leadership development

Navigating the first 90 Days: A Detailed Guide to Executive Onboarding

Learn the best practices of executive onboarding and how you can create a stellar process within your organization.

Matthew Reeves

CEO of Together

Published on 

October 10, 2023

Updated on 

Time to Read

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Leadership transitions mark significant milestones in an organization's journey. 

The successful integration of new executives can pave the way for groundbreaking strategies, innovative ideas, and revitalized energies. But the challenge of seamlessly embedding these new leaders into an organization's fabric is no small feat. 

Enter executive onboarding – a strategic process designed to ensure that these transitions are smooth and set the stage for lasting leadership success.

What is executive onboarding? 

Executive onboarding isn't just about welcoming a new leader to the fold or giving them an overview via a company handbook. It's a thoughtfully constructed process, pivotal to ensuring that freshly appointed executives find their footing and effectively integrate into their designated roles in the organization.

Consider executive onboarding as a nexus, bridging an executive's accumulated experience and knowledge with the specialized requirements and nuances of their new role. Given the substantial influence that executives hold over an organization's strategy, culture, and overall trajectory, the depth of this process goes far beyond the administrative aspects often associated with standard employee onboarding.

New executives are thrust into a realm where every decision echoes through the organization. Here, executive onboarding shines as a guiding light, steering executives as they wrestle with these early challenges, ensuring they find their balance, adapt, and lead with conviction.

But there's no universal playbook for executive onboarding. Each process requires tailoring, crafted considering the distinct strengths of the executive, areas for growth, and the specific challenges inherent to the organization and its industry.

The goal? To swiftly transition the executive from a newcomer to an integral component of the leadership team, perfectly in sync with the company's goals and aspirations.

Emphasizing the importance of culture is non-negotiable in this process. Even the most accomplished executive can falter if they're out of step with the organization's cultural heartbeat. This makes it imperative for the onboarding process to prioritize cultural acclimatization, ensuring that leaders not only understand but also embody and advocate for the company's core values and practices.

In essence, executive onboarding lays the groundwork. It equips the new leaders with the necessary knowledge, resources, and connections, cultivating an environment where they can drive growth, foster innovation, and ensure the organization's long-term prosperity.

Why is executive onboarding important?

When we discuss organizational transitions, especially at the executive level, the stakes are high. The effects of these transitions reverberate across departments and often influence the company's trajectory for years to come. 

At a foundational level, executive onboarding serves as an accelerator. Instead of waiting for leaders to naturally and gradually adapt, onboarding programs propel executives to their peak performance in a shortened timeframe. 

At the executive level, a few months' worth of delays or missteps can equate to significant lost opportunities, financial setbacks, or reputational risks. By streamlining the leader's integration into the company, organizations stand to gain quicker decision-making, strategic alignments, and achieving business objectives.

Retention is another essential facet of this conversation. While executive turnover is a reality that all companies face, it's also an expensive one. From direct hiring costs to the more intangible expenses associated with knowledge gaps or disrupted workflows, the financial implications of losing an executive are substantial. Effective onboarding doesn’t just help a leader adjust; it solidifies their connection to the company, its culture, and its mission. This bond dramatically reduces the likelihood of premature exits, ensuring that the organization reaps the benefits of its executive hires for the long haul.

Another critical element to understand is the risk mitigation aspect. Leadership transitions, by nature, come with a degree of uncertainty. New executives bring fresh perspectives, strategies, and working styles. While this is beneficial, there's always a risk of misalignment, especially in the early days. A robust onboarding process helps smooth out these potential mismatches, align the executive with the company’s ethos, and ensure a harmonious working relationship with existing teams and stakeholders.

Finally, consider the ripple effect. An executive's decisions and strategies don't operate in isolation. Their influence cascades down the organizational ladder, impacting teams, departments, and even the rank-and-file employees. When an executive is onboarded correctly, the positivity of this influence is maximized. Their strategies align with the company's objectives, their decisions are informed, and their leadership style resonates with the organization's culture. This benefits the executive and fosters a positive and productive environment for everyone involved.

Executive onboarding plays a vital role in organizations

Organizations are akin to complex ecosystems where each element, particularly leadership, profoundly impacts the equilibrium. 

Given the magnitude of influence an executive wields, ensuring their seamless integration is paramount. Executive onboarding is more than a mere initiation; it's a strategic endeavor aimed at optimizing an executive's influence and ensuring that they, and by extension, the organization, hit the ground running. The structured approach of executive onboarding is designed to address various key facets:

Cultural integration 

One of the recurrent challenges executives face is understanding and aligning with the company's cultural nuances. 

Company culture, comprising values, beliefs, rituals, and behavioral norms, influences every aspect of an organization, from decision-making processes to interpersonal interactions. Effective onboarding is instrumental in ensuring that the new executive is familiar with and deeply ingrained in this culture. By doing so, it accelerates the executive's acceptance and ensures they resonate with the organization's ethos. This, in turn, leads to more informed decisions congruent with the company's values and beliefs.

