Inside the Messy Middle: Leadership Lessons from the Field

11 Leading with Context, Credibility, and Humanity with Sahana Shenoy

Meet Sahana Shenoy, a highly competent Product Management and Technical Program Management Leader with nearly two decades of cross-functional leadership experience. Sahana has led large scale initiatives across e-commerce, supply chain, healthcare, among some of the industries, and she's overseen multi-billion-dollar portfolios and helped build platforms that are used by hundreds of millions of people globally.
Top five takeaways from this remarkably insightful conversation:
1. People over Process.
Sahana shares how a team that hadn’t shipped code for a year wasn’t suffering from a technical gap but a trust breakdown:
“The team had slowly… stopped trusting each other… conversations had become more about defending positions than solving larger organizational problems.” She rebuilt trust first—then delivery automatically followed!
2. Small actions make a big difference.
Her leadership shift came from showing up repeatedly and reliably:
"Being present when there is a problem, being there for your team, showing up consistently and, making sure you're inclusive consistently. All of these small consistent actions actually made the difference..."
3. Expect high standards, but with humanity.
Her identity and caregiving experiences expanded her leadership lens:
“Best leaders today… are a combination of high standards with humanity.” Ask before assuming. Context matters.
4. Making rationale travel as fast as the decisions they support.
Global teams often receive decisions without the “why”:
“Decisions travel pretty quickly… but the rationale… doesn’t travel along with it.” Middle managers carry the invisible labor of translating in both directions...."
5. Using AI as a thought partner, not a replacement.
AI accelerates prototyping and thinking, but critical thinking and judgment still sits with humans:
“AI is only as effective as the human expertise and data behind it.” She encourages teams to use AI to amplify thinking, not replace it."
 
Connect with Sahana on LinkedIn - https://www.linkedin.com/in/sahana-s-05bb9517/ 
Subscribe to Sahana's Substack - https://substack.com/@sahana722010 
Connect with me on LinkedIn - https://www.linkedin.com/in/meenakshi-iyer-northstar/ 
Learn more about NorthStar Solutions and Services LLC - https://www.northstaratwork.com/ 

10 Elevating Purpose and Humanizing Technology with Seema Sreenivas

Meet Seema Sreenivas, a dynamic program management leader with more than a decade of cross-functional leadership experience in the Healthcare policy and systems space in the public sector in the US. Her career has been centered on improving operations, driving meaningful outcomes, and leading teams through change with clarity and purpose. She brings a thoughtful perspective on leadership, growth, and how to create lasting impact within organizations. 
Five key takeaways from this refreshing conversation centered on people, purpose, and human-centered tech:
1. Leading through lived experienceSeema’s leadership was profoundly shaped by her parents’ ESRD journeys. Their experiences pulled her toward mission-driven work in healthcare and grounded her leadership in empathy, service, and purpose.
2. Leading with empathy Seema's upbringing as a first‑generation Indian American gave her a unique lens on language, culture, and belonging. She leads with grace for those whose first language isn’t English and brings compassion into cross-cultural, multi-generational environments.
3. Humanizing technology to inspire dev teamsOne of the most powerful practices she introduced was bringing patients and nurses into quarterly PI events—helping developers reconnect with the mission behind their work. This shifted morale, motivation, and clarity across teams.
4. Navigating red tape with purposeIn public-sector environments, progress can be slow. Seema kept teams energized by anchoring them to the mission and focusing on consistent delivery, cost savings, and stakeholder alignment.
5. Staying open-minded as a leadership practiceHer biggest advice for middle managers: enter new environments with openness, curiosity, and a willingness to observe before taking action or initiating change.
 
