Executive transition playbook first 100 days
Executive transitions are among the most critical moments in an organization’s lifecycle. When a leader steps into a new executive role, it impacts not only the strategic direction but also the organizational culture, stakeholder relationships, and overall business performance. If managed poorly, transitions can lead to disruptions such as loss of institutional knowledge, diminished team morale, and financial challenges.
The reality is that many executive transitions don’t go as planned. According to Harvard Business Review, 50% of new executives fail or leave within 18 months, potentially costing the organization up to ten times their salary. Additionally, Korn/Ferry reports that only 30% of global executives are satisfied with their onboarding process. These statistics underscore the need for a strategic approach to ensure successful leadership transitions.
Several years ago, I worked with the new CFO of a $6B division of a $40B manufacturing organization. She transitioned from corporate headquarters to a division, which had a markedly different culture. Her challenge was not only adjusting to a new environment. It meant embedding herself in an unfamiliar culture, building trust with her C-suite peers, and establishing herself as a strategic advisor to the CEO—all while leading a team uncertain about its future.
To further complicate the transition, the division was being acquired, and her team faced nine months of incredibly heavy work with no guarantee of securing future roles in the new organization. Despite these challenges, by receiving the right executive advisory transition support, she navigated the complexities, built trust quickly, and inspired her team to stay committed, even when the nine months turned into 18.
Executive transitions are pivotal moments for organizations. They require careful planning, clear communication, and focused support to ensure a smooth and successful transition. Below are four key considerations for senior leaders to manage transitions effectively and with confidence.
1. Understand the ecosystem: stakeholder mapping and engagement
As you step into this new role, understanding the organization’s ecosystem is one of the first and most crucial steps. Every organization has its own dynamics—how departments, teams, and individuals interact, how decisions are made, and where power and influence lie. It’s important to map out not only formal authority but also informal networks and relationships. This will help you navigate internal politics, align your strategies, and avoid potential pitfalls that could derail your efforts.
Stakeholders are key to your success—both in the short term and for the long-term execution of your vision. Their support can unlock resources, enable smoother decision-making, and lead to faster buy-in. However, if you don’t identify and understand key stakeholders early on, you risk spending valuable time and energy in the wrong areas or missing out on insights that could shape your strategy.
I recently advised a new SVP of R&D for a $50B pharmaceutical company who was transitioning into this role from academia. We’ll call him Nate. One of his first areas of focus was understanding and connecting with key stakeholders in this highly matrixed organization around the world. Nate formed relationships, sought to understand their roles and areas of expertise, and learned what was important to them. This enabled him to speed up what is often a daunting transition and quickly become embedded in the business.
Navigating the ecosystem can be tricky, especially when not all stakeholders are immediately visible. Some people may wield significant influence without holding formal authority, while others may be new to the organization or going through their own transitions, which could affect their willingness to support yours.
Executive ecosystem checklist:
- Identify key stakeholders: Identify both formal and informal influencers. Understand their roles, influence, and how their priorities align with yours.
- Conduct listening tours: Engage stakeholders through one-on-one conversations. Listening to their concerns, needs, and aspirations will give you a broader view of the challenges and opportunities ahead.
- Understand motivation and metrics: Recognize what each stakeholder needs to achieve and how they measure success. This understanding will help you align goals and collaborate effectively.
- Build relationships early: Establish trust by engaging with key stakeholders from the start. Understanding their perspectives and setting the foundation for collaboration is essential for a smooth transition.
2. Communicate a compelling vision: aligning and inspiring your team
In your new role, one of the first things you’ll need to do is communicate a clear and compelling vision. This vision should not only align with the organization’s broader goals but also provide your team with a clear direction. As a senior leader, your ability to communicate this vision effectively will be pivotal to driving alignment and motivating those around you.
It’s about more than just outlining a plan—it’s about inspiring action. Crafting a vision that resonates with your team and stakeholders gives them a sense of purpose and direction, especially during a time of uncertainty. Your communication needs to go beyond clarity; it must be compelling and motivating. The clearer and more inspiring you can be, the more quickly you’ll build the trust and commitment necessary to lead your team forward.
Nate communicated his vision with passion and energy that inspired others. He also showed genuine curiosity and care for the organization and people within it, so they wanted to buy into his inspiring vision and deliver on it.
Executive vision checklist:
- Align with organizational goals: Ensure your vision is aligned with the strategic objectives of the organization. This alignment ensures that you and your team are working toward shared long-term goals.
- Communicate clearly: Convey your vision in a way that resonates with your team and stakeholders. Use your communication skills to inspire confidence, trust, and action.
- Inspire and motivate: Use your vision not just as a roadmap but as a source of motivation. Help your team see their role in achieving broader goals, making the work meaningful and engaging.
