Product Tribes AMA #5 — Mig Reyes

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This is the transcript of Ask Me Anything Session with Mig Reyes on Product Tribes community, August 8, 2019


Mig Reyes is a Director of Product Design at Sprout Social in Chicago, IL, USA. There, he and his team of 19 are researching and designing social media publishing and analytics products.

He’s spent the last decade of his career leading and making at several design-driven brands, including Trunk Club, Basecamp, and Threadless. Outside of work, Mig has connected design communities serving as a President for AIGA Chicago, teaching, and starting the Chicago chapter of CreativeMornings.

He enjoys photography and writing about business, leadership, creativity, and culture. You can find him on Instagram and Twitter as @migreyes.

Mig, thank you for joining us today!

Hi everyone! Excited and honored to be here. Greetings from a hot and sunny Chicago, IL, USA.

Since you’ve challenged us on Twitter to ask about something different than design, here goes: Tinker Hatfield said that experiencing life through travelling is kind of like building a library for creativity. Judging by your Instagram, you could probably relate. Could you share how your travels affect your work?

I love this question, and it’s been something I’ve been really intentional with as I’ve grown in my career.

To design is to create for people — all kinds of people. From all kinds of perspectives.

Traveling is exposure to different cuisine and sights, sure, but also exposure to how other people solve similar problems. I intentionally try to learn the transit and subway system every city I visit. You learn how other countries handle accessibility — e.g. Tokyo plays unique chimes at every stop so folks who are blind know where they are.

The landscape and the way a city looks and works are incredible inputs and influences on how we make things at the workplace.

It’s also how we can stretch and grow ourselves, throwing ourselves into unfamiliar places and seeing how we manage through it.

In a way, it’s a parallel to earning seniority in a career. How well can you navigate the unknown? Measuring that is a useful way to determine how mature (senior) someone is.

I too was going to start with some non-design related questions. Piggybacking off of the travel question, it looks like you and I have some passport stamps in common. Any travel plans remaining in 2019?

Yes! I’m spending a week in London for the very first time. I’m excited, it’s no doubt an incredible city for design, fashion, and culture.

And, I get to watch my very own Chicago Bears play (American) football in (an actual) football stadium! I welcome tips and advice for museums, sights, and other design-centric experiences.

Steering back to the work ground: You seem to encourage designers to try every craft connected to design. Why is it important?

You may not be an expert at motion, writing, visual design, information architecture — but it all adds up to one experience. I’m always encouraging others to explore and try new things.

1. Empathy for others.

Learning just how hard it is to do something on your own is a surefire way to earn trust and respect in others that do that very craft. If you find yourself having friction with another team, say Sales, Engineering, or Marketing, try doing their job.

2. Personal growth and career forking.

You also may not know you love doing something until you simply try. Studying as a traditional graphic designer, I never thought I’d enjoy writing — UI copy, essays, daily prose — until I tried!

I would be interested in what your favorite design and non-design books are.

Fun question!

I’m asked this often, so I made this resource.

Hands-down, far and away, one book that nearly transformed my skills and career trajectory was Revising Prose, which was recommended to me by my boss Jason Fried when I worked at Basecamp.

Books on writing helped me learn how to focus, be ruthless in editing, and prioritize.

Another one that changed my perspective on advertising is Scientific Advertising, which you can get a free PDF if you search online. It approaches marketing and advertising from a no B.S. perspective, which I think is needed greatly in our industries.

Since you’ve mentioned Basecamp, it is very well known for amazing books and content that they deliver. Where did it come from? How to build a company that wants and knows how to share the inside knowledge? And keep it nice and simple while comprehensive at the same time!

Basecamp is a fiercely opinionated place to work. It’s why I loved my four years there, and why I believe their philosophies on building businesses and products resonate with so many.

They’re not afraid to say what’s on their mind.

Working at Basecamp was like an MBA. It was there that Jason Fried empowered me to transition from a brand and marketing designer to a product designer. He let me become a manager for the first time in my career. Basecamp is predicated on trust in every employee — but to grow, you’ll have to jump in the deep end yourself.

There is no marketing team at Basecamp, which means there are no “content calendars” or any such mention of creating materials for the public.

It’s simply the Basecamp ethos to share what you learn. The learnings you discover while building, making, and messing up — those are the byproducts that earn more customers, and attract incredible talent to want to work at your company.

Inside of Basecamp is much like the perception outside: it’s constant sharing of learnings. Most people I worked with then are still there today, because of that kind of nurturing culture.

I would like to know what is your opinion on remote-work, as I know you worked for Basecamp, which is fully remote. I also went through the Sprout Social job board, but I see the positions are only on-site. Could the Sproutsocial be fully remote? Do you see any limitations in remote-work, e.g. in design process?

I currently manage two designers remotely, and a third will be transitioning to remote as well!

Having worked remotely full-time for four years, there are incredible benefits and freedoms paired with expected challenges.

All of Basecamp is run remotely; I don’t see major limitations. Remote work feels better when more people can participate in it. If there are a few outliers, those particular employees can feel like secluded satellites.

Work feels calmer when everyone is remote.

You can take your time to think, at your own pace.

Writing matters.

I’ve brought up writing a lot. Since you can’t have in-person meetings, Basecamp hires people who have phenomenal written skills.

Offsites and outings are really important to building bonds.

You’re not with people every day, so week-long team offsites really helped. We discussed key topics as a team, but mostly used the time for feasting together, chatting together, and spending leisure time together.

