Brian Bailey Preface to the Revised Edition

You Might Enjoy Working Where I Work

I always chuckle when people conclude an announcement about their new job with “By the way, we’re hiring!”. It makes perfect sense, of course. We all want to work with people we know and we’re naturally feeling pretty great about the company we just joined.

But in the back of my mind, I’m thinking, “How do you know if you’re really going to love it there?” More importantly, “How do you know you’re going to stay?” It’s pretty common in the technology world to see another post about a year later, about another company, with another by the way.

That came to mind last week as we started recruiting for a developer position at Pingboard, the place I work. I’ve posted about jobs before and reached out to friends about them, but there’s only so much a link to a job posting can tell you. If I was on the other side of the link, there’s a lot more I’d want to know.

In February, I will have been at Pingboard for three years. When I’m trying to decide about a place to work, I look at four things: the problem, people, place, and practice. Here’s why I work at Pingboard and why you might enjoy it, too.

Problem

Pingboard is the place for everything you need to know about the people you work with. From the web and our mobile apps, everyone in the company has quick access to the org chart, contact info, who’s out sick or working remote, birthdays and anniversaries, and who knows Ruby or loves to bike. Why is it we can get any answer in seconds outside of work, but not at work? We believe that democratizing company information is the first step to being more effective and happier at work, and more connected to your coworkers.

It’s an interesting, challenging, and relatively unique problem to solve. It’s also one that companies think is worth paying for. We have a growing number of customers in diverse industries and locales. They are typically hiring rapidly and care deeply about their employees and their culture. They’ve reached the point where no one knows who’s who and who does what anymore.

We’ve made great progress (and many mistakes), and yet we feel like we’ve barely even started. There are so many ideas just waiting to be built.

People

Our team is still small. That means that everyone plays a significant part and each hire is taken very seriously.

My coworkers have many similarities in the things you’d like to be similar, and a lot of variety in everything else. They are smart, focused, encouraging, humble, friendly, and always willing to help. They’re also interesting, curious people with full lives outside of work - travelers, music lovers, gardeners, woodworkers, hockey players, dancers, and more.

Our co-founders bring a lot of experience and a history of success. With that comes maturity; we hire slowly, are cautious with money, and always maintain perspective. But they’re also willing to rethink anything. They know what they don’t know and relish asking questions and learning from others.

Along with that comes a commitment to transparency. Everyone in the company works with the same set of information, including revenue, expenses, metrics, and how much is in the bank. All questions are welcomed and answered.

Who you work with matters more than anything else. At Pingboard, I am constantly learning from my coworkers and enjoying their company.

Place

We have our own space in one of Austin’s best neighborhoods. It’s in a old house with hardwood floors and windows that actually open.

We’re surrounded by great restaurants, coffee, and eclectic food trailers. We do meetings walking through the neighborhood and at picnic tables outside our favorite coffee shop.

Everyone has the option of an adjustable desk and the equipment of their choice. We also have unlimited vacation and the freedom to work remotely when the mood strikes.

Our office is a unique, casual, slightly quirky place that quickly feels like home.

Practice

If you’re joining an engineering and product team, the way software is planned, developed, tested, and shipped matters a great deal. Here’s a brief overview of our process.

We practice Kanban, which encourages continuous flow, team ownership, and focus. We use Trello for project management to make it easy to know the state of each story (in progress, code review, testing, blocked, live), as well as potential problem areas (too many stories in progress or awaiting deployment.) All development stories go through code review and continuous integration tests must pass before they’re ready for human testing and review on staging.

Our 2-week cycles begin with a kickoff meeting on Monday and end the following Friday with a company-wide meeting where we demo (and celebrate) the work.

On Monday, Wednesday, and Friday, the whole team walks the Kanban board together. This meeting replaces the daily standup we’re all familiar with and, in our case, it’s been a massive improvement. We simply start at the right side of the board (stories awaiting release) and work our way backward. Every card is reviewed to make sure the status on the board is accurate, answer any questions about it, add checklist items as needed, and clear any blockers. The focus is on how can we work together to move stories across the finish line.