Goal alignment 

The vision and mission of an organization provide the compass guiding its journey. 

For an executive, aligning with these objectives is non-negotiable. The onboarding process ensures this alignment by meticulously detailing the company's strategic objectives and how the executive's role fits into this grand narrative. By elucidating the bigger picture and providing clarity on both short-term and long-term goals, onboarding ensures that executives are not working in silos but are contributing toward the organization's overarching mission.

Stakeholder engagement 

Executives, by virtue of their role, interact with a myriad of stakeholders, both internal and external. 

Building and nurturing these relationships is pivotal. Whether it's internal teams, board members, shareholders, or external partners and customers, each interaction holds significance. Effective onboarding programs recognize this and facilitate introductions and engagements with these stakeholders. By setting the stage for these interactions, onboarding ensures smoother collaboration and faster relationship-building, essential for an executive's efficacy.

Faster ROI

The recruitment of top-tier executives often entails a substantial investment. 

Naturally, the organization seeks a return on this investment through strategic decisions, innovation, and leadership that propels growth. A well-orchestrated onboarding process significantly reduces the time it takes for executives to become fully operational. Providing them with the resources, insights, and tools from the outset ensures that they quickly transition from the learning phase to the execution phase, leading to quicker ROI.

Clearly establishes responsibilities 

While job descriptions provide an overview, the actual scope of an executive's role is multifaceted. 

Clear delineation of responsibilities is crucial to avoid overlaps, conflicts, or gaps. Effective onboarding programs meticulously detail these responsibilities, ensuring that the executive fully understands their mandate. This clarity enables them to prioritize and delegate and also ensures they can focus their expertise and energy on what truly matters, driving efficiency and ensuring impactful contributions.

A Free Checklist to Build a Stellar Preboarding Program

5 best practices for onboarding executives

The complex nature of executive roles demands an approach to onboarding that is comprehensive and strategic. 

Not only are executives responsible for pivotal decisions that determine the trajectory of an organization, but they also influence its culture, stakeholder relationships, and overall morale. So, the onboarding process for executives must be tailored, systematic, and agile, ensuring that the new leader is equipped with organizational knowledge and aligned with its vision and culture. 

Drawing insights from various expert sources, we've outlined some best practices that can significantly enhance the executive onboarding experience.

1. Create an onboarding plan for executives 

An onboarding plan for executives acts as a roadmap, delineating the trajectory of the executive's early days in the organization. 

Instead of leaving the executive to navigate the labyrinth of a new organization unaided, a structured plan offers guidance, ensuring that they understand company dynamics, key stakeholders, and organizational objectives. The plan should encompass key meetings, orientation sessions, skill development modules, and feedback loops. By personalizing the onboarding experience to cater to the unique needs and skills of the executive, this plan accelerates the executive's journey from a newcomer to an integrated leader.

2. Offer executive coaching

The leap to executive roles often comes with unprecedented challenges. While their vast experience equips them with industry knowledge, the nuances of the new organization can still be overwhelming. 

Offering executive coaching can be invaluable here. Through coaching, new leaders gain insights into company dynamics, potential challenges, and strategies to overcome them. Coaches act as a sounding board, providing unbiased feedback and strategies to manage complex scenarios, making the transition smoother and more efficient.

3. Ensure cultural immersion 

Executives need to resonate with the organization's cultural ethos to be effective. 

Beyond the official company values listed in manuals, every organization has unwritten norms, rituals, and beliefs. Ensuring cultural immersion involves introducing the executive to these nuances. This might involve storytelling sessions about the company's history, informal meetings with long-standing employees, or cultural workshops. A deep understanding of the cultural fabric helps the executive make decisions aligned with the company's ethos.

4. Foster stakeholder relationships from the get-go 

An executive's efficacy is often tied to their relationships with key stakeholders, both internal and external. 

From teams and departments within the organization to external partners, investors, and customers, these relationships determine the ease with which the executive can execute their mandate. Introduce the executive to these stakeholders early on, setting the foundation for collaborative endeavors. Organize meetings, luncheons, or even offsite team-building events to facilitate these introductions.

5. Implement feedback loops 

Continuous feedback is the cornerstone of improvement. 

Regular feedback can guide their actions and decisions, especially during the early days when the executive is still familiarizing themselves with the organization. Implement a structured feedback mechanism where the executive receives inputs from their peers, superiors, and even subordinates. This 360-degree feedback provides a holistic view of their performance, shedding light on areas of excellence and potential improvement arenas.

By integrating these best practices into the executive onboarding process, organizations pave the way for a seamless transition, ensuring that the new leaders are well-acquainted with their roles and primed to drive growth and innovation from the outset.

Why mentoring is crucial for executive onboarding

Mentoring, a revered practice rooted deep within organizational and educational settings, has risen to particular prominence in executive onboarding. 

