I jotted down some lessons I picked up in 2015. Most of these relate to my work at Barrel. I wanted to post them in case others out there may find them relevant or helpful.

Structure and Planning Can Be Liberating

I believe more and more that “playing things by ear” is overrated and that the notion of freely figuring out what to do on the go can actually get in the way of spending time in a meaningful and rewarding way. I tried a few different things this year to give more structure to my schedule and to plan ahead as much as possible. Some examples:

• Our management team at Barrel started plotting out all major meetings and appointments a quarter in advance to give us a better sense of how the coming months would play out. These include team meetings we need to prepare for, meetings with our CPA, as well as any business travel or conferences. Forcing ourselves to look 3 months ahead gives structure to the upcoming quarter and helps us anticipate the workload in terms of meeting prep as well as availability for taking on other responsibilities.
• We instituted a morning daily huddle for the management team with a consistent structure that we follow. The three of us share each of these: 1) small victory from previous day; 2) top priority for the next 24 hours; 3) areas we’re stuck or find especially challenging; and 4) daily measures (accounts receivables and any new business activity). These happen at 9:37AM on the dot and last for about 15-20 minutes. We also end with a daily affirmation that we repeat together to feel centered on our mission and responsibilities. The huddle not only helps us sync up each morning and inform each other on what’s been happening, it’s also a great mechanism for helping us to plan out our day ahead.
• We put a lot of work into some HR-related processes, namely our comp review system and our new employee on-boarding. With very clear structures, scripts, forms, and other pieces in place for these, there’s no more scrambling to get these done last minute. We just follow the process as we’ve laid out (we made some early tweaks based on feedback and experience) and this makes things very easy.
• On a personal level, when going on vacation trips, I’ve found that some basic planning can lead to a much more enjoyable experience. Some things I’ve tried to jot down:
  • A list of restaurants to hit up
  • 1 or 2 activities to do each day
  • Some thoughts on when to go to bed and when to wake up each day
  • Groceries to pick up, especially if we’re staying for a few days at a hotel or AirBnB
  • What the transportation situation will be like and how much time we can expect to spend in transit

Having a plan doesn’t mean you always have to stick to it. But what it does provide is relief from having to make a slew of decisions in real-time. Instead, planning puts in structures to automate certain tasks and activities, allowing you to focus your energy on the most important matters (or to simply focus on enjoying yourself). By adhering to this type of discipline, I believe you set yourself up to feel less constrained and freer.

Listening is Teaching, Talking is Learning

I picked up the wording for this lesson from my wife Melanie, who came across it in a book by author Deborah Meier. The idea of listening as a way to teach really resonated with me because I don’t think I’ve been a great listener at Barrel.

I’ve often relished being the know-it-all with rapid-fire answers and instructions for anyone who came to me with questions. What I’ve realized from observing and tweaking my behavior is that people are more likely to understand and learn new things when they’re prompted to think deeply and figure things out on their own. While it may seem convenient and efficient for me to bullet list how an employee can resolve an issue or approach a problem, it’s likely that what I tell them may not be clearly understood or completely absorbed. So rather than answer a question with an answer (or command), I’ve found that asking the question right back and patiently listening to the person think things through can open the door for a richer discussion and a more valuable learning experience. As I listen, I might ask follow-up questions and also pepper in words of encouragement or praise.

Long-term, I think fostering this type of communication will help the team become more confident about problem solving on their own and figuring things out without having to come to me. I also think it’ll help expose me to different perspectives and to understand the different ways people see the same problem. I’m all for relinquishing the feeling of being the one with all the answers (which, by the way, is a very limiting mindset to have), especially if it means we can have team members who feel empowered and supported in figuring things out on their own.

