Microsoft: Leadership, Management, and DesignOps

My contribution as head of product design and research in 2 groups at Microsoft fit roughly into the following three categories of work that helped keep our teams happy, healthy, and productive during extreme change due to the GitHub acquisition.

• People — taking care of our team day-to-day, coaching, fostering inter-team relationships, recruiting, etc.
• Process — how our team was working, establishing design methodologies, ceremonies, and practices between disciplines, from Design to Engineering to Product Management, from Research to Content Strategy... basically cross-team relations, empowerment, and DesignOps.
• Purpose — co-create product strategies with Product and Engineering peers, stakeholders, and executives, develop and embed organizational design culture and principles, raise the quality bar, and tell the team's story.

TL;DR: my focus was on designing the design process and creating conditions in which design could flourish.

Please take the time to read what my colleagues wrote about working with me below.

LEADERSHIP & MANAGEMENT

I led two remote-friendly teams of product designers, researchers, and copywriters (five and seven team 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 focused on strategic projects with GitHub (post-acquisition) for Azure Boards (Atlassian Jira compete) in the Azure DevOps Services group and 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.

As a people manager, empowering people on our team to do their best work depended on the details. How complex was the problem? Which designers were paired with which PMs and which engineers?

1. Initially, I owned all of the decisions, worked in the weeds, and participated deeply in all aspects of execution.
2. As trust developed within our team and with our colleagues in product management and engineering, I began to delegate execution but was still involved with final decisions.
3. Finally, I provided context & direction but fully delegated decision making & execution to the designers on our team.

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 product management and engineering. I'm a designer who codes. I speak engineering. This went a long way to create bridges and bonds with the engineers on our team.

DESIGN EXECUTION

Because the teams were small, I made contributions as an IC, 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.

DESIGN SPRINTS

I ran Design Sprints for our teams and other groups at Microsoft (Teams, One Note, and Education) to rapidly develop prototypes and validate ideas.

TEAM ACCOMPLISHMENTS

• Azure Boards baseline research study

  Our goal was to improve our understanding of how Azure Boards was viewed relative to our competitors.

• Azure Boards Design Sprint ("Loved by developers")

  We had a huge opportunity and goal to tell the "GitHub, Azure Boards, Azure Pipelines" story. Modern development teams outgrow GitHub Issues and go to Atlassian for Jira. There was no reason Azure Boards couldn't be a clear and viable alternative considering the GitHub acquisition. Jira is a low bar though — it is not loved by developers. The high bar... the north star... is to be the work management tool that modern development teams love to use. We came out of the sprint with a clear idea of how we could make Azure Boards the work management tool of choice for development teams.

• Azure Boards Work Item redesign

  The work item is at the core of the Azure Boards experience for developers. It presents users with important information, yet collaboration, functionality that our competitors offer, is missing. A social, collaborative work tracking experience is table stakes for software development tools. We wanted our work item experience to be the best in the market, and that starts with a modern work item that is a dynamic, living document with collaboration front and center.

• Azure Boards reskin

  Details to come...

• Azure Boards OKRs extension

  Details to come...

• Azure Boards GitHub app integration

  Details to come...

• Azure Boards UX/UI “paper cuts”

  Details to come...

• “Project Paper” - GitHub Pages v2 prototype

  Details to come...

• App Center onboarding

  Details to come...

• App Center service landing pages

  Details to come...

• App Center illustration refresh

  Details to come...

• App Center baseline research study

  Details to come...

• App Center design library

  Details to come...

• App Center yellow padding (UX/UI “paper cuts”)

  Yellow padding is a user experience-focused product review. The process ensures that we are providing a good, consistent user experience. The process is done with designers, product managers, and engineers. Area PMs create a list of all user flows, assemble screenshots and create a Figma mockup. Participants walk through mockup and critique. We capture feedback in Figma and then synthesize the raw feedback to find common themes. We then align feedback to product initiatives.

• Care and feeding of designers (presentation and deck)

  

THINGS THAT COLLEAGUES SAID ABOUT WORKING WITH ME

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 leader and supportive 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, he 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.

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)

Jared is a wonderful collaborator and sprint facilitator. He facilitated a highly complex design sprint with cross discipline stakeholders from Teams, Education, and Office to build bridges and provide a foundation for collaboration. His expert facilitation kept the focus on the customer, making sure we solved the right problems. It generated much excitement for the future, not least from our developers who immediately shared sprint mocks with their teams!

Jared has a calm confidence that puts everyone around him at ease, even in the most stressful situations like a huge messy design sprint. His passion for user-centered design comes through in everything he does.

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

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, 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 Thanks 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. Thanks 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)