The personalized approach of mentoring bridges gaps between what executives know and what they need to understand about their new roles. Leveraging mentoring in the onboarding process taps into the experiential knowledge of seasoned professionals, enabling new executives to sidestep pitfalls and harness best practices that took years for others to cultivate. 

Let's delve into the multifaceted advantages of mentoring in executive onboarding.

Knowledge transfer

At the helm of any organization, executives must quickly decode the company's dynamics, understand industry shifts, and adopt best practices that align with the company's vision. Here, mentors emerge as a reservoir of knowledge. They provide new executives with insights that textbooks or training modules might miss – the unwritten codes of the organization, the historical reasons behind specific practices, or the nuances that differentiate this industry from others. This rich tapestry of insights ensures that executives don't just know the organization but understand its soul.


The age-old adage, "It's not what you know, but who you know," holds particular resonance for executives. Their ability to effect change, drive innovation, or resolve conflicts often hinges on their connections within and outside the organization. With their extensive tenure and relationships, mentors can introduce new executives to crucial stakeholders, potential allies, or even industry experts. These connections, often nurtured over years, can prove invaluable in propelling the executive's agenda and solidifying their position within the company.

Navigating challenges

Every executive, irrespective of their past accomplishments, will encounter challenges unique to their new role or organization. 

These challenges, if not navigated wisely, can become stumbling blocks. Having faced and overcome many such challenges themselves, mentors provide guidance, offering strategies and perspectives that help the executive make informed decisions. Their counsel can range from handling team conflicts, steering through organizational politics, or even advising on strategic decisions based on past experiences.

Confidence building

The early days in any role, especially as pivotal as an executive position, can be daunting. Doubts can creep in, and decisions can seem overwhelming. In such times, mentors act as a pillar of support. Their vote of confidence, rooted in experience and wisdom, can boost the executive's morale. 

By offering guidance, sharing their own tales of trials and triumphs, and being a sounding board for ideas, mentors ensure that new executives not only make decisions confidently but also grow into their roles more seamlessly.

Step-by-Step Checklist For Enterprise Mentoring Programs

Step-by-step guide for creating an executive onboarding plan

The significance of executive onboarding is underscored by the weight of responsibility these roles hold. 

Successful onboarding ensures that executives don't just integrate into their roles but excel, driving organizational success. Such a process, however, cannot be left to chance. It demands a tailored plan crafted after understanding both the executive's role and the broader organizational canvas. 

This blueprint, once aligned with both the executive's and the organization's objectives, lays the foundation for a successful leadership transition.

Conduct a training needs assessment

Begin with a comprehensive assessment to gauge the executive's skills, knowledge, and potential gaps. This isn't about questioning their capability but understanding where they are versus where they need to be in their new role. Such an assessment helps in creating an onboarding plan that specifically targets areas of growth, ensuring a smoother transition.

Set clear objectives

Delineate the goals for the onboarding process using the SMART criteria. Establish objectives that are Specific, Measurable, Achievable, Relevant, and Time-bound. For instance, "Understanding the company's main revenue streams by the end of month one" might be a tangible objective. Such clear goals set the tone and direction for the entire onboarding journey.

Curate resources

Equip the executive with resources tailored to their needs. This could include strategy documents, organizational charts, past performance reports, or industry research. The goal isn't information overload but providing them with tools to aid their decision-making processes.

Introduce the organization

Provide the executive with an in-depth understanding of the organization, beyond just figures and facts. Share the company's history, cultural nuances, values, and strategic goals. Organize sessions with key personnel who can provide macro and micro perspectives of the organization's functioning.

Develop a plan for skills development

Identify skills that the executive needs to develop or sharpen. This could be based on the initial needs assessment or feedback from initial interactions. Prioritize these skills and offer avenues for their development, whether through workshops, courses, or coaching sessions.

Schedule orientations for teams and departments

Facilitate meetings between the executive and the teams or departments they'll work with. These sessions aren't just about introductions but understanding team dynamics, ongoing projects, challenges, and opportunities.

Set up 360-degree feedback

Incorporate a 360 feedback mechanism involving peers, subordinates, and superiors. This holistic feedback provides the executive with insights into their impact, areas of improvement, and strengths from multiple perspectives.

Organize regular check-ins

Establish a regular cadence of check-ins between the executive and their immediate supervisor or a designated onboarding guide. These sessions are platforms for reviewing progress, addressing challenges, and recalibrating objectives if necessary.

Provide ongoing learning

Recognize that onboarding isn't just a phase but an ongoing process. After the initial onboarding period, the emphasis should shift to continuous learning, ensuring that the executive remains at the forefront of industry changes, organizational shifts, and leadership methodologies.

Foster leadership success and organizational growth with Together

Navigating the intricate dynamics of a new leadership role is challenging, and while executives bring a wealth of experience, they still need guidance tailored to their new environment. 

Here's where advanced mentorship platforms like Together come into play. Together not only assists executives during the transitional phase but also embeds them into the fabric of the organization.

Together isn't just another tool in the leadership toolkit; it’s a game-changer. While most platforms offer standardized mentorship, