— Blueprint | Herding Cats Edition

Linda Eliasen

Linda Eliasen is a renown product and visual designer, illustrator, creative director and writer.

HelpScout Alt


Toggl Plan:

I first heard about Linda when she quit Dropbox after burning out. Having worked in Mailchimp during its starting years and then transitioning to Dropbox, she seemed to be living the fabulous startup life in the booming Bay Area. Suddenly she realised something needs to change. I first heard about Linda when she quit. After a brief detour in UENO and UsTwo, she’s settling into her new role in HelpScout. We sat down in her home in Brooklyn to talk about leadership, imposter syndrome, burning out and what does it feel like to be in charge.


Toggl Plan:

What drew you to HelpScout?


They reached out to me and talked about being a remote company and I was just really intrigued by that. I didn’t really know what I was going to find when I talked to them. I didn’t know if it was going to turn out that the recruiting email I got was sent by a robot or if it was actually a real person on the other end. But as soon as I talked to them I felt they were just so kind, and wonderful. And they care so much about their product.

I can compare it to when I was at MailChimp in the very early days when there were only 50 or fewer people and everyone just had a very specific role, knowing what they wanted to accomplish. Everybody I spoke to there had that same grasp of their product and what they wanted to build. It was really refreshing and nice.

One thing that I really liked that my new boss said to me is that he’s hoping to keep me uncomfortable for as long as he can. I think that that’s an important place to keep your employees, especially us younger employees. We like to be challenged. We want to grow. We want to learn. We don’t like stagnancy. I think it’s really good to just give people a list of ways that they can improve. We want that. We need that.

I had been in agencies for the last year and a half. I really liked my time at UENO a lot but I was ready to focus in on one product again with one team because I really like that in-house vibe. I don’t want to say that it’s like a family because we have our own lives and our own families, but it does feel like a unified force working for the same thing.


Toggl Plan:

How do working in an agency and working in a tech company differ? What do you think?


Oh man, it’s so different working in an agency versus working in-house. When you’re working in-house, you have time to chew on your problems a little bit longer. Once you’ve done that you have the ability to test and to iterate. You’re not just working off in a silo and then handing it over and saying, “Okay, we’re done. We did it.”

—When you’re working in-house, you have time to chew on your problems a little bit longer.—

It’s a labor of love a little bit more so in an in-house place. In an agency environment oftentimes I felt like I was faking it, not in a super disingenuous way, but just in the way that you have to pitch to a new client and you have to spend a few weeks just getting to know everything about them, their competitors. You put all of this intense energy into a very small moment of that company’s existence and then you just have to say good-bye to that work or to the relationship if you don’t win the work.

It can be emotionally taxing for me I think. I really like to be able to spend time improving the things we’re working on and watching them grow.


Toggl Plan:

Do the leadership styles in those different fields differ also?


It depends on what company you’re in more than anything. Every company is just a different relationship.

I think that the agencies that I was at, they were very different from normal agencies. We still had structure. We had product managers and overall leaders who were driving the company’s force. But at the end of the day at an agency, your goal is to make money and to stay open. That means a lot of times taking on work that everyone isn’t that excited about necessarily. It’s all about trying to be a team player and to pull your weight and be there for each other even when all of you are not maybe super stoked about the work that you’re doing, which is a challenge.


Toggl Plan:

But to you, what is a good leader?


The leaders that I’ve had that are great, especially in an in-house situation, they care a lot about the users or whoever the people that we’re serving. We care a lot about them and they are putting the users’ needs first and have a clear vision for how they want to help those people. Because I think from there, then it just becomes this trickle-down effect to everybody who’s in the organization and figuring out how to give them a sense of purpose on that same mission.

The best leaders that I’ve worked for have just provided the most clarity I think in who we’re here to serve and how we’re going to do it. It’s kind of simple once you break it down like that, but they can give you a clear list of things that you need to work on to help with that mission. If you are missing pieces in your own toolbox, then they can tell you how to work on those things so that you can grow as an individual. My favorite bosses that I’ve had had a knack for doing that and for providing that kind of clarity.