3. Develop a strong strategic plan: laying the foundation for long-term success
A strong strategic plan to guide your transition and ramp up your impact is essential as you step into your new leadership role. This plan should outline your immediate goals, long-term objectives, and key milestones to mark progress and success. It’s important to approach planning with an understanding of the organization’s broader strategy and how your goals align with it. While your experience gives you strategic insight, remember that flexibility is key. Transitions come with uncertainty, so your plan should adapt to evolving challenges.
As you lead through change, creating a clear roadmap helps you set expectations and provide clarity for your team. At the same time, no plan is without risk. Identifying potential challenges and understanding how to manage them proactively will set your organization up for success in both the short and long term.
Nate sparked bold, future-focused thinking on his team while communicating long-term strategic priorities related to wise investment and growth. He advocated for impactful portfolio investments while engaging in open dialogue to ensure his team contributed meaningfully to, and owned, the strategy.
Executive strategy checklist:
- Set clear success objectives: Define what success looks like in the first 6–12 months. Engage your leadership team in setting achievable goals that align with the broader strategy.
- Identify potential barriers: Recognize challenges such as misalignment or lack of support and create contingency plans to navigate them.
- Develop a flexible roadmap: Create a strategy that balances structure with flexibility. Build in checkpoints to reassess and adjust as needed.
4. Evaluate, build, and engage the team: ensuring alignment and high performance
As you settle into your new role, evaluating and aligning your team is critical. Assess whether the team structure is equipped to execute your strategic plan. Do you have the right people in the right positions? Are there gaps or development opportunities? Building a high-performing team isn’t just about filling positions—it’s about fostering collaboration, psychological safety, and shared ownership of your vision.
Nate quickly built trust through openness, thoughtfulness, and respect while encouraging collaborative thinking and cross-functional idea sharing. As a result, his team was positioned to lead significant initiatives that will positively affect the future of the business.
Executive team checklist:
- Evaluate and align the team: Assess your team’s structure and capabilities against strategic goals to ensure the right people are in the right roles. Identify development areas and align efforts.
- Foster a culture of collaboration: Create an environment where open communication and constructive conflict are encouraged. This enables better decisions and teamwork.
- Invest in building a high-performing team: Continuously develop your team’s skills and collaboration to ensure alignment with your broader strategic goals.
Set the stage for true transformation
Stepping into a new executive role is more than a leadership shift—it’s a pivotal moment for both you and the organization. The challenges are significant, and the stakes are high, but this transition also offers a powerful opportunity to shape the future. The actions you take early on establish your credibility and influence, setting the tone for your leadership from day one.
How you navigate these early challenges will define both your immediate success and your long-term legacy. This transition isn’t just about managing change—it’s about actively shaping it. By embracing a structured, strategic approach, you can turn uncertainty into a clear roadmap for growth and transformation.
The more you invest in understanding the organizational ecosystem, building your team, and aligning your vision, the better equipped you’ll be to lead with confidence, inspire loyalty, and drive the organization forward.
Ultimately, this transition is not just a phase to endure—it’s a defining moment that can elevate the organization and set the stage for sustained success. Make it count.
Related content
Related content
Technology choices are often made under pressure - pressure to modernize, to respond to shifting client expectations, to demonstrate progress, or to keep pace with rapid advances in AI. In those moments, even experienced leadership teams can fall into familiar traps: over-estimating how differentiated a capability will remain, under-estimating the organizational cost of sustaining it, and committing earlier than the strategy or operating model can realistically support.
After decades of working with leaders through digital and technology-enabled transformations, I’ve seen these dynamics play out again and again. The issue is rarely the quality of the technology itself. It’s the timing of commitment, and how quickly an early decision hardens into something far harder to unwind than anyone intended.
What has changed in today’s AI-accelerated environment is not the nature of these traps, but the margin for error. It has narrowed dramatically.
For small and mid-sized organizations, the consequences are immediate. You don't have specialist teams running parallel experiments or long runways to course correct. A single bad platform decision can absorb scarce capital, distort operating models, and take years to unwind just as the market shifts again.
AI intensified this tension. It is wildly over-hyped as a silver bullet and quietly under-estimated as a structural disruptor. Both positions are dangerous. AI won’t magically fix broken processes or weak strategy, but it will change the economics of how work gets done and where value accrues.
When leaders ask how to approach digital platforms, AI adoption, or operating model design, four questions consistently matter more than the technology itself.
- What specific market problem does this solve, and what is it worth?
- Is this capability genuinely unique, or is it rapidly becoming commoditized?
- What is the true total cost - not just to build, but to run and evolve over time?
- What is the current pace of innovation for this niche?
For many leadership teams, answering these questions leads to the same strategic posture. Move quickly today while preserving options for tomorrow. Not as doctrine, but as a way of staying adaptive without mistaking early commitment for strategic clarity.
