Brian Bailey Preface to the Revised Edition

On Board

Next month, I’m thrilled to join Pingboard, a new Austin startup.

Pingboard sets out to solve one of the core problems faced by small and medium size companies: how to add, update, organize, and harness employee data. The problem looks like disparate Google spreadsheets and a hodgepodge of information silos; the result is overworked studio managers and disconnected employees.

I’ve had the privilege of working on interesting products during my time at Gowalla and, more recently, Return Path. My focus has been on consumer apps, but I’ve long been fascinated by products that solve problems for people at work. Watching and learning from great services like Intercom, Sifter, Basecamp, Asana, Slack, and Editorially is an ongoing pastime. As a product manager, I’m eager for the challenge of creating tools that make the hours we spend at work easier, more productive, and when possible, more enjoyable. I’m grateful for the chance to join this talented, thoughtful team building a great product and company in my favorite city.

If Pingboard might solve problems your company is currently facing, let us know and we’ll follow up with you. We’re currently running pilot programs with a few companies, but will be opening things up soon enough. This is just the first step forward.

I’d love to learn from you, too. Office managers who craft a thriving, productive culture out of chaos deserve great products that put them first. Startups and growing companies deserve solutions without the baggage that typically comes with “business software.” How can Pingboard made your work and your company better? Drop me a note and let’s talk.

Read more about the vision behind Pingboard in this post from Bill Boebel, Founder and CEO.

P.S. For those of you who know me through Uncommon, there is much in the works as we continue to reimagine online community together. See you on the front porch.

Meetings Shouldn't Be Free

If a company’s most valuable asset is the time and talent of its employees, why is it easy to schedule lengthy meetings with multiple participants? Increasing the cost and effort involved in arranging meetings would make them rarer and more valuable.

Though meetings are often necessary and productive, they can become the default response to uncertainty. If there are questions or unknowns and the next step isn’t clear, a meeting is organized with everyone who has a stake in the decision or might contribute to the conversation.

The problems with meetings are well known. They are typically longer and include more people than needed. The decision making process is sometimes made more difficult, not less. Also, meetings interrupt work and focus, meaning the time before and after what’s blocked out on the calendar is negatively affected as well.

What if there was a cost associated with each meeting? Imagine if a 30-minute meeting with three people cost $50, and each additional person was $10. Adding 30 minutes doubles the cost. So, an hour meeting with four people would be $120.

The amount itself doesn’t matter. The currency doesn’t even have to be dollars. The key is that each team (or possibly individual) in the company has a quarterly balance to pull from, a balance that covers a minimal number of meetings.

If sending out a meeting invitation reduced a finite resource (and it does, this just makes it explicit), there would be second thoughts about whether this specific meeting was worth it. Maybe the meeting could be limited to 30 minutes if the topics were sent out beforehand. Perhaps only four people are required, not six. Maybe the question could be summed up in a succinct email instead.

This assumes that the cost is associated with arranging the meeting, but it would be interesting if there was a cost for attending as well. “Sorry I had to decline your meeting request, but I only have two left for the quarter and I’m saving them.”

There would need to be company-wide visibility into the meetings taking place (a good thing in its own right) and a great incentive to not go over, anything from rewards for success to actual budget impact on the negative side.

The result would be fewer, better meetings, insight into the number and cost of meetings across the company, and people thinking through which ones are truly worth it.

Picking Up Where You Left Off

A challenge in any side project is the limited amount of time you can dedicate to it. Evenings and weekend are always shorter than you wish they were, and that time is usually already filled with friends and family, errands and excursions, and the rare break from our tools of choice.

The small and inconsistent amount of time itself isn’t the primary challenge, though. It’s how that breaks your flow and momentum. Whatever the side project is—a novel, piece of furniture, open source project, app, travel journal, garden, or website—when you find a free moment to work on it, the first thought is, “Now, where was I?”

Day jobs are great at maintaining that context hour after hour, week after week. Everything is familiar and the thread between what you worked on yesterday and what you should work on next is strong.

Take a week off from your day job, though, and you find yourself adrift. People returning from vacation often talk about spending a few hours or even longer “catching up” or “getting back in the groove”.

