Momentum with Sidekick

Leading With Intention IRL With Dani Rombough

Talent doesn’t grow on its own. It’s shaped by systems, sponsorship, stretch, and leadership behavior. In this episode, Bonny sits down with Dani, a senior leader in planning and inventory management at major Canadian retailers, to explore what talent and leadership development really looks like inside high-performing companies. Building on the ideas from our Talent Trap conversation, we go deeper into what shapes leaders over time, how development happens in practice, and what it takes to build capability at scale. Through candid reflections and practical examples, Dani shares the moments, mentors, and mindset shifts that shaped her and how she now intentionally develops others. Key Takeaways: ➡️ You Are the System. Leadership behavior shapes culture more than strategy. The habits you reinforce, especially under pressure, determine how talent grows. ➡️ Coaching Is a Leadership Discipline. Coaching builds judgment, ownership, and long-term leverage, especially in complex organizations. ➡️ Intentional Energy Builds Sustainable Performance. Protecting high performers, re-engaging plateaued talent, and creating stretch for emerging leaders requires deliberate attention. Listener Challenge: Dani left us with a powerful reminder:every day, the people on your team go home and someone they love may ask them, “How was your day”?  As a leader, youhave more influence than you may realize in shaping how they answer that question. Even on the hard days, how are you creating an environment where people feel challenged, supported, and seen? Now reflect on your own leadership journey: Who invested in you and how are you paying that forward? What habits or behaviors are shaping the experience your team has every day? Because leadership isn’t just measured by results. It’s also reflected in how people carry the day home with them. Tools & Resouces: ➡️ Decide who to Delegate to with the Skill/ Will Matrix [https://www.bitesizelearning.co.uk/resources/skill-will-matrix-leadership-style] ➡️ How to delegate like a CEO [https://www.linkedin.com/posts/annemarie-durbin-162b7a20_delegations-leadership-ceo-activity-7388547049602035712-IVL0/?utm_source=share&utm_medium=member_desktop&rcm=ACoAAAI5E1UBOItSwQ5u8jaWs2TZLPeNPi3mhsw] by Eric Partaker ➡️ Learn about the Leader Member Exchange (LMX) [https://www.masterclass.com/articles/lmx] theory. ➡️ Make your feedback more effective with the SBI- Method [https://www.ccl.org/articles/leading-effectively-articles/closing-the-gap-between-intent-vs-impact-sbii/] ➡️ Avoid defaulting to a Performance Improvement Plan [https://www.forbes.com/advisor/business/performance-improvement-plan/] to quickly Our Guests Dani Rombough  [https://www.linkedin.com/in/daniellerombough/?lipi=urn%3Ali%3Apage%3Ad_flagship3_profile_view_base_contact_details%3BJgJlAA%2FYQmewzRyDKv0aFA%3D%3D]is a retail professional with over 15 years ofexperience in planning and inventory management at major Canadian retailers. With a strong track record of driving results through data-informed decisions and team development, Dani brings both analytical expertise and people-focused leadership. In addition to a successful corporate career, Dani co-founded a math tutoring business operating across multiple cities. Dani is known for an authentic leadership style and a passion for building high-performing teams and fostering growth. Our Co-Hosts Bonny van Rest [https://www.linkedin.com/in/bonnyvr/] Strategic Thinker. Bold Challenger.Grounded Visionary. Bonny is a strategist, facilitator, andco-founder of Sidekick Consulting who believes momentum is built in the middle of the mess. With a background as a CMO and over a decade of experience across startup and corporate environments, she’s known for her sharp thinking, no-nonsense mindset, and ability to turn big ideas into grounded action. Bonny brings a calm presence, clear direction, and just the right amount of edge to move things forward—with intention. Production by PRCPRN Studio [https://prcptn.com/]. Directed by Giuliana DiBonaventura [https://www.linkedin.com/in/giuliana-dibonaventura-148a69132/]

