pushing designer in the process, because I think it has a bigger impact earlier has been much easier to do when you have a set of cross-functional squads of design, where a designer is matched to the PM, match with an engineer, matching the researcher, because everybody’s just, it’s one team and everyone understands the value of that.

And so, that’s been, I think. Whereas I’ve been on this journey to try and make design impactful and arguably push it earlier in the process. I think one of the realizations I’ve come to recently is like the organ, like the, the ship, like the way that we also work with partner functions is incredibly important to how effective you can be in that place.

Christian: For sure. Yeah. Did you find that having these smaller teams, smaller squads allows design to get involved earlier? 

Jamie: Yes. I’m going to say yes. What has been interesting, you can set up the groundwork for, for that to be effective, but, um, I think there’s also an aspect of like culture where you need to really have.

The designers who are often, you know, in these enormous organizations. And I have only experience of Microsoft at that scale, but even up until we were a centralized design organ, actually, arguably were challenged by some of the kind of aspect of not necessarily having as much impact early as we would’ve liked to.

We weren’t design wasn’t a function that was kind of involved earlier in the process, of the product or doing to either. I think it is up to you much more now, but certainly my time, it wasn’t then you could set up the kind of groundwork for success and for involvement early, but you also need to often guide a set of designers or design group into.

Feeling comfortable in that space as well. And so I would actually say, I can say this openly they would agree with me themselves, the designers on my team. It took a while to climatize, to the fact that like, they suddenly had the ability to impact and to be part of that early process, much more than they had in the past.

And it was a bit of a, oh, okay. I can do this now. So the moment which was really exciting. It was exciting for me to see that, we’re working on it right now. It will get better and better as we get better and better. 

Christian: Yeah, that’s interesting. I’ve never thought about it that way, because everyone talks about, we want the seat at the table.

We want to make a difference. We want to get involved earlier, but when you get that, how does that change your, your daily life? It as in your job, right? It changes your job almost completely because suddenly, suddenly what’s more important for you as a designer to do is to get involved earlier. You, you need to do more strategic thinking.

You need to be in those early conversations with other business stakeholders versus I just need to deliver some, some design work. So it’s kind of like careful what you ask for, because you might just get it yeah. 

Jamie: A hundred percent, a hundred percent. And like, I know the designers in my group are a hundred percent capable of doing that delivery, understanding that strategic partnering with the PMs and engineers that we work with on that.

And actually having a unique perspective that the other groups don’t have on the experience. They come from a kind of user kind of focused kind of angle that always will. I think it’s really interesting. Like you’re totally right. And I think that’s some of the, kind of like the shifting and adjustment that has taken needed to be a bit of a mindset shift as well.

And as much as it’s been, what’s also been interesting when I, even, when I worked within the bigger Oregon developer tools with, with kind of much, much more people the program management and engineering by and large have always been open to design’s involvement.

It’s just been a capacity of like, how do we get to there? How do we get early? And I think one of the kind of changes I re like I really understood this year is like, actually, you really need to think about how the teams are structured to allow for that to happen. Um, and so the partners we have in PM and engineering are like more than happy to have designs involvement at that early stage.

We don’t feel any resistance in that capacity. And that’s great. Like, that’s super great. And I don’t know if it’s part. My working with the leadership in those things as well as it is just the designers that we have on the team are very, you know, like they’re highly capable of stepping into those strategic places too, but it’s a, you know, kind of pivoting into this, but it’s interesting because it sort of touches a little bit on the conversation that was had again, having this week, we wanted to designers about the idea of sort of, and this is kind of probably quite a familiar term for maybe some people like the idea of the kind of full-stack designer and is that important and, uh, a company as large as Microsoft we have people that are happy to not do that.

Strategic thinking, you know, people that are kind of happy to be kind of designers almost in the truest sense of the word where, where the craft is, the thing that defines them as a designer and that’s it. But I do see in large parts of our company, certainly that the need for that evolvement or that the need for that to evolve into more of this kind of like business focused business thinking designer.

And certainly we have design leaders at the very highest level who are driving that and push that. And, you know, Jonah’s starting VP diff design in Microsoft is one that definitely Springs to mind as somebody that’s very passionate about the idea that design is a business function and should be involved at these early stages.

but it, as you kind of touched on earlier, Christian, it pushes us to think about what the designers core functions are. and one of the things that I have noticed recently, this is part of that conversation is the. The importance of research and research being a kind of skill that designers can wield.

Um, because often again, we complain and worry about design being a small discipline within a huge software organization research, or even smaller, like, you know, they’re half the size of design. And so like they’re even more challenged by some of the things that we talk about and , the levels of kind of ratio and of what they can get to.

So I, something I’ve definitely noticed a trend of and it’s maybe not that uncommon, but it’s certainly something that’s kind of happening in Microsoft at the moment is the desire slash neat for designers to be able to wield some research skills, to be able to, I think, to be able to qualify a lot of the design decisions that we make.

we’re incredibly, data-driven credibly research driven to do more of that. We need more people doing those things, if that makes sense. Um, so. 

Christian: So I think we should go back to talking about full-stack designers and all that, but just before I, I have a question too, regarding something that you said earlier, you said they might be required a slight organizational change in order to allow design to get involved a bit earlier.

So my question to that is, is there for therefore, do you think it’s not possible for that change to be driven from the design sides? Does it have to be first some sort of an organization change there in order for design to be able to get involved earlier? 

Jamie: It’s an excellent question. I have, I have an opinion on it and this is just my opinion, but like I would say that, I think now there’s kind of two parts of my answer, I suppose.

I think, yes. I think that to see designs impact earlier in the product making process, we probably need to have. We have need to think about where we’re designed sets and, and who it works with most closely. and I think that, you know, there’s lots of different ways of organizing design teams and there’s this kind of like, you shouldn’t organize them depending on the business need and things like that, but they’re kind of, you know, broad, the broad shapes are kind of embedded or more centralized.

And having been part of both, I’m seeing much more effective, early design participation in a, in an embedded team. And that said I think that there is definitely, there’s definitely ways of making a centralized design team, but I think much more like a more impactful or involved earlier in the product process.

Um, it probably requires a lot more advocacy on the part of the design leader and maybe just. Any design leaders that work underneath them, and also a great relationship with PM and engineering to understand why that’s important. if you embed everything the value is immediately apparent because you can see the squats working together as one they’re responsible for the same things.

They’re accountable for the same things. They’re engaged in the same process that trying to, they’re trying to work towards the same goals. If you do it as a centralized. You have to proxy for some fat, you have to make sure that everybody’s aware there’s an alignment aspect where you’re always reminding people.

This is why it’s important that designers involved does this. And this is why it’s important. This is why it’s important. This is just my experience, but certainly that’s the sort of the shift I’ve seen. 

Christian: Yeah. We’ve, I mean, we’ve had quite a few heads of designs and design directors on the podcast and every single one of them says the same thing.

So something along the lines of the work that I do is I don’t push any pixels. Obviously I don’t do that anymore. But the work that I do is, is the work that’s required to allow the designers on the ground so to speak, to do the work that they’re here to do, there has to be someone at the top to frame design, to advocate for it, evangelize if it’s necessary and the older the organization in the more.

 The less design driven it is the more you need someone at the top to kind of pick, pick that battles and fight them really. 

Jamie: Yeah. Yup. Yup. Absolutely. Just, you know to make sure that design is represented at all of the touch points or the moments that the organization comes together to make sure that people remember, you know, like the, remember the importance of design as a discipline as part of what we’re doing.

Um, no, I totally agree. And it’s been interesting, I think, and this is maybe somewhat of a function of my remote aspect of it because the whole time I’ve worked at Microsoft, I’ve been five-year years worked from east London. And my team has always, almost always been based in and around Seattle with the leadership kind of based in and around Seattle as well.

So again, when you talk about a design leader needing to have, uh, needing to pick those battles and reminders, so then advocate for design at the kind of highest level. When I’m working eight hours separately, that’s always a challenge. Like that’s always a challenge to do when you’re having to sync with those other, oh, the other leaders in the organization.

Whereas I can see how quickly we’re getting to that point already with an embedded model. And it doesn’t require so much of me having to do the advocacy. And so much of that kind of, I have a group of people I work with very closely. They understand that the team understands that and we’re sort of often going, 

Christian: yeah, that makes total sense.

Let’s go back to full stack, but let me first ask you this. If I go on your website, the only thing you see, I thought that was so funny when I was doing my, my research says, like go into a website, the only thing you see is a Swiss army knife.

And I thought, I think I know what that means, but I’m going to ask him, so tell me about this Swiss army. 

Jamie: Well, no, you know what, so it’s w so the Swiss army knife. It’s interesting. I think so when I put the Swiss army knife in, there has a sort of, you know, cause I think when you’re a younger designer, there’s always, everyone’s always doing their own logos and they’re doing their own, this and that.

And they’re trying, they’re trying to kind of set their personal brand. And I think before personal brands were even a fun and cool thing to have and an important thing to have, they’re not just finding cool. I think, you know, designers were trying to define themselves through, and always show off some of the craft or, or even talk about some of the way that they designed and, and the Swiss army knife.

One of those things where I was trying to think of a way that I could, Sort of visually depict my impression of my background and your right, essentially. That was my longest. And I actually, oh, I don’t know where it is now. I have a small five-year-old son now. And so leaving Swiss army knives around the house and stuff, it’s just something that’s not really done, but somewhere I have it.

And you can in fact, get you a Swiss army knife personalized. So there was no Photoshop involved. That was literally, I got, that’s why this type of graphy is a little shonky because it was done by the company that directs that, that make it. But yeah, I got a Swiss army knife with my name printed on it, as a, as you say, as a way of depicting the iHub at that point up until that point.

Anyway, I had a variety of, of different backgrounds and different things that I’d done. and arguably, that has only proliferated since then. And so I guess the Swiss army knife is still kind of applicable. Yeah. I, the interesting thing about that when we talked a bit talking about generalists and full-stack designers as well, I was super nervous about using that as a.

Representation of myself. There was definitely a time when I made that image and I use that to represent myself that like being a generalist, actually, wasn’t a good thing. You kind of want it to be a UI designer or you wanted to be a UX designer or you want it to be a typography for graph brand.

Like we had those, the industry at that point was like, being a specialist or someone super good at one particular area, it was actually more benefit, like was, was judged to be better. I think that in a funny way has flipped on its head. And I think the idea of this kind of generalist or this full stack designer is, is been around for a while and is only, only becoming more important, I think.

And, and just for the reasons we talked about earlier, the tools are cheap. Anybody can pick up Figma. you can watch a bunch of videos about how to use it. the skills that we now need to learn and to understand are much, much different. So yeah, this be nice. This is the depiction of me as a generalist back then.

Christian: I don’t anything’s exchanged. No, that’s good. It’s probably has evolved. As you said, you’ve added another tool to the, 

Jamie: I need, I need to, I think I only had something like six or seven of those different things, poking out this just how mean I need the bigger one now the one with all the bits. So that’d be my update.

Keep an eye on that, that your logo is coming soon. So it’s, 

Christian: it’s interesting you said in the past it was very important to have one skill to be really good at that. I think it also comes down to what the organization you’re working as part of needs, because I can think off the top of my head of a lot of startups that I’ve worked with, that didn’t really have the budget for a, an individual.

Or UI designer, strategist and all that. They just needed one person who could do it all. And I also can think of quite a few large companies that had the budgets and have the organization structure to support all of these different roles that could be done by one person, but they would prefer to have them separate.

So it’s a, I think it also comes down to the organization you’re working as part of, I am a big, big, big fan of generally sell I’ll openly admit I am one. but with that being said, I think it’s really important to have one thing that you’re really good at. So you’re kind of like a T-shaped, you’re a generalist, but it’s more of a T-shaped generalist if 

Jamie: you will.

Yeah, I think probably everybody is even if they don’t quite realize what that T bit is, but normally it comes from the background that has gotten them to where they are. Like, as you say, I think that. We’ve we joke quite a lot. We have a lot of very talented interaction and technical interaction designers on my team at the moment.

And we joke quite a lot that I’m doing a visual designer because I’m the one with the visual design background. And I make, and spend quite a lot of time helping the team with kind of, the direction around design systems or I cannot graphy or color or, you know, type of wifi and things like that.

And so, that’s yeah. I say, as you say, we’re all probably T-shaped and sometimes it’s good to sort of sit back and figure out what your kind of where your depth is, but, our top of our tee is getting wider. I think maybe the kind of like, I dunno, that’s probably the, 

Christian: the Vista the vertical line.

Yeah. Right. We’re supposed to know these are, 

Jamie: but back in the day, I probably wouldn’t have done, but yeah. It’s not ever, it is apologies to any time photographers listening yet definitely should know that. But yeah, the vertigo is probably getting shallower. I think that’s the thing that I’m certainly seeing anyway, in the experience I’ve had at the moment, 

Christian: It’s not only technical skills, it’s getting wider than that.

Like the top, the horizontal line is getting wider because now. Unlike I’ll agree. 10 years ago, soft skills are becoming really important for a designer that wants to work at that intersection of design and business wants to be part of those conversations a bit earlier on needs to build trust with the rest of your organization needs to understand how to frame design and talk about design from the perspective of whoever you’re presenting to.

So all of these are soft skills. They’re not technical skills. You really learn by sitting down and watching a tutorial. It’s more through experience. So we’ll talk about soft skills a bit later, as part of the, you know, the, the, the end of podcast question, but what do you think that, that is becoming more and more important in terms of 

Jamie: soft skills?

Yeah, no, that’s so, as you say, like, I ha you know, soft skills. Everything you need, if you want to be at that intersect. Because if you think about, if you think about it, like, the, the sort of activities that you’re doing at this early stage are in practice and hopefully not all the time, but in practice.

And hopefully there are much more of these kinds of collaborative, white boarding activities that prioritization activities there, they’re not productive activities that necessarily need you to have a graphic design or any kind of creative background whatsoever. Everyone could pick up a pen and draw on a whiteboard and put up post-it notes and things like that.

And again, that comes back to that sort of like, how do we define what it is that makes design design or makes interaction, design, design, and again, you know, in a way, this is a little bit back to what I was talking about earlier, where the sometimes designers need a bit of time to claim the ties to this new way of working, and then the kind of things that they’re being expected.

Bring to a meeting or, or kind of a conversation or a workshop. and you’re right. Like soft skills are super like invaluable. Um, and in a lot of times, because actually I think I’m okay to say this, but not everybody is blessed with a skill in soft skills. Particularly if the discipline they’re working in doesn’t necessarily need, require them to have soft skills, you know?

And, and so like being, uh, a great facilitator or a great Collaborator a brilliant user I’d like advocate for the user or the customer. We talk about a lot insight, Microsoft is enormously important. It’s a huge thing of how I believe design again, can be impactful early in the process.

How design becomes important to business. I think the one thing I. Really learned through my time so far Microsoft is, is just framing how we talk about it. This is not like rocket science. You know, it’s not rocket science, but I came into Microsoft, not fully understanding this as well as I now understand it.

And, and in part that’s because I was very quickly having conversations with engineering leaders and PM, PM leaders about why it’s important. And I saw how they talked about the importance of their work. And we talked about this inside Microsoft a lot, but I think it’s very common.

It’s like most large organizations and it’s just the idea of impact, the idea of impact. It’s just it’s in some ways to describe it, very simple. It’s like you have, you do things, but why do you do things? We talk about activities and impacts. So you do things, every day, every week you’ve done something.

 It is sadly rare. that we regularly sit and talk and think, and sort of analyze ourselves about why we’re doing those things. It’s not always rare and it depends on kind of like the seniority of designer you are or the type of designer you are, we will avoid a lot of trade secrets here.

We will often come round to kind of like these review processes we have with insight Microsoft. And we’re asked to describe the impact that we had over a given period. And that is hard P designers, every, almost every single person I’ve worked with on those sorts of appraisal processes, really struggled.

And in fact, I’ve worked with managers and in teams to try and clarify how design can talk about impact or how design can take impact. And I have a kind of like, I have an opinion, which I know is not, um, not the same as some of the people I worked with, but, um, I’m happy to go there anyway. and I think this is it’s interesting. I think this is more true in my more recent team. I, I actually believe to an extent and just to be clear it’s very easy to talk about impact when you were saying I moved to metric eight to, from zero to 20 or something. And we by NPS score from zero to 40, over a given period.

And I see our partner disciplines in, in PM and engineering able to very easily talk and look at, but point out rather tangible statistics or metrics that they have shifted the needle on. And, and that can be great. That can, that’s a very easy way of understanding the impact of the work that they did.

Design I think has a harder job because it often is. Involved in some of the things that are talked about at the end sort of later on down the line or they’ve been involved early, but like, how do you quantify what the impact of that, of the design of being in that initial kind of workshop was?

And so we tend to look at the sort of the end game, almost what did we deliver? You know, what do we deliver from a kind of like output and assets and red lines? And I’ve seen so many kind of those conversations where someone’s kind of like, I deliver this, this, this, this, this isn’t a huge bullet pointed list.

And I was like, well, why, and is this a blank? look how like, uh, okay, so we need to kind of unpick it all. And I spend a lot of time talking with designers about how we pick that and try and get to the nugget of like why the work that they did. And it’s always there. Do you know what I mean?

It’s like the five why’s it’s like, you just keep asking until we get to this nugget of like, why it’s important, but the thing that. I know that I’m, you know, I’m not maybe alone, but certainly I’m not always in agreement with people I work with about is that I do, I do believe that design and I believe there’s more and more now, the way that my team is organized as embedded teams with squads, I believe that the impact of the work that they collaboratively do should be attributed to the designers as well.

Like I believe that like design should be able to say, you know, our NPS score went from zero to 40 again. we can draw a line to the work that we did around NPS where something or usability, that was an NPS theme, to saying that actually we can say we contributed towards that, that, that metric.

 but it’s hard, I would say, like, it’s hard to find those hard things that people feel good about saying. Yes, eight to be that thing and draw a line back to some design work or some design involvement. Maybe even the same for research. I’m not sure maybe, or maybe not. I don’t know.

That’s an interesting 

Christian: one. Well, the way I think about it is in any other industry, if you want to talk about impact, you would count the impact of the entire team. So this goes both ways. It’s, it’s it’s whatever the PMs and the engineered team is talking about in terms of improvements. Design has likely had an impact on that, but the other way around as well, because I sometimes talk to designers and ask, well, what’s the impact here?

Okay, well, we’ve moved metric a to metric B who’s. We are, well, we, the design team who else? Cause you can’t ship products. You just you’re a designer. So surely the is the testers is the analytics team is everyone else. And analogy is if you build a, uh, who gets credit, just the brick layers.

It’s the architect, it’s the brick layer. It’s the carpenters is everyone else. And similarly I find because design is a team sport and that’s why I think it’s interesting. Sometimes I have conversations. Well, who’s more important in a productive, there’s no such thing.

There is no such thing. Everyone is a piece of the puzzle. And without the piece of the puzzle, regardless of which piece of the puzzle, that is not a complete puzzle, that doesn’t make sense. Exactly. So I also think it should go the other way where designers should give more credit to the remain, to the rest of their teams.

And I’m wondering how are you empowering your teams on a daily basis to talk about design too, whichever stakeholders they need to talk about design to it from the perspective of, of impact from the perspective of here’s what this team has achieved over this period of time, how are you doing?


Jamie: do we know? So well, it’s, I mean, so it’s interesting. I like, again, this comes back to this idea of like, how do you shape the team as well? It’s much easier to say this team achieved this and this team have these different pieces of a puzzle that achieved this. And without that piece of puzzle, obviously the puzzle isn’t clear as much as you do that, when you have distinct squads and like, but your question was how do we kind of empower design or, or talk about it on a regular basis?

One of the things that we set out to do, um, this is another example. So one of the things that we set out to do when we were. We w when we set up this kind of squad model, which we’re doing now was that, we have regular check-ins for the entire team. So there’s a couple of things, actually.

Um, we do a regular check-in every month for the entire team, and everyone brings together and we walk through experiences that the cross-functional teams have worked on together. And a lot of time it can be a designer and a PM presenting it, but the engineer will also be there. Like, it is very much like a, a group effort.

So whenever we’re sharing, it’s not designed, did this thing, or PM did this thing, or engineer built this thing. It’s like, everybody feels like it’s a, I hope everyone feels anyway , that it’s something that they all worked on. And they’re all seeing the benefits of that. The other thing that I really enjoy.

At the moment is we do a weekly what we call UX review. It’s not a sort of a particularly snazzy name or particularly kind of like clever format, there’s a need sometimes to do some form of kind of UX gate, um, for experiences coming through that, the work that we’re doing and what I’ve been really in the past when I’ve done those as a centralized designer work, what what has happened is we’ve had without a bunch of incredibly talented, very senior designers and one or two PMs kind of walking into this environment and showing their work and often with the engineers.

And sometimes those conversations are great. And sometimes the conversations are quite spiky. And. It wasn’t until kind of close to my end at my time at dev tools that I heard some lateral feedback, that those are quite scary things to step into. This is a bunch of my colleagues and people I knew well and friends of mine.

And I certainly thought, and I was always very careful to try and be as inclusive and low stress, although there’s a kind of function of those forums where it was a kind of go, no go aspect. If it really wasn’t up to snuff, we needed to ask them to come back and do some work on it.

Um, but I heard laterally that those are quite there were, they had, they have been quite kind of imposing intimidating forums to step into as a PM or engineer. The thing that we’re doing now is, uh, is like from the get-go a completely cross-functional conversation. And so like every UX review that we have every week, We’ll have the experiences that the PM engineer designers will bring in, but it’s like the room is full of like engineers asking questions about the user.

We’ve got PMs asking technical questions. We’ve got designers ask and it’s a really much more, um, Lively vibrant conversation, I think. I think there are less intimidating and maybe find out later, I don’t know, after, 

Christian: after they listen to this, they’ll 

Jamie: tell me exactly what 

Christian: all you on about 

Jamie: this.

I’m expecting a lot of that. Hopefully all positive. So 

Christian: totally. We were talking earlier about soft skills and I like to use that as a segue, into talking about hiring and portfolio reviews and all of that from the perspective of a manager. And what do you see a lot of designers do wrong? What do you see a lot of designers do, right.

And all of that, but let’s, let’s use the soft skills, a breach. How do you, cause it’s easy to look at a portfolio and say, this person has a technical. But he’s much harder to look at a portfolio and say, this person is a great communicator, or this person knows how to frame design for stakeholders.

It’s so hard. So how do you even find out about that before you hire 

Jamie: someone? Well, that’s interesting cause that last bit of the question is the really tricky bit. so yeah, so I think I mentioned this before we’re hiring or have been hiring a lot of people at the moment.

I’ve been doing a lot of these sort of thinking and conversations at the moment and I’ve kind of, you know, the, I guess , it comes back to a little bit about what we were talking about earlier. Like the, what I see now in the sort of skill sets of folks coming through and looking to join our team is By-in-large kind of like the same set skills everybody has.

Everybody kind of understands that they have to do a bit of research on sound stands. They have to talk to the users. Everyone understands that they have to do where our friends don’t understand that they have to have feedback. And the challenge then is because it becomes, it becomes a bit noise and I’ll be, I’m going to be frat very Frank. 

It becomes a little bit noise. And so, you know, we’ve just listed me today, finished hiring for four roles. So that means I probably have talked to 40, so plus people and I’ve looked through just now countless CVS and portfolios and online things as well. So, um, what I think sets folks apart, and it’s just what you were alluding to is the F you know, is the storytelling aspect, like what.

That they can bring to this thing that they’re sharing with us. And that doesn’t have to be something that had millions of users. It doesn’t have to be something that they could, you know, had a whole research team working on before they worked with the whole research team and they did all this validation.

There’s almost always something like unique to the way either the way that they approached it or the project itself, because humans are inherently interesting and different and fickle and weird things. And that’s, what’s great about being a UX designer. We get to work most of the time with human beings who are very difficult people, things and drawing that out of their work is the things that have always set folks up.

And then the ones that I’m like, okay, actually those are the people that I really want to bring in for an interview. And even then sometimes that doesn’t work sometimes even then sometimes you think you’ve got a great storyteller and it transpires that, that isn’t quite the case, sadly, in the moment.

And I think it is, it is, again, it comes back a little bit to the why a little bit, it’s sort of like when the, when you’re sitting down and you’re thinking of like, from the perspective of the people applying, like when you’re sitting down and thinking about like how you want to set yourself apart, via online, be it in the conversation we have as an informational screen, be it in the interview itself you are uniquely different to the next person that hiring manager will talk to.

Um, what is it that you can help them with you buy and, you know, I think that we have, we’ve had so many portfolio presentations that I’ve asked the team to sit through and they’ve given me great feedback, there are a couple probably that were just brilliant storytelling and just stuck in the mind of everybody.

Um, and it’s, I think that you talked a little bit about like how when you’re looking for people, again, this comes back to this soft skill idea, and it comes back to like how design continues to be an important function in software as the tools that kind of like as all democratized and the skills are all democratized.

How does design or interaction design or UX design, whatever you want to call it, become unimportant function. It will, I believe it will become through the skills that folks bring through things like, as you say, storytelling and like advocacy for, and so when you see those people start to pop up on portfolio reviews, you’re like, okay, those are the ones that want to try and get on the team because I think they are, they’re not, I think everybody can be taught these skills, like to be clear, like, I think you can learn this stuff, it’s practice and things like that.

Some people come in to these things inherently easier. They just feel more comfortable in those environments and doing that kind of work. I enjoy that kind of work. I think that’s why I like being a designer. I like telling stories. Yeah. 

Christian: Well, would you say that storytelling and all those soft skills is something that shines through face-to-face or in an interview, but in order to get the interview.

It’s probably still the technical work. It’s the technical skills. Would you say that 

Jamie: sort of, but if you think like yes and no. Like I think as I say I think that there is, I think technical skills, my honest opinion, technical skills, by and large, particularly things like Figma, particularly in, uh like if you’re applying for somewhere like Microsoft or one of these other big tech companies know that you will come into an environment where there is almost certainly like a very strongly defined design system, things like that, that, that will kind of, I’m not going to say restrict your creativity, but they will guardrail what you’re able to do as an interaction as I like, that’s just, I’m pretty confident in saying that’s probably prevalent across the other big tech companies that exist as well.

It’s certainly the kind of case inside Microsoft. And so, I remember the portfolios that I review where they’ve tried to kind of like, you know, you’re showing. You’re trying to take the person, like take the viewer of this portfolio on a journey or through a story. Like, so if you’re going to do a case study don’t make it.

There’s a, not like we don’t, we have sadly little time to read the, kind of that to understand the real technical skill that you have. We will make very quick judgment calls about those things based on what you sort of share on in that portfolio. But like, if you can hook with a little story and maybe make that story just slightly quirky or unique or something to you or some way you approached it.

You’ll probably be more likely to kind of have a conversation with a hiring manager after that. And maybe if you can have that conversation that goes, well, maybe even an interview after that and who knows. but yeah. It’s I am. Yeah. I’m always looking for something a bit different when I’m looking at it.

Cause there’s so much that’s that sensei and it’s the same. And it comes a little bit to sort of, you know, when I graduated 20 years ago, gosh, that’s a terrifying thing almost 20 years ago. Yes. It was 20 years ago. There, there wasn’t any of the courses that there are existing in things like UX and UI design interaction, design there’s courses.

I don’t think that, you know, that go back and further in the discipline was a sort of nascent thing. I know talented designers inside Microsoft. Who’d been there for sort of 30 plus years and came in with a background as kind of artists and could have print designers and worked on some of the very first UI stuff.

But before that was even a thing. and I think that one of the challenges probably for the education. established it’s these days is that there’s. So they’re filling the market with kind of people was round about the same sort of skills. So like, maybe it’s interesting, like with this idea of soft skills, like what are the skills we can equip young designers with to have them stand out? and there were some colleges do that. Well, some colleges focused on the technical stuff, you know, dependent on their, 

Christian: yeah. Well, I think that if more people think the way you do, which is it’s a question then frightening, potentially it could be potentially, it’s maybe easier to get into design.

Bye call me by coming from a different background. So if the texting, the technical skill is not that important, I mean, obviously it’s important to have that baseline fundamental, but if what’s more important is how we can build relationships with people, how you can foster trust, how you can talk about, or I can still tell a story, all of that.

Then you might be able to do to start in design from another industry as well. 

Jamie: And you know what, that’s a great segue cause actually it touches a little bit on this question. You can ask me, I think at the end of, by like what the self skill is, is it, but also it reminds me that, you know, And I think to start with, this was a function of a little bit of working in such technical design areas.

So, you know, I was design manager for developer tools for years and now we’re working in design manager for effort machine learning tools at Microsoft, trying to find folks that had a mixture of interaction, design skills, a bit of those research skills, and also had an understanding of ML.

I’m thinking about kind of most recently the kind of to hiring up and doing that sort of Venn diagram is finding that people in the middle of it’s super hard. So you start to think actually one of the most important bits and what are the least important bits and what are the beats I can teach people on the role, what are the bits that like leads on our team can help support kind of like designers without maybe some of those kinds of like, when I say technical, I mean, when you say technical to me, Technical as in, to kind of come to understand this kind of AIML space, but it’s really a kind of the design craft skinless, as well as the cross goes to.

I was thinking about across dev tools in ML. Like I have, I think I might be one of the only people with an actual arts graphic design background that I’ve hired into one of these teams. They almost, almost all of the brilliant people that we’ve brought into Microsoft have come through a, what we call non-traditional background almost all of them and many of them.

And I can’t think of one that hasn’t flourishing. Do you know what I mean? Cause they can, they have the, the guidelines and the foundation of a, kind of like a good structure around a craft and an understanding of that. And it comes a bit back to that design idea that you’re kind of working within guardrails and these big companies.

Um, but they also come in with a slightly different, like a different approach and if perspective things, and I think that’s really interest. 

Christian: Well, let me know what you think about this. Cause you said earlier that Venn diagram, when you look to hire someone, most of the time you have a problem that you need solved or, or that you need to field.

And then you, you have a specific person in mind. And whenever someone in an interview is kind of like that person that you have in mind, that’s the person you would try to hire. So if, if it’s a matter of the person I need to hire is a person that kind of fits what we need here. Do you think that on the, on the side of someone who’s looking for a job, it’s also a matter of focusing.

So first of all, thinking, well, what type of, what type of work do I want to do? Which do I want to do consumer, do I wanna do enterprise? Do I wanna do super technical stuff? Do I want to do, and then polishing your skills and everything else that you need around that to match the type of job that you want to do or.

You just go as wide as possible, cast the fishnet as wide as possible and hope you’re going to catch something. 

Jamie: Um, it’s probably the former Christian, I think. And I think, although I’m like personally, I wish it was the latter and that people were able to do all sorts of different creative things and that, that would allow them to get whatever job they wanted.

Having sat in the design hiring managers sort of seat for the last couple of months. I know that I have preferred candidates and been more interested in the candidates that have a more enterprise bent to the work that they do the kind of enterprise kind of business to business, internal tools stuff.

And it’s, and it’s, it’s a sad fact of like, and it’s, it’s not a sad fact so much, but it’s like, I’m thinking kind of thinking about the candidate as I’m looking at this stuff, because I also want them to be successful. I want, I don’t want them to come into a design team in Microsoft in this. Consumer and other types of work that Microsoft does anyway.

Um, but I w I wouldn’t want them to come into this very specific space and not succeed and be a struggle and really, really struggle. I feel like, you know, in seeing that I’m taking the opportunity away from a bunch of people that may not have that background, but want to get into AI and ML space or, or developer tools as well.

But as you say as a hiring manager you’re kind of balanced with, normally, if you have an open role, you are, you have a gap. And that normally means that things are like leaking all over the place. And you’ve got PLN engineering asking you for when that design is going to start.

And these are all things that I’ve been experiencing the last couple of months, like how quickly can we fill that role? There’s always an, a speed, a speed up that you’re very rarely sitting with an open job position going, I just fancied hiring a designer it’s always, like, we need to fill this role as fast as possible.

I mean, I, I think I’ve been very lucky in the last, as I said, the last one, the rules I’ve been hiring for is that we hired so many. We had three, three for my team and one for a partner team. And the advantage of having a few open at the same time is that you, as you say, you might meet somebody and you’re like, this is that perfect person for that thing.

But then you might need even more perfect person, but you’ve got a little bit more latitude. Like we have a little bit more latitude in the type of work that we’re doing to sort of go, actually, let’s put that this other person in this place, or let’s put this, you can figure it out often when you’ve got one role as you’ve described, you’ve got one gap that you’re trying to show that you’re probably just trying to fill that gap in the same, with the same shape of person that you lost or that’s moved on from the team as well.

So, yeah, it’s an interesting. I love 

Christian: change the topic a little bit. Something that I wanted to ask you is you’re a manager. Now a manager is a different career path than the one of an individual contributor than the one of someone who’s sitting in Figma all day and delivering or meetings, reviews, whatever it is, I would assume a lot of your day is spent around managing one-on-ones hiring, maybe all of that.

So, but get one day know, a few years ago you were a designer too. And at some point you’ve decided to make that shift into management. And I’d like to talk a bit about that. why have you done it and how do you think looking back, what was the, what was it at that point that made you want to move into management versus staying a country?

Jamie: So I can only, so, so here’s, that’s an interesting, so I I’ve just started doing a bit of mentoring on the ADP list website and I have to say I’ve had a lot of people already coming to me saying, I w either I want to be a manager or I’ve been made a manager and, or even just asking me kind of consider the questions to that.

My journey to management was actually genuinely, uh, I was incredibly lucky to have a manager I had at that point or a skip level manager. So someone, someone moved out of our team and we spent a good deal of time in dev tools, trying to find an alternative to that director. And I was working, I was kind of co-leading the team at that point with the other very senior design manager on the team.

 And I just had a conversation with the VP of program management and he’s, you know, he said, would you be interested in, in taking this on? And I was incredibly lucky for him to, I think he saw a mixture of kind of a bit of people skills that obviously design an understanding of design and also a kind of an aptitude around technical that he thought would fit well for that.

So sometimes, you know, the step into management is circumstantial and I guess mine was circumstantial and I’m kind of like, I, you know, it wasn’t my five to 10 year plan. Probably I came into Microsoft as an IC. I was enjoying being an IC and I didn’t also, I, you know, I don’t think one of the other things I say to other people as well, I genuinely don’t believe you have to step.

I don’t know if this is true everywhere. I know it choose at Microsoft and I know it’s true. I know it’s not true everywhere as well, actually, as is my point. you shouldn’t have to step into management to continue a career like, cause it’s very, very different and I, I. Experienced that very quickly, you very quickly go from yeah.

Working in Figma. And gosh, we used illustrator back then. Um, and I’m into just talking about appraisals and figuring out team structure and having one-to-one with kind of unhappy members of the team and trying to figure out how you can help them support them. and I. I sort of grown to love that bit.

I think you have to sort of love a bit of that. I know lots of people that have stepped into management and really not enjoyed it and wants to go straight back to IC or, or have, you know, in, in some cases we’ve lost talent to the company because they couldn’t, they didn’t feel like they could step back an IC.

And I think there’s like a very old school way and I don’t think this is don’t exist, just Microsoft. , but I think that generally in industry or business, it is seen as a step down, if you go into management and then decide you don’t like it anymore. And I think that’s totally broken because I think that companies will continue to lose.

Great, great, great talent. If, if we don’t and it’s not the companies say that that’s how it should be, but we don’t say that it can be different. We don’t say that enough. You know, like we don’t push that enough and people still have this. Nugget in their head where they think they can’t can’t stay at company because they cause they don’t want to be a manager anymore.

And I think that’s a real shame, but I’ve stuck at it. I was incredibly lucky to work with some really talented managers at the time who really helped me on my kind of like a management or management manager transformation journey, as well as having a brilliant manager myself who would help me with that too.

So, but yeah, it was a circumstantial change that ended me doing this. Fair 

Christian: enough. Yeah. All right. Let’s go to the end of podcast questions. You might already have answered this one, but I’ll ask again, just in case you have a different answer. So what’s one skill that you wish more designers with.


Jamie: it is different. Um, and I think I was thinking about this earlier, that curiosity, I wish, and it comes back to why I think, uh, why I think the shape of designers needs to change. And I, like, I think I, I wish more folks were more curious about the different things. Of making products. Like I wish more designers were more curious, like, and that they were more curious about research and how to get involved in that.

They’re more curious about like, how do we measure things and keep a track of that measurement? They were more curious about like the the code that goes in to building the thing that they’ve designed to figure out, how do we keep a track of that and help the engineers Polish it like, like all of that for me is curiosity.

I’m incredibly nosy. and I’m curious, I think it comes from my mum, uh, who won’t ever listen to this, so I can safely say that. And then, and I think that I’ve just, that’s helped me connect lots of dots, I think in the past. And it’s helped me build relationships in spaces that aren’t naturally designed, because I’m just curious about what they’re doing and how that ties into what we’re all trying to do together.

This is not thinking about my team, but just in general, I’d love. If more kind of designers were more curious about what else goes on in that organization and how, how they might be involved or even just informed about it. 

Christian: Okay. Curiosity is an answer we haven’t had before.

So I like that one. That’s pretty good. Yeah. What’s one piece of advice that’s has changed your career for the better. 

Jamie: So yeah, I mean, this is, this is somewhat easy. We’ve touched a little bit on this as well. And it probably was that moment where I became a manager of the dev tools team in, in, in Microsoft.

And it’s when I started working with my manager back then. And although he wasn’t a designer he pushed me to think about why for everything. It’s the idea of activities to impact. And as like that, for me, the idea of impact when you get it unlocks everything unlocks, like it helps you really think about even your day to day or week to week.

What is the most important thing I could be doing now? X, like for me, it’s for the team, for the designer, it could be for the project for, you know, everyone has a different answer to that, but like, why am I doing this thing? I can always come back to this idea of like, we are only given eight hours time in a day.

And so you have to try and make sure you’re using it as wisely as you can. I think, yeah, that’s so it’s just keep thinking about why I think is the thing that I I’ve always been remote reminded of. 

Christian: Good. That’s a good one. I don’t think we’ve had that one either. So you’ve got two out of two. Jamie, this has been such a great conversation in case anyone wants to follow up or they want to know more about you, where can they 

Jamie: reach out?

Well? So, yeah, I am on LinkedIn and you’ll feel free to reach out yeah happy to chat there. also I’m, I’m enormously enjoying the conversations I’m having on ADP list at the moment. If you want to have a chat with me there about any of the stuff we’ve just talked about or anything else to do with kind of like design or management or any of those things, then I’m happy to kind of like, yeah.

Happy to chat to you. Amazing 

Christian: Timmy, once again. Thank you very much for being part of the design mitzvahs, this journey. This has been really cool. A great conversation. We’ll catch 

Jamie: up soon again. Okay. Thank you.

Christian: What a season? This has been 10 shows, 10 fantastic conversations about the value of design, how we can become better and more efficient and more effective at our work. How can we set our best foot forward when looking for work? We’ve also talked a lot about building trust with your product team and your internal stakeholders.

We’ve talked about learning how to use daytime metrics to your advantage. This has been a season packed with knowledge. I am beyond excited for season three next year. And until then, I’d appreciate it. If you could leave the podcast a review, and if any of these conversations has been useful to you, I hope you’ll share them with your community.

I’ll sign off for now. And thanks a lot for listening. I cannot wait to bring you 10 more of these conversations in the next season.