Walking the board is indicative of how we approach development and design in general. It’s a highly collaborative environment. Everyone is comfortable asking questions, spontaneous whiteboard sessions are the norm, and there’s little arrogance or argument. We’re all on the same page and share a common goal: to continually get better at how we work together (including improving what’s outlined above) and our respective skills, so that we can deliver an amazing product to our customers.

Growing the Team

Right now, we’re hiring a Senior Rails Developer and two sales positions. I wrote this thinking about the roles on the horizon, though. As we grow, there will be room for developers, designers, product managers, support and QA specialists, writers, and more (as well as Marketing, Operations, etc…). Each of these will play a big part in our future.

Over the past year, two great friends that I’d worked with previously joined our team. That turns out to be a fun and addictive experience. If you’re reading this, you’re likely a friend, too (and if not, we probably should be!). If you’re ever curious about the possibility of working at Pingboard, I’d love to talk (say hi on Twitter or email hi at brianbailey.me). It might lead to something right away or plant a seed for a year from now.

We all want work to work on problems that are challenging, rewarding, and interesting. We want to work alongside people we respect, enjoy, and learn from. We want to work in a great environment and look forward to the week. And we want to work somewhere that works smartly and doesn’t prioritize process over people.

We’ve done a lot of work over the past three years to make Pingboard that sort of place. There’s still plenty to fix and figure out, and I’m sure there always will be, and that’s part of the fun, too.

Maybe it’s the sort of place you’re looking for.

Horizontal and Vertical Communities

Communities take many different forms, but most can be classified as horizontal or vertical.

A vertical community is driven by aspiration, a mix of wish and ambition. There is a desire to emulate and embrace what the best of the community represent.

Vertical communities rely on celebrities at the top of the scale. Sometimes these are celebrities in the pop culture sense, but every community has a form of celebrity, the people who attract the lion’s share of interest. They are the reason most try a service and why they return.

Celebrities define success for the community and motivate those who aspire to achieve the same status. Vertical communities often have a score of sorts and a person’s status relative to others is fluid.

The heart of horizontal communities, on the other hand, is affinity. People are drawn by a sense of belonging and commonality. There’s an inexplicable feeling of being at home.

There aren’t superstars and followers, brands and audiences. Everyone is equal.

The aspiration of a horizontal community is for the community itself to grow and thrive. Success and sacrifice are shared, and status is a reflection of what the community has achieved, together. It might be a park restored, voices heard, legislation passed, or bringing something new into the world.

Though we experience horizontal communities regularly with our friends and neighbors, they are rare online. Something is missing. Nearly two years ago, I wrote a post on Svbtle to see if others felt the same way.

Since then, a strong, delightful community of kind and creative people has formed around this idea we call Uncommon in Common. I’m working with a few friends to build an online home for Uncommon. Meanwhile, the community itself has taken root. We’ve had gatherings, mailed postcards around the world, and shared meaningful, memorable stories via a weekly dispatch.

If you’re curious about slow, thoughtful, horizontal communities in a sea of real-time, vertical, social networks with insatiable needs for our attention, reach out or send me a note. There is much to be done.

Is There Anybody (Else) Out There?

Every few months, it seems a new, beautifully designed project launches featuring interviews and profiles of designers.

Cheers and high fives to anyone who pulls it off. Bringing something new into the world is a great thing.

I’m struck, though, by how many of these feature the same group of designers, people who speak and write in high profile venues and who have been profiled many times before. They, too, are wonderful people who have earned their success. Their stories, perspectives, and advice are very valuable.

But there are so many other voices out there. Designers are some of my favorite people. I’m amazed by (and envious of) their talent, but they are endlessly fascinating people, with a unique way of looking at things and wildly diverse interests. Even better, they are humble and honest about their craft and struggles.

We would all benefit from widening the circle of people who we hear from on the topics of art and design. So, I took 5 minutes and put together this list of people for the next project about the life and work of designers. All are delightful and worth hearing from. Plus, they will each tell you about 20 others you should talk to (and insist that they are less talented than all of them).