Why build versus buy is the wrong starting point
One of the most common traps organizations fall into is treating digital strategy as a series of isolated build-vs-buy decisions. That framing is too narrow, and it usually arrives too late.
A more powerful question is this. How do we preserve optionality as the landscape continues to evolve? Technology decisions often become a proxy for deeper organizational challenges. Following acquisitions or periods of rapid change, pressure frequently surfaces at the front line. Sales teams respond to client feedback. Delivery teams push for speed. Leaders look for visible progress.
In these moments, technology becomes the focal point for action. Not because it is the root problem, but because it is tangible.
The real risk emerges operationally. Poorly sequenced transitions, disruption to the core business, and value that proves smaller or shorter-lived than anticipated. Teams become locked into delivery paths that no longer make commercial sense, while underlying system assumptions remain unchanged.
The issue is rarely technical. It is temporal.
Optimizing for short-term optics, particularly client-facing signals of progress, often comes at the expense of longer-term adaptability. A cleaner interface over an ageing platform may buy temporary parity, but it can also delay the more important work of rethinking what is possible in the near and medium term.
Conservatism often shows up quietly here. Not as risk aversion, but as a preference for extending the familiar rather than exploring what could fundamentally change.
Licensing as a way to buy time and insight
In fast-moving areas such as AI orchestration, many organizations are choosing to license capability rather than build it internally. This is not because licensing is perfect. It rarely is. It introduces constraints and trade-offs. But it was fast. And more importantly, it acknowledged reality.
The pace of change in this space is such that what looks like a good architectural decision today may be actively unhelpful in twelve months. Licensing allowed us to operate right at the edge of what we actually understood at the time - without pretending we knew where the market would land six or twelve months later.
Licensing should not be seen as a lack of ambition. It is often a way of buying time, learning cheaply, and avoiding premature commitment. Building too early doesn’t make you visionary, often it just makes you rigid.
AI is neither a silver bullet nor a feature
Coaching is a useful microcosm of the broader AI debate.
Great AI coaching that is designed with intent and grounded in real coaching methodology can genuinely augment the experience and extend impact. The market is saturated with AI-enabled coaching tools and what is especially disappointing is that many are thin layers of prompts wrapped around a large language model. They are responsive, polite, and superficially impressive - and they largely miss the point.
Effective coaching isn’t about constant responsiveness. It’s about clarity. It’s about bringing experience, structure, credibility, and connection to moments where someone is stuck.
At the other extreme, coaches themselves are often deeply traditional. A heavy pen, a leather-bound notebook, and a Royal Copenhagen mug of coffee are far more likely to be sitting on the desk than the latest GPT or Gemini model.
That conservatism is understandable - coaching is built on trust, presence, and human connection - but it’s increasingly misaligned with how scale and impact are actually created.
The real opportunity for AI is not to replace human work with a chat interface. It is to codify what actually works. The decision points, frameworks, insights, and moments that drive behavior change. AI can then be used to augment and extend that value at scale.
A polished interface over generic capability is not enough. If AI does not strengthen the core value of the work, it is theatre, not transformation.
What this means for leaders
Across all of these examples, the same pattern shows up.
The hardest decisions are rarely about capability, they are about timing, alignment, and conviction.
Building from scratch only makes sense when you can clearly articulate:
- What you believe that the market does not
- Why that belief creates defensible value
- Why you’re willing to concentrate risk behind it
Clear vision scales extraordinarily well when it’s tightly held. The success of narrow, focused Silicon Valley start-ups is testament to that.
Larger organizations often carry a broader set of commitments. That complexity increases when depth of expertise is spread across functions, and even more so when sales teams have significant autonomy at the point of sale. Alignment becomes harder not because people are wrong, but because too many partial truths are competing at once.
In these environments, strategic clarity, not headcount or spend, creates advantage.
This is why many leadership teams choose to license early. Not because building is wrong, but because most organizations have not yet earned the right to build.
This article was originally publish on Rotman Management
IN OUR CONSULTING WORK with teams at all levels—especially senior leadership—my colleagues and I have noticed teams grappling with an insidious challenge: a lack of effective prioritization. When everything is labeled a priority, nothing truly is. Employees feel crushed under the weight of competing demands and the relentless urgency to deliver on multiple fronts. Requests for prioritization stem from both a lack of focused direction and the challenge of efficiently fulfilling an overwhelming volume of work. Over time, this creates a toxic cycle of burnout, inefficiency and dissatisfaction.
The instinctive response to this issue is to streamline, reduce the number of initiatives, and focus. While this is a step in the right direction, it doesn’t fully address the problem. Prioritization isn’t just about whittling down a to-do list or ranking activities by importance and urgency on an Eisenhower Decision Matrix; it also requires reshaping how we approach work more productively.