Strategy Is Not the Plan

What if “strategic planning” is actually the reason your strategy isn’t working?   In this episode, Bonny and Nora unpack one of the most widely accepted, and rarely questioned, concepts in business: strategic planning. In this episode, they challenge the assumption that strategy and planning are one and the same and explore how confusing the two can lead to false progress, endless motion, and teams that are busy but not actually winning. Through a candid, real-time conversation, they explore the tension between strategy-first and emergent strategy, and land on a modern approach: treating strategy as a set of intentional, testable hypotheses that evolve through disciplined execution and reflection.    Key Takeaways:   ➡️ Strategy is not the plan: Strategy defines how you believe you’ll win; it’s an intentional set of choices and trade-offs. Planning is a set of activities that gain momentum and test those choices.  ➡️ False progress feels productive: Without clear strategic choices, even the best plans can create motion without direction and success becomes accidental.   ➡️ Emergence requires intention: Strategy can be set upfront or emerge through action, but only becomes real when leaders stop, reflect and choose.   ➡️ Agility is disciplined learning: Adapting isn’t about constant change; it’s about building a cadence to reflect and evolve with intention.     Strategy + Planning + Cadence = Momentum    Listener Challenge:  Before your next planning session, pause and ask:  1️⃣ How do we believe we win?  If it sounds like a list of initiatives, you’re planning not strategizing  2️⃣ What needs to be true for this strategy to work? If you don’t know, you can’t learn  3️⃣ What would make you intentionally change direction? You might pivot too soon, or too late.     This week, don’t start with the plan. Start with the choice.  Resources / Tools: ➡️ Define your winning strategy with Roger Martin’s Choice Cascade [https://rogerlmartin.com/thought-pillars/strategy]   ➡️ Roger Martin on Strategy is not Planning [https://www.youtube.com/watch?v=iuYlGRnC7J8]   ➡️ Browse EOS Worldwide [https://www.eosworldwide.com/accountability-chart-download] for tools like Vision/Traction Organizer (V/TO) [https://www.eosworldwide.com/vto-download], and the 90 day world [https://www.eosworldwide.com/blog/leading-in-a-90-day-world]  ➡️ Download your OKR or OGSM Template [https://www.whatmatters.com/resources/ogsm-vs-okr-whats-the-difference] to help you plan.   ➡️ Assess your Why, How, What with Simon Sinek’s Golden Circle [https://simonsinek.com/golden-circle]    Our Co-Hosts: Bonny van Rest [https://www.linkedin.com/in/bonnyvr/]  Strategic Thinker. Bold Challenger. Grounded Visionary.   Bonny is a strategist, facilitator, and co-founder of Sidekick Consulting who believes momentum is built in the middle of the mess. With a background as a CMO and over a decade of experience across startup and corporate environments, she’s known for her sharp thinking, no-nonsense mindset, and ability to turn big ideas into grounded action. Bonny brings a calm presence, clear direction, and just the right amount of edge to move things forward—with intention.  Nora Griffiths [https://www.linkedin.com/in/nora-griffiths-16676577/]  People-Centered Leader. Strategic Integrator. Dynamic Optimist.   Nora is a purpose-driven leader, facilitator, and co-founder of Sidekick Consulting who believes that bold and meaningful impact is accomplished when done together. With deep roots in business development and operations, she’s known for her people-first lens and her talent for uncovering insights and ideas that translate swiftly into action, driving both people and performance. Nora brings a rare blend of energy, empathy, and clarity to build momentum that truly matters.  Production by PRCPRN Studio [https://prcptn.com/].  Directed by Giuliana DiBonaventura [https://www.linkedin.com/in/giuliana-dibonaventura-148a69132/]