They can also talk about how they do it better than I can. I encourage you to check out their book on the subject if you’re interested in learning more! On a personal note, remote freedom helped keep my work environment fresh, which helped me think differently every day.

Basecamp seems to be a totally different animal in the software development world. Can you tell us a bit more about the development process in Basecamp?

Perhaps a shorter answer here; Basecamp recently wrote everything they know about building products. It’s free online here!

Much of what I’ve learned in my career is covered in their free book. I promise they’re not paying me to plug them.

Could you tell us more about your CreativeMornings project? How did it affect your work life?

Starting the Chicago chapter of CreativeMornings was one heck of a project.

If you’re unfamiliar, CreativeMornings started in New York by Tina Roth Eisenberg, otherwise known as Swissmiss online. It’s a monthly breakfast lecture series that brings together creatives in a city for coffee, food, and inspiring talks.

While there’s well over 100+ chapters today, I started CreativeMornings Chicago as the 5th chapter.

Starting a community from scratch is like building a company and organization. I had to recruit volunteers, find venue spaces at a $0 budget, and convince Chicago’s best talents to speak at these events — again, for $0.

I had to learn how to make and market a movement. I was bearing the load from social media posts to putting away chairs at the end of events. Learning how to inspire a team to help me and delegate was a critical learned skill.

What I learned from starting and running it for 2 years, though, is all of that hard work was for the community. Thanks to CreativeMornings, people met their future employers, spouses, and best friends, all while finding a dose of inspiration.

In a fun turn of events, I was later asked to be a speaker myself at CreativeMornings. It’s one of my favorite talks to give. You can watch it here:

I’m proud that our chapter is still around, 8 years later.

I’m really curious about the shift in the design industry right now and the growth of in house design teams. Do you think there is still a place for agencies and freelance designers to be successful and how do you think they can innovate and not fall into famine mode when so many companies are turning to their in house teams?

My peers and I have been noodling on this for some time. You’re right; there is a shift in design, and building teams in-house is something to take note of.

Starting my career, it wasn’t an exciting prospect to say you worked in-house. That narrative has reversed. We have organizations like Facebook and Google who have really been public about building up design teams. The likes of design-founded companies like Airbnb further that case.

There’s absolutely a place for agencies and freelancers to be successful, though I think you’ll have to be honest with yourself on the kind of work you’re looking to do. As a hiring manager myself, I don’t often see freelance UX or product designers. That could be a symptom of the Chicago market — I’d love others to weigh in there.

The freelancers I know largely maintain their body of work with brand, marketing, and advertising. I suspect this has to do with the temporary nature of the work.

In product, deep knowledge of users, customers, and a history of what’s worked and what hasn’t is required. You’re hard-pressed to get that level of depth from a freelancer.

Since you’ve mentioned not being afraid to say what’s on our minds: People love to talk about success but you seem like a brave guy. Could you share a story of your most difficult challenge and a lesson learned from it?

The most difficult challenges in my career are more around people, relationships, and organizational challenges than they are about designing work.

I’ve not shared this publicly before!

After four years, I felt stale at Basecamp. Stuck, not doing my best work. My team knew it, too. Leaving such an incredible company, coworkers, and leaders felt like career-suicide. But leaving to work on fresh problems, become a manager of bigger teams, and meet different types of talented people at all my future jobs absolutely grew me.

I also left Basecamp with no plan. No next job lined up.

I bought a Leica and traveled a bit. That’s where my passion for travel and photography started — leaving the most important thing I knew.

I could relate. What I’ve learned in my career is that — surprise, surprise — not everybody has to have the same opinion. Period. And for marketers, and I suppose designers too, empathy is one of the most important values, isn’t it?

In fact, I’ve left jobs twice in my career with no plan — and just enough money in the bank to hopefully find my next job.

It’s part of the theme of throwing yourself into the unknown and trusting yourself you can make it work.

In Sprout Social, you’re all about the customer and you’re very open about your values. I remember you having your brand story at the first scroll of your home page. How does that affect your business strategy? Would you say building genuine relationships with your audience is rewarding?

Absolutely rewarding, and why Sprout exists. There’s a lot of bad business practices and customer experiences with no heart or humanity behind it. We want businesses to be better, and that starts with a shared mission that we’re all better when we’re connected, as real people.

In the design process, there are many roles, researcher, designer, developer….and so on. Is there a particular role or group more forgiving and allowing people to make more mistakes than others? Especially for people who have diverse but not specialized experience wanting to break into the whole design and innovation world.

What I think is important to call out here is the sense of one being “more forgiving” than another.

Every job is hard.

That’s why I encourage people to try every role in product development, and see where your strengths lie. My director partner and I quite literally redesigned the org structure of our team after we spent a lot of time with every single individual designer to learn their own strengths, opportunities, and growth aspirations.

No matter the role, you’re going to make mistakes. Instead of competing on whose role is more forgiving (or which role feels more important), can we instead create a culture where failure is considered learning, and celebrated?

All sports teams have defined roles, and successful teams know the value of each position. The same principles can apply toward product development teams.

Any advice for new designers coming up right now?

I asked about 40 of my friends and mentors the same question.

And in that tone, our last question (that we ask all our guests): What is one thing you would like the Product Tribes community to remember?

We build products for people.

The most rewarding jobs we have in our careers are because of the people.

Be good and be kind to people, and spend your time learning about others. Your best work will come out of that.

Join Product Tribes — community of experienced product designers, managers, and developers.

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