Navigating Major Programmes

How do you champion an authentic leadership style in a sector that’s slow to adapt to change? Infrastructure Ontario President and CEO Angela Clayton has traversed this career journey by building a robust network while maintaining a deep dedication to continuing education and an iron-clad work ethic. She joins Riccardo and Shormila for a candid conversation about career growth and what it means (and doesn’t mean) to be a woman in leadership in this male-dominated industry. 

Angela has seen the benefits of prioritizing community and collaboration in many facets of her career. She reflects on her history of learning on the job and how employer-supported professional development has transformed her trajectory. She and the hosts dig into the practical realities of leadership in major programmes and the mistaken assumption that great individual contributors naturally become great leaders. She also speaks frankly about being the only woman in the room, and how essential trust in hard-earned champions, while it doesn’t negate impostor syndrome, certainly puts it into perspective.

The discussion also explores IO’s evolution over time, Angela’s approach to her transition to CEO, and her future plans for pursuing more impact-driven work. Discover this successful industry innovator’s take on the shifts leaders must make as they navigate new roles and her thoughtful advice for women aspiring to excel in infrastructure.

Key takeaways:

• How a strong network creates career opportunities, and why getting the job is only the beginning;
• The pitfall of assuming technical excellence translates into project and people leadership;
• How to think about “diversity hires” without tokenism—and what real sponsorship looks like;
• The culture and mandate evolution of Infrastructure Ontario;
• The mental shift required when moving from PM issues management to CEO vision and culture development.

Quote:

“[Former peers who now report to me are] some of my most trusted advisors. They have the history of the organization, and it’s so valuable to have that institutional knowledge.” - Angela Clayton

The conversation doesn’t stop here—connect and converse with our community via LinkedIn:

• Follow Navigating Major Programmes: https://www.linkedin.com/company/navigating-major-programmes/
• Read Riccardo’s latest at www.riccardocosentino.com
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• Follow Shormila Chatterjee: https://www.linkedin.com/in/shormilac/
• Follow Angela Clayton: https://www.linkedin.com/in/angelafclayton/ 

To what extent is leadership success contingent on specific industry expertise? Marcia Medrano began her career in buildings, not transit. Yet, her experience developing and guiding teams, budgets, and procurement projects is proof that people management is not bound by sector—as long as you’re willing to make the most of the experts around you.

In this episode of Master Builder, Riccardo and Shormila sit down with the Executive Vice President of Capital Projects at Metrolinx to explore what it takes to rise to leadership without pretending you’re an expert in everything. Marcia traces her path from architecture and vertical infrastructure to transit delivery and the core lesson that’s shaped her career: big infrastructure delivery is fundamentally about people—building trust, aligning teams, and getting things done. Marcia doesn’t hesitate to push back against conventions and assumptions. Choosing to leverage her parallel expertise rather than be daunted by a new sector, she often asks, “Why not?” Over and over, she sees the question unlock progress in new and exciting approaches for the infrastructure industry.

The three experts hold a candid discussion about impostor syndrome and women in leadership, the superiority of alliance projects, and the importance of transparency on all sides of a major programme. They call out the danger of blindly following rigid structures and the shifting of the status quo as the Canadian infrastructure industry dives into ever larger and more ambitious projects. Throughout it all, Marcia champions a new understanding of steering the ship, and all the assets that come along with “leading like a woman.”

Key takeaways

• The relationship-building and human connection that underpin infrastructure delivery success;
• How transparency drives success, however varied a team’s expertise and experience; 
• Why incentivizing on-the-ground solutions and cooperation outweighs claims that stall progress at every turn;
• The importance of updated governance and project-wide empowerment on the owner side of collaborative contracts;
• What’s poised to change for women in infrastructure leadership.

