Learning to Let Things Break
Executive Design expert Emily Henlein shares how she advocates for ‘indirect actions’ to prioritize wellbeing and why future designers have a secure seat at the table.
“Oh man, I haven’t finished this project and I said it’d be ready by EOD.”
“Geez, I have 30+ Slack messages after taking the day off.”
“I really should step away and go for a walk, but I can probably just wrap this up first.”
This concept of the “ideal worker”, or someone who will put the needs of the business above all others (mostly personal and private) is a mentality that has plagued many of us, especially working from home. A looming need or anxiety to be a perfect worker 100% of the time is one of the primary reasons people experience burnout.
Emily Henlein (Executive General Manager of Design at Xero) built her career working at tech giants like Amazon and Microsoft, doing scrappy, nose-to-the-grindstone work daily. She’s experienced some intense, invigorating work environments, but it wasn’t until she moved into managerial and directorial roles that she understood the real meaning of work-life balance, and why telling people to take leave or walk it off doesn’t set the foundation for a healthy workplace.
Rather than these “direct actions” to prioritize well-being, she shares her lightbulb moment when discovering that a lot of the opportunities lie in “indirect actions” such as stepping out of a meeting you don’t need to be in or by actually letting a project slip (God forbid), to highlight a space where the process needs to be improved.
dscout: Could you talk us through how you got into this and how your path affects how you lead and grow a team and think about your work today?
Emily: I was actually on a path to becoming a lawyer. I had all my applications filled out and I was going to do environmental law—I literally had them all filled out on my bed. But then I went abroad to New Zealand and when I came back I decided that I was going to do something creative instead.
I can remember almost as clear as day walking on the Abel Tasman trail and saying, "I don't want to do law.” It turned out that a good friend of my husband's sister was running a design arts college in Christchurch, New Zealand. I ended up getting an accelerated degree in communication design and photography.
Later on, during the first dot-com boom, I saw that my friends from college were making six-figure salaries and I thought, "What the hell am I doing working at this interior design shop?" So I told my husband, let’s figure out a way to get back to the States.
A year later, we were living in Seattle, WA and starting to figure out what would be next. I took a job with a small boutique design firm in Pioneer Square and that was the beginning of my design journey.
It was during my master’s program at the University of Washington when the head of design from Amazon came to speak. Due to my type-A nature, I went right up to her after the meeting and was like, "I’d love to learn more about Amazon.” She gave me her email.
I sent her my resume and portfolios from design school and within a week she invited me to lunch and suggested that I interview for a role. I went to the Amazon headquarters, survived the rigorous interview process, and ended up landing an entry-level design job there.
Just over a year in, several of us got shoulder tapped to move into this startup inside the company. We were tasked with designing frontend experiences on the Amazon platform for companies like Marks and Spencer, NBA, and Diane Von Furstenberg. Turns out, looking back, this was actually the start of the AWS incubator.
A few years in, I decided I wanted to have kids, but the environment at the time was not conducive to starting a family—super long hours, high-stress days. This was a decision point for me in my career and I started looking for opportunities that would give me a better work-life balance.
I decided to shift to something new and ended up going over to Microsoft to work for MSN. It was there that I had one of my biggest learning moments. Coming from Amazon, I came in with a bit of arrogance that really showed itself in meetings. My boss at the time actually pulled me aside and said, "You're being a real ass in meetings. I need you to just stop talking and listen."
It was a really sobering moment because you’re in this mindset where you can do no wrong and had he not done that, I could have kept going on this self-fulfilling track, therefore missing the opportunity to learn how to be an effective and empathetic manager.
Though I had extremely valuable experiences there, I decided that I needed to take a break from corporate politics. My family and I went to India and we spent six weeks doing yoga training and Ayurvedic medicine. After I returned, I took a director position at Yellow Book, which became Yell UK. That's when I actually started to lean into what it meant to be a design leader.
This idea of workerism and the “ideal worker” is pervasive across industries. Is there something that you think about the creatives in design and user research that makes it particularly sinister?
Honestly, it's only really become obvious more recently because in previous gigs we had some amazingly flexible setups.
At Yell UK and at Sears Home Services, you could work from home and you only had to be in the office on certain days—which makes a big difference. The companies were ahead of their time. Back then, it was huge because you could go and exercise and spend time with your family, and you could easily work your schedule around your life.
I didn't really start to understand the reality of burnout and stress until later on in my career. There was one meeting where I actually had an aha moment, because the whole focus of the meeting was how do you prioritize wellbeing?
The realization came to me as I was listening to people speak about their experiences. It turns out, we’d been focusing on the obvious wellbeing tactics. By looking at it in a very obvious and straightforward way, like trying to put more breaks throughout the day, encourage more walking meanings and advocate for a day off a week, we were ignoring an opportunity to lean into the micro-moments where it’s the indirect actions you take each day that could create the real shift.
What are some indirect actions that affect wellbeing? For example, that feeling that you have to attend every meeting, even the ones that have over twenty people and where won’t actually add real value. Or, putting your hand up for something that you want to do, but don’t actually have the bandwidth to do?
When we start to focus on the indirect actions, we can start to understand how the things and events around us might play into what we bring to our work. For example, if I’ve just had a tense conversation with my child who is homeschooling, how will that affect the meeting I’m about to walk into and should I still even attend that meeting? So, maybe it’s best that I don’t attend.
Skipping that meeting or asking your team to shift around priorities to give you space to do things you want to do are indirect things that affect your wellbeing. But oftentimes they are harder to vocalize because they, at times, contradict the standard way of working.
You're not as cognizant of these opportunities because you’re ingrained to do it, which kind of comes back to the concept of the ideal worker. People do things because that's what they think that they should be doing. Why? Because that's what an ideal worker does.
Those are the habits that I feel we need to focus more on. I tell my organization, which is almost 180 people now: “Own your time and do what you need to do.” This language is important because it gives the person total autonomy.
I’ve missed meetings recently because I decided to go and do yoga and I was honest about it. And I really debated being honest about it, but then thought, “just say it.” I've tried to show up as a vulnerable leader in the system, but I do think there's that indirectness. Taking initiative to elevate these indirect actions that are affecting our wellbeing may actually spark more change in our colleagues.
As EGM, are you doing any coaching to ensure your team takes those indirect actions to prioritize their wellbeing?
To both myself and my direct reports (which are mostly GMs and head ofs) I'm very clear with them that you've got to get really crisp with your boundaries.
One indirect action that I’ve seen is designers picking up work that should typically be handled by their product peers. Whether it’s the creation of a roadmap or setting up the right discovery process, I often see folks step outside of their boundaries to just get it done vs. letting it break so that the right action can be taken to fix it.
Actions like these perpetuate a system where people focus more on getting the task done, even if it’s not their job instead of just letting things break. I've started to get pretty vocal around letting some of these structures fall apart when they’re not working.
The earlier you can identify that the structure needs to break, the sooner you can bring the change needed. Change is what most structures or situations need. But that's been one that's very tough for the tech industry mindset to embrace. It's not easy to see something broken and be like, "okay...let's just let it be broken."
When I say let things break, what I typically mean is with the process. For example, if you're working through the product process and there's an enormous amount of slack around a particular problem you're solving, or there seems to be way more meetings and a lot more people involved than need to be, then it may actually need to break to better identify where the problem is and short circuit the system to do things differently.
Product is a team sport. If things aren’t working, you have to figure out where the primary issue is. If you let it break, the group can then come together, address the issue, and change.
By doing this, we can react very quickly when we put something out that customers are unhappy with. For example, at Xero we do work for the small business and accounting world, we have to be really sensitive and empathetic to the fact that for an accountant or bookkeeper, they spend their full day in our software and have calculated their time for tasks to bill their clients.
So when we make tweaks to font sizes or where things appear on the page, that actually changes the way the data presents itself and it could have a significant impact on the customer’s workflow and time it takes them to complete a task.
For a small business owner, they don’t have the capacity or time to learn how to do something in a completely different way. We have to roll things out with an additional layer of customer sensitivity that isn’t nearly as common as major B2C companies.
In B2B, what we're working through now is how do we balance the future experience and those benefits, with the initial change difficulties our customers experience when we make adjustments.
There’s a lot of conversations about the ROI of design. From your experience, having scaled it in a variety of industries and org types, do you feel design has a seat at the table and how do you see it evolving for the future?
I was actually reading an article yesterday about how, with where the world is heading, design will need to be the centerpiece of problem solving.