With a side project, though, it might be a week or more since the last time you worked on it, every single time you work on it. Plus, you usually only have a few hours; any time spent getting back into the flow is a waste.

What can you do to sustain momentum with side projects and get into the flow quickly? Here are a few ideas that might help.

Find the right place to stop

I love reading about how people write and one idea struck me recently as something that would be helpful for any project. The idea is to stop in the middle of a page or paragraph, no matter how well it’s going, so you have a place to start the next time you write. Some authors stop when they reach the day’s word count, even if it means not finishing the sentence. Others stop during a particularly interesting and enjoyable section. This way, they will be eager to return to the story and with the foundation already set, have no problem getting started. It’s the perfect answer to the question, “Now, where was I?”

Be intentional about where you stop for the day. If you’re designing a web page or screen for an app, for instance, try stepping away from the laptop after you’ve made significant progress, but before it’s complete. The next time you dive in, it will be much easier to start.

You still might need a little direction, though.

Leave a trail

Everything is so clear when you’re in a state of flow that it seems like it will be effortless to pick up where you left off, no matter how many days pass. More often than not, though, it’s difficult.

After be surprised by this way too often, I finally decided to take a preemptive step. Now, when I’m wrapping up for the day, I spend a few minutes making notes for my future self. What are the next three things I was going to do if I wasn’t out of time? What problems still need to be solved that I will have forgotten about next week? What steps do I need to reproduce to get my local testing environment in this state again?

Notes like these are enormously helpful when you have an hour or two to spare and don’t want to spend half of the time retracing your steps.

Choose the smallest way forward

Sometimes anything is better than nothing. Keep a list handy of small tasks that are perfect for when time is short or things just aren’t clicking. A little progress is better than growing frustration with a blank page, canvas, or screen.

Your side project, and the time you invest in it, are both so valuable. I hope something here helps you get the most out of every hour you invest in your craft. If you have methods that work for you, please share them.

The Block Plan

My house is swimming in college brochures and data as we search for the perfect school for my son. Since I loved college and am fascinated by the academic world, I’m enjoying this part of the process a lot (more than the part when we drop him off at the winning school, I suspect).

I’m especially intrigued by the ways colleges distinguish themselves. There are a handful of schools that operate on a block plan (the most prominent one is Colorado College). I had never heard of this approach and though my son remains unconvinced, I think it’s very clever. Not just as a way to run a school, though, but potentially as a way to run a business.

The block plan works like this. Each students takes a single course at a time and the entire campus operates on the same schedule. The classes meet Monday-Friday and last for 3.5 weeks. They end at noon on Wednesday of the fourth week. Students have the afternoon off, plus Thursday and Friday, then start a new class on Monday (a few classes are “double-blocked” and continue for another 3.5 weeks).

With the block plan, students focus on one class and subject for the month. Professors have greater flexibility in when and where a class takes place since it can’t conflict with another class (some are held off-campus or in the case of an astronomy class, meet in the evenings).

What would a block plan at work look like?

The block plan reminds me of development sprints which typically last for one or two weeks. I wonder what would happen if that concept was expanded to include the whole company and lasted for a longer period of time.

  1. On the first Monday of the month, the entire company gathers together over breakfast (this would likely work best in companies with fewer than 20 people).

  2. Each person or team briefly describes their goals and commitments for the month (they have previously shared an in-depth version to get feedback). Everyone is encouraged to narrow the focus as much as possible to a single thing. Instead of making small progress on many different tasks, they seek out a larger goal that can be reached (or shipped) this month; a significant, measurable success for the company and its customers. This could include things as diverse as a new feature, customer satisfaction goals, marketing and press efforts, improvements to internal tools and processes, new hires, and investor outreach.

  3. On subsequent Mondays, everyone comes together to provide a quick update, noting successes or new priorities (updates are made to the shared document throughout the month as well). While acknowledging that things can change rapidly in a small company, there is a strong commitment to stability. Any changes to the plan are publicly acknowledged, other priorities dropped, and the person or team “compensated” in some fun, small way for the shift.