In our work, we have found that three critical factors lie at the heart of solving prioritization challenges: tasks, tracking and trust. Addressing these dimensions holistically can start to address the root causes of feeling overwhelmed and lay the foundation for sustainable productivity. Let’s take a closer look at each.
You’re buckling in for an overseas flight in a brand-new Boeing 777. The pilot comes on the PA: “Ah, ladies and gentlemen, our flight time today will be six and a half hours at a cruising altitude of 33,000 feet. And I should mention that this is the first time I have ever flown a 777. Wish me luck.”
Before setting foot in the real world, pilots, military personnel and disaster response teams use intense simulations to learn how to respond to high-intensity challenges.Why should we place corporate leaders and their teams in situations without first giving them a chance to try things out? The risks are huge — new strategy investments can run into the hundreds of millions of dollars. BTS offers a better way to turn strategy into action: customized business simulations.
‘Now I Know What it’s Like to be CEO’
A customized business simulation of your enterprise, business unit or process, using real-world competitive dynamics, places leaders in a context where they step out of their normal day-to-day roles and gain exposure to the big picture. Participants make decisions in a risk-free environment, allowing them to experience critical interdependencies, execution best practices and the levers they can use to optimize their company’s key performance indicators. It takes the concept of a strategy and makes it personal, giving each individual the chance to see the direct impacts of their actions and the role they play in strategy execution.
Leading corporations are increasingly turning to business simulations to help build strategic alignment and execution capability when faced with the following business challenges:
- Key performance objective and new strategy implementation.
- Accelerating strategy execution and innovation.
- Improving business acumen and financial decision making.
- Transforming sales programs into business results accelerators.
- Leadership development focused on front-line execution.
- Implementing culture change as tied to strategy alignment.
- Modeling complex value chains for collaborative cost elimination.
- Merger integration.
Within minutes of being placed in a business simulation, users are grappling with issues and decisions that they must make — now. A year gets compressed into a day or less. Competition among teams spurs engagement, invention and discovery.
The Business Simulation Continuum: Customize to Fit Your Needs
Simulations have a broad range of applications, from building deep strategic alignment to developing execution capability. The more customized the simulation, the more experience participants can bring back to the job in execution and results. Think about it: why design a learning experience around generic competency models or broad definitions of success when the point is to improve within your business context? When you instead simulate what “great” looks like for your organization, you exponentially increase the efficacy of your program.
10 Elements of Highly Effective Business Simulations
With 30 years of experience building and implementing highly customized simulations for Fortune 500 companies, BTS has developed the 10 critical elements of an effective business simulation:
- Highly realistic with points of realism targeted to drive experiential learning.
- Dynamically competitive with decisions and results impacted by peers’ decisions in an intense, yet fun, environment.
- Illustrative, not prescriptive or deterministic, with a focus on new ways of thinking.
- Catalyzes discussion of critical issues with learning coming from discussion within teams and among individuals.
- Business-relevant feedback, a mechanism to relate the simulation experience directly back to the company’s business and key strategic priorities.
- Delivered with excellence : High levels of quality and inclusion of such design elements as group discussion, humor, coaching and competition that make the experience highly interactive, intriguing, emotional, fun, and satisfying.
- User driven: Progress through the business simulation experience is controlled by participants and accommodates a variety of learning and work styles.
- Designed for a specific target audience, level and business need.
- Outcome focused , so that changes in mindset lead to concrete actions.
- Enables and builds community: Interpersonal networks are created and extended through chat rooms, threaded discussions and issue-focused e-mail groups; participants support and share with peers.
Better Results, Faster
Well-designed business simulations are proven to significantly accelerate the time to value of corporate initiatives. A new strategy can be delivered to a global workforce and execution capability can be developed quickly, consistently and cost-effectively. It’s made personal, so that back on the job, participants own the new strategy and share their enthusiasm and commitment. This in turn yields tangible results; according to a research report conducted by the Economist Intelligence Unit and sponsored by BTS, titled “Mindsets: Gaining Buy-In to Strategy,” the majority of firms struggle to achieve buy-in to strategy, but those that personalize strategy throughout their organization significantly outperform their peers in terms of profitability, revenue growth and market share.
Business Simulations: Even More Powerful in Combination
Comprehensive deployment of business simulation and experiential learning programs combines live and online experiences. The deepest alignment, mindset shift and capability building takes place over time through a series of well-designed activities. Maximize impact by linking engagement and skill building to organizational objectives and by involving leadership throughout the process.
Putting Business Simulations to Work
Simulations drive strategic alignment, sales force transformation, and business acumen, financial acumen and leadership development, among other areas. A successful experiential learning program cements strategic alignment and builds execution capability across the entire organization, turning strategy into action. Results can be measured in team effectiveness, company alignment, revenue growth and share price.
Learn more about business simulations
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