And Keegan Jones, just because there can never be too much Keegan Jones.

One Year Later

One year ago, my sister, Laura, passed way. Such a sad time that was, so much hurt and heartache at the loss of a uniquely wonderful person.

Trying to process it all that weekend, I wrote Saying Goodbye to a Sister. I included a link to a memorial fund, as her medical expenses had grown quite large.

And that’s when the Internet gave me one of life’s great gifts, the gift of slowly coloring the edges of a dark and painful experience with goodness and warmth. More and more, when I look back, I think of those things, good deeds in a weary world.

I’m grateful for people like Om and Semil, so genuine in their concern and offers of help. Someone posted a link to the post on Hacker News of all places, and next thing I knew, strangers were donating to the memorial fund. Friends gave beyond their means.

Daniel wrote “I’m placing Laura under People I’m Sad I Never Got The Pleasure of Knowing,” and others sent similar thoughts. She would’ve enjoyed their company and stories greatly. I wish I had shared her more in the present tense.

Then there is Anna, Nicki, and Clare, who in inexplicable ways, played the part of comforting sisters from great distance, with their care and thoughtful, encouraging words delivered at just the right moments.

I was reminded that week of the immense power of the Internet to knit people together from far off locations and divergent perspectives. It’s easy to forget that; I don’t think I will again. That potential, always there, but sometimes hard to find amidst the noise, is part of the inspiration for the Uncommon community.

I delivered a eulogy at Laura’s memorial service. It was largely based on the essay, but I added a coda that I’ve been thinking about as the anniversary approached.

We can learn from those that leave us early. I feel like we have to. Laura’s life was a constant reminder that there is another way to be.

The first reminder is this: Be present

Laura loved to spend time with people. She was never in a hurry to leave the table. She didn’t want moments with friends and loved ones to end.

The second is: Be kind

Laura loved everyone. She saw and respected each person’s value. She never judged others and couldn’t understand people who did. It broke her heart when people weren’t respectful of those who saw things differently.

The third is: Be who you are

In a world that tells us that nothing is enough, that we should never be satisfied with ourselves or our life, Laura found peace and happiness in who she was. Laura had dreams and she had regrets, but she also knew that she was, at that moment, who and where she should be.

And the final reminder is this: Be willing

When I think of my sister, she was, above all else, willing. Willing to try anything and go anywhere. Willing to love and willing to hurt. She was willing to change all of her plans at a moment’s notice and willing to be there for you no matter what. She was willing to be lost and willing to be found.

One of my favorites parts of the past year has been seeing Laura’s spirit and example, her kindness, presence, and willingness, where I might have missed it before. I saw it as Lisa left the states for an adventure in Berlin and when Radhika said yes to an invitation to travel from London to Austin to perform. I see it in Allison’s joy in life, Erin’s poetry and non-profit work for young women, and Wesley’s genuine love for people, conversation, and exploring new cities. And I see it now in my son’s college choices, each 1,800 miles or so away.

My great joy has been watching four friends who each live to travel, which my sister loved more than anything. People travel for a variety of reasons, but there’s a kind of travel that feeds your soul; travel that you’re incomplete without. I see that in the very different adventures Lora, Jennifer, Keegan, and Cassie have embarked on around the globe. I’m inspired by the possibility they see around every corner and their taste for the unknown. My sister’s life was defined by her six-month trip around the world with a girlfriend, and each update from Cassie’s current journey with her own friend makes me smile.

In the end, I’m thankful for friends. Thanks to everyone, so many I haven’t mentioned here, for your kindness. I only hope to live up to your examples when given the opportunity.

What Project Management Tools Are Missing

If you’re building an app or website, you’re likely using a tool to manage the process, such as Basecamp, Trello, Pivotal Tracker, GitHub Issues, or Sprintly. Some teams use a combination of these (one for big picture planning, one for specific tasks, for instance) and also incorporate more specific apps like InVision for design feedback.

