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.
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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.
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I recently read an HBR article discussing why the traditional approach to leadership development doesn’t always work.
It stated that instead of traditional methods, the best way to identify, grow and retain leaders to meet today’s demands is to “Let them innovate, let them improvise and let them actually lead.”
Over the past 30 years, as we’ve partnered with clients facing a vast range of challenges, we’ve seen the truth behind this – that people learn best by actually doing. That’s why business simulations are such a powerful tool: they allow people to do and lead within a risk-free environment, and condense years of on-the-job learning experience into a few days, or even hours.
We also know that learning is not just a “one and done” situation – it is a continuous experience. In many cases, a learning journey, which blends a variety of learning methodologies and tools over time, is the most powerful means of shifting mindsets, building capabilities and driving sustained, effective results.What a learning journey looks like depends entirely on the context of your organization. What challenges are you addressing? What results are you driving for? What does great leadership look like for your organization?
To bring this to life, imagine the following approach to a blended learning journey for aligning and developing leaders – in this scenario, within a financial services firm: Financial technology has “transformed the way money is managed. It affects almost every financial activity, from banking to payments to wealth management. Startups are re-imagining financial services processes, while incumbent financial services firms are following suit with new products of their own.”
For a leading financial services company, this disruption has led to a massive technology transformation. With tens of thousands of employees in the current technology and operations group, the company will be making massive reductions to headcount over the next five years as a result of automation, robotics and other technology advances.
This personnel reduction and increased use of technology is both a massive shift for the business as well as a huge change in the scope of responsibility that the remaining leaders are being asked to take on moving forward. As such, the CEO of the business unit recognizes the need to align 175 senior leaders in the unit to the strategy and the future direction of the business, and give them the capabilities that they need to effectively execute moving forward.
To achieve these goals, BTS would build an innovative design for this initiative: a six-month blended experience, incorporating in-person events, individual and cohort-based coaching sessions, virtual assessments and more. Throughout the journey, data would be captured and analyzed to provide top leadership with information about the participants’ progress – and skill gaps – on both an individual and cohort level, thus setting up future development initiatives for optimal success.
The journey would begin with a two-day live conference event for the 175 person target audience, incorporating leader-led presentations about the strategy. The event would not just be talking heads and PowerPoint slides, but rather would leverage the BTS Pulse digital event technology to increase engagement and create a two-way, interactive dialogue that captures the participants’ ideas and suggestions. Participants also would use the technology to experience a moments-based leadership simulation that develops critical communications, innovation and change leadership capabilities, among other skills.
romAfter the event, participants would return to the job to apply their new learnings. On the job, each participant would continue their journey with four one-on-one performance coaching sessions, in addition to a series of peer coaching sessions shared with four to five colleagues. They also would use 60-90 minute virtual Practice with an Expert sessions to develop specific skill areas in short learning bursts, and then practice those skills with a live virtual coach. Throughout the journey, participants would access online, self-paced modules that contain “go-do activities” to reinforce and encourage application of the innovation leadership and other skills learned during the program.
As a capstone, six months after the journey has begun, every participant would go through a live, virtual assessment conducted via the BTS Pulse platform. In three to four hours, these virtual assessments allow live assessors to evaluate each leader’s learnings from the overall journey and identify any remaining skill gaps. The individual and cohort assessment data would then lead to and govern the design of future learning interventions that would continue to ensure the leaders are capable of implementing the strategy.
As you can see, this journey design leverages a range of tools and learning methodologies to create a holistic, impactful solution. It’s not just a standalone event – each step of the journey ties into the one before, and the data gathered throughout can be used well into the future in order to shape the next initiative .
Great journeys or experiences like this can take many forms. In addition to live classroom and virtual experiences, there is an ecosystem of activities, such as performance coaching, peer coaching, practice with an expert, go-dos, self-paced learning modules, and more, that truly engage leaders and ensure that the learnings are being reinforced, built upon, practiced and implemented back on the job. We find that these types of experience rarely look the same for every client. There are many factors that determine which configuration and progression will make the most sense. There is one common theme that we have found throughout these highly contextual experiences, however – that the participant feedback is outstanding and the business impact is profound.
Leading with Purpose, Part 1
Most CEOs I speak with are not 100% at peace with their company’s purpose. As the market, their people and their business evolve, so will their purpose. As some of the best companies of past and present show us, there is strength, and even magic, in a great company purpose. What is also clear, however, is that this magic does not come from just having a “purpose” or “vision,” but rather from how well a company is executing against their purpose.
When Southwest Airlines (which has been profitable for 45 consecutive years, and on FORTUNE’s list of World’s Most Admired Companies for 24 straight years) was first starting out, their mission was to make flying affordable.1 They rallied their people on the idea that a grandmother should be able to affordably buy a ticket, at the drop of a hat, to get on a flight to see her new grandchild. This simple mission led to the “Southwest Effect,” which transformed the airline industry, and continued to be a lens with which the Southwest leadership team made key decisions.
Today, Southwest’s vision has evolved: “To become the world’s most loved, most flown, and most profitable airline.” And they are executing on this vision. They continue to drive superior shareholder returns against all industries on the S&P 500 (as they have for the past 44 years), and in 2018 were named the top low-cost airline in JD Powers customer survey reports for the second year in a row.
As the Southwest example highlights, great company purpose combined with a leadership team who will build the work-flows, culture, processes and metrics to live up to it can be an enormous employee motivator. But we have also experienced, both at BTS and with our global clients, that a good company vision and purpose on their own are not sufficient – employees need them to be even more personal to them as an individual. I remember a lunch I had twelve years ago with a 24-year old new hire who was my direct report. After some small talk he looked at me and said, “Why are you here? Why have you spent seven years with the same company?”
I’ll never forget that lunch. It was the first time I had been asked the question, and it was the beginning of a new decade where our employees were much louder and more active about wanting to reflect and spend time on our mission and purpose, linking it to their personal values and the impact they strived to have in the world. Luke, that 24-year old new hire, has made me and our company better as a result of his question.
In the last decade, there has been a growing emphasis in the business world on finding a deeper motivation to unlock greater meaning at work. For some this may sound ‘fluffy,’ or as one executive we spoke to commented, “Is this just the next version of the pursuit of vision and values? It sounds great on paper but too often makes little real difference as it tends to stay on the wall, rather than live in your heart.”
Yet your people spend the majority of their life at work and with colleagues. At its best, a sense of purpose is a way of bringing meaning to their work and understanding the contributions they are making to the company, as well as greater society. It makes sense, then, that employees who are clear on their personal and professional purpose end their work day invigorated and proud of what they’re doing instead of exhausted by mindless work that is bereft of real meaning.
According to a recent PWC study, 79% of business leaders believe that purpose is central to business success – but only 34% use their organization’s purpose as a guidepost for their leadership team’s decision-making. Signs that your workplace may be lacking organizational purpose are distracted employees and a lack of comradery. These are significant factors – so why don’t more organizations devote time to developing clear purpose and values? Well, developing organizational purpose is no easy task, and much of it starts with your own personal purpose. If you’re unsure of what exactly your own personal purpose is, have no fear – in the next two installments of this blog series, we will offer simple steps to help you uncover your personal and organizational purposes and get closer to leading through the lens of purpose.