Beyond that, there’s just so many things. I think that anybody who communicates really well and who’s very honest, and transparent, also tend to be able to find a way to get you to do your best work. I’ve had some horrible bosses who just say, “Make something awesome.” It’s this vague idea of awesomeness that you’re kind of working towards. But I think a good leader would say something like, “This is what awesomeness looks like and I’m going to empower you to get there and I’m also going to trust you do it the way that you see best fits.” To be given that kind of responsibility gives you pressure but in a good way, where you’re empowered to do it on your own.

—To be given that kind of responsibility gives you pressure but in a good way, where you’re empowered to do it on your own—


Toggl Plan:

But what do you think was your burnout to some extent due to bad management?




Toggl Plan:

If you can’t answer that, it’s okay.


No, it’s okay. I think it’s been long enough that I can answer it. Because honestly, at the time when I experienced burnout I was a designer. I wasn’t a leader at that company. I hadn’t had a leadership role yet in a company, so I think I didn’t have an ability to fully empathize with my managers and now that I have that experience, I can look back and empathize and say given the circumstances, I don’t know if I would have done a better job managing myself. Oh God. Those were dark times.

In the times I experienced burnout it was because of the lack of the things that I just told you about. It was a lack of a clear mission. I just felt like vaguely being told what to work on and when but there was no why involved. When things weren’t done quickly or to the expectations of other people, it was made very personal.

Oh God. Those were dark times.


Toggl Plan:

Yeah, I can imagine. I have my personal experience with burnout.




Toggl Plan:

As I think many women our age must have. It’s very easy to feel not good enough or feel the need to constantly prove yourself. I’ve always contemplated a bit whether or not my managers could have at least noticed that there might be a problem.


Looking back on the way I was acting back then, I do wish that I had more of an empathetic or sympathetic person in leadership. I think I was just showing all of the signs of burnout and of imposter syndrome. I was lacking confidence and I wasn’t doing my best work at the time by any means.

But it kind of created this downward spiral because I wasn’t given what felt like a safe space to talk about it or to be that person. Even when I tried speaking to HR, it was more like the company was trying to protect itself from any negativity that might come from me. It just caused this downward effect where it just gets worse and worse and worse until you don’t see any way out other than to leave and to spend some time by yourself.

—I wasn’t given what felt like a safe space to talk about it or to be that person.—

I think that women do especially have a hard time with that because the way that we work and the working model as it’s structured is set up for a male-dominant, patriarchal society. Women have only been in that world for a few decades and it’s only been the last couple of years that it’s been okay to start talking about these kinds of things. We still have a long way to go, but I feel it every day that people feel there’s something wrong with them, and so they must do all these things to fit in quickly or else.

I read some study not too long ago about the effects that stress has on women specifically. It turns out women are 30% more prone to have heart attacks due to stress - I mean I’m probably completely misquoting that, so by all means put something in the footnotes that clarify - but because of not just the ways that we work, but in our expectations of carrying emotional labor and doing other menial tasks around the office.


Toggl Plan:

What kind of leader are you based on your experience working mostly in a male-dominant tech field?


I’m still figuring it out to be honest. I still feel like a junior leader, learning how to do this.

So far the things that I’ve tried to do is just to get people to talk to each other a lot, to open up as many channels of communication as possible, and to make sure that if somebody’s work is struggling that they’re not just being left in the dark.

I don’t want people to do work that isn’t great and then say, “Okay, well, thanks for trying. We’ll have somebody else do it instead,” because I’ve had that happen to me in the past and it just feels awful.

Instead I’m opening up a critique channel, where I get them involved with other designers who might help them figure out how to solve those problems for themselves. Because I think that for example I’m very sensitive to people potentially feeling left in the dark or don’t know what they need to be working on or why. I’m working hard right now to just make sure that everybody understands exactly what they’re meant to do and how they’re adding value to the company.


Toggl Plan:

Is there something you’re nervous about starting work in a remote company?


