Guest Bio Boomie Odumade is a senior engineering leader and fractional leader of Engineering who builds high-performing, secure, and resilient engineering organizations. She coaches engineers and engineering leaders, partnering with them to grow their capabilities and reach their goals. Outside of work, she’s active in the tech community, mentors youth, and enjoys salsa dancing, exploring creative adventures with her kid, and building LEGO botanical sets. Episode Summary In this episode, Boomie builds four LEGO models that reveal her philosophy on engineering leadership. From her personal life to the best and worst team experiences, she shares insights on clarity, alignment, and the balancing act CTOs face in today’s rapidly changing tech landscape. The conversation dives deep into managing AI adoption, addressing fear at all organizational levels, and why transparency—balanced appropriately—is critical for team success. Episode Overview In this conversation, Boomie builds four LEGO models that reveal her philosophy on engineering leadership: Personal Introduction Boomie shares her life outside work through physical activity (salsa dancing, half marathons), quality time with her kid, building LEGO botanical sets, and self-care through hiking and theater. Best Team Experience: The Power of Direction Using a boat model, Boomie illustrates what makes great teams work: clarity and direction, leaders who guide without micromanaging, teams aligned and moving together, and celebration of wins that prepare for the next challenge. Worst Team Experience: Misalignment and Roadblocks Her model captures the dysfunction patterns: being pulled in multiple directions with inconsistent information, disempowering micromanagement, “us vs. them” mentality, and the resulting roadblocks and demotivation. The root cause? Lack of shared context, goals, and understanding of how different teams contribute to success. The Silent Objection Problem Boomie reveals a powerful observation: people nod in agreement during meetings, then express their real concerns in smaller groups afterward. Why? Fear of looking less knowledgeable, challenging leadership, or being “that person” who always questions things. The solution is creating explicit safety for questions and concerns. Meeting Structures That Work Two types transform teams when done authentically: retrospectives that create safe spaces for real feelings and accountability for change, and monthly all-hands that reinforce shared goals and create leadership touchpoints. The warning: fake retrospectives that don’t lead to change erode trust. The AI Leadership Challenge Boomie addresses the dual fear problem: executives afraid of falling behind, engineers afraid of losing jobs. Her approach balances showing both capabilities and limitations, presents the full context (including “AI deleted the database” stories), and focuses on business case specific to the team’s actual needs and structure. Addressing Fear at All Levels With engineers, she builds relationship and trust to surface concerns. With leadership, she finds words that show understanding while positioning as a partner focused on shared goals—whether those goals are fear-based or not. The CTO Balancing Act Boomie’s final model captures leadership as four simultaneous balances: business goals vs. people needs (these don’t compete), transparency vs. information control (people imagine the worst without enough info), hands-on involvement vs. delegation (don’t stunt growth), and burnout prevention (taking care of yourself, your people, and the business together). Connect with Boomie * LinkedIn: linkedin.com/in/odumade * Fractional Leadership Services: techbees.me * Slack Communities: Active in SheTO, Rands Leadership Slack, and other tech communities Key Takeaways * Great teams share three essentials: clarity, direction, and alignment * The “us vs. them” dynamic stems from lack of shared context and goals * Silent objections in meetings are more dangerous than voiced concerns * AI adoption requires acknowledging fears at all organizational levels * CTO leadership is fundamentally a balancing act between business, people, and sustainability * Transparency reduces anxiety—when people don’t have information, they imagine the worst * Creating psychological safety for questions prevents surface-level agreement that masks resistance This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit herdingsquirrels.substack.com