Quote

“Challenging our own biases of the things that we know and the things that we don’t know is part of challenging the status quo.” - Marcia Medrano

The conversation doesn’t stop here—connect and converse with our community via LinkedIn:

• Navigating Major Programmes, Season 2 Episode 6 with Lawrence Rowland: https://navigatingmajorprogrammes.transistor.fm/s2/23 
• Follow Navigating Major Programmes: https://www.linkedin.com/company/navigating-major-programmes/
• Read Riccardo’s latest at www.riccardocosentino.com
• Follow Riccardo Cosentino: https://www.linkedin.com/in/cosentinoriccardo/
• Follow Marcia Medrano: https://www.linkedin.com/in/marcia-medrano-34a2962a/ 

How is AI poised to transform our workflows and working relationships in the coming months and years? There’s no question that large language models have had an enormous impact on our lives—and most of us have barely scratches the surface of what is possible with these powerful tools. In this episode, Lawrence Rowland joins Riccardo to unpack all that’s changed since his last appearance on the podcast in 2024. Lawrence is a veteran of project management with a laser focus on AI transformation and strategy. Together, he and Riccardo explore numerous angles of working with these inhuman (but increasingly capable) agents on everything from research to reporting to improving coworker interaction.

The conversation stays grounded in practice: the pair drills down on the massive shifts in AI in merely months, why token budgets matter, and the growing ability of programs to self-prompt and think outside the boxes of our requests. Lawrence shares the fascinating way he uses AI—to synthesize methodologies, generate playbooks, pressure-test thinking, and reveal tacit insights missing from current project narratives.

The two AI buffs also confront the human side of the transition, including where accountability falls when work is partially automated and what “transformative AI” might mean for careers and organizations. Less about hype and more about adaptation, Lawrence and Riccardo’s conversation hones in the theory on constraints. They remove the rose-tinted glasses and speak to redesigning workflows based on a practical, vital question: where is AI genuinely better, and where are humans still essential?

Key Takeaways:

• How agentic AI shifts work from prompting to task-level execution;
• The reasoning capacity of AI tools based on token budgets and model capability;
• The concept of underwriting in retaining human liability in AI-dominated work
• How theory of constraints and bottleneck thinking helps decide what to automate vs keep human;
• How AI can improve communication and project alignment by translating complex work for different audiences.

Quote:

“Either you’re checking the AI or the AI is checking you, and getting used to that will set you up for the new economy.” - Lawrence Rowland

The conversation doesn’t stop here—connect and converse with our community via LinkedIn:

• Navigating Major Programmes, Season 2 Episode 6 with Lawrence Rowland: https://navigatingmajorprogrammes.transistor.fm/s2/23
• NBER “Economics of Transformative AI Workshop, Fall 2025”: https://www.nber.org/conferences/economics-transformative-ai-workshop-fall-2025
• arXiv “Some Simple Economics of AGI” by Christian Catalini, Xiang Hui, Jane Wu: https://arxiv.org/abs/2602.20946
• SSRN PDF “Some Simple Economics of AGI”: https://papers.ssrn.com/sol3/Delivery.cfm/6298838.pdf?abstractid=6298838&mirid=1
• Follow Navigating Major Programmes: https://www.linkedin.com/company/navigating-major-programmes/
• Read Riccardo’s latest at www.riccardocosentino.com
• Follow Riccardo Cosentino: https://www.linkedin.com/in/cosentinoriccardo/
• Follow Lawrence Rowland: https://www.linkedin.com/in/lawrencerowland/ 

What can a long career in urban transit reveal about collaboration, contracts, and system integration? In this episode, Evgenia and Shormila guide a wide-ranging conversation with transit veteran Ron Aitken. The discussion ties together his nearly five decades of experience in Canadian and international infrastructure projects.

Ron is an expert in what makes complex urban transit work: clarity of requirements, disciplined change control, and the relationships and experience on both sides of the contract. Examples from Vancouver and abroad illustrate the outcomes of effective collaboration, a concept that existed (and succeeded) long before it was being written into the alliance and collaborative contracts presently in vogue. Risk balance, project definition, and synergy have always impacted major programmes.

The industry is evolving, and this conversation doesn’t shy away from exploring that. Owners are taking back certain systems integration responsibilities and accepting more risk. Interface and requirements management are becoming more essential, and the adoption of new AI tools is transforming scheduling and delivery across the board. Throughout their broad dialogue, Ron reinforces a simple but oft-overlooked fact: delivery models matter, but the culture and the people matter more.

Key Takeaways:

• Why procurement models don’t guarantee success;
• How early automated transit programs forced teams to build delivery capability, not just technology;
• Why trust and respect must be built quickly—and why experience on both sides of the contract is non-negotiable;
• How systems integration drives risk in urban transit—and why “systems first” scheduling and access planning matters
• The approaches that can mitigate and even abolish claims in major projects.