Working remotely so far has been great. I have full control over my own world right now. I can just take care of things as they need to be dealt with and I can stop and have this conversation with you, which is great.

There’s a lot about it that’s really wonderful. But what worries me about it the most is the fact that in a studio you’re in the same environment as other people. That that’s how the culture is built and that’s how relationships are formed. When you’re in a remote environment, you have to almost fabricate those same experiences that you would have in an office environment.

—When you’re in a remote environment, you have to almost fabricate those same experiences that you would have in an office environment.—

I’m trying to figure out how to get people to have casual conversations as well as the important ones about design challenges and other things. I’ve been tackling it just by getting people to show what they’re working on in Slack regularly. Also setting clear expectations with the rest of the company that if they see something on Slack, that isn’t the best time to jump in and do a formal design critique. And that if they’d like to talk about something further, we should set up a different time to talk about that.

I’ve had a few little tiny bumps in the road already. For instance, one designer is in Australia, another designer is in Dublin. It’s 6 AM in Australia, it’s 7 PM in Dublin, so to get those two designers to share their work with each other, somebody’s going to have to come on early and somebody’s going to have to stay late. But you have to just say, “I’m sorry guys. This is just for today. Make up for the time as you need to.”

It’s definitely an interesting challenge. I can’t wait to see where I’m at six months from now.

Another really challenging thing about it though is working with junior level people. I don’t think it’s as possible to work with young and new designers, which is hard if you’re a person like me who really wants to mentor and keep that fresh energy around. Because sometimes I feel like my own taste gets old and I want to work around younger people. But it’s difficult to do that because you have to manage yourself, and you have to be a very open and honest communicator, and you have to be the kind of person who puts themselves out there. Those are the soft skills that you acquire after a few years of your career.


Toggl Plan:

As you’ve been in lots of different companies in very different stages, what does it take to maintain the culture when you grow?


Actually, I’ve just been reading this book called Powerful by Patty McCord.

It’s something that’s been driving me nuts probably since I was at Dropbox because culture is such a popular thing to talk about and it’s such a thing when you’re junior designer to feel like, “Oh, I’ll be great at discovering a good culture fit.” Everyone has their different definition for what a culture fit is. I’ve heard some companies describe it as a person you’d want to get a beer with or whatever. You’re rolling your eyes and you should be.

It’s taking me some time to figure it out. Because early days at MailChimp we had a really strong culture there, like incredibly strong. It was so wonderful. I would get together with our lawyer, and our IT guy, and somebody from frontend and we would all have game nights on Sunday nights. We were all very different. But we liked to be around each other.

I also, after I left, I ended up doing some freelance work for one of the people who ran the mobile department. He’s married and has twins. Him and I didn’t have anything personally in common. You would never see us at a bar together, but we still enjoyed that working relationship enough to carry it out after I left.

I don’t know how they did that because by the time I got to Dropbox, you’re just seeing lots of the same type of people. It’s not just a Dropbox problem. It’s like an all of Silicon Valley problem, where it’s a lot of dudes who are around the same age, who act pretty much the same. A lot of these people are friends of mine and I’m not saying that it’s all bad. It’s just how do we create that culture and keep hiring for it in a way where we’re creating an actually diverse environment..

—It’s just how do we create that culture and keep hiring for it in a way where we’re creating an actually diverse environment.—

This book that I read – can I actually read you what it said?


Toggl Plan:

Of course.


Okay, so she talked about how in Netflix they decided to continue hiring for the right culture fit. Instead of using the ‘would I grab a beer with them’ model, they wanted to hire people who had good judgment. To them, good judgment is ‘the ability to make good decisions in ambiguous conditions, to dig deeply into the causes of problems, and to think strategically, and to be able to articulate that thinking.’

That’s such a weird way to think about culture, but I think that it’s the perfect model to apply to every person from every walk of life and to say will I be able to enjoy working with this person. Are they going to have the communication skills necessary to work with anyone and to be able to articulate their points clearly when they are solving problems?