Each of these has its own approach to tracking tasks and progress, sharing images and documents, and enabling discussion. Once you choose the best tool for your team and establish a workflow, you can turn your focus to building great products.

A few months later, it’s common to encounter increasing frustration with your choice and start to wonder if you made a mistake. Conversations start happening in other tools, a Google Doc becomes the de facto backlog, and people start adding work to the project tool after they’ve finished it. I’ve had this experience many times over the years, with a variety of products and team sizes.

In these moments, changing the tool is rarely the right decision. I’ve seen teams fall into a cycle of evaluating, choosing, trying, and discarding tools. We blame the tool for what are really team issues, dysfunctional processes, or simply a failure to be persistent and consistent in how we use it. More often than not, changing how we define features, discuss them, make decisions, and communicate is what’s required to improve things. The tool has only shined a light on something we’d rather not face.

That said, I’ve recently become convinced that it’s time for these tools to evolve. They do an excellent job of providing a centralized place for project tracking and discussion, but there’s been little innovation outside of increasing flexibility (for example, making it possible to group tasks in different ways).

There’s a missing piece. These tools are enabling discussion, but they’re not helping with decisions.

What needs my attention?

In a large project, conversations are spread across hundreds of tasks. One person may be responsible for a task, but the discussion is where decisions are being made: from defining the feature initially and finalizing copy to debating design and implementation details. Inboxes overflow with notifications about these conversations, but unless you respond in realtime, it’s very difficult to know where your attention is needed. Which update was just to keep me the loop, which is asking for my opinion, and which is waiting on my decision? Every comment is treated the same as every other comment.

What was the decision?

The result is that the only way to find the actual decision within a discussion is to read the discussion. Making it possible to revisit the reasoning behind a decision is a great thing; requiring that someone read through the debate about button color and placement to find the moment when an option was chosen is silly. Offering the ability to close a discussion or mark it resolved is of little use if the resolution isn’t clearly documented.

Whether the discussion is tied to a feature or page, or something smaller, it’s common to have multiple questions and answers in the conversation. Sorting through this is a time-consuming challenge. Are we waiting for someone else to vote? Which decisions have been made and which are still being debated?

The result is:

  • Time wasted going through every discussion and image or document someone was notified about to see if they need to comment
  • A lot of people chiming in, but little clarity on decisions
  • Too much notification noise, making it easy to miss critical updates
  • The true status of a task is hard to discern, as the complexity and outstanding issues are surfacing within the discussion

Smarter Tools

There are manual processes that help with each of these things. You might make sure that a story or task is small enough that lengthy discussion and multiple questions are unlikely. Anytime a decision is made in a thread, you could add special formatting and update the beginning of the topic, the story description, and/or the original spec.

But our tools should be smarter, too. Choosing who to notify on a comment is an example of a helpful bit of flexibility that does little to solve the underlying issue. It isn’t any more effective than it is with email threads; there’s no clear responsibility and people tend to err on the side of including anyone remotely involved.

A few ideas:

  • Add different comment types, such as Question, Answer, and Vote
  • If someone wants to quickly survey the team about something, provide a simple thumbs up/thumbs down interaction and vote tally, instead of the weight of 8 different +1 comments and notifications
  • Provide the ability to assign a question to someone within a discussion, while adding others who need to be aware
  • Require a summary when a question is marked closed or resolved, which is displayed next to the question, with the discussion hidden by default
  • Provide a dashboard view of discussions that are in progress, prioritizing those that are awaiting a decision, as well as ones that require a response from you

The next evolution of project tools might be found in one of the current offerings, a product already focused on team communication like Slack, or an entirely new app. Whichever it is, I can’t wait.

Note: This is just a start. There is much that could be done for product management generally, from improving the spec process to shepherding an idea through definition, writing, design, development, testing, releasing, and sharing. If you and your team have come up with clever solutions to these sorts of challenges, whether manual or technological, reach out on Twitter or by email. Also, if you work on a project tool and want to talk, I’d love to lend a hand.