Quote:

“I recommend to people just starting their career: get yourself a helmet and boots and find your way out onto the site” - Ron Aitken

The conversation doesn’t stop here—connect and converse with our community via LinkedIn:

• Follow Navigating Major Programmes: https://www.linkedin.com/company/navigating-major-programmes/
• Read Riccardo’s latest at www.riccardocosentino.com
• Follow Shormila Chatterjee: https://www.linkedin.com/in/shormilac/
• Follow Evgenia Jilina: https://www.linkedin.com/in/ejilina/ 
• Follow Ron Aitken: https://www.linkedin.com/in/ron-aitken-a9275468/ 

What would it take to prioritize major programme outcomes over more familiar factors like price and procedural fairness? This is the question posed by Peter Weltman, the guest host on this Uncharted Conversations episode. Peter notes that Canada’s infrastructure industry is struggling to maintain what it already has, much less build what it needs next. Iterating is likely to fail, so what are the alternatives?

Co-hosts Shormila, David, Melissa, and Riccardo quickly surface the real tension: “outcomes” are often harder to define, measure, and defend than cost—and public procurement systems are deliberately built for political optics and to avoid the perception of discretionary decision-making. Together, the panel explores why technical merit often fails to meaningfully influence selection and why innovation tends to get squeezed out when projects are seen as fixed scope from the beginning.

From there, the conversation widens beyond RFP mechanics into bigger levers: risk appetite for unsolicited proposals, whether Canada needs an “infrastructure venture fund” for ideas, and the value of portfolio thinking. Canada may not be ready to blow up the whole system. However, examples—including new financing entities and development-partner models—both within and beyond infrastructure highlight alternative pathways that are already emerging.

Key Takeaways

• The problem with reducing “value for money” to competitive pricing in major projects;
• The difficulty in defining “outcome-based procurement” beyond cost;
• How better technical discrimination can prevent price from dominating “best value” selections;
• The potential for more rigorous schedule and delivery certainty evaluation through risk analysis;
• How entities might catalyze more innovative deal structures than classic linear procurements.

Quote:

“How do we create the incentives to build the capacity to do things in a more innovative way, realize more budget, more benefits?” - Peter Weltman

The conversation doesn’t stop here—connect and converse with our community via LinkedIn:

• Follow Navigating Major Programmes: https://www.linkedin.com/company/navigating-major-programmes/
• Read Riccardo’s latest at www.riccardocosentino.com
• Follow Riccardo Cosentino: https://www.linkedin.com/in/cosentinoriccardo/
• Follow Shormila Chatterjee: https://www.linkedin.com/in/shormilac/
• Follow Melissa Di Marco: https://www.linkedin.com/in/melissa-di-marco/
• Follow Peter Weltman: https://www.linkedin.com/in/peter-weltman/

Behind every major programme is a project manager—but how do they get there? For a practical and informative conversation on the current PM job market, Riccardo sits down with Mukhtar Kadiri, whose extensive project management experience has culminated in his work as a Program Director and Career Coach, where he helps project management professionals compete for high-compensation roles in the industry.

Though the hiring environment for PMs today varies by niche and region, competition is heavy across the board, and Mukhtar recommends all job searchers have a strategy—that they approach the search like a project in itself. He and Riccardo explore how candidates can use AI to make the most of their application process and the essential steps to get a foot in the door. Mukhtar has tips for employers and hiring managers, as well.

Job searching is a skill, Mukhtar stresses, and this episode offers actionable ideas of how to approach the work intentionally. Specific and backed by plenty of real-world experience, Muhktar’s perspective is essential listening for employees and employers alike, whether they’re currently on the job hunt or planning to begin searching in the future.

Key Takeaways

• How today’s PM job market is changing competition, screening, and expectations;
• The five-part strategy, from application to highest offer, that hones your job search skills;
• Why you need to pitch differently to recruiters and hiring managers;
• How to utilize AI beyond asking it to write your cover letter for you;
• The traits employers should emphasize to win the best candidate.