Connect with Seema on LinkedIn - https://www.linkedin.com/in/seema-sreenivas-25407a47/ 
Connect with me on LinkedIn - https://www.linkedin.com/in/meenakshi-iyer-northstar/ 
Learn more about NorthStar Solutions and Services LLC - https://www.northstaratwork.com/ 

09 Building Credibility with Clarity & Commitment with Abhinav Roy

Meet Abhinav Roy, an accomplished portfolio delivery lead with international experience in the banking industry and financial services industry, helping teams and organizations build the capability, clarity, and confidence to deliver at scale. With his support, they learn how to shift perspectives, embrace change, and create meaningful transformation. His global experience spans India, Europe, the US, and Australia, and he wears many hats - Enterprise Agile Coach, Leadership Coach, and a Certified Yoga Instructor!
4 key highlights in this deeply honest and reflective conversation: 
1. Vulnerability is a leadership accelerator, not a liability.
Abhinav’s turning point came when a team member told him he appeared “very robotic” and overly certain. That moment pushed him to show more of his human side — honesty, imperfection, presence. This experience reshaped his coaching style into what he calls hands‑on leadership — mentoring, modeling, and being human alongside his teams.
2. Culture and identity shape how we lead — and how we’re received.
Growing up in a disciplined academic family in Bihar, India, and later working across India, Europe, the US, and Australia taught Abhinav to deeply respect context. He learned to interpret directness, silence, disagreement, and feedback through a cultural lens — a skill that makes cross‑border collaboration far more effective.
3. Middle managers carry invisible emotional labor — and credibility is the antidote.
Abhinav names the unique tension of the messy middle: “Absorb the ambiguity from the top and the frustration from the bottom.” This constant orbiting around others can erode one’s sense of center. His antidote: build credibility through clarity, commitment, and doing the right work even when no one is watching.
4. AI becomes empowering when you engage with it.
Abhinav moved from skepticism to hands‑on experimentation, building and breaking his own AI app to truly learn how it works. As he put it, “I built it, deployed it, broke it, built it, deployed it… the best way for me to learn AI was to do it myself.” His biggest insight: AI isn’t the threat; “staying incurious… that’s the threat.”
 
Connect with Abhinav on LinkedIn - https://www.linkedin.com/in/abhinavroy19/ or at https://www.perspectivecatalyst.co/ 
Connect with me on LinkedIn - https://www.linkedin.com/in/meenakshi-iyer-northstar/ 
Learn more about NorthStar Solutions and Services LLC - https://www.northstaratwork.com/ 

08 Leading with Intention and Integrity with Tezeswari (Tez) Nettimi

Meet Tezeswari Nettimi, who goes by Tez, an award-winning technology and transformation leader with experience in driving IT modernization and strategic program delivery. A parent of two active teenagers, she is passionate about creating community impact through leadership, innovation, and mentorship. This straight-from-the heart conversation highlighted Tez's values-based, servant leadership and her commitment to leading with intention and integrity.
Here are three key takeaways from this amazing conversation:
1. Lead with intention, not intensity.Tez emphasizes that sustainable leadership comes from clarity, prioritization, and intentionality, not just working harder or putting in more hours. As she put it, “Sustainability and performance comes not through intensity. It’s about longevity,” a reminder that boundaries and self‑compassion are essential for leaders and their teams.
2. Empower teams instead of having all the answers.A defining lesson from her early leadership experience: you don’t need to be the expert in everything. Your job is to bring the right people together, create psychological safety, and enable their strengths. True leadership is in being that enabler of collaboration and outcomes.
3. Consistency builds trust, and trust builds influence.As organizations get flatter and AI-driven, influence matters more than authority. Tez highlights that clear communication, active listening, and consistent values‑based behavior build trust—and trust is what gives leaders real influence across cultures, generations, and hierarchies.
 
Connect with Tez on LinkedIn - https://www.linkedin.com/in/tnettimi/ 
Connect with me on LinkedIn - https://www.linkedin.com/in/meenakshi-iyer-northstar/ 
Learn more about NorthStar Solutions and Services LLC - https://www.northstaratwork.com/ 

