Location: Portland, Oregon
What’s your background and how did you get into management?
It’s not conventional. In the second half of the 90s, I began dabbling with open source technologies. In particular, with Linux and Perl. During this time, I was also a high school dropout painting houses for three years.
The idea of working in tech didn’t appeal to me. I equated that with working on a tech campus, in a small cubicle, in Silicon Valley. It was an environment that I was familiar with; my father did (and still does) work on a tech campus, in Silicon Valley (in hardware).
Being a rebellious anarcho-punk teen, my goal for myself was to avoid that type of career. All I wanted to do was play music in a punk band and do something “creative.”
My first business was a mail-order sticker company. I wanted to sell stickers online, so I figured out how to build a website where people could browse a small inventory and place an order. An “order” was a row written to a CSV file on an FTP server. I didn’t get many online orders.
Fast forward to 2000, I relocated to Portland, Oregon and got a job – with a (sigh) cubicle – at IT events management company. Within a few months, I started to build out a few intranet sites for the organization of 200 people. This kept leading me to learn more about languages like PHP, too.
In 2001, the company’s software department invited me to join them and start working on ASP/ASP.NET sites. I did this for a few years and then decided I wanted to focus more on using open source technology. So, I started a new company called “Planet Argon” for freelancing & moonlighting projects.
After a short trip to a small software consulting business, I decided to quit and go full-time freelancer in early 2004. For most of that year, I was learning how to win work with clients. Most of this work was in PHP, Python, and Perl.
In late 2004, Derek Sivers, founder of CDBaby, introduced to Ruby on Rails. This started me down a path that would change my life. In 2005, I started blogging, a lot, about what I was learning and how I was using Rails under the name, “Robby on Rails.” I had a design partner, Allison, who was contributing to our client projects, too.
Within six months, we found ourselves booked solid with new projects; it didn’t take long for me to see that we couldn’t handle them all ourselves. In late 2005, we hired our first employee and within two months we grew a team of eight people working out of our attic. This was the start of Planet Argon, the agency.
Once we became employers, I found myself in my first management role and have been leading Planet Argon, full-time, for the last 14 years.
We still don’t have cubicles…but now we deal with the pros and cons of an open office.
A lot of what we focus on these days is helping companies with existing (Ruby on Rails) applications make them better and more maintainable.
What are the biggest challenges you face?
Recruitment over the last few years has been a big challenge for us. While we’ve made some great hires, we find it difficult to recruit more senior developers. We can’t quite afford to match salaries of larger tech VC-backed companies based on the west coast.
Another challenge is finding developers that enjoy making existing things better (vs. shiny new things). There are plenty of developers that throw around, “we need to rewrite” or “we need to rebuild.” It’s not as easy to find the developers that find enjoyment diving into a bit of a mess and helping to untangle it.
Those folks are extremely valuable and are, in my not so humble opinion, the true heroes of our industry.
What is your approach to hiring?
When we interview developers, we’re trying to find humans who will work great with other humans. The idea of having anyone who only focuses their attention on their code isn’t feasible. So, we try to get a good read on their personality and communication skills.
Can they explain technical concepts to non-technical people? How confident are we that they’ll align with our core values? Are they humble and hungry? Will they be good team members?
What’s your advice for managers who are just starting out?
Even your smartest and most autonomous employees have a deeply rooted desire to be led. If I had a chance to go back and offer myself advice 13 years ago, it would be something along the lines of, “Hey, Robby! Yes, listen a ton… and delegate outcomes to the team… not tasks.”
What’s your workday like and how do you manage your time, emails, etc.?
I’ve always been an early-bird since a kid; my first job was a paper route. This required getting up at 5:30 am. I had to fold newspapers, organize them into my shoulder my bags, and ride my bicycle around to toss papers on people’s doorsteps. There was something so tranquil about those slightly-dark hours of the morning. Fewer cars around, fewer people, the sounds of the birds waking everyone up…I grew fond of this time of the day.
Fast-forward ~27 years, I still enjoy the early mornings.
A typical workday involves me working for about an hour from home to triage my inbox, organize my todo list, and determine what today’s highlight will be. My highlight is a task will make the biggest impact on the company. I don’t respond to many emails at this time–only urgent ones. I lean on my todo app, Things, to prioritize my day. This usually happens along with my first cup of coffee.
I then stop working and go to the gym. I’ve found that if I allow myself to get somewhat exposed to the day first, and then subject myself to an intensive workout, it’ll help reduce my stress.
After a cool-down, I head into the studio to work with the team. The rest of the day tends to be a combination of some one-on-ones, pairing with a junior developer on a ticket or two, and dedicated time to focus on my highlight of the day.
As an example, today’s important task was to respond to your interview questions. Yesterday, I wanted to make sure that I led a really productive and collaborative development team-wide meeting. The previous one was rated a bit lower than normal–so I was determined to correct that and it ended up being one of our best in several months.
(Yes, we have everyone rate each of our team meetings on a scale of 1-10)
One of the things that I’ve learned is that as rigid as I would like to be with my time, that should mainly apply to external groups (i.e., clients, prospective clients, recruiters, peers, etc.). However, being available to listen and help our internal people (developers, coworkers) is something that I believe we need to see as a big aspect of our responsibility. People need to be led. They need to be heard. They want our time.
What’s a personal habit that contributes to your success?
Tracking how much water I’m consuming each day seems to be helping.
As mentioned earlier, I start my day off by setting what my highlight of the day will be. During the week, it usually ends up being a company-related highlight…but there are occasionally personal ones, too. Sometimes, I need to focus on a few personal tasks during the middle of the day, so being intentional can be helpful.
Before I leave for the day, I review what I wrote down in the morning to see if there was any deviation. I will log a few things that I noticed in my team. (i.e., positive, not so positive, confusing, etc.)..and figure out if I should share in an upcoming one-on-one and/or if I should share some praise at our next company-wide standup meeting, which we have each Monday morning.
If you could recommend one book to managers, what would it be and why?
One of my favorites that I read in the past year was The Coaching Habit: Say Less, Ask More & Change the Way You Lead Forever by Michael Bungay Stanier.
It really helped me rethink how to approach my one-on-one meetings with employees. There are several tips on how to ask better follow-up questions, how to keep your mouth shut and invite people to speak, ways to communicate that you’re listening, not offering up unsolicited solutions, and following through on things for your people.
Most importantly… not offering to solve their problems. “Let me know if I can help you” and/or “Have you tried/considered…?” is something that I’m trying to stop doing…and so should you.
“…and what is your biggest challenge here?” is a great question to ask your people. They’re the ones with the problem and the know how to find a solution. Work through that together…but coach them to their own solutions.
What is your approach to mentoring and coaching members of your team?
To expect more out of myself than I do out of my team. If I can’t show that I’m becoming a better human on this big planet, a more productive manager, a more successful coach, then who am I to be trying to cultivate this in others? This means a lot of self-reflection, being vulnerable with my team members, and sharing my progress.
When I interact with members of my team, I’m always experimenting with new things that I’ve learned about. If anything, it keeps things fresh for all parties.
Where can we go to learn more about you? (LinkedIn, Twitter, GitHub)
This series asks engineering managers to share their experiences with the intent of helping other engineering managers learn and improve. Have someone you want to see featured or questions you think we should ask? Contact me.