3 Introspective Reflections, as I Transition into a New Challenge

Executive Transition Framework: 7 Lessons from VP Strategy Execution & Chief of Staff Role

Author Byline
By M. Mahmood | Strategist & Consultant | mmmahmood.com [mmmahmood]​

Leadership transitions into hybrid roles like VP of Strategy Execution and Chief of Staff demand rapid adaptation across multiple dimensions simultaneously. These positions, while intertwined, require distinct skill amplification and mindset shifts. My 18-month journey revealed that success hinges not on pre-conceived notions but on intentional learning, relationship craftsmanship, and authentic self-awareness.

The origami cranes in the featured image symbolize this deliberate folding of leadership capabilities, each crease representing a lesson learned, a skill honed, and a relationship strengthened through conscious practice.

Mastering the Duality: Strategy Execution and Chief of Staff

As I take on my next challenge to create and capture value for Enterprise solutions, I spent some time over the weekend asking myself a few "exit interview" type questions. Here is what I learned through an introspective lens.

What did I learn over the last 18 months, as VP of Strategy Execution and Chief of Staff?

As the title may suggest, these roles while intertwined, require varying skills to be amplified. It took me a hot second (i.e: a little bit of time) to adjust to the environment, people and most importantly managing expectations. Aural skills, for the purpose of understanding the needs and point-of-view of others was critical; be it during business planning cycle or introducing the leadership team to a new approach (thinking or framework). Listening and empathizing can lay a solid foundation to craft relationships, making it easier to make mutually beneficial decisions.

The duality of these roles creates unique pressure. Strategy execution demands analytical rigor, systems thinking, and outcome orientation. Chief of staff requires political savvy, facilitation skills, and emotional intelligence. Amplifying both simultaneously stretches any leader, requiring conscious development of underutilized capabilities.

Aural skills i.e listening to understand rather than respond—emerged as the foundational capability. Whether navigating business planning cycles or introducing new frameworks, the ability to hear unstated concerns, detect underlying motivations, and appreciate diverse perspectives determines whether you build coalitions or create resistance.

The Business Planning framework (updated for 2023) emphasizes stakeholder alignment as prerequisite for execution. Chief of staff roles operationalize this principle daily, translating executive vision into organizational action through relationship craftsmanship.

Navigating Ambiguity: The Consultative Mindset

To make sense of ambiguity, consultative mindset, along with strategic thinking were more prevalent, as most of my projects ended being NDA (non-disclosure agreements). Analytical skills came in quite handy to make assertions and inferences from data at hand. As such the entire gambit of skills, from hypothesizing to materializing came into play.

Working under NDAs creates unique constraints. You cannot discuss projects openly, seek broad input, or transparently share rationale. This forces reliance on small-circle consultation, data-driven inference, and strategic intuition. The consultative mindset becomes essential—asking probing questions, synthesizing fragmented information, and making informed bets with limited visibility.

Analytical skills transform from nice-to-have into survival tools. When you cannot discuss details, you must derive insights from patterns, anomalies, and implications. Hypothesis-driven thinking becomes standard: form educated guesses, test through limited experiments, validate with tight stakeholders, and scale what works.

The entire skill gambit, from hypothesizing to materializing. activates, as uou are not just strategist but translator, facilitator, and execution partner simultaneously. The Strategy Execution framework (updated for 2023) captures this comprehensiveness, emphasizing that execution is not downstream of strategy but interwoven with it.

This ambiguity management approach proves valuable beyond NDAs. In any complex organization, perfect information is rare. Leaders who thrive are those who make quality decisions with incomplete data, using consultative methods to fill knowledge gaps while maintaining strategic direction.

The Power of "No": Boundary Setting and Expectation Management

It is almost as important to state what the project is not about, to manage outcomes and expectations. This also suggests the power of tactfully saying "No". (Credit: Tomas Ageskog)

The most underrated leadership skill is the ability to say "No" gracefully. In strategy execution and chief of staff roles, requests pour in constantly: new initiatives, ad-hoc analyses, meeting invitations, advisory asks. Without boundaries, you dilute focus, burn out your team, and fail to deliver on priorities.