Embrace the Ups and Downs and Keep Moving

These things happened in 2015 at Barrel:

• Heavy turnover (over 10 people quit or were fired in a span of 5 months)
• Lost one of our biggest clients
• Suffered record monthly losses
• Billing disputes with clients
• Low team morale due to overstaffing

Sounds like a pretty crappy year, right? And yet, 2015 was, in my mind, one of the most exciting and memorable years. It definitely sucked to experience the things I mentioned above, but at the same time, these low points prompted us to reflect and change our ways. And as we faced other challenges, we got better at bouncing back. Rather than feeling sorry for ourselves and writing things off as hopeless, we kept at it and tried new things. Here are some things we accomplished:

• Instituted a new interviewing and recruiting process that added new talented and strengthened retention
• Added a roster of clients in the healthy lifestyle space, an area in which we’re working to establish ourselves as the go-to digital agency
• Put in place a much more robust and structured expense management system to help us keep overhead down and find savings by cutting wasteful spending
• Workshopped and streamlined our project management workflows and deliverables, helping improve client experience
• Instituted new ways of resourcing team members on projects and also expanded our network of freelancers/contractors to help augment our capacity

My main takeaway from the ups and downs of this year is that it’s unproductive to fret and dwell on the downs. Crappy things will always happen in one form or another. Some may be preventable and work itself out while others may come out of nowhere and smack us in the face. Either way, I’ve gotten much better at taking these things in stride and focusing my energies more on the actionable steps we can take to move the company forward. We’re not going to have the solution or happy outcome for every bump we hit, but I like the idea of building an organization that is confident in its ability to overcome setbacks, to learn from them, and to be stronger, so that whenever we look back in a few months or in a year, we can honestly say: “Wow, we’ve changed a lot and come a long away.”

Dig Deeper to Identify and Address the Underlying Problem

I find that I’m the type of person who, when confronted with a problem, likes to jump on a solution as quickly as possible. In many cases, my eagerness to take action has served me well. But I’ve found that as I come across more complex challenges, my tendency to embrace rapid-fire solutions is sometimes counterproductive.

Where I’ve fallen short is in the questions I ask upfront. Rather than probe deeper into a problem to find out why it’s important, how it’s impacting the organization, and who potentially needs to be involved, my first line of thinking might be along the lines of “Is there a tool that can help us?” or “How do other companies handle this?” And right away, my focus shifts from closely examining our situation to wondering which web app will solve all our challenges. I’ve come to see this as a rather dangerous line of thinking. Putting too much faith in a tool, a new hire, or any other silver bullet solution is likely to lead to disappointment. I’ve learned this the hard way, and yet, I find it hard to let go of my ways.

This lesson contains a few takeaways:

• Beware of the sexy, seemingly easy solution
  The alluring web app that promises to alleviate all my problems while putting everything in the cloud? Adopting a tool, especially for an entire organization, is never a cakewalk and it’s important to understand the commitment required to make it work. In many cases, a new tool may not be the solution at all, and instead, the best course may be to tweak whatever homegrown solution we have going already. The same applies to hiring someone as a way to solve a problem. Without properly understanding the underlying issues, hiring someone to come in and fix everything can lead to disastrous results. I wrote about the pitfalls of hiring to solve a problem a couple years ago but have acted contrary to my own advice several times since.
• Map things out
  If it’s a workflow problem, writing down all the steps to the existing workflows or even diagramming it is a very helpful first step. For example, before going to look for tools, I could map out an existing process to better understand what works well and specifically which areas give us trouble. For other problems, I think writing in detail about the problem can be a useful way to identify gaps or underlying issues that may be easier to address than originally thought.
• Always ask “how can we do this better?” as a baseline
  I found that starting with this question, rather than a prescriptive “how can we automate this” or “how can we cut down the cost of this” makes it easier to explore a variety of solutions rather than being zeroed-in on finding a specific solution.

Part of effective problem solving, I’ve found, is to have patience. And by patience, I don’t mean passivity or inactivity, but instead, a persistent and disciplined focus to gather and analyze data, ask meaningful questions, and to think both short and long-term about the impact of potential decisions. I know this is an area I’ve struggled with time and time again, but I think having greater awareness of my own behavior in problem-solving situations will allow me to pull back and employ a solid framework to identify and address underlying issues.

Parting Thoughts

My hope with these lessons is that they become institutionalized into the culture at Barrel. One way I can personally contribute is to continue modeling certain behaviors and seizing every opportunity to share these lessons or to highlight and praise behaviors that help advance these lessons. The better we, as a company, can tie specific examples to these lessons, the easier they’ll be to explain and share.