Design leadership, strategy, and planning

Philosphy on leading design teams

I manage and lead design strategy and execution of core initiatives like Conversation Intelligence and Agent performance at Observe.AI while mentoring a team of designers. Following is my philosophy for leading design teams. 

I like to think of design leadership as comprised of the following buckets:

  1. Setting up team vision and direction
  2. Mentorship and coaching
  3. Design and product strategy
  4. Design operations
  5. Culture

Setting up team vision and direction

The goal of setting up a vision for the team is to optimize for impact over busyness. While we all work on individual projects, knowing how our efforts impact the business is essential.

At Observe.AI, we organized ourselves into functional pods responsible for different business metrics like an increase in new logos, improvement in retention, etc. While we aligned ourselves to overall company goals, I realized we needed different design strategies for different pods. 

My responsibility was to develop the design strategy and vision for the user experience for core initiatives. To that end, I created artifacts like design principles and vision documents to align cross-functional stakeholders with design teams. We did this as a collaborative exercise with inputs from leadership, product management, machine learning, and engineering leads. This ensured the entire team was on the same page concerning design decisions and tradeoffs, and we could scale our decision-making process efficiently. 

Example: Conversation Intelligence

Artifacts
  1. Design principles (Poster | Document)
  2. Vision deck
  3. Memo
Impact
  1. Enabled cross-functional team members to align on product and design decisions confidently. 
  2. Provided clarity on the direction and set boundaries for the relevant projects for each team/pod, which also helped distribute tasks and initiatives between teams.  

Mentorship and coaching

I was responsible for mentoring three designers and enabling them to lead independent initiatives within different functional pods/teams.

I generally follow the following framework when guiding team members:

  1. Most problems are either related to motivation or ability. 
  2. Motivation problems can be dealt with through coaching, providing clarity, removing roadblocks, or managing conflicts. 
  3. Problems of ability can generally be solved through teaching and training. To that end, I frequently organized sessions where I taught skills around AI+Design, communication, time management, building trust with cross-functional teams, etc. 
  4. Sometimes individuals may find the task too difficult; in such cases, we can deal with them by redistributing workloads, managing expectations with cross-functional teams, or providing additional support.   
Impact
  1. Enabled fresh graduates and experienced team members to deliver multiple large projects within and often even before schedule. However, not all projects get done on time. Recalibrated when the team needed additional time or clarity and coordinated with product and engineering counterparts accordingly. 
  2. Enabled team members to run initiatives independently.
  3. Provided a safe space for the team to voice their concerns.

Design and product strategy

I was responsible for setting up the design strategy and worked closely with product management counterparts to develop the product strategy and roadmap. 

To that end, I worked on the following initiatives

  1. Figuring out gaps in the product from user research, competitive/market research, sales wins/losses, etc., along with product management and leadership teams. 
  2. Prioritizing initiatives based on their impact on key business metrics, existing product gaps, and new opportunities.
  3. Creating product design and user research roadmaps. 
  4. Breaking down large initiatives into multiple projects and features and prioritizing them.

Design operations (DesignOps)

I was responsible for managing design operations for multiple design initiatives for the team. Worked closely with product management and engineering teams to manage timelines and ensured design and research projects went through enough feedback cycles and were delivered on time with the right quality. In case of capacity problems, I was also responsible for reorganizing projects and hiring. I worked closely with leadership and HR teams on capacity planning, creating job descriptions, interviewing candidates, and evaluation. Have also been involved in hiring for the product management teams. 

Impact

  1. Enabled fresh graduates and experienced team members to deliver multiple large projects within and often even before schedule. 
  2. Ensured all projects got enough feedback before going into development. 
  3. However, not all projects get done on time. Recalibrated when the team needed additional time or clarity, needed more fidelity, and coordinated with product and engineering counterparts to manage the change accordingly. 
  4. Streamlined hiring and capacity planning in collaboration with leadership and HR teams.

Culture

As a senior design team member, I ensured a positive team culture within the design team and cross-functional teams. While building a great culture is always a work in progress, I received recognition for this initiative from multiple team members and leadership. 

 Building a great culture is about small things like celebrating wins, mourning losses together, celebrating personal milestones, reinforcing good behaviors, and sometimes giving harsh feedback when needed – as long as the feedback comes from a place of positive intent to improve the person or the process. It also means encouraging your team to do more than they think is possible, actively caring about their growth, and setting the right example by doing instead of preaching.

I’ve aimed to build a culture of high performance, extreme ownership, a bias for action, and empathy within the team.