Design Management Sessions & Techniques

Starting in 2008, I began a transition into design management. While maintaining sharp skills with design tools, UX, and visual design, my focus transitioned into mentoring, growing, recruiting - and most importantly - retaining designers. Keeping them inspired, happy, and challenged. I’ve led teams as small as 1 and as large as 20. Often I designed right along with the team or we pair on projects together.

Over the years I’ve discovered, developed, and found some pretty good methods for helping designers thrive. It’s a tricky balance between letting them have agency and control over their work, but also helping guide and mentor in areas they need improvement in.


I use the Radical Candor book by Kim Scott (Google, Apple) as my initial framework. I give a copy of the book to each designer and ask them to take some time to read it. We discuss certain chapters and ideas presented. It’s a great foundation, but its not for everyone and often you have to adjust according to the personality of the designer. I care deeply and challenge directly, and I want my team to, as well.

This book and framework doesn’t work in all company cultures, however, so discretion and application of the principles is on a case-by-case basis.

The other method I use to understand each designer’s personality and interaction styles is this amazing workbook called Understanding Yourself and Others: An Introduction to Interaction Styles and its companion book Understanding Yourself and Others: The Temperaments. I’ve found pretty much every designer (or person I work with) fits into one of these four interaction styles, and it helps both the designer and me work better together, and the team work better together.

Weekly 1:1

The weekly 1:1 is perhaps the most important session a designer can have. Here’s where they can give me, the Design Manager, candid feedback about how I’m doing. I follow a fairly strict format at first, then open up the session to their Q&A. This is their time, so I generally let them direct it after I’ve been able to get a few answers out of them regarding their growth, job happiness, and more.

Generally I start out with 1hr, but as we get know each other better, we often trim it to 30 minutes.

I create a shared document with Dropbox Paper or Google Sheets, which the designer is invited to. They’re expected to fill out each week. It takes about 5 minutes. Here’s a sampling of the weekly questions I ask each team member, and how I track the happiness of each designer week to week.

Weekly Design Team Meetup

In this 1hr meeting, we, as a team, discuss our work, design trends, process, and anything else people have on their minds. This is the one time, we as as team, meet where we don’t do design reviews per se and just talk candidly and openly. As its an open forum, I keep notes in a shared doc with any action items and outcomes.

While all this seems like a lot of meetings, it’s not. This is how teams gel, work their problems out, and create the best experiences for customers.

Weekly Design Team Review

The magic happens in this 1hr 30 min workshop! Team members bring in their work to share and get feedback on and collaborate with. Nearly 100% of the time, a designer leaves with better implementations, different directions, and problems solved. Whether is feedback on a logo, or far more complex interaction problems in SaaS to solve, the team comes together to solve those.

Bi-Weekly Design Team Retro

In this 30 min session, every other week, we, as a team, discuss the good and bad of how our team, our projects, and our company, and ourselves - are doing. I keep notes in a shared doc the entire team has access to (here’s an anonymized sample). The process is taken from any agile/scrum book:

  1. 5 minutes silently writing on stickies what’s going well

  2. Sharing, one-by-one, those stickies. All notes are captured in a share doc

  3. 5 minutes silently writing on stickies what’s not going well

  4. Sharing, one-by-one, those stickies. All notes are captured in a share doc

  5. 5 minutes silently writing on stickies improvements to address what’s not going well

  6. Sharing, one-by-one, those stickies. All notes are captured in a share doc

At the end of the session, we have a list of things we’d like to tackle for next week. The real trick is tracking these and staying on top of them. It’s always best to take volunteers and assign them so you build a real sense of teamwork to solve problems.