My guest today is design executive Kim Lenox. Kim is Vice President of Product Design at Zendesk. In her 20+ year career, she’s also led design teams at top global organizations such as LinkedIn and HP. In this episode, we talk about the difference between management and control, leading geographically dispersed teams, and taking handwritten notes on digital devices.Listen to the full conversation
Jorge: Kim, welcome to the show. Can you tell us about yourself?
Kim: I am leading a product design team at a company called Zendesk and we create software for customer support companies. Companies that use customer support software, and I got into this particular role about a year ago, but I have been working in software product design for over 20 plus years.
Jorge: We’ve been friends for a while and I’ve been following your career as you’ve moved up to higher levels of responsibility in your career path, and I’m very intrigued on how someone who is leading teams of designers in organizations, how you go about managing your information and making… helping make it make sense to you.
Kim: Yeah. I think it actually starts way back when I was a child. My home environment was rather chaotic growing up and I found that I was… in order to handle that chaos, I was organized, I was structured even as a child and I would be able to kind of maintain the calm by having things organized, and I wasn’t a messy child, I wasn’t a rebellious child. I was a “getting things done” child which sounds kind of strange, but that… when I hit my college years, I found that I was the one managing the photography lab, managing the gallery, always taking leadership roles, and I thought that that was because I was good at it and it actually was because I wanted to control things because as a child I didn’t have a lot of control over things, and so what I found in my first software design or software company role, I was a international product manager, and so there’s a lot of control there, right, you’re managing the schedules, you’re managing the features, and so I found that I leaned more towards controlling type of work.
Again, I wasn’t necessarily very good at it in the beginning because I took the approach of kind of command and control, which is not how you motivate people, which is not how you get things done, but I can thread back the leadership all the way to my childhood.
Jorge: Well it’s fascinating. I was going to ask you about this difference between managing and control. Can you elaborate on that?
Kim: Yeah, that’s interesting. There is no control, I have learned and it is… for me now it’s more about paying attention to the right things at the right time and letting the other things go. There’s so much information when you think about social media, when you think about the news. I find that I will have media diets where… especially when I was pregnant, I didn’t want to know what was going on in the world because I was so emotional with who’s growing beings in me that I needed to protect my emotional state, and so I find that that plays into how much information I have day to day is really about what is the right thing that I need to know right now and planning for the future, but not trying to consume it all. I have to be very selective.
Jorge: What I hear you describe is setting up the conditions that allow for things to evolve in a desired direction as opposed to try to force them somehow.
Kim: Yeah, that’s a good observation. Yeah.
Jorge: I’m also hearing that focus is a very important part of that, and I’m wondering, in this time when we are exposed to things like social media and the news and the influence that that has in our lives and we have some degree of agency on how much we do that, right, like we can say, well, I’m leaving Facebook or whatever, but I’m curious how that plays out at work. Like how do you determine what to pay attention to and what not to?
Kim: Yeah. Throughout the different companies that I’ve worked at, I found that having a shared understanding of what our goals are, not just my team’s goals, but the goals of my partners. Once we have that in mind, we can think about things in a long term, this is the vision, this is where we’re all headed together, and then here’s the near term things that we’re going to do and here’s the short term things that we’re going to do and then being in agreement and then we all head in that same direction, and then being able to do check ins with each other to make sure that we are still aligned as new information comes about, maybe we had a plan and the technology stack won’t allow that or we want to accelerate something that we can’t achieve on our own, and so how do we mitigate that.
I think it’s really about… the focus is really about finding alignment first and then reminding each other continuously of, this is what we said we are going to do, are we still in agreement that this is what we’re going to do? Okay, let’s pawl ahead.
Jorge: As a leader, I know that you are dealing with teams that are all over the world, right, and I’m wondering about when you say finding alignment, that requires communication, right, and it requires getting everyone to understand what the vision is so that you can all move forward in alignment. I’m wondering about communication styles… interpersonal communication styles, and getting alignment especially with folks who are remote. How that works.
Kim: Yeah. Where I am now at Zendesk, I have eight offices around the globe, only two are in the US and so it’s seven different countries, so there are a lot of cultural differences as well as just differences in work styles and… so it’s all very different, and so what I try to do is adapt my style to the group that I’m working with. I think that helps to find empathy for one another and recognize that we are different and that we communicate differently and try to understand how we communicate and what our communication styles are that I think setting that precedent is really important, and then the tools that we use, we rely heavily on virtual tools.