To me that is starting to make the most sense as far as finding the right culture fit. Because culture is starting to be a bullshit way to just hire more people who look like you. I think that we need to get as far away from that as possible.

At Help Scout we don’t offer referral bonuses for this specific point. Not to end up blowing up in a culture that feels clone-like. We don’t do that because we want people to actually find the right people for the job.


Toggl Plan:

What would you search for in a person when hiring and how would you test what Patty McCord mentioned while doing that?


It’s really hard. You have to have conversations with people about things that they’ve worked on. Like what I am interviewing designers, I have them show me a couple of projects that they care about. A lot of times I’ll say it doesn’t have to be related to the job that they do. Just have them break it down and see how well they’re able to do that.

—You have to have conversations with people about things that they’ve worked on.—

A lot of people find it very challenging to take something from beginning to end and to relate back to you in a way that feels almost like story or that anybody could understand it. That’s the first thing I look for, especially in a world where I’m going to have to be working asynchronously. I want to make sure they clearly have the ability to communicate their ideas to me.

Another thing that seems like a no-brainer, when you’re viewing somebody’s portfolio with them, just asking them why. Instead of, “Oh, how did you do that? That looks so cool,” or, “How does this work? Break it down for me,” to just take a step back and say why did you do this and why not this. If they have clearly informed thinking behind their answers, that’s always a good sign, especially if it’s around the users that they’re designing for.

Also, I tend to break down the barrier of I’m the interviewer and they’re being interviewed. I’ll just start to speak a little bit more casually and see if they can pick up on that, not that’s it’s a deal breaker if they don’t, but to see how easy it is for them to level with me like a human being.


Toggl Plan:

What do you think are the biggest mistakes you’ve made as a leader?


I feel like I haven’t been leading long enough to really know. I think I still have that imposter syndrome.

If anything, my biggest mistake has been that I make assumptions. I think that people who feel like they’re an imposter in some way, tend to make assumptions on what is needed of them or when to step in and when not to and to assume that you’re annoying somebody. All of these little things that we make up in our heads have nothing to do with the work and everything to do with our own insecurities.

—All of these little things that we make up in our heads have nothing to do with the work and everything to do with our own insecurities.—

I regret ever giving into that voice because it’s never productive. It’s always just there to annoy you and to keep you from being productive. That would be one of my biggest problems so far.


Toggl Plan:

What do you think is the single most important thing about leadership?

—One thing that a lot of leaders, especially if they’re in an ownership position,forget is that the level of responsibility they have over the product does not match everybody else’s; and it shouldn’t.—

I’ve been in some places where every single person on the team is expected to carry the responsibilities of that product as if it’s their baby, their whole life. I think that this is a problem that especially comes with early stage startups as they’re transitioning. When you’re starting out and there’s a few people in the room, you all have to have that personality and you have to care that much about what you’re making or else it’s just not going to happen.

As those companies transition into the 20s, 30s and beyond, you’re going to have to start hiring people who are there for their own career and for their own purposes, and for their own needs. I think that it can be really difficult for some leaders to let go of those expectations and to allow people the ability to work on things for their own-wise and to take a step back.

I’ve also been in a situation where I’m in a very big company and I’m trying to care that much about the product as if it was my own. If you’re doing that, on the other side of it, as the individual, you’re kind of buying yourself pain in a way. You don’t have all of the control and you don’t have the say at the end of the day for how things are going to go. Yeah, It’s a two-sided relationship. I would say that that’s probably one of the biggest mistakes that I’ve seen some leaders make.

Also, it’s knowing when to let go of certain people. That’s another thing that that book Powerful talks about, the people that are perfect for your company at a certain stage might not be perfect down the road.

That’s one thing that I’ve heard from my own bosses a lot when they’ve had to let people go, most often they say, “I should have done that a year ago or two years ago.” You care so much about them as individuals, you don’t want to hurt them in any way, so you keep them around. But I think it’s good to be honest with yourself and what the company needs and to I guess pull the trigger when the time is right.

—It’s good to be honest with yourself and what the company needs and to I guess pull the trigger when the time is right.—

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