Quote

“Job searching is a skill” - Mukhtar Kadiri

The conversation doesn’t stop here—connect and converse with our community via LinkedIn:

• Follow Navigating Major Programmes: https://www.linkedin.com/company/navigating-major-programmes/
• Read Riccardo’s latest at www.riccardocosentino.com
• Follow Riccardo Cosentino: https://www.linkedin.com/in/cosentinoriccardo/
• Follow Mukhtar Kadiri at https://www.linkedin.com/in/m-kadiri/ 

What happens behind the scenes before a project bid is even accepted? The delivery outcome component of major programmes is fascinating, but a lot occurs long before procurement, design, and development get underway. Taking a step back, and behind the curtain, Riccardo, Shormila, and special co-host Evgenia Jilina, Colliers’ Transit Regional Sector Director, dive deep into what happens before the Request for Proposal is published. 

The three infrastructure professionals explore the competitive, resource-intensive work that happens upstream: strategic positioning, RFQs and RFPs, partnership decisions, and the internal calculus of whether a proposal is worth the investment of pursuing at all. They break down why “winning” a project is rarely about a single submission moment. Preparing a proposal can cost millions, pull top talent off active work for months, and take months or even years—a lengthy span of time where assumptions, teams, and even the market can change. 

They make the case that capture planning is so much more than paperwork—it’s the training plan behind the goal: the structure that helps organizations choose which opportunities to chase and show up with the right partners and narrative when it counts. Together, the panel tackles the uncomfortable tension at the heart of public procurement. It’s a system designed to prevent influence, yet meaningful early interactions help clients clarify needs and bidders understand the real problem. In the end, a strategic but authentic engagement approach inevitably weighs into the final decision. Real success is so much more than a lucrative “win”: it’s a mutually beneficial relationship where client, bidder, and the public recipients of the infrastructure all triumph. 

Key Takeaways: 

• Why capture planning is essential to success, not a waste of time and money;
• How organizations decide which pursuits are worth prep that costs millions, months, and their best players;
• What successful early engagement looks like before an RFQ or RFP is issued;
• Why early conversations should be reframed as “engagement” rather than “influencing”;
• How to build bid teams around strengths and gaps instead of searching for a unicorn.

Quote:

“The stakes are high…you’re expected from day one to start on a project that’s bigger than the GDP of some small countries.” - Shormila Charterjee

The conversation doesn’t stop here—connect and converse with our community via LinkedIn:

• Follow Navigating Major Programmes: https://www.linkedin.com/company/navigating-major-programmes/
• Read Riccardo’s latest at www.riccardocosentino.com
• Follow Riccardo Cosentino: https://www.linkedin.com/in/cosentinoriccardo/
• Follow Shormila Chatterjee: https://www.linkedin.com/in/shormilac/
• Follow Evgenia Jilina: https://www.linkedin.com/in/ejilina/  

What does it take to become a celebrated leader in infrastructure? With more than four decades of experience in the public and private sectors, Bruce McCuaig is ideally suited to answer this complex question. He joins Riccardo to reflect on leadership, delivery, and building major programmes that “matter now and one hundred years from now.”

Bruce shares what has shaped his philosophy: an enduring enthusiasm for the legacy of transportation projects, a belief in multidisciplinary teamwork, and a practical approach to collaborative management of risk. He breaks down key qualities of senior leadership: listening and guiding, not seizing control and credit. 

Riccardo and Bruce’s conversation explores the recent shift in Canada toward alliance delivery models. True to his leadership style, Bruce argues that while a broad toolkit of procurement and contracting approaches is useful, collaboration is essential to every successful project, whatever the model. He advocates for giving “fearless advice,” supporting teams with training, and empowering them with trust. In the end, a united approach that puts the public’s best interest front and centre throughout every project ultimately leads to legacies worth building.

Key Takeaways

• How a far-ranging career builds judgment, adaptability, and impact across sectors;
• Why listening is a paramount skill every leader needs to possess;
• How to develop a culture of collaboration on every major project;
• Approaching risk as shared and holistic, rather than “ours vs. theirs;”
• The skills hiring teams should prioritize when filling infrastructure leadership roles

Quote:

“Sometimes, there might be a Eureka moment where the senior leader can say ‘this is the solution!’, but [more often], it’s about helping the team get to a solution.”  - Bruce McCuaig

The conversation doesn’t stop here—connect and converse with our community via LinkedIn:

• Follow Navigating Major Programmes: https://www.linkedin.com/company/navigating-major-programmes/
• Read Riccardo’s latest at www.riccardocosentino.com
• Follow Shormila Chatterjee: https://www.linkedin.com/in/shormilac/
• Follow Bruce McCuaig: https://www.linkedin.com/in/bruce-mccuaig-a1749549/ 

When we view Indigenous communities not as risks to be managed but as partners in building stronger, more sustainable, and more profitable infrastructure projects, what changes? In this episode, Shormila speaks with Matthew Jackson, Hydro One’s Vice President of Indigenous Partnerships. Matthew has spent more than a decade working with the Indigenous communities impacted by energy sector projects. He has seen firsthand how that essential mindset shift can unlock both reconciliation and commercial success. 