Zoom, Slack, Google Docs, and the expectation of my team and most of the other teams at Zendesk that I’m aware of, all the ones that I’m aware of, require you to have a core business hours and be flexible in your time to maybe have an early morning call or a late evening call, but those are the exceptions, and so we function in an asynchronous manner, and so I will post something perhaps on a Sunday night in preparation for my staff who’s in Melbourne and Copenhagen, my managers are there, and by the time I wake up they have responded and then the rest of North America and other areas will respond, and by maybe Tuesday morning we will have a solution together.
From Sunday night to Tuesday, we’re not… if we’re all in the same room we could solve this quite quickly, until we allow for that time to make decisions and there’s no stress, there’s no pressure. If there’s something really critical, I will WhatsApp somebody or they will WhatsApp me especially if there’s a travel engagement and something didn’t get approved and they are heading to the airport, of course, reach out to me at a crazy hour, that’s completely acceptable.
Generally we let people work in their business hours, which I think is really important. As far as the communication, we have an annual get together, an offsite where all of the designers, all of the researchers, front end engineers that are on my team, content strategist, we all get together and we spend time together. We have meals together, we do workshop ideas together, and that’s something that culturally Zendesk has encouraged since before I arrived, and so it’s really important to be able to break bread and get to know one another so that when you are in those asynchronous communications and you’re not necessarily having a voice conversation where you can refer intonation and you can infer what somebody is meaning through their voice or through their body language on Zoom, you don’t necessarily see that in Slack. Emojis help, but it’s not necessarily enough.
Knowing people well enough to know when they’re joking or know when they’re upset is really important, and that happens because we actually spend time together.
Jorge: I remember reading this book called, The Year Without Pants by Scott Berkun. It’s a great title and it’s about a year that he spent working for Automattic, the company that makes WordPress, and they’re a fully distributed company. I think they don’t even have a headquarters anymore.
Jorge: They do the same thing, or they did when that book was being written, and I remember him saying that they pick an exotic location every year for the team to meet at, to like to…. like entice them, and for much of the same reasons, right, like this idea that you get a better sense for who people are by interacting with them in a physical space as opposed to something like Slack.
Jorge: That goes a long way to helping build alignment. I would expect… one challenge that a lot of folks have is keeping track of commitments, so the things that you have committed to or that other people have committed to you, and I’m wondering if that’s something that is kind of top of mind for you and if so how you manage that?
Kim: Yeah, in the work context we have program managers, we have design operations folks and we have annual planning, quarterly planning, we have all of the design work in JIRA because that’s something that our engineering counterparts have, and so we can just… they can scoop up our work and bring it into their roadmaps and it has a natural flow to it, and so I can see from my leadership team what’s happening on all of their teams.
When we have…. occasionally we’ll have somebody… one of our product partners that needs something that was unexpected and we can look at what everyone is working on and be able to say, oh, this person is rolling off of this particular project in another week or so, we can now move them to this urgent matters for just a few weeks. We generally will allow the designers to… because they’re in their isolated location, we will have them paired with their engineering product partners in those locations, but occasionally we do have something where a project comes up that doesn’t have an eng… it doesn’t have a designer assigned to them and the design work still needs to get done. We’ve had somebody in Montpellier doing work for the Copenhagen team or we’ve had the San Francisco team helping the Dublin team and that is enabled to happen because we are tracking who’s working on what.
Jorge: That’s great. One of the challenges that I have seen folks deal with in those systems is that… in systems like the one that you’re describing is that some folks are more proactive about updating their status and updating projects, and I’m wondering if that is a challenge that you’ve encountered and if so if you have found ways of getting the information that gets put into those things to become consistently useful.
Kim: Yeah, for Zendesk when I arrived a little more than a year ago, they weren’t doing the tracking. They were assigning a designer to a product manager and they were working in… they’re isolated products, but we announced the product suite called the Suite, which is a collection of products, and so we’ve been doing a lot of product integrations since the announcement. It’s been a year now since the Suite came out, so now we are really required to work in the same design space and work on the same scrum teams and do a lot more alignment, and so because of that, I introduced JIRA last year and the team has been evolving it over time, and at first there was some resistance and then I tried to explain that we can be more adaptable when we have staff members who are stalled on a project, we can keep them busy with something interesting somewhere else on the team, but if we don’t know that they’re stalled, if we’re not visually being able to see that, then it’s hard to know.
Now they are doing regular quarterly planning and we’re able to really see what’s going on, and most of the management piece of it that you were describing is done by my direct reports, the managers that are leading the teams, and so that makes I think it easier for the designers who don’t necessarily want to work in it, but some of the designers are very organized and structured and prefer to track things and others are less so, and so again, it’s about adapting your style to that person’s style to see what works for them and what works for you.
