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Microsoft: Leadership, Management, and DesignOps

March 01, 202010 min read

TL;DR: All of the work that I did as head of product design and research in 2 groups at Microsoft fits roughly into the following three categories that helped keep our team happy and healthy.

  • People — taking care of our team, fostering inter-team relationships, recruiting, etc.
  • Process — how our team was working, establishing design methodologies, ceremonies, and practices across disciplines, from Engineering to Product Management, Research, Content Strategy... basically DesignOps.
  • Purpose — co-creating strategies, forming design principles, telling the team’s story.

As a head of design my focus was on designing the team and creating an environment in which design could flourish. The designers on our team designed the products.

I led two remote-friendly teams of product designers, researchers, and copywriters (five and seven members) who hailed from Seattle, San Francisco, Los Angeles, Boston, Berlin, and Barcelona. I played a handful of different roles as a manager: mentor, friend, sometimes bearer of bad news, career advisor, and proud colleague. I worked with both teams to establish our design culture and facilitate ceremonies, processes, and relationships to make us more effective. Our work was primarily on strategic projects with GitHub (post-acquisition) for two organizations in the Developer Services group: Azure Boards (Atlassian Jira compete) ands App Center (Google Firebase compete).

I focused on a couple of things day-to-day:

  1. Design team dynamics: process development, enabling and encouraging cross-discipline collaboration, hiring, and people management
  2. Broader team dynamics: partnering with heads of product and engineering and their teams on product vision, direction, priorities, and execution

Jared is a design visionary and fantastic people manager. He loves solving problems and cares deeply about craft. He's the kind of manager you feel lucky to have on your side. He's great at recognizing strengths and creating opportunities. Within an organization going through multiple reorgs with lots of ambiguity, he kept the team grounded and productive, and I felt supported. I'd highly recommend working with him if you ever get the chance.

Brooklyn Brown - Senior Product Designer (direct report)

Jared is an inspiring cross-discipline leader and supportive design mentor. He is thoughtful and considerate of the needs of his directs, peers, and users alike. He cares about and values people above all else, and that comes through in everything he does. Even though he is a highly skilled product designer, as a manager, he always gives his team space to learn, grow, and do good work. Consequently, he elevates everyone around him by providing encouragement and focused, well-articulated feedback. He is curious and open-minded, always learning from others and seeking out new insights. As a leader, Jared listens deeply and isn't afraid to speak up and make decisions when necessary. He advocates for cross-discipline collaboration and effectively aligns organizations around shared values and goals. He is a thought leader—strong opinions loosely held—and he's right… a lot. I'm definitely keeping an eye out for opportunities to work with Jared again!

Erika Johnson - Product, Interaction & UX Designer (direct report)

If you ever get to work with Jared, you’ll see that he’s from the future. He’s strong at seeing what’s next and keeping on top of trends. He has a talent for seeing the big picture, keeping projects on the rails, and giving just enough feedback to ensure the project is on target while giving designers the space to create. He’s drama free and focuses on what is right for the product and team. He’s a risk-taker, and willing to put himself out there to ensure a project’s success — while seeing all sides of the picture. He’s easy-going, empowering, curious, supportive, and a straight shooter. I’d work with Jared again in a heartbeat. I’m jealous of the people that still get to work with him. If you get the chance — you should work with him too.

Cheryl Hooper - UX Designer (direct report)

Because the teams were small, I was able to make contributions as an IC as well, including projects on issue tracking and work management, road mapping tools, CI/CD, and the future of platform-as-a-service for websites and apps in GitHub. And I ran Design Sprints for our teams and other groups at Microsoft (Teams, One Note, and Education) to rapidly develop prototypes and validate ideas.

Thank you so much for facilitating our “OneNote in Teams” design sprint last week! We literally could not have done it without you. Your expert facilitation brought 3 orgs together (Education, OneNote, and Teams) to problem-solve as one team. This sprint built bridges between our orgs, providing a foundation for us to collaborate more closely going forward. It also generated so much excitement for the future, not least from our developers who I heard have already been sharing sprint mocks with their teams! 😊

But most importantly, our user-validated solutions are going to make it easier for our customers to use OneNote in Teams! And that’s what it’s all about.