Stating what a project is not about provides clarity. It manages expectations upfront, prevents scope creep, and focuses resources on what matters. This negative definition is as important as positive articulation. When launching OKRs, we explicitly stated: "This is not about individual performance management. This is not about creating bureaucratic overhead. This is not about replacing existing planning processes." These clarifications prevented misunderstanding and resistance.

Tactful "No" is not rejection but redirection. It acknowledges the request's merit while explaining capacity constraints, priority misalignment, or resource limitations. The formula is: validate + explain + redirect. "That is an important initiative (validate), but our current OKR rollout consumes our full bandwidth (explain). Let us revisit in Q3 once the foundation is solid (redirect)."

This skill proves particularly crucial in chief of staff roles where you represent the executive office. People interpret your "Yes" as organizational commitment. Therefore, every agreement must be deliberate and aligned. Saying "No" protects the executive's time, your team's capacity, and organizational focus.

The Negotiation Mastery framework (updated for 2020) complements this principle. BATNA thinking applies: what is your best alternative to saying yes? Walkaway discipline applies: what is your limit? ZOPA discovery applies: what is the overlap between their request and your capacity?

Blueprint Creation: Defining Process in Undefined Roles

Lastly, this role was a fairly new setup in the organization, so there was no blueprint to follow. This was both a curse and a blessing in disguise, as I was able to define process and ways-of-working. As an example: Having successfully introduced and implemented the Objectives and Key results (OKR) framework, to effectively manage a billion dollar business, highlights how new value can be created and captured.

Entering a newly created role presents a unique paradox. The absence of a blueprint means no constraints but also no guidance. You are simultaneously architect and builder, designing the plane while flying it. This is both curse and blessing—the curse of ambiguity, the blessing of autonomy.

The OKR implementation exemplifies blueprint creation value. When no process existed for aligning a billion-dollar business around measurable objectives, we designed it from first principles. We defined OKR cycles, established review cadences, trained leadership, and built tracking systems. The result was not just a framework but a new organizational capability.

Blueprint creation requires balancing structure with flexibility. Too rigid, and the process breaks under real-world complexity. Too loose, and it fails to provide direction. The sweet spot is "minimum viable process"—enough structure to guide action, enough flexibility to adapt.

The Free Business Resources (updated for 2026) provides templates that accelerate blueprint creation. Rather than starting from scratch, adapt proven frameworks to your context. This balances innovation with reliability.

This experience translates directly to entrepreneurship. Starting FlexMed Solutions and md-konsult.com required defining processes where none existed: client onboarding, project delivery, quality assurance. The blueprint creation skill—defining process in ambiguity—proves equally valuable in startups and corporate innovation roles.

Self-Reflection: Navigating Role Transitions and Authenticity

What could I have improved upon, during my tenure?

To start off, I did not have any pre-conceived notions about my role. This was good in a sense that I did not carry any baggage. On the flip side, it also highlighted the fact that initially I was flying blind and lacked a sense of direction. Not sure if I would change it, as adjustment period was quite short.

When I took this role, I was transitioning from a very tough project, where I had to provide clear guidance every day and the buck stopped with me. This role was almost a polar opposite of that, where I served more as a facilitator and coach. Imo, it was a mixed bag, as cycle time to make decisions were prolonged. During the transition, adjust to the needs of the role, but stay your authentic self.

The transition from directive leadership (where the buck stops with you) to facilitative leadership (where you empower others) presents psychological challenges. The shift from daily clear guidance to coaching and facilitation feels like losing control. Decision cycles lengthen. Outcomes feel less direct. Authority becomes influence.

This transition was a mixed bag. On one hand, facilitative leadership builds sustainable capability and reduces dependency. On the other hand, it feels slower and less certain. The key insight: adjust to the role's needs while staying authentically yourself.

Authenticity does not mean rigidly applying one leadership style. It means bringing your core values and strengths to each role while adapting your methods. If your strength is analytical rigor, apply it to facilitation—use data to guide discussions, structure to frame decisions. If your strength is relationship building, apply it to strategy execution—use trust to drive alignment, empathy to navigate resistance.

The adjustment period was blessedly short, suggesting that flying blind without pre-conceived notions accelerated learning. Without baggage, you observe reality more clearly. Without rigid expectations, you adapt more fluidly. This becomes a meta-lesson: sometimes the best preparation is no preparation—just principled responsiveness.

Core Nuggets: Actionable Leadership Principles

A few nuggets to share...