Jorge: I’m thinking back to the opening part of our conversation where you talked about this drive you had when you were little to organize things, and it sounds like, man, this sounds so organized. It sounds fabulous, but you’ve been describing so far the operation of your team and that is one relationship or one set of relationships that you have to deal with at work. Call it like the folks who, kind of report in to you, and I’m wondering if and how the systems vary with your communications to the folks that you report to, so your stakeholders, the people who are kind of up the organizational ladder from you.
Kim: Yeah. The communication usually comes through program management. They will have our corporate top five initiatives that they track regularly, and so those… that information gets reported I think weekly statuses and within those are the design work that’s being achieved or blocked or whatever might be happening, and it’s a typical program management email that has a green check mark for something going well, a triangle that’s yellow if there’s some concerns and then a red x box, if there’s like this is a problem, and so for the executive team they can quickly skim and see that, okay, what we said we were going to do, everything’s on plan or oh this thing has a triangle, what’s going on here? Oh there was a delay with some technology. There was a delay with… we didn’t hire somebody fast enough perhaps, and so you can get kind of a visual of that.
The design leadership team is able to see quite frequently regular design work that’s in progress, and then we have regular check-ins which are specifically on the direction of the overall program, so in those design critiques we see little bits of information, a snapshot of a current project, but on a… probably a quarterly basis we see the bigger programs and those bigger programs are where my chief creative officer is attending and he’s able to see what’s happening, and then I also meet with him weekly. I meet with the global head of design weekly, and I also have monthly and bimonthly and quarterly meetings with the engineering execs and the heads of product and all of those things. I have a full calendar of one-on-ones to make sure that what my team is doing is meeting the expectations of my partners.
Jorge: If I were to summarize what I’m hearing from you, it would be that it’s essential to tailor the means of communication and the places where that communication happens to the needs of the audience who you, or the interlocutors who you will be communicating with, right? So you interact differently with the folks who report to you than you do with your stakeholders around the world base, and set up the conditions so that that works.
Kim: Yeah, and my peers in product… the product executives, the engineering executives, we meet twice a year and we’ll do planning and strategic alignment and we’re always looking at what’s happening in the competitive landscape and how we need to adapt and how our… what our plans were and how we’re actually building up to that plan. Are we actually meeting those expectations or do we need to pivot in some way?
Jorge: So it’s about visibility and accountability.
Kim: Also, I think really critical is just finding alignment, making sure that we are all in alignment. The company Zendesk was founded by three Danish founders, and the Danish culture is very consensus driven, and so we spent a lot of time in building relationships and having conversations around our shared vision, so it’s not a top-down mandate. It’s really about it coming from all directions and great ideas. It comes from every direction, it’s really about us making sure that we’re aligned, and that comes through conversation.
Jorge: That’s great. Like if I were to draw a little diagram of it, sounds to me like there are at least two dimensions here to the form that the information environments take. One dimension is who you’re communicating to within the levels of the organization, right, so whether it’s folks in your team or whether it’s stakeholders and the other dimension has to do with culture. This idea that you’re bringing up that some organizations because of contingent reasons like the culture of origin of the founders or whatever have particular cultures that lead to different styles of communication.
Kim: Yeah, absolutely.
Jorge: Before we started recording we were kind of joking around and talking about how we had just seen our respective set of kids off to school, right?
Kim: Mm-hmm (affirmative).
Jorge: One of the things that I’m always interested in is how we take these things that we learn at work about managing our information and apply them to our personal lives and things like dealings with our families, the folks that we live with, our friends, et cetera. Have you taken any of the things that you’ve learned in your career managing folks in organizations and applied them to your personal life in some way?
Kim: I suppose I have, but I know that I use some of the software tools. I was using OneNote for a while at work and I’m still using it as a home based to do list. I was using Trello for a while for work and I also had a Trello board for personal things as well. I definitely try different software, and I’m not answering your question yet, but I just recently got an iPad Pro so it has the stylus and I’m taking notes for work on that now because what I was finding is… first of all I have to write my notes.
I have a lot of memory recall when I am writing conversations down, and it’s really a visceral, very important part of my work style, and what I was finding was on paper, I wasn’t… every three months I would change notebooks, and so I would walk around with two notebooks because most of the things that I’m doing don’t get done in three months, and even if it’s the end of the month and you start a new month you still have to reference back, so I got this iPad to be able to help my work style, and so that’s my latest tool.