Thanks again for bringing our 3 teams together to work as one. You’ve positively impacted all 3 orgs.

Mila Byrne - Principal Design Manager and UX Lead (colleague)

One of the most significant impacts I had in our groups at Microsoft was bringing the product management, engineering, and design disciplines together - pairing people with the problem spaces where their skills and interests best aligned. I’m a huge proponent of “starting together, working together, and finishing (measuring) together,” and I spent a lot of energy helping people on our team forge relationships with their counterparts in other disciplines.

Jared, you are our customer-obsessed, strategic product designer extraordinaire. You were the integral part of the engineering, product, and design leadership triumvirate that transformed the Azure Boards’ vision. Valentina and I would have been lost without you. You are the Google of design, team process, and customer-focused thinking. No matter the topic, you always have an idea, a link, or a vision to share.

Steven Borg - Principal Group Program Manager (leadership team colleague)

Simply put, you're a fantastic collaborator. From my interactions working with you on both Boards and ACE, you're open-minded, an articulate communicator, and incredibly encouraging. You're also an incredible leader and visionary. You know a good idea when you hear it, but at the same time, you know how to gently put a bad idea to rest. Recently, during a meeting, when you were put under pressure to work on something you didn't agree with, I admired how level-headed you were and how you continued to be respectful despite the frustrating circumstances.

PS Thank you for always encouraging me behind the scenes. Whether it's on a presentation or being the only woman in the room, I appreciate it. It goes a long way.

Evangeline Liu - Program Manager (colleague)

I've really valued having you on the team. You've been a really great partner, whether that be executing on some design work, bringing in the power of the group, or having a forward-looking chat about what's possible.

I've really appreciated how you've been able to quickly jump into the problem spaces that have come up over time, provide some design experience to orient us, connect the team with appropriate expertise and even take up some of the design work personally. I've been thankful for your flexibility, depending on the needs of the project or players. We could just have a quick consultation chat and keep moving or engage more deeply.

I've really valued the energy you bring to the leads team to help us challenge our mindset to help us work towards being more competitive, have a better product, and improve how we work. A small but powerful thing here is the sharing and discussion of tweets you find from the community. Continue pushing that way in a way that helps us make the transition from talk to action.

Alex Nichols - Senior Program Manager (colleague)

You've been an invaluable, customer-focused team member as we built up a vision for a complete relaunch of Azure Boards as a simplified, modernized product. Where we often felt the need to jump to design, or pictures, you pushed back on product to deliver a customer-focused vision that achieves business objectives. When we were looking at what it would mean to change our navigation to reduce "it's confusing" NPS comments, and we found that it was the fundamentals of our product that needed change, you didn't hesitate to drive for the right results for the customer and help advocate on leadership team to put together a vision that would actually be impactful. You also demonstrated this in the face of pressure from your peers on the leadership team to "just start drawing pictures" for modern Azure Boards, and this resulted in us building a stronger muscle around iterative learning going forward.

Over the past few months, you've also done an incredible job of building up a design team with the skills and passion for helping the team build a vision and MVP for Azure Boards. Thank you for being such a fearless leader, and helping us to build a better relationship between the product, design, and engineering teams!

You are a disruptive thinker who is always focused on making sure we are designing/building the right features for the customer. You are continually pointing back at the customer and questioning our assumptions, which makes for a much better user experience and has been invaluable in planning out what the future of Azure Boards could be.

Ali Tai - Program Manager II (colleague)

Our team accomplished a significant amount of work together. Highlights include:

  • Azure Boards baseline research study
  • Azure Boards Design Sprint
  • Azure Boards Work Item redesign
  • Azure Boards reskin
  • Azure Boards OKRs extension
  • Azure Boards GitHub app integration
  • Azure Boards UX/UI “paper cuts” initiative
  • “Project Paper” - GitHub Pages v2 prototype
  • App Center onboarding
  • App Center service landing pages
  • App Center illustration refresh
  • App Center baseline research study
  • App Center design library
  • App Center yellow padding (UX/UI “paper cuts” initiative)
  • Care and feeding of designers (presentation and deck)

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