Ownership & Accountability IRL with Carlton Yearwood

In this episode, Bonny and Nora are joined by Carlton Yearwood, whose experience spans Fortune 200 and the Big 4, the US Marines, government, coaching, and ministry contexts. Together, they challenge a common myth: ownership and accountability aren’t performance tools — they’re a cultural operating system.   Why do leaders say they want ownership but design against it? Why is it so seemingly hard to achieve? What does accountability look like in high-stakes, high-performing environments? And how do you balance psychological safety with high standards?  Packed with real-world examples, this episode offers practical, field-tested ways to build cultures where accountability is modeled, ownership is chosen, and leaders stop carrying it all alone.   Key Takeaways:   ➡️️ Stop demanding accountability. Start designing it into how your team works.   ➡️️ Look in the mirror first. Accountability starts with you, not your team.   ➡️️ If you don’t own the why, your team never will. Clarity drives commitment.  ➡️️ Don’t just assign work, foster owners who drive outcomes.  Listener Challenge:  Pick one accountability ritual you want to practice over the next month.  Don’t make it a memo or a big speech. Choose something small, consistent, and actionable that helps build a culture of accountability. Give it four weeks, trust the process and let it take hold. Practice it, model it, and see what happens.  Our Guests   Carlton Yearwood [https://www.linkedin.com/in/cyearwood/]   Carlton brings a uniquely grounded perspective on leadership and culture, shaped by a career that spans the U.S. Marines, community service in New York, senior executive roles at Fortune 200 companies, and leadership at a Big Four firm. As a former Chief Ethics and Diversity Officer and now Senior Partner at True Blue Inclusion, he’s spent decades helping organizations translate values into real, lived culture — advising leaders across industries on what it truly takes to build accountability, ownership, and high-performing teams.  Our Co-Hosts  Bonny van Rest [https://www.linkedin.com/in/bonnyvr/]  Strategic Thinker. Bold Challenger. Grounded Visionary.   Bonny is a strategist, facilitator, and co-founder of Sidekick Consulting who believes momentum is built in the middle of the mess. With a background as a CMO and over a decade of experience across startup and corporate environments, she’s known for her sharp thinking, no-nonsense mindset, and ability to turn big ideas into grounded action. Bonny brings a calm presence, clear direction, and just the right amount of edge to move things forward—with intention.  Nora Griffiths [https://www.linkedin.com/in/nora-griffiths-16676577/]  People-Centered Leader. Strategic Integrator. Dynamic Optimist.   Nora is a purpose-driven leader, facilitator, and co-founder of Sidekick Consulting who believes that bold and meaningful impact is accomplished when done together. With deep roots in business development and operations, she’s known for her people-first lens and her talent for uncovering insights and ideas that translate swiftly into action, driving both people and performance. Nora brings a rare blend of energy, empathy, and clarity to build momentum that truly matters.  Production by PRCPTN Studio [https://prcptn.com/].  Directed by Giuliana DiBonaventura [https://www.linkedin.com/in/giuliana-dibonaventura-148a69132/]

Fractional Leadership IRL with Dave Berney

In a world of constant change, why are we still designing leadership teams for stability? In this episode, Bonny and Nora explore why leadership roles can no longer be designed for stability in a world defined by uncertainty, volatility, complexity and constant change. Joined by Dave Berney, fractional CFO and CEO/founder of HAB Strategy, the conversation challenges the assumption that senior leadership must always be full-time and permanent.  Together, they unpack how fit-for-purpose, fractional leadership helps organizations navigate growth, complexity, and risk more effectively. And as a fractional leader, what motivates him and what he’s learned along sharing with those interested in pursuing the fractional life. Drawing on real-world examples from finance and operations, the episode explores how fractional roles create flexibility, accelerate learning, and enable smarter decisions without locking companies into outdated org designs.  Key Takeaways:   ➡️ The old assumption that leadership must be full-time is breaking down: today’s uncertainty demands flexible leadership capacity, not fixed org charts.  ➡️ Start with the business problem, not the title: ask what expertise your business needs right now before deciding who to hire.  ➡️ Fractional leadership reduces hiring risk: companies can test leadership needs and learn before committing long term.  ➡️ The future of leadership is blended: high-performing organizations combine full-time and fractional talent to match expertise to evolving business needs.  Listener Challenge:  Before you make your next leadership hire, pause and ask yourself: “What expertise does my business actually need right now, and for how long?” Then design the role around the problem you’re trying to solve, not the title you think you’re supposed to fill.  Our Guest: Dave is the CEO and Founder of HAB Strategy. As a CPA and ACA he has worked with companies big and small, from giants like Grant Thornton, US Bank and Pfizer to smaller & fast growing North American startups like GANDER Social, InFlux Technologies, Unlimited Life and more. He’s married with two young kids but still finds time to play sports like ball hockey, hurling and snowboarding, and do business mentoring in the business networking group Sound of C.  Our Co-Hosts: Bonny van Rest [https://www.linkedin.com/in/bonnyvr/]  Strategic Thinker. Bold Challenger. Grounded Visionary.   Bonny is a strategist, facilitator, and co-founder of Sidekick Consulting who believes momentum is built in the middle of the mess. With a background as a CMO and over a decade of experience across startup and corporate environments, she’s known for her sharp thinking, no-nonsense mindset, and ability to turn big ideas into grounded action. Bonny brings a calm presence, clear direction, and just the right amount of edge to move things forward—with intention.  Nora Griffiths [https://www.linkedin.com/in/nora-griffiths-16676577/]  People-Centered Leader. Strategic Integrator. Dynamic Optimist.   Nora is a purpose-driven leader, facilitator, and co-founder of Sidekick Consulting who believes that bold and meaningful impact is accomplished when done together. With deep roots in business development and operations, she’s known for her people-first lens and her talent for uncovering insights and ideas that translate swiftly into action, driving both people and performance. Nora brings a rare blend of energy, empathy, and clarity to build momentum that truly matters.  Production by PRCPRN Studio [https://prcptn.com/].  Directed by Giuliana DiBonaventura [https://www.linkedin.com/in/giuliana-dibonaventura-148a69132/]