  4. Projects are finished and shipped by Tuesday of the fourth week.

  5. The final Monday morning update is moved to Wednesday. Each person or team recaps the month and what they accomplished. Finished work is shown off and successes cheered.

  6. The rest of Wednesday is set aside for planning the next month with leadership input, individually and within small teams.

  7. The fourth Wednesday also includes a special event to celebrate the month, such as a lunch or outing.

  8. Finally, everyone has Thursday and Friday off, a four-day weekend once a month.

The time off provides a breather after a month of focused work dedicated to a large goal. It allows for short getaways, but also the scheduling of weekday tasks that are hard to fit into a work week. The entire company being off at once removes the sense of missing out, the need to keep an eye on email, and the dread of returning to work that’s piled up. Plus, having just finished a project, minds are slightly less occupied.

I actually think that one four-day weekend a month is better than another ideal, the four-day workweek. It makes it more likely that people do something ambitious with the time off and provides more of a reward to work toward. Plus, it’s easier to adapt it to friends and family who are on the normal schedule. There would still need to be room for other vacation days, of course.

The four-day weekend is admittedly the most problematic part of the idea. At many companies, you can’t just close for two days each month and weekends may have service commitments, too. Plus, 24 days off a year plus additional vacation time is unheard of in America.

I think it could work in the right sort of company, but it would be rare. One option would be to make it a three-day weekend, another would be to rotate who gets the time off so it becomes a four-day weekend every other month.

What does the block plan accomplish?

  1. It brings the rhythm of the calendar and seasons into our work. What was accomplished in July? What are the goals for September? Sometimes work can become disconnected from the world around us, like cubicles in windowless offices.

  2. Assures that a marker is reached and celebrated once a month.

  3. Makes the whole company a team and puts everyone and the work they do on the same level.

  4. Provides a healthy mix of support and accountability.

  5. Creates a cadence to work. A new month is always a new beginning and often a new project. The end of the month is a time for celebrating and getting away.

  6. People are trusted and valued. Each plays a significant part is setting the priorities for the month and is given the freedom to accomplish the goals as they like. Changing priorities is a big deal. A few days a month are set aside to focus on friends and family, exploration and relaxation. It’s so important, in fact, that everyone is going to do it.

Finally, the idea works well within offices, but also for distributed teams as physical presence isn’t required. More effort would need to be put into celebrating milestones, though. The fourth week would be a great option for a semiannual retreat, gathering in one place for the final push and then relaxing together over the long weekend.

With the block plan, I believe more would be accomplished of more significance, people would be more invested in one another, there would be less of a sense of work being a treadmill of to-dos, and people would thrive. If you’ve seen something similar in practice (or try it), I’d love to hear your thoughts.

An Unfinished Idea

I’ve noticed a common thread in recent essays and conversations about ideas. When the topic turns to creating something new, the ideas themselves are talked about as commodities of little value.

“Ideas are easy,” we’re told. “Anyone can come up with ideas. Execution is what matters.” An idea that doesn’t result in something tangible is a failure. There is a right way and a wrong way to create, and only one is worthwhile.

We sometimes forget about the wonder that comes from false starts and messy mistakes; the joy found in an absurd idea and the gumption of those willing to try regardless. My father’s house and yard were filled with testaments to successful experiments and ideas gone wrong. A visitor was never quite sure which were which. He loved that.

Ideas are becoming another form of productivity, something to be implemented and measured. Instead of celebrating the madcap and unattainable, or the stack of first chapters and partial canvases, they are seen as a waste of time. We belittle unfinished ideas, as if we’re not all unfinished ideas.

Ideas should never be limited to what’s possible.

Does what we create have value if no one else ever sees it? What if it is never finished?

Bringing something new into the world is one of life’s great joys, of course. That should always be encouraged and celebrated. The extra push to stop chasing perfection, let go, and share it, is a good thing.

Yes, real artists ship. They also have ideas that are never realized and work that lies unfinished. They have dreams they can’t describe and plans that don’t make sense.

We’re all trying in our imperfect way to express the inexpressible. We’re all real artists.

Originally written for Uncommon in Common’s weekly dispatch.