9 Tips to Have a Better Out of Office Hours Experience with your Mentor

Do your homework, take notes, be flexible, and many more

Getting ready for dat OOOH chat

Over the course of the last few months I’ve had the opportunity to talk to 7 designers through the awesome Out Of Office Hours community started by Dustin Senos. Shout out to Jonas Downey, Maya Benari, Jonny Mack, Shaun Tollerton, Adam Saint, and Greg Beldam for volunteering their time to speak with me.

Out of Office Hours has given me a window into the design world like never before. OOOH pairs professionals in the tech industry with young students and professionals like myself. Who would have thought talking to real designers is better than sitting alone reading a bunch of design articles all day?! 😂

Here below are a few things I’ve learned along the way that will help you have a better experience when/if you sign up to talk to someone from the industry…

Be prepared

Here I am on vacation doing some homework for my next OOOH call!

Do your homework on the volunteer you are scheduled to hangout with. Google their name. Scroll through their Twitter and Instagram accounts. Look them up on LinkedIn. Read their blog posts. Try to find them speaking at conferences on YouTube or Vimeo. Take notes as you do all this and prepare some questions based off what you find. Trust me this will make your conversation 10000% better because you have done your homework and know what this person is all about.

For example — By doing my homework before hand, I found out that Maya Benari had extensively worked on the US Web Design Standards during her time in the USDS. I was working on a design style guide at that time and we were able to talk more about that topic in depth during our call.

Take notes

A few of the many pages of notes I took with my Boogie Board 📝

Taking notes helped me better internalize the great advice and resources I was being given through each conversation. I have gone back to specific points that each designer I have talked to has made every once in awhile when I’m designing something at work or at school. Taking notes also is a great way to show the designer you are talking to that you care about what they are saying enough to write it down. I’ve learned that taking good, concise notes is a skill that needs practice just like anything else.

Don’t try to impress

Like the songbird of our generation says, “B$*%! be humble” (Shoutout Kung Foo Kenny). A few times I found myself trying to impress the designer who I was hanging out with by mentioning an article I had just read or talking about some really niche thing I learned in design school just for the sake of impressing them. Sometimes I even found myself getting into “interview mode”. This is not an interview. There is nobody to impress just lessons to learn. Sit, listen attentively, and have fun talking to some of the most talented designers in the industry.

Stay flexible

Designers are busy people and don’t get put off if they have to reschedule! Especially the talented ones that have offered to give some of their time to mentor us. I found myself being put off when one of the designers had to reschedule. My mind began racing as to why he was moving the meeting.

“Do they still want to meet?”
“Did they look at my portfolio and realize I’m a scrub from Indiana that has no idea what I’m doing trying to be a designer?!”
“Am I bothering them by asking to reschedule for another open time?”

Nope. Professionals in the industry are just busy. Realize that and stay flexible around there packed schedules. They still want to talk to you just be patient and understanding.

Find a quiet place with good WIFI

My friend Matthew Robert Anderson in his quiet place.

When I talked to Maya Benari I was at a loud Starbucks with poor WIFI. It affected the conversation because we constantly had to stop, wait for the Internet to catch up, and then repeat the last thing we said. We eventually just gave up on the video chat and Maya graciously called me on the phone and we finished our conversation that way. Find a quiet nook or office room to chat with your mentor and make sure the place has a strong WIFI connection.

Tell them beforehand what you are interested in talking about

I’ve found that shooting them a quick email before talking with a few questions or things I am interested in talking about is a great way to get the most out of the short time you have with each mentor. By doing this before the call you are able to prepare them to know what resources and pieces of advice they might be able to offer you in that specific area. It usually works better than putting them totally on the spot with random questions.

For example — I emailed Jonny Mack letting him know I was interested in learning about what it was like to work on a huge product like the Google Cloud Platform, before we met. He was able to be prepared to talk about his work at Google and what it was like designing with a diverse team that has many people involved during the design process.

Do a debrief afterwards

After a 30 min or hour long conversation there is a lot to think about. I’ve found the best way for me to retain the information I’ve just talked about is to take 5 min after the call to write down some quick thoughts, clean up my notes, and unload my mind before going through the rest of my day. Try it out next time you talk to someone!

Say thank you

A few of the thank you letters I sent out to Out Of Office Hours volunteers

Seems like a no brainer right? You would be surprised at how many people miss this easy step to make a great impression. Send an email or write them a short note thanking them for taking time to meet with you. They aren’t getting paid to do this and they are already busy people. The least you could do is thank them for their time!

Stay in touch

Some designers that you talk to will only want to talk once but I’ve found many are very open to staying in touch. This is especially true if you express that you are interested in talking more. “Talking more” means different things to different people so make sure you are clear with what that looks like. For Jonny Mack and I, we met once and I reached out to him again a few weeks later to talk more. We are now staying in touch about once a month and I’m learning a ton from our short conversations over Google Hangouts.

In conclusion, if you are a young designer and haven’t heard of Out of Office Hours sign up right now!!!! You won’t regret it. Hopefully these tips will help you have a better experience.


I’m on the world wide web at haydmills on everything 👋

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