It’s not Trello, it’s not OneNote, it’s this new thing of taking notes, and I’m finding it very useful because I will have a conversation with someone and they will say, “Oh, what’s going on with this particular project?” And then I say, “Hold on, let me look.” And I can reference back to the conversation that I had with another stakeholder, and I’ve got my notes there. There’s still a few little glitches that I want to be able to have check-boxes and check things off the to do list, but it doesn’t actually… I can’t do a search for a checkbox and I can’t do a search for a checkbox that has completed, so I’ve got some ideas for the software company that worked on them, but to your question about what things in my work life have I brought into home life, I-
Jorge: Or vice versa, right, I made it by… It might go the other as well.
Kim: Yeah, I think it is a blend. I can’t say that I necessarily have certain things that I’ve brought into the home life, but there are things that are… the way our family functions is definitely to accommodate my role as the VP of product design. My husband became a stay at home dad when the twins were one and now they’re nine and a half, and so he’s going on quite a few years of being a stay at home dad, and that has really enabled me to take on these additional levels of leadership as my career has grown, and I could not do this role without having a stay at home dad. Absolutely not.
When something comes up and I need to hop on a plane or I need to stay late or whatever might come up, I know that I don’t have to juggle his career as well. We don’t have to worry about hiring people outside that might change their career paths and leave us. He’s a fixed, very important person that can help me succeed and help the family succeed, so that’s been really important for us, and I can hop on a plane in a moment’s notice and he’s got it. He can take care of things.
Jorge: Well that’s great. I want to come back to something you said just because I’m also an iPad Pro note taking nerd and I’m curious as to what app you’re using for your notes on the iPad.
Kim: Yes. Well, based on my Facebook requests that you responded to, I ended up getting… there was a couple of different ones. One was GoodNotes and the other was Notability and I ended up buying Notability first and so that’s the one that I’m still using, but I kind of like some of the different templates that good notes have, but I haven’t been able to play around with it yet. I want to… what I found worked for me with the iPad Pro is I bought it before I went on vacation and so I could try it out without having to really listen to somebody, I could just test it out and so I got Notability first and so far that’s been working pretty well. I’m not a fancy sketch noter by any means.
I envy the folks that do that, but I have found that I’m able to reference back to sketches that I do and have a conversation face to face and be drawing together with someone, and then later on, say I’m sketching with a designer and then later on I meet with their manager and I say, “Oh, this is what we talked about.” And we can reference back to that. I can do that on paper too, but this seems a little easier and I’m having some of my direct reports ask me to send my notes to them, and so they say, “Hey, can you send that?” And I can just turn it into a pdf and send them whatever I’ve jotted down.
I want to get to a point where I don’t have my MacBook anymore. I want to use just the iPad Pro, but what I’ve found is that in a Zoom context, I can’t necessarily put up a video and be sketching at the same time, and so I still need to have my laptop, but my laptop is turning into more of a Zoom device and there are a few things in the iPad, Google calendar that I can only do on my Mac and the other device, and sometimes I cannot share my screen when I’m at the offices, share the screen onto the conference monitor. That’s more of a technical thing than I need to talk to IT about, but overall I’ve been really pleased with it.
I do find that when I’m meeting with somebody in a video, which is frequent, I feel the need to let them know that… I show them my iPad, and I say, “Hey, I’m taking notes, so if you see that I’m looking down, it’s actually me referencing the notes.” And I didn’t actually tell people that when I was writing on paper, and I think it’s because I’m a little more enamored by the technology. As I’m writing I can see that I’ve… they’ll add some more color to something and I’ll try to squeeze some words in and so my notes are quite messy, but now I can actually select that text and move it and then make room for the new stuff, and so as people are talking, I’m selecting stuff and moving it around and laying out my page basically that I ordinarily couldn’t do on paper, and so I’m finding that I am looking down more.
I need to do a little retro with my staff and see if how annoying that is or if it’s actually noticeable or not, because when I was on paper, I was always… I can look at somebody and take notes on paper without looking at my notes, but on the iPad I’m looking down more often.
Jorge: Well, Kim, this has been really fabulous. If folks want to follow up with you, where should they go?
Kim: I am on Twitter, uxKim, K-I-M and LinkedIn. Those are… You can go to the Zendesk design blog page as well. I think it’s design.zendesk.com and, yeah, that’s pretty much it.
Jorge: Well, fabulous. It’s been wonderful having you here. Thank you for your time.
Kim: Yeah, thank you so much, it’s been great chatting with you.