The Talent Trap: Lead With Intention, Not Habit

Your best person is exhausted. Your steady performer is coasting. Your eager learner isn’t growing. And … everything still comes back to you.  In this episode, Bonny and Nora challenge a hard truth: the Talent Trap isn’t about having the wrong people on your team. It’s about how leadership habits quietly shape the system your team operates in. When you default to speed, safety, and star players, you reinforce dependence, overload your best talent, and stall capability across the team. Through a relatable case study of Alex, Maya, Chris, and Sam, we unpack how misdirected leadership energy, not lack of talent, creates fragility.  This isn’t about working harder. It’s about leading differently.  Key Takeaways:   ➡️ You are the system. Your leadership habits shape how your team behaves. What you step into, avoid, or default to reinforces patterns, even when your intentions are good.    ➡️ Build capacity, not just results. Results today don’t guarantee capability tomorrow. High-performing teams aren’t built by leaning on your star players. They grow when you intentionally develop skills, judgment, and confidence across the team.  ➡️ Coaching beats managing. Managing keeps work moving. Coaching builds judgment, ownership, and confidence and reduces long-term dependency.   ➡️ Leadership energy is finite. Where you spend your energy determines who grows. If it all goes to urgency or your top performer, capability stalls elsewhere and you stay the bottleneck.  Listener Challenge:  This week, take a moment to map your team on the Skill/Effort Matrix. How would you assess each of your team members current skill level and how much effort are they putting in?     With that:   Protect your “Maya.”  Have the honest conversation with your “Chris.”  Design a stretch opportunity for your “Sam.”  And ask yourself: What leadership habits am I reinforcing without realizing it?  Tools & Resources:  ➡️ Decide who to Delegate to with the Skill/ Will Matrix [https://www.bitesizelearning.co.uk/resources/skill-will-matrix-leadership-style]  ➡️ How to delegate like a CEO [https://www.linkedin.com/posts/annemarie-durbin-162b7a20_delegations-leadership-ceo-activity-7388547049602035712-IVL0/?utm_source=share&utm_medium=member_desktop&rcm=ACoAAAI5E1UBOItSwQ5u8jaWs2TZLPeNPi3mhsw] by Eric Partaker  ➡️ Learn about the Leader Member Exchange (LMX) [https://www.masterclass.com/articles/lmx] theory.   ➡️ Make your feedback more effective with the SBI- Method [https://www.ccl.org/articles/leading-effectively-articles/closing-the-gap-between-intent-vs-impact-sbii/]  ➡️ Avoid defaulting to a Performance Improvement Plan [https://www.forbes.com/advisor/business/performance-improvement-plan/] to quickly  Our Co-Hosts  Bonny van Rest [https://www.linkedin.com/in/bonnyvr/]  Strategic Thinker. Bold Challenger. Grounded Visionary.   Bonny is a strategist, facilitator, and co-founder of Sidekick Consulting who believes momentum is built in the middle of the mess. With a background as a CMO and over a decade of experience across startup and corporate environments, she’s known for her sharp thinking, no-nonsense mindset, and ability to turn big ideas into grounded action. Bonny brings a calm presence, clear direction, and just the right amount of edge to move things forward—with intention.  Nora Griffiths [https://www.linkedin.com/in/nora-griffiths-16676577/]  People-Centered Leader. Strategic Integrator. Dynamic Optimist.   Nora is a purpose-driven leader, facilitator, and co-founder of Sidekick Consulting who believes that bold and meaningful impact is accomplished when done together. With deep roots in business development and operations, she’s known for her people-first lens and her talent for uncovering insights and ideas that translate swiftly into action, driving both people and performance. Nora brings a rare blend of energy, empathy, and clarity to build momentum that truly matters.  Production by PRCPRN Studio [https://prcptn.com/].  Directed by Giuliana DiBonaventura [https://www.linkedin.com/in/giuliana-dibonaventura-148a69132/]