How Not to Apply for a Design Job

John Freeborn at UXDX Community: The UX of Career Building: Failing Forward in Tech. Video: https://youtu.be/-Dw0MIH0sWI

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 listen to me

[00:00:08] All right. Thank you, Kevin. Thanks for the intro. My name is John Freeborn. This is how not to apply for a design job. Why should you listen to me? Let's get into the introduction. I've worked in design for a long time. I've been a hiring manager and worked at all levels of design. I've had all the titles and worked a lot of places. And my career path has not been a straight line. It's been pretty messy. I've made every possible mistake that you're going to see in this deck. This is not a shaming game here. I'm bringing all of my personal experience to the table. I've had a few wins. I've worked at some great places. Hopefully some of this experience can help you all. Let's get into it.

Episode one: the grievous errors

[00:01:07] Episode one, the grievous errors. This is the most obvious of all the mistakes, but shockingly, I see it all the time. You have to include a link to your portfolio. I need something to look at as a design manager. It sounds a little silly to even put this at the beginning, but it happens all too often.

[00:01:36] Everybody is password protecting their portfolios these days. You have to include a password if you want me to look at a portfolio. Again, it's a no-brainer, but you'd be surprised how often this happens. And this really just throws a wrench into the whole process. I have to go and ask, if I'm really interested. And the chance of somebody else getting in front of me before you do, because I'm waiting on a password, just lowers your chance of success.

[00:02:09] This one, and the disclaimer is here, I've done this more than I care to admit: applying for a role that you are unqualified for. This really is common. And that leads into this obvious question: how do you know if you are qualified for a role? The first bullet point should probably be in bold here: read the job description. You really have to understand what the role is. You have to be honest with yourself, and you have to look and decide: do I have these? Are the bonus things really bonus, or am I looking at the requirements?

[00:02:56] Job descriptions these days have gotten aspirational. I've seen them. People are asking for 12 years of Figma experience when Figma hasn't existed for that long. They're asking for a video editor who knows Ruby on Rails and who also does lighthouse keeping. If you see things like that, you should probably just run the other way. But if the job description is well written, really take stock of it and ask yourself if you have the majority of those skills.

[00:03:32] A little data, and I think this is relevant in the world that we live in these days. I've seen this before, and I've seen it anecdotally in real life: women tend to apply for roles less often than men, especially if they don't feel like they meet the qualifications. Women will apply for a job if they meet 100% of the qualifications, where men will apply if they meet 60%. I'm sorry: women will apply 60% of the time where men will apply 100% of the time. It's very odd, and I'm probably guilty of this as well, but job descriptions are really a wish list. They're a dream. Do not cut yourself off from an opportunity, because you don't need every bullet point in that job description. You really should take it all into context. I think it's relevant, and I hate to see people not going for something because they didn't hit two bullet points that maybe weren't that well thought through when the job description was written.

[00:04:47] This is where it gets a little more interesting. I have had several situations where I had a live job posting and someone reached out to me on LinkedIn and basically accused me (luckily they did this not publicly) of not reviewing their portfolio. They told me in a LinkedIn message that I didn't review their portfolio and that I wasn't being professional. I think it's just an interesting thing, to approach someone that way and question their professionalism without any facts.

[00:05:25] A second situation happened, again thankfully not public. A candidate reached out to me on LinkedIn and accused me of not knowing my own job description, said that they were totally qualified and that I made a bad decision. You can feel that way. I've felt that way at times. I'm not suggesting you shouldn't stand up for yourself, but you should take into account what kind of reaction or outcome you want from an interaction like that. The design world is very small. You never know where you're going to cross paths with someone again. Or maybe that design hiring manager moves to another company, and the perfect role becomes available in that next opportunity for you. You want to make sure that you're bringing the best possible outcome to any situation. And sometimes you just want to be aware of how you're coming across. It's strange that I've seen these more than once.

Episode two: annoying but not fatal

[00:06:38] The second set here are things that I would call more annoying than fatal in terms of applying for jobs, but I've seen them a lot. Again, I've done this multiple times: applying for multiple roles at once, at varying levels. A bigger company maybe has a senior design role and a mid-level design role and a junior design role, and especially as a younger designer, I probably just applied for all three. It does not really bode well for how you view yourself as a designer. It gives the company a strange input, as if you don't know where you are in the hierarchy. It's just one of those things that I've seen often.

[00:07:36] No cover letter. Over the years I've come to decide I don't need a cover letter. Just show me what you do. Don't tell me. I'm sure different hiring managers have a very different point of view on this, so do not take this as gospel. But the reality is, as a design manager, I have very little time to review your applications. If your portfolio isn't good, the cover letter is not changing my mind. If the portfolio is good, or I have some questions, maybe a cover letter gives me some context, but it's not really changing my decision.

[00:08:24] This is something I did for a really long time: showing every single project you've ever done in your portfolio. It's really hard as a design manager or hiring manager to look at a portfolio with 40 projects. You don't know where to start. My assumption is your best projects are probably at the top, but there's no guarantee of that. I also might just be visually interested in some random thing, and maybe that's not your best work. You really want to take into account the time that a design manager has in hiring. I've heard stories that each application gets three minutes. I try to spend a little more time on my reviews, but it's going to vary wildly. What I realized is that I really wanted to craft a story with my portfolio. And when I limited my projects to a much smaller group, I just got more interviews.

[00:09:31] This section is kind of funny, but these are all real things. Immediately trying to connect with someone on LinkedIn after you've applied. I've done this. We've all done this. We're all trying to get an edge. I totally understand it. It's not going to lose you a job, I don't think, but I don't know how much it helps.

Moving forward and the hiring manager's side

[00:09:54] How do you move forward? That's a complicated question, especially in this job market. There are layoffs, bad managers, toxic workplaces. If you've worked in this field long enough, you will experience some of these downsides. I myself have been laid off. I've been forced out. I've quit jobs when I maybe shouldn't have. I've been part of acquisitions, which sounds cool, but if you're not on the founding team, it really just means you're not going to have a job when they downsize. Just take a deep breath, figure out what your value really is, and then move forward. I know in this current environment it's really, really tough, so I empathize.

[00:10:46] The hiring manager is in an interesting spot, and I did a lot of this in a recent job, where we would post a role and get hundreds of applications within 24 hours. When you are a hiring manager, hiring is a big part of your job, but you still have the actual design work and product reviews and all the other things that you're working on. It's really like a second job. You want to put yourself in the shoes of that hiring manager. Understand that they are going to have very little time, and you want to be as focused as you can with your application. You want to tell a story and really express your experience. It's really about having a little empathy for the hiring manager, which I know is a little hard to do these days when you just get rejection letters, but it's important.

My hiring process

[00:11:52] When I'm hiring, this is my process. Given everything I've already told you, this is maybe helpful in terms of how it goes. The first thing I look at is a portfolio. I intentionally don't look at a resume. I intentionally don't look at other stuff. I really just want to look at their work. I want to see if it makes sense for the kind of work we're doing. I want to understand what's important to them as a designer, what their taste level is, what their skills are. Even what projects they choose to put in a portfolio, in what order, tells me a lot about who that designer is.

[00:12:39] If that goes well, then I go and look at the resume. I'm looking for confirmation. I'm trying to understand their path as a designer and what they've worked on, and I want to see how they articulate some of their design experience. It's a data point, though. I'm not looking for some magic thing in a resume. It's really a continuation of what I saw in the portfolio.

[00:13:11] The next step is probably one of the most important for me. I call it a screening call. Sometimes I call it a humanity check. I'm intentionally getting on a phone call, not a video call. I do that to limit bias. And I really just want to have a conversation. I want to talk to the person who's applying. I try really hard to defuse the nervousness in these calls. I really just want to have a chat. I'm not asking them to pitch. I want to talk to them. Sometimes these go better than others, but ultimately my goal is to learn a little about who they are as a person.

[00:13:59] If this call goes well, I move folks forward into a portfolio presentation. This is their opportunity to get in front of the design team, show a few projects, and demonstrate how they do what they do in that environment. This is not a rehash of their entire portfolio online. I've seen some folks try to take that tack, but it's really a deep dive into a couple of projects. These sessions sometimes go 30 minutes, sometimes they're 45, sometimes an hour, but you really need to be focused in these. This is showtime.

[00:14:44] The last stage has different names at different companies. Some companies call it HQ day, even though everything's done virtually now. There are different titles for it, but it's basically the last stage before a decision is made. Hopefully you're getting to talk to different people across the organization, not just the design team, but maybe a product manager, maybe other high-level staff at the company. Once you've had the opportunity to talk to all these different people, my process is to take all of the data from all the different people you talked with, put it all into the pot, and decide where I'm at. Every company does this really differently. I don't want to get into the nuances of all the differences, but the goal is to get a viewpoint from various people that I trust on how this candidate would perform in the job.

[00:15:48] And then of course the step that is the most stressful is the final decision. This is the hardest part for a hiring manager, and I understand; I've been on both sides of this. You should remember that whatever the result of this decision, the design community is small. You never know when you're going to cross paths again. This isn't all about your skills. Obviously I'm trying to find someone who has the skills to fit a job, but it's also about culture. It's also about personality. It's also about the company, the makeup of the team, projects that are coming in the future, the maturity of the design culture of the company, and half a dozen other things that you don't care about but I have to take into account in filling a role. You should not take this as your self-worth. It's way more complicated than that, and oftentimes out of your control. It's hard.

What have we learned

[00:16:53] What have we learned here? Please include a portfolio and a password. If I don't have that, you're not moving forward in the process. Apply for roles that match your experience. Be realistic, and apply for things that are a good match. Don't attack the gatekeeper. Please don't do things like I described. We're all just trying to find a good job, hire good designers, take care of people. It doesn't help.

[00:17:33] Tell me a story. As a hiring manager, I am a human being. Human beings are wired for stories. Help me remember you. Tell me something. Don't show me a barrage of things that I will forget.

[00:17:53] And the last piece, and this comes back to my comment about empathy before: the hiring manager experience is really important. If you are a designer of any stripe, or especially a designer in the UX field, you understand user flows, you understand personas. Bring some of that to your hiring process. They are in a very unique situation with a lot of stress. Help them help you.

[00:18:27] And the last piece: I'm going to jump into Q&A. Hopefully there are some questions. While I do Q&A, I do have a few other slides, because I've worked with a lot of smart people over the years, and I asked a few of them to weigh in on things that they do in their hiring process. That's about it.

Q&A

[00:18:52] Host: Excellent. Thank you very much, John. I guess it's a very topical one, because everybody's asking about jobs right now and how they can stand out. I might just start there, and if anybody has any questions, please do write them in, because I know we got a few comments and questions on the last talk, so please keep that up. I'm going to start off with the first one, because you mentioned how important the portfolio is, but you also said, "Don't show me everything." Do you have any guidelines for people? Because it can be hard, when you're putting together your portfolio, to decide what aspects you're trying to highlight. Is there any guidance you can give people on what they should keep and what's not necessarily as important?

[00:19:37] John: Yeah, I think the thing that I look for is projects that have a deep level of complexity. And this is one of the hardest things: I want real-world experience. Usually when you're working on a big project at work, you have your path, you have your process mapped out in your head. We all know what the Double Diamond is. I've seen it in way too many portfolios. But the more interesting stuff is when things go wrong and how you adapt to those situations. And I think this comes back to the storytelling piece. You really want to build case studies or projects that show that journey, that tell an interesting story. And in an ideal world, those stories end in impact and you can show some data around that.

[00:20:40] I understand that's really hard, given maybe where you were sitting or what opportunities you might have had. But if you can find, let's say, four case studies or projects that you feel really strongly about, those would be the kind of things that I'm looking for as a hiring manager. I don't want to see some cookie-cutter thing that may be beautiful but doesn't really get into how you actually do real design work. Does that answer the question? Is that helpful?

[00:21:17] Host: Yeah. I love the impact approach as well, and what the underlying problem was, because maybe it's not the prettiest solution. Maybe you're B2B and there's a lot of data on the screen, but that's what was needed for that use case. The other one, just on the portfolio: how much should a person share about how much they did? Because I've seen so many portfolios, and my first question is, "Well, this is a big product. You didn't do everything." I'd love to know what exactly your role was and where you fit in. What's your advice on that?

[00:21:57] John: I agree, that's really hard, especially when you're working at an enterprise level. I think it's really important that people are up front about what their role was. A pretty standard case study template includes a line early on about what their role was on the team and what they were responsible for. And the thing that I'm looking for as a hiring manager is: you make that statement, "Okay, here's what my role was," and then you're telling the story and showing me where you had impact along the way. Obviously, if you're working at a bigger company, you're leveraging design systems, you're leveraging branding guidelines, you're leveraging all these resources to make that design. But the thinking and the process and the decisions are the part that I'm looking for, and that helps me understand how you think and how you work as a designer.

[00:22:58] Host: Would you advocate for putting in a few more iterations, rather than just "here was the problem, here's the solution"?

[00:23:03] John: I love seeing iterations. I love seeing what wasn't chosen and why. I think those are often more interesting than the actual final results.

[00:23:14] Host: Yeah, brilliant. I'm going to jump to the other one, because you mentioned not chasing up straight away on LinkedIn. You were saying it's not necessarily a negative, but it can be distracting. But as you said, and I've seen this as well, when we put up a job posting, it's instantly hundreds of applications. It's very hard. How do you try to stand out from the crowd? Do you have any suggestions on what people can do?

[00:23:48] John: I do think reaching out on LinkedIn or other networks isn't the wrong thing to do if you have a legitimate, honest question. I've done this in the past. If a hiring manager posts something, I will generally go down the path of applying, and then you can do a follow-up. I think it's how you approach the follow-up. It's not just, "Hey, look at me, I need your attention." It's engaging with them contextually. Maybe it's a deeper question about the job description, maybe it's a question about the company. I think there are other ways to reach out too: maybe using your network to talk to other designers who work at the company, not necessarily the hiring manager. There are ways of finding an angle without necessarily going straight to the gatekeeper for that attention. I fully understand, and I have fully done, the LinkedIn reach-out. But I do think it's the how, not the fact that you're doing it. It's really coming with some empathy, with "I understand the problem here, and let me ask a question that's actually meaningful."

[00:25:24] Host: Great. There are two examples I thought I would share that I saw done really well. Somebody reached out to my network and asked somebody else to contact me and give me a live reference. Unprompted, somebody from my network said, "This person's great. You should check them out." I thought that was good. And the second one: somebody was looking for a job, so they had time, and they said, "Look, I'll come in and work for one week with your team. I'm that excited to work on this. I know that's the best way I can show it." That put them at the top of the pile. I know it's not everybody's taste to give out free labor, but it was something to try to get them to the top of the queue. They'd been looking for months and decided they had to take drastic action, and that worked for them.

[00:26:14] John: I have done that as well. If a colleague knows that I have a connection on LinkedIn, I will actually reach out on the candidate's behalf, which is another way of going about it, and which also feels a little more helpful than self-aggrandizing.

[00:26:34] Host: Right. And I guess the last question that I have is around the final interview, your HQ day. What are you trying to get across? Do you have advice? Is it that you're trying to show agency, likability? Because at this point it's probably less about the skill sets and more about the personality.

[00:26:58] John: Yeah, there's definitely some personality at the HQ day. You're going to be in meetings with people you've never had any contact with, so there are a lot of variables. I think it's really about being open. There's this age-old thing that you're interviewing them too, and that's a real thing. You really want to be super aware of what those conversations look like. The way I try to run an HQ day is I want it to feel as much like the real job as possible.

[00:27:36] John: What I'm looking for in those conversations is: are they going to bring value? Are they going to be a collaborator? Are they going to be someone who listens and takes things in, as well as being helpful and part of the team? I'm generally not looking for someone to come in and blow my mind at that point. If I bring them to that stage, I have pretty high confidence that they will be good at the job, that they have the skills for the job. At that point we're checking for all the other stuff. I've already decided as a hiring manager that they are close and they are skilled. It is a lot of the intangibles at that point.

[00:28:26] Host: Brilliant. Well, that actually brings us to time. I just want to thank you once again, John, for sharing, and I hope everybody out there enjoyed it as much as I did.