07 Looking back to Pause and Reflect with Host, Meenakshi Iyer

What our six guests have taught us about Humanity, AI, and Leading at the Messy Middle
In this special retrospective episode, I, your host, Meenakshi Iyer, am inviting you to pause and reflect, to take in, and synthesize the biggest insights from our first six conversations on this podcast. In the American philosopher John Dewey's words, "We do not learn from experience...we learn from reflecting on experience."
This episode weaves together the most powerful themes shared by our six previous guests: Padmini Nidumolu, Meshia Adams, Shreya Kaushik, Dr. Elena Bozylinski, Leanna Holmquist, and Kristján G. Mathiesen.
The bottom line? The messy middle is where leadership is being redefined — and its leaders are rising to meet the moment. In an AI‑enabled world, it’s these leaders in middle management who are the most equipped to connect strategy, context, people, and performance.
Six recurring themes:
the invisible emotional labor middle leaders carry every day
why empathy, trust, and authenticity are becoming strategic leadership skills
how clarity, context, and communication shape team culture
what AI is changing — and what it never will
the role of identity, culture, and lived experience in how we lead
the courage it takes to grow, evolve, and lead through ambiguity
🎧 Listen in for a thoughtful and inspiring look back — and a powerful reminder the messy middle is where true leadership is!
 
Connect with me on LinkedIn - https://www.linkedin.com/in/meenakshi-iyer-northstar/ 
Learn more about NorthStar Solutions and Services LLC - https://www.northstaratwork.com/ 

06 Leading With Your Whole Self with Kristjan Mathiesen

Meet Kristján G. Mathiesen (KGM), an "Icelander living in the States", an innovative tech leader who prioritizes being genuinely human in this AI-first world! He leads with humor, empathy, and curiosity to connect with people and help them feel confident in technology. His love for teamwork shapes how he shows up at work and in life. These are 3 of the many remarkable Kristján shares in his usual unassuming and authentic manner:
1. Being genuinely human is a leadership superpower.
Kristján’s biggest turning point was realizing he couldn’t “play the manager.” The moment he stopped performing and started showing up as his real, imperfect, human self, trust deepened and relationships transformed.
2. Context, culture, and connection shape how people work.
Having lived across Iceland, the UK, and the US, Kristján brings wide‑angle empathy to global teams. He sees how culture, identity, and background influence expectations—and why genuine curiosity and connection matter more than ever.
3. Empathy takes energy - and it makes all the difference!
Being human at work takes energy. Emotional presence doesn’t clock out at 5 PM. But when teams reciprocate with trust, humor, and openness, they create the kind of culture people want to stay in—especially in an AI-driven workplace.
 
Connect with Kristjan - https://www.linkedin.com/in/kristjanmathiesen/ 
Connect with me - https://www.linkedin.com/in/meenakshi-iyer-northstar/ 
Learn more about NorthStar Solutions and Services LLC - Unpacking Leadership™ at the "Messy Middle"

05 'Staying frosty' in the age of AI with Leanna Holmquist

Meet Leanna Holmquist, an intuitive product leader shaping how humans and intelligent systems communicate and is passionate about making AI actually usable by humans. She specializes in AI enablement, product ownership, and NLP behavior modeling, blending technical depth with a sharp instinct for language and user experience. In this powerhouse of an episode,
1. Don’t Let AI “happen to you" - "stay frosty"!
Leanna’s core message is that AI is reshaping work, but leaders - especially in the messy middle - should not be passive recipients of that change. Instead, they should stay curious, experiment thoughtfully, and understand where AI can genuinely help their teams. “Don’t let AI be a thing that happens to you… stay curious, stay frosty.”
2. Middle Managers are more essential than ever; AI doesn’t replace the human layer
Despite headlines predicting the collapse of middle management, Leanna emphasizes that AI cannot replace the human-centered leadership functions that managers provide - psychological safety, context-setting, coaching, and navigating resistance. “Middle managers bring something AI never will… psychological safety… knowing when teams are overwhelmed.”
AI may automate coordination tasks, but the orchestration layer - the glue that turns strategy into outcomes - remains deeply human.
3. Successful AI adoption is a cultural transformation, not a technical one
Leanna stresses that most digital transformations fail not because of technology, but because of people. AI adoption requires clear guardrails, ongoing enablement, and constant feedback loops - not just tool access. “Technology alone does not transform organizations - people do.”
Connect with Leanna on LinkedIn
Connect with me on LinkedIn
Learn more about NorthStar Solutions and Services LLC
 

04 Being a lifelong learner with Dr. Elena Bozylinksi

Meet Dr. Elena Bozylinski, a highly accomplished, cross-functional Program Management Leader, who is the epitome of leader being a lifelong learner. In this episode, Elena shares how she went from technical roles to program leadership, revealing how continuous learning, and leading with emotional intelligence and influence, have shaped her career trajectory. These are three main takeaways from this conversation:
1. Lifelong learning is a career accelerant — especially when done intentionally
Elena's journey from technical roles to program leadership, an MBA, a PMP, and ultimately an EdD (while raising two kids) reinforces a powerful message: continuous, structured learning opens doors. It helped her break ceilings, expand her career, and even step into teaching. Elena's story shows us how continuous learning is integral to career advancement and enrichment.
2. Leading in the “messy middle” is emotional labor, not just task-related labor
Elena surfaces what most project and program managers feel but rarely name: the invisible work of coaching leaders, smoothing cross‑functional friction, and navigating politics without formal authority. Influence, trust, and emotional intelligence are the real engines of delivery.
3. AI is here — but humans stay in the loop
Elena’s stance on AI is pragmatic: learn about AI from credible sources, follow discerning thought leaders, and stay curious. Don’t outsource your own judgment. Our job as leaders in middle management is to integrate AI thoughtfully and while keeping people and context at the center.
 

03 Isolating Signal from Noise with Shreya Kaushik

Meet Shreya Kaushik - a software engineer at heart, a working parent to a five‑year‑old, and a leader in middle management, navigating the challenge of isolating signal from noise, whether in corporate dynamics or the fast‑moving world of AI. In this episode, she shares grounded, insightful reflections in her trademark matter‑of‑fact style.
1. The “messy middle” is defined by invisible labor and competing pressures Shreya highlights what senior leaders often miss: mid‑level managers shoulder heavy operational work, emotional labor, and the constant task of translating expectations across the org. They juggle their own need for clarity and purpose alongside that of their teams, all while context‑switching and striving to lead with empathy.
2. Identity work and mentorship reshape how leaders show up
Her experience in the Building My Runway program helped her release the pressure to influence and instead lead with self‑awareness, empathy, and grounded confidence. She now sees leadership less as “proving yourself” and more as “showing up with intention,” especially as a working parent who understands the emotional realities others carry.
3. Adaptability is the new leadership currency — especially in an AI‑driven world
Moving across different cities in India, experiencing different languages and cultures, while growing up, built a resilience that now helps Shreya navigate rapid shifts in an AI-first workplace. That adaptability, she notes, is becoming essential for leaders at every level.
Connect with Shreya on LinkedIn
Connect with me on LinkedIn
Learn more about NorthStar Solutions and Services LLC

02 Holding it all together with Artemeshia Adams

Meet Artemshia "Meshia" Adams, a highly-accomplished People Ops and HR Leader! In this episode Meshia drops real‑world wisdom on authenticity, emotional labor, and modern, global leadership - showing how empathy, equity, and trust can reshape teams, cultures, and careers, especially in today's AI-enabled workplace. 
1. Empathy and authenticity are essential leadership tools.
Being misunderstood—especially by controlling personalities—pushed Meshia to see through others' “self‑intoxication,” and lead with empathy, and stay real while navigating identity, code‑switching, and inclusive leadership.
2. Middle managers carry heavy, invisible emotional labor.
She spotlights the burden of holding sensitive information, shielding teams during change, and ensuring “schedule equity” so global collaboration doesn’t unfairly strain certain regions or individuals.
3. Influence grows through trust, adaptive communication, and intentional AI use.
Meshia builds influence through relationships, tailors communication across generations, uses AI for learning and ideation, and challenges leaders to rethink outdated definitions of what “good” looks like.
Connect with Meshia on LinkedIn
Connect with me on LinkedIn
Learn more about NorthStar Solutions and Services LLC