On This Episode of No Doubt, Let’s Go!
In this episode between Coach Reggie and Leslie Ogoe, focus on effective program management, design operations, and agility within tech and creative organizations.
We discussed the evolution of program management from advertising to tech, emphasizing the importance of building trust, understanding company culture, and tailoring communication and tools to the needs of different stakeholders.
Leslie highlighted the need for structure that accelerates rather than hinders teams, advocating for trust-building, listening, and collaborative problem-solving over rigid processes.
The discussion covered strategies for bridging communication gaps between design, product, and engineering, prioritizing work through customized dashboards, and using tools like Asana and Claude AI to streamline workflows and personal productivity.
Leslie shared insights on helping teams focus on true needs and objectives by filtering out corporate noise, using tight briefs, and maintaining flexibility through regular check-ins and feedback loops.
The conversation also addressed overcoming perfectionism in design, fostering continuous improvement, and the role of empathy and advocacy in building inclusive communities, such as the Black by Design ERG.
Leslie concluded with advice for designers and creators to persist through challenges by staying focused and resilient, reinforcing the value of progress over perfection and the importance of adapting processes to support both professional and personal growth.
Program Management Evolution and Value
The discussion compared program management in advertising a decade ago to its current state in tech companies like LinkedIn, Google, and Spotify. In advertising, teams served a single client and could experiment with new processes for several weeks without much resistance. Now, the value of program management depends on whether a company is led by engineering, design, or product, making the environment more political. Trust and cultural currency are now essential for program managers to be effective, as teams are more likely to challenge new processes if they don’t trust the person introducing them.
Building Structure Without Red Tape
Effective program management should provide structure to help teams move faster, not slow them down with administrative overhead. Instead of relying on spreadsheets and rigid processes, Leslie focuses on building trust and listening to team needs. Trust enables smoother adoption of processes, and listening helps identify underlying tensions. Leslie advocates for starting with trust, then listening, and only then introducing structure tailored to the team’s needs.
Bridging Gaps Between Teams
When communication breaks down between design, product, and engineering, Leslie’s first step is to frame challenges as shared opportunities, using inclusive language like ‘our opportunity.’
He avoids finger-pointing and encourages collective ownership, asking open-ended questions to help people dream beyond constraints and fostering collaboration and buy-in. This approach shifts the focus from blame to joint problem-solving and encourages stakeholders to contribute ideas.
Portfolio Visibility, Intake, and Prioritization
Leslie helps leaders and teams manage multiple concurrent projects by tailoring information delivery to the recipient’s preferences, creating dashboards with only the necessary information for each audience. Tools like Asana are used to provide both detailed and summary dashboards.
He blocks and tackles for designers, ensuring they get what they need quickly and aren’t bogged down by unnecessary details. The intake process is streamlined to match designers’ workflows, and Leslie emphasizes the importance of understanding how leaders process information to avoid overwhelming them.
Use of AI Tools (Claude) in Workflow and Personal Life
Leslie uses Claude, a generative AI tool, for meeting notes, scheduling, and as a tutor for his MSW studies. He uploads documents and has Claude generate actionable outputs, such as a scholarship calendar that updates weekly and sends reminders.
He values AI for providing next steps and breaking down complex topics, especially when he feels unsure or shy about asking questions. He is cautious about connecting AI to too many external sources, preferring to maintain control over his data.
Personal Development and Career Transition (MSW Studies)
Leslie is pursuing a Master of Social Work (MSW) as his ‘third act’ after careers in production and program management.
He wants to leverage his diverse experiences, including his corporate background and African family heritage, to help others by listening and providing support.
This transition is motivated by a desire to be proactive and make a direct impact, drawing on lessons learned from his previous roles.
Scaling Design Teams and Encouraging Early Feedback
To help design teams deliver at scale, Leslie encourages designers to share imperfect work early to get feedback. He advises designers to leave ‘holes’ in their projects for others to add value and to provide context for their decisions, recognizing that design leaders may lack day-to-day context.
This approach fosters collaboration, ensures alignment with company goals, and helps designers feel supported rather than isolated.
Clarifying Team Needs and Objectives Amid Corporate Noise
Leslie helps teams identify their true needs and objectives by asking ‘why’ and ensuring they feel comfortable questioning processes. He uses a tight intake brief to focus teams and acts as a broker between stakeholders and designers, preventing stakeholders from bypassing necessary structure.
He stresses that organization and process should not be seen as negative, but as tools to provide consistency while allowing for flexibility when needed.
Agility, Feedback Loops, and Pivoting
Leslie and Reggie discuss the importance of agility, planning for change, and feedback loops. Leslie uses 20% check-ins to assess project direction and avoid over-investment before full commitment.
He emphasizes the need to balance being a good partner with setting boundaries, knowing when to say no, and being willing to pivot without remorse. This approach helps teams adapt quickly and avoid wasted effort.
Applying Professional Skills to Personal Projects
Leslie applies his program management skills to his passion project, Notes of the National, a community centered on wine, music, and travel. He and his wife run it like a small agency, with check-ins, weekly plans, and structured programming.
They use tools like Google Maps to organize events and have pivoted their approach over time, shifting from parties to brunches and tastings as their interests and capacity changed. This demonstrates the transferability of professional skills to personal endeavors.
Work-Life Balance and Capacity Management
Leslie manages his capacity using a ‘nutrition wheel’ or pie chart model, allocating 100% of his time across different activities. As priorities shift, such as when school is in session, he adjusts the size of each ‘slice’ rather than removing activities entirely.
This flexible approach helps him maintain balance and avoid overcommitting, recognizing that he cannot do more than 100%.
Common Roadblocks for Design Teams and Overcoming Perfectionism
Leslie identifies perfectionism as a major roadblock for design teams. He advises teams not to seek perfection but to seek understanding, encouraging them to share work early, collaborate with stakeholders, and accept that mistakes are part of the process. He stresses that working in silos is counterproductive and that progress comes from iterative feedback and learning from failures, which can lead to greater long-term success.
Building Inclusive Communities (Black by Design ERG)
Leslie discusses co-leading the Black by Design ERG at LinkedIn, emphasizing empathy, listening, and understanding the unique challenges faced by underrepresented groups. The group supports both individual and collective needs, while also demonstrating business value to the company. Building an inclusive community requires balancing social impact with organizational goals and ensuring the group has a tangible impact.
Advice for Designers and Accidental Agilists
Leslie’s advice to designers and accidental agilists is to ‘keep low, stay firing’—focus on your craft, persist through challenges, and accept that the journey may not be smooth. He encourages resilience, continuous improvement, and not being discouraged by setbacks or opposition. The key is to keep moving forward, stay grounded, and maintain a commitment to learning and progress.
