Out Of Office Hours — Expanded Notes

When someone does what you want to do better than you, ask them for help.

A Little Context

I was working as a Client Relations Manager in the Pacific Northwest when I fell in love with product design and decided I wanted to build beautiful software for a living.

The decision came after after two years of working in the tech industry and filling various roles that fit me like the sweaters I get from my in-law’s every Christmas: okay in some spots but overall just not right.

I came to product design very organically. I grew up using technology, paying special attention at how it worked and why it worked the way it did. I’d fiddled around in Adobe Creative Suite in high school so heavyweight production tools weren’t too daunting. While my brother spent his time building stuff out of wood and metal in his backyard workshop I’d be hacking together Flash animations or the soundtrack for an imaginary film in the now-defunct Adobe Soundbooth.

Last summer, in between customer service tickets and onboarding trainings, I got a Slack message from my friend Joshua Clemans about a tool he was using to mock up our company’s website.

“It’s called Sketch. Check it out.”

Boom.

Queue Google searches for “free Sketch tutorials”, “product design”, “UX design”, “UI design” ad infinitum. I probably spent more time on Medium and the Inside Intercom blog that week than I did on Facebook.

During this time, I realized two things:

Digital product design is a real role.

If I wanted to be in that role, I needed to learn a lot.

A UX/UI Designer position had been vacant for a few weeks at my company and I heard they were having a really hard time filling it. Knowing how desperate our team was, I drafted a proposal to my manager (himself the VP of Product) that basically said “Here are some courses on design and frontend web development. If I took these courses, I could fill that role.” While the team ended up hiring a UX Designer, I was able to get approval to take six months of design and frontend courses through Thinkful, all on my company’s dime. My role hadn’t official changed — I was still a client service manager — but part of the deal was that, if I made significant progress in my courses, my team would consider a transition to a product and/or design role sometime in 2017.

Needless to say, I put everything I had into those courses. Learning became my absolute priority. I began to connect with the larger design community on Twitter and Medium and ran into Out Of Office Hours. I signed up immediately.

Out Of Office Hours

On Monday I had my call with Amanda Conrad, the Director of Product Management at true[X]. I was intrigued about the whole process and a bit nervous that I would speak to someone who was so far ahead in their career that they would be dismissive of my newcomer questions. Amanda, however, was extremely friendly and engaging. We talked about our backgrounds and found that we shared similar stories about moving into Product. Here are the four questions I prepared in advance as well as the (very!) condensed version of her super thorough answers:

1. What are some of the mistakes that someone new to product management or design should watch out for?

• Prioritization: as a newcomer it can become very difficult to see beyond the immediate needs or feature requests. If you want to become an excellent product designer you will need to develop a shared vision of the software that you want to ship. The key word her is shared: the vision must be a synthesis of the various stakeholders (customers, business development, engineers) and you will be a part of this vision if you intentionally seek to connect with these stakeholders.
• Process: having a good design process from the start will not only make your job easier but will also enable you to support your team better. A clearly-defined process provides guidelines that will increase your efficiency in everything from user research to handing off mockups to an engineer.

2. You’ve done both product management and UX/UI design — how important is it to clearly distinguish between the two roles?

Amanda explained that, particularly for a newcomer, a hybrid UI Designer/Product Owner role can be a great place to start and learn from both disciplines, allowing you to further specialize as you progress in your career. It also depends on the people and the team: for some people, the combination of responsibilities might be too much; similarly, in some instances a hybrid role might be indicative of a dysfunctional team that needs to define roles more clearly. Overall, if it’s a small enough team and you can handle both responsibilities, embrace the opportunity to learn both.

3. What key skills should product managers and designers seek to cultivate?

As Amanda explained, PMs usually come free three main areas:

• Business: people who want to apply business strategy to the entire lifecycle of a product.
• Engineering: developers who want to go beyond “only coding” and be involved in the entire lifecycle of a product.
• Design: designers who want to go beyond putting together mocks and be involved in the entire lifecycle of a product.

A great team will have all three kinds of product managers. Therefore, regardless of your background, you should work to cultivate skills in business, engineering, and design.

4. If you were hiring a new designer, what would you look for in their portfolio?

Beyond the essentials of clean, useful, and usable designs, a strong candidate’s portfolio will show proficiency in three areas:

Writing:

• How do you think through a problem?
• Can you turn customer/business initiatives into an actionable proposal?
• Can you write and document your work in detail?

Speaking:

• How do you propose a solution?
• Can you clearly articulate specific design, business, and customer decisions to people who are outside of any one of those areas?

Design:

• Do your designs provide actual solutions?
• Is it clear that they fit in the larger product process (user research, biz strategy, etc.)?
• Can you code your designs?

Overall, a great portfolio will showcase a synthesis of all of these things.

Lastly, Amanda gave me great piece of advice:

Become the person who knows who to talk to when a question or problem comes up. You can only do this if you get to know the strengths of everyone on your team by investing time and effort in getting to know them personally.

Even though I only signed up for a 30-minute chat, we ended up talking for almost an hour. I am very grateful for Amanda’s willingness to listen to my questions and for her thoughtful answers and advice. Also, many thanks to Dustin Senos ✌️ for putting together @ooohours. I can only hope to one day give back to the community as much as I’ve been given to.

Lastly, I hope my still-ongoing story serves as encouragement to others who are keen to learn design and code for fun or switch careers entirely. With so many great and accessible resources out there, we no longer have excuses to not learn something if we really want to.

Find something that you’re good at, someone from whom you want to learn it, and don’t be afraid to ask questions.

Santiago