April 23, 2020

Stephen Olmstead

Constantly learning, growing, and adapting… forever

April 23, 2020

I can't believe this happened — Stephen Olmstead from InVision took part in our design conversations

Stephen is a designer and researcher by background who is currently VP of Product Strategy at InVision App

As an early employee, he helped found and build out InVision’s core research, product management, partnerships, community engagement, and corporate development practices. He’s a saved sinner, husband, father of three and occasionally podcasts about design, faith, and life at


I currently oversee our design and product management teams for our Studio and Craft products. I’m a part of what some refer to internally as the InVision 'OG crew’. I started when we were about 30 employees. It's hard to believe that 4 years later we’ve grown to 700+ folks fully distributed around the globe.


I started at InVision as a product designer but quickly took on the role of ‘infrastructure builder’ within the company at our CEO’s request. I was blessed to have been given the opportunity and trust by senior leadership to build out several teams in rapid succession hot on the heels of our Series A and B rounds. I founded our original research, product management, customer experience, and partnership practices.


To be honest, I’m not A+ at any one thing, but I think I’m B+ in a fair amount. That sort of ‘degraded polymath’ mentality has enabled me to touch and shape a fair amount of the business over the years. I’ve really enjoyed mapping out unknown and complex areas for the business, putting into place connective structures/processes that make that unknown tangible, hiring people who are WAY better at a given area than myself, and then getting out of the way as quickly as possible so those far more skilled individuals can be successful.


My current role is a bit of a ‘circle of life’ moment for me as I’m now back in the product (where I got my start) working on leading development of tools that serve the community I love so much.

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It definitely can be tough at times, and the balance is never perfect (but that's life in general eh?). There are really two coping mechanisms here that I typically lean on:


  1. Аccepting that context switching is not a cost-free endeavour, but it IS a muscle that gets stronger over time
  2. Аcknowledging that building a product (and an organization) is not a solo endeavour, you live and die by the team no matter how strong an individual is.


With regards to the former: I once asked the founder of the agency I used to work for how he managed to keep his head straight when he had to manage so many separate arms of the business at the same time. I remember feeling panicked thinking about the load balancing feat that was required of him to keep the business not only operating but successful. I’ll paraphrase his response, he said: “Multitasking isn’t real. You can only do one thing well at any given moment. Micro-tasking, however, is VERY real and it's a muscle that you learn how to grow and build over time with orders of magnitude.” His point here, which always stuck with me, was that context shifting between tasks is often the most difficult thing for a person to accomplish effectively. You can grow that muscle and ability over time, but if you try to do too much, too early, you’ll crush yourself under an unbearable weight.

With regards to the latter (and mitigating that weight) — it's all about the team.

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There’s NOTHING that I do in my daily work that can be entirely attributed to me as a victory

think we live in a world where far too often individuals get lauded as if they did all the work themselves. In my experience, that's never the case when building products and growing a business. I’m 100% dependent on working in concert with my teammates to achieve the focus and forward motion we all need to drive towards success. By myself I fail; united with the team we do our best work.

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Our goal has always been to create the go-to design platform for teams and individuals building digital products. Our roadmap is informed by feedback from our community and our own real-world usage. We’re grateful that InVision has incredibly high penetration in the market today. That enables us to sit with, and observe teams and individuals of all shapes and sizes to regularly find out what parts of the workflow are optimal and which parts are ripe for improvement. We pick those areas of greatest opportunity and focus on how we can fix those problems. At the same time, we are constantly aware of the need to grow anything we tackle into a long-term sustainable part of our business model.


One of the unique value props that InVision has as a fully distributed organization is that we can literally recruit from anywhere in the world. It’s one of the most powerful advantages for us as an organization in finding the right people. I think it says a lot about a person when they value the location most that enable them to be present with family, friends, community, and culture over the location that allows them to lock in a job they love and that pays well. But in a distributed org you can have both- so that's super powerful.


In the early days, I played a much more active role ‘people vetting’. Thankfully today we have an excellent product recruiting team that does a lot of the heavy lifting here. We’re big fans of creating a space where we can work side by side with candidates who are considering a career at InVision. We frequently do paid projects as part of the hiring process based on real-world items we’re solving for. This gives us the ability to not only see how someone solves a problem but also how they work with a team in real-time.

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The number one thing we look for in candidates is a humble spirit

We believe as an org that none of us has ever arrived as masters of our craft- we’re all constantly learning, growing, and adapting… forever. There’s always something we can teach others and, in-turn, be taught. And all of us are going to make mistakes from time to time- that's okay, that's human. That parts of the process of evolving as individuals and as a group. And acknowledgement of that creates a sort of ‘common grace’ for everyone in the team to lean on each other, make mistakes, learn from them, and lock in on that central vision. We don’t always agree on everything, but we trust and support each other during healthy disagreements.

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Clear, consistent, and frequent communication is the key to success with a remote team. If you’re not updating your teammates regularly and engaging in a healthy, live feedback process, you’re effectively working in a vacuum. As a remote team, we live and die by our ability to communicate with one another effectively.

Team Communication

The digital tools we use most for communication and collaboration are Slack, Zoom, and InVision itself (dogfooding for the win!). As a general rule, we start with Slack as our most frequent form of communication. If something takes longer than a few sentences to explain or review in Slack we’re very quick to drop a ‘/zoom’ command in Slack and pull each other into ad-hoc video calls. As a remote org, the ad-hoc video call is our substitute for the ad-hoc in-person meeting. It works very much the same, but there are (in my opinion) healthier boundaries and expectations around these. It's expected that these calls will be short, respectful, and to the point. We use InVision itself to work collaboratively as a team. Most frequently this takes the form of asynchronous feedback on designs in InVision as comments or synchronously if we’re doing live reviews on early collaborations/redlines in Freehand.

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A big part of remote work is leaning into and embracing the diverge/converge way of doing work

We’ll typically allocate one part of the day for teamwork (convergence) and another part of the day for deep, personal focus work (divergence). My team, for example, has a pretty wide array of timezones reflected in it. I’m west coast US, but half of my team is European. This means that our convergence time works best during my mornings and their afternoons. Our divergence time works best for them during their mornings and my afternoons.


Surprisingly time zones are a lot less work to manage then many folks would think, especially if you subscribe to the value of the above model. I happen to be a big believer in it. I think we all need a protected space to do focused work based on earlier team input/feedback. There’s a certain rhythm to it that affords a hyper-productive cadence. Focus time is a frequent casualty of war in physical offices due to how easy it to ambush each other and interrupt the flow. I don’t miss that one bit.


Working with Design Trends

The great thing about building products for product designers is that they’re not shy about letting us know what they need! And we are always hungry for that feedback. We encourage everyone within the organization to be chatting with users regularly (we even have a program called ‘delicious empathy’ where InVision foots the bill for lunch/dinner with employees/users to facilitate this). In general, it's a pretty straightforward process to discern major trends based on a blend of user feedback, incoming support requests, and strategic business strategy conversations. Customer empathy is so incredibly key here: at the end of the day, it's about working with our customers to get them what they need to be most successful.


That being said, there is certainly further nuance to this equation. There are some product opportunities and trends that don’t readily float to the surface. This is where the ‘skate to where the puck is going’ analogy works well. Human beings are natural problem solvers. When we feel pain or some sort of lack in our lives, it's natural to generate solutions. These solutions are often made out of necessity from raw materials that are accessible, not optimized or with scale in mind. I often refer to these as ‘duct tape’ solutions.

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Duct tape solutions can frequently be prescriptive

They’re beautiful in that they capture the raw essence of guerrilla problem solving, but they’re rarely optimal in execution. In cases like this, it falls on our team to probe deeply to truly understand the base needs that need to be met. Once we understand those base needs we can back into the solution. Practically that looks less like: ‘Okay our customers want X, let's build that.’ and more like ‘The reason why our customer want X is because of Y. How do we solve for Y?' Its a subtle, but important reframing of the problem that seeks to eject prescriptive behaviour while empathizing with the core need. When we understand the core need we can channel our efforts effectively to design an optimal solution.

Hiring Process

I think domain knowledge is incredibly important. We are big fans of hiring a LOT of ‘crossover’ designers for this very reason; folks that started or have played the role of designer at some point in their career but are now making a disciplinary switch or have a desire to explore something new (that's what happened to me). I think that's super healthy for any organization. These contextual switchers bring with them the wealth of knowledge of a subject matter expert (SME). That industry prowess largely makes up for any greenness that they lack in their new chosen field of focus.


Now this obviously is not always possible or the case, so upleveling domain knowledge, not folks new to the industry (but who rock their respective discipline) is equally important as well.

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We have an internal training program we call ‘Xenia’ that is designed to introduce and educate everyone in the company to the finer points of our industry

Familiarity with the industry absolutely is a major plus for anyone going through the hiring process. I’d expect this to be the same for any other industry where the focus/disciplines are swapped. Example: When I was in the healthcare space I’d place more weight/confidence in hiring a designer who had familiarity with the nuances of the healthcare problem space or a similar space (like FinTech which is also highly regulated) than one who was totally new to it. There are, of course, totally reasonable exceptions to this which have to be accounted for on a case-by-case basis.


Our Xenia training is run by some excellent teammates here at InVision, this effort was spearheaded by the excellent Dennis Field whom I’ve had the privilege to work with for several years now (he also has a fantastic course on Skillshare that you might enjoy). Xenia covers everything a new employee needs to know. From how to get access to software/hardware you need to do your job, how to set up your employee perks (such as your monthly Cafe card, healthcare benefits, etc), introduction to slack channels, executive video meet-and-greets, as well as group exercises designed to lead you through learning and growing in maturity in using the tools we produce and make as an organization. It also contains significant sections designed to introduce folks to the community and to help folks understand and develop a sensitivity to working with our core audience and user base. It takes about a week to complete for all new employees.


4 Tips for Young Designers

  1. Build an authentic peer network you trust one small, selfless give at a time. The more you do right by people, the more those people will do right by you. Do good without expecting anything in return even when you’re busy, that reputation will open many paths naturally for you as you continue to grow. Many of those paths will be completely unexpected/unknown prior to doing that good, and yet those paths are often the most important to unlock.
  2. Being A+ at one specific skill is overrated. Being B+ or A- at lots of things lets you take on almost any problem. For goodness sake, don’t torture yourself pursuing A+ unless you’re one of the rare less than 1% of the population that can pull that off. Embrace your complementary skills and lean into that multi-talent nature. You’ll have to get creative with how you brand that, but ultimately you’re the sum of your strengths, you’re not defined by one single skill that you have in the workplace (and if you are, that's a precarious place to me in my opinion).
  3. Extremes are easy, balance is hard. Always strive for balance. Spoiler: you’ll never achieve it, but it's a worthy pursuit. Balance means making sure you are very clear about priorities. I’m a nerd. I have a ‘priorities matrix’ that is clipped to the office window that reminds me every day that Faith > Family > Health > Career is the order I’ve determined. I struggle daily to keep this prioritization but the pursuit of accountability is a good one to have. Find someone who will talk to you candidly when you ask them ‘What priorities do you see in my life? Does my walk match my talk?’. That person is invaluable. For me, that person is my wife. Keep them close and nurture that relationship always.
  4. Our greatest strengths are also our greatest weaknesses, be cognizant of the flipside of each. Some folks always see the glass half-full, others always half-empty. There’s always an underlying opposite truth to your strengths or weaknesses. Sit with that and come to grips with it. If you’re being overly pessimistic with yourself, you need to understand the strengths that you have and lean into those versus wallowing in what you think you can’t do. Conversely, if you’re overly confident, a dose of humility will go a long way when you realize the strength you often trumpet is most likely also your Achilles heel.

Advice for Product Makers

  1. At their core, great products provide an insane amount of utility while requiring the least amount of energy. If you can put one finger on the scale and see a mountain rise up on the other side, you’re onto something. Good products are powerful tools of augmentation; when you use them, you feel like you’ve been given a superpower. Summoning your first Uber, having your first FaceTime call with your family while travelling halfway across the world… these all feel a bit like stepping into Tony Stark’s Iron Man suit and taking it for a spin.
  2. The value prop of a great product is understandable at a glance. It is immediately cognitively digestible. I believe, in many ways, this has as much to do with knowing how to message the value of your product as it does with the way you build it. Many well-built products have fizzled simply because their builders didn’t know how to bullet point out the value for cognitive consumption by the market. Messaging, marketing, and understanding your target audience is so crucial to giving your brand new product the runway it needs to succeed.
  3. There is no replacement for an extreme passion and empathy for the market by the builders themselves. I’m convinced that if you’re not completely geeked out about the space you’re building for, you’ll never be able to tap into that ‘extra level deeper’ that all great products (and the brands behind them) inevitably possess. Maybe I’m a romantic, but I don’t think this can be faked… you either have it or you don’t. That level of passion shines brightly in your product. It shows in the attention detail, the love of craft, the way you interact with your audience, the compassion and sensitivity you show to meeting their needs. The best products are built by the makers that actually use and needed the product in the first place. They weren’t looking for a bright idea to market, they WERE the market. They evolved that passionate muse into a viable business that simultaneously let them scratch an itch while (hopefully) making money while doing it.


Books upon books have been written on this topic does a much better job than I can convey here. But those are some general guidelines I’ve found to be helpful over the years.