Like whether it's climate change related, AI-related, getting water to a village, you name it—they're all design problems at their core. Of course, other functions like engineering are tackling them as well, but they’re interesting design problems at the heart of it.
At Xero, we’re very fortunate that design has quite an amazing seat at the table. All of the GMs of design sit on the product leadership teams of their respective product groups and are active and engaged members and partners.
We're building out a strategic design arm that's intentional, because we believe that design can be quite a powerful asset, especially at the start of a conversation. I think we're also lucky in that, at Xero, there's a lot of openness to try new things and do things in a different way.
However, when you examine a topic like burnout, I’ve noticed that people in different countries are in varying mental states depending on their experience during COVID-19. For example, when you talk to people in Melbourne, who have been in lockdown for 290+ days, they've actually got wellbeing and self-care fatigue. So, that's the other angle we need to dig into how to be creative when everyone’s in a different place mentally. And what does creativity look like in constrained or taxed environments and life feels busier than ever.
Another aspect that crops up with ideal workerism is this question of, “Well, do you feel this way because you’re just not doing what you love?” Thoughts on this?
That's actually a really interesting point and something we're doubling down on with my leadership team currently, because my latest questions are, "Do you have joy in your job?" “Are you thriving in the product group you're sitting in?”
We recently went through this exercise talking about the idea that joy and thriving are very different. I have joy in my job. I love the people. I love my peers. I love my team. I enjoy the problem-solving here, but are we thriving? I would say across the board, that was the piece of the puzzle that we are now trying to solve.
Xero sounds like a really unique, wonderful spot, and not every place is like that. Do you have any advice for an individual contributor somewhere who wants to start thriving instead of surviving but doesn’t know how to advocate for themself? "
Be mindful of the percentage of energy you're putting into your job, and if you need to work at a reduced percentage for a finite time, then work at that pace.
The reason I like this idea is because in and of itself it’s still a form of work. However, instead of dedicating all of your energy reserves to your job, you’re safeguarding some for your own wellbeing when it matters. More importantly, because it matters.
I think we often fall into the trap of short changing ourselves on what this personal advocacy looks like. For example, it’s not as simple as making a rule for tools down early on Friday or taking a walk. We need to go deeper. Tactics that have worked for me include insisting folks look for ways to put two-hour breaks in their day, and in fact, I recommend this over the pockets of 30-minute-breaks that never really allow you to find your flow or truly step away if that’s what you need to do. Or do something totally unrelated to work— read a book, go for a walk, just sit and breathe.
Taking a break from the grind of your job can shift your perspective in more powerful ways than using the free time to work on another task in your to-do list. Sure, crossing a thing off your to-do list can be quite satisfying, but it’s likely not bringing you the real shift you need.
While we’re all adults here, it’s not really easy or effective to just tell folks what to do—are you exercising? What about doing yoga on your next break? Maybe sign up for an online class? The suggestions are all well-intended, but they’re not actually working. It's like there's another lever that has to be pulled and that was my ‘aha’ moment in direct vs. indirect actions. Change the taxing habits you’ve formed doing your job. Evolve those. Then, I think you'll start to see real change.
As you start to shift these habits, it may feel like you’re not working as hard or as intensely as you were previously. It might mean that you’re not going to answer every Slack as soon as it comes in. Instead, you might turn Slack off until the end of the day or attend fewer meetings. The goal is to change the activities in your day-to-day that cause the stress and then pay attention to how it affects you.
As you start to ask for the space you need, another issue that ends up happening is that the hamster wheels start spinning in your head. That anxiety rises and you're like, "Oh no, I'm not doing enough."
There's something cognitive that needs to shift in our system. No one needs to know you're working differently today. No one actually needs to know how you get your work done, we need to create a system where you can own that you’re chilling out a bit today, doing what you need vs. the “I need to be doing it all” mindset that often persists.
I often tell folks to ask for what they need. I think that’s actually resonated quite well with the team because it puts the onus on them versus management telling them what they think is right. I can't quite put my finger on it, but the individual has to own it. They need to own their time and then feel empowered to do what they want with it.
Stevie Watts is the Content Strategist at dscout. She enjoys telling compelling user research stories, growing social channels, and exploring all things video production. As a newer Chicagoan, you'll likely find her at a concert or walking her corgi, but undoubtedly heads down looking at Google Maps.
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