• Be your authentic self and contribute by empowering others
• Amplify your aural skills and listen to understand
• Craft relationships as its always easy to have a conversation with a friend
• Say "No" and state your position. It helps the other party understand, for a good dialogue to ensue.

These four nuggets distill 18 months of learning into actionable principles.

Be your authentic self and contribute by empowering others. Authenticity builds trust. Empowerment builds capability. Combined, they create followership that transcends positional authority. People work for leaders they believe in and who believe in them.

Amplify your aural skills and listen to understand. Listening is not passive reception but active sense-making. Understanding before responding prevents defensiveness, surfaces real issues, and builds psychological safety. In strategy execution roles, where you facilitate decisions rather than make them, listening becomes your primary tool.

Craft relationships as its always easy to have a conversation with a friend. Relationships are not transactions to be optimized but crafts to be cultivated. Invest time, show genuine interest, deliver on commitments. When challenges arise, friends tell you the truth and support your success. In chief of staff roles, where informal influence matters more than formal power, friendship networks become essential.

Say "No" and state your position. Clear boundaries enable good dialogue. Ambiguity breeds misunderstanding and resentment. When you state your position clearly, others can respond constructively. They may disagree, but they know where you stand. This clarity accelerates negotiation and alignment.

The Negotiation Mastery framework (updated for 2020) reinforces this principle. ZOPA (Zone of Possible Agreement) cannot be discovered without clear positions. BATNA cannot be assessed without knowing your walkaway. Saying "No" is not conflict but clarity.

Integration and Application: Now, On to the Next Set of Learnings

Now, on to the next set of learnings.

Leadership is iterative learning. Each role teaches different lessons. Strategy execution taught process and systems. Chief of staff taught influence and facilitation. The enterprise solutions challenge will teach new capabilities—perhaps sales excellence, product innovation, or market creation.

The transition between roles is itself a skill. Extracting lessons, codifying principles, and applying them to new contexts accelerates development. This article represents that codification—turning experience into principles that guide future action.

The meta-lesson: leadership excellence is not about mastering a single role but about accelerating learning across roles. Each transition is a crucible that forges new capabilities while testing existing ones. Those who learn fastest, adapt most effectively, and remain authentic throughout, achieve sustained impact.

The Business Planning cycle (updated for 2023) parallels this personal planning cycle. Just as organizations need strategic plans, leaders need development plans. The three questions—what did I learn, what could I improve, what principles will I carry forward—provide structure for personal strategic planning.

Synthesis: The Chief of Staff as Organizational Architect

The Chief of Staff role, particularly when combined with Strategy Execution, positions you as organizational architect. You design processes, facilitate decisions, align stakeholders, and ensure execution. You are simultaneously strategist, operator, and coach.

This architecture role requires unique humility. You enable others' success more than your own. Your wins are invisible—smooth processes, aligned teams, executed strategies. Your impact is measured through others' achievements.

The OKR implementation for a billion-dollar business exemplifies this architecture. The framework becomes the blueprint. Training and facilitation become the construction. Sustained execution becomes the completed building. The architect's name is not on the building, but the building exists because of the architect.

The four nuggets—authenticity, listening, relationship crafting, and clear positioning—are the architect's tools. They are not flashy but essential. They do not draw attention but enable greatness.

As I transition to enterprise solutions, these tools transfer. The context changes but the principles remain. Listen to understand customer needs. Craft relationships with enterprise stakeholders. Say "No" to misaligned opportunities. Stay authentic while adapting to enterprise sales dynamics.

Final Reflection: Leadership as Continuous Transition

Leadership is perpetual transition. Each role, each project, each quarter presents new challenges requiring adaptation. The 18-month VP Strategy Execution and Chief of Staff role was a transition. The enterprise solutions role is a transition. Every day is a transition from what you were yesterday to what you must become tomorrow.

The key is not avoiding transitions but embracing them as learning opportunities. The exit interview questions—what did I learn, what could I improve, what principles will I carry forward—should be asked continuously, not just at role endings.

The origami cranes remind us that leadership is craft, not science. Each fold is a choice. Each choice shapes the final form. Random folding produces chaos. Deliberate folding produces art. The art of leadership is making deliberate choices about identity, relationships, and value creation—choices that serve others while transforming yourself.

On to the next set of learnings indeed. The journey continues.