A Beginner's Life

Coming Out Of The Desert

6 min read

A few years ago, it was the Wild West.

Everyone was fighting battles on multiple fronts. Engineering, Product, Marketing, Support, Design – each team was massively underwater, our resources strained beyond their limits daily. There was no time to breathe, because if we let off the gas pedal, we would lose. A lot of problems had to be “problems for another day” because they didn’t rise to the level of the largest current fire.

Slowly but surely, we are emerging from this era. As we bring new resources to bear, we are able to spend time on things we could have only dreamed about a few months or years ago. You’d think, with the immediate fear of extinction lifted, anxiety levels would be at an all-time low.

Not for me. This has been the scariest time I’ve encountered in my Wistia tenure.

In the past, projects were borne of necessity. We tackled the biggest fires and lowest hanging fruit, because there was so much of it to tackle. Systems were created and scaled only when, without them, the wheels would fall off the bus and we would fall into chaos.

Today, our to-do lists are increasingly self-determined. We can make the choices on what to focus on, instead of them coming from an obligation or a looming deadline. While support is still a constant need, for example, we are building headroom to make it possible for all to contribute to the company’s future along the lines of their personal passions.

For the first time, I am spending my time thinking, “what should we be working on?” Which is an exciting and scary question to ask.

We’re trying a number of things to make this transition as successful as possible (I’ll only comment on those that I influence personally).

We’re meeting more often. Or at least that’s the goal. I’ve historically found the concept of most meetings repulsive. I now admit that I couldn’t build a strong connection to my colleague’s work without them. There are also huge benefits to working out our biggest questions first in private sessions, where the more obvious (and therefore often overlooked) questions can be asked, and assumptions questioned, without the influence of large group thought.

As we’ve grown, there is also the new challenge of interpersonal relationships. “Rough edges” between teammates could once be solved by a single conversation. They are now such an inextricable web that they have no solution and require constant vigilance instead. These relationships, in particular, do not come naturally to me, and I’ve made it a goal to talk with everyone I work closely with at least once a week. This constant interaction will make it much easier for them to say “you know, something has been bothering me…” when it is necessary.

Transparency has risen to a primary goal. In the past, information traveled around on an as-needed basis. You know what we learned? This made people uncomfortable, and uncomfortable people are more likely to snipe, gossip, and criticize. They don’t feel empowered to participate directly, so they use other, less productive channels.

We’ve pursued processes that make the sharing of information and gathering of feedback easy. Instead of using active yet siloed tools like email, I’d suggest making access to information (and the process of giving feedback) democratic, yet passive. A Trello card and GitHub issue can be sought out and openly discussed, but can also be safely out-of-mind for those with less interest. Despite having more on-going projects across the company, it is easier to be informed than ever.

We’re challenging how it’s been done before. It has been an important time to examine critically how we do things, since we have new powers and opportunities that would never have entered the conversation a few years ago. Certain avenues were previously closed to us because of a lack of resources, and the danger is we’ll stick with what we know instead of branching out.

As an example, the concept of spending money is something I have to actively make part of my problem-solving repertoire. It’s great to be scrappy – but I am sometimes blind to a better solution staring me in the face, simply because it costs money money_with_wings.

Our new path, while a bit smoother than it was in the past, is not without pitfalls! Many of these are totally new to us, and are things that our limited size and scope helped us steer clear of in the past.

Losing connection with the customer experience. This one keeps me up at night. How do we avoid the all-to-common “ivory tower”, where our team size and resources growth insulate us from our customer’s feedback? How do we maintain a focus on building great product, instead of slipping into a quagmire of mediocrity?

This isn’t something that can ever be fully solved, but we can adopt values and practices that create strong connections with our incredible customers. All Hands Support, a practice we still religiously follow thanks to Mercer’s hard work, reminds us there are many customer problems to solve, and that focusing on the mundane can be more valuable to our customers than the shiny and new. Customer Storytime, a weekly lunchtime series Elise created, is an example of something that was there, valuable and staring us in the face, for years until a new member of the team stepped up and made it happen.

Spreading ourselves too thin. New team members bring new ideas and new passions, and audience growth has led to more opportunities than ever. As a result, we are being pulled in more directions. We have to be careful that the volume growth in projects doesn’t outpace the bandwidth we have for critical review – otherwise we could find ourselves working on projects that haven’t been properly thought out (I’m definitely guilty of that!).

Adopting a fear of failure. One sad refrain I’ve heard again and again, in slightly different form, is how success can breed a fear of failure. Our larger audience means when we fail, we fail bigger, which can be scary. It’s also possible to only work on the comfortable, which works…until it doesn’t.

Rituals like our Show and Tell, where work in progress and lessons learned can be shared openly by every member of the team, create a culture that is more accepting of feedback and failure. Our leadership also values learning, and the sharing of that learning, over short-term success. I’m really proud of our recent Top Hat Tuesday review. The shuttering of a content endeavour, and acceptance that we didn’t “kill it”, was tough but oh-so-necessary.

So here we are, still chugging along. We’ve found some amazing folks to join us, co-workers who are dedicated and awesome at what they do (by the way, you should too).

The Wild West is gone. But it’s been replaced with a new world with it’s own exciting challenges. I’m pumped to see how we navigate it.

P.S. Every week, I send out a short newsletter with links to my favorite articles. When I write a new essay, that will be included as well. Sign up to get your copy.