Today, more and more organizations are recognizing how vital Indigenous perspectives are to Canada’s infrastructure and economic expansion. Many project failures stem from a broken starting point: the assumption that Indigenous communities are an obstacle rather than rights-holders and value-creators. Transitioning from an oppositional to a partner relationship transforms the timelines, governance, and outcomes of major programmes. Today, Hydro One conducts business with Indigenous communities through a 50/50 equity partnership model—an approach that is rebuilding trust, accelerating decision-making, and reducing environmental and safety impacts.

Shormila and Matthew’s conversation provides practical advice for leaders and teams. While Hydro One’s approach cannot be cut and pasted across the industry, key components of their method are transferrable. Matthew encourages teams to engage early, lead with transparency, and be open to a new way of working. Hydro One’s marked acceleration of green-lighted projects proves the undeniable positive impact of this approach.

Key Takeaways 

• How shifting from “Indigenous risk” to “Indigenous opportunity” changes project outcomes;
• The revenue, work safety, and environmental benefits of being willing to try new approaches;
• The strong Indigenous leadership that led to Hydro One’s success;
• Advice for the new generation of infrastructure professionals pursuing Indigenous relationships;
• The realities of continuing social segregation, even in recent years.

Quote:

“The future of this country is bright if we can embrace that Indigenous opportunity and that Indigenous value.” - Matthew Jackson

The conversation doesn’t stop here—connect and converse with our community via LinkedIn:

• Follow Navigating Major Programmes: https://www.linkedin.com/company/navigating-major-programmes/
• Read Riccardo’s latest at www.riccardocosentino.com
• Follow Shormila Chatterjee: https://www.linkedin.com/in/shormilac/
• Follow Matthew Jackson: https://www.linkedin.com/in/matthew-jackson-957a3b24/ 

How do you know if you’re a good leader? In engineering, like any profession, leadership is so much more than just getting your team to do what they’re told. In this episode of Navigating Major Programmes, Riccardo and Shormila shift their focus to a broader topic: people management. Reaching beyond assessments and management styles, the two long-time leaders unpack their experiences so far. They explore the difference between managing contractors and direct reports, the importance of feedback delivery, and the need for empathy that flows in both directions—up and down the chain of command.

Their conversation winds through self-reflection, organizational structures, and the dearth of training for technical experts thrust into people-management roles as the only path for advancement. Along the way, they discuss how leadership evolves over time (and often through mistakes), why emotional intelligence takes deliberate work, and what makes people management uniquely demanding—especially when you’re delivering hard news while still remembering there’s a human on the other end.

They also dig into the realities of leading within complex systems: how to motivate and retain people across generations, why “tone from the top” shapes culture more than any slogan, and how leaders can adapt their style to the individual in front of them. Therapy, organizational design, and the impact of AI on early-career technical roles all receive their due consideration in a thoughtful, candid episode that recognizes leadership is a lifelong practice—not a just title.

Key takeaways

• The role of empathy in business, relationships, and company culture;
• Why self-reflection is essential to every leader’s development;
• Recognizing when to adhere to and when to throw out the org chart;
• Navigating disconnection from direct reports in enormous corporations;
• The negative impact of distilling rational reasoning as decisions descend from the top.

Quote

“Creating corporate culture…all starts from the leader—the tone from the top.” - Shormilla Chaterjee

The conversation doesn’t stop here—connect and converse with our community via LinkedIn:

• Follow Navigating Major Programmes: https://www.linkedin.com/company/navigating-major-programmes/
• Read Riccardo’s latest at www.riccardocosentino.com
• Follow Shormila Chatterjee: https://www.linkedin.com/in/shormilac/
• Follow Riccardo Cosentino: https://www.linkedin.com/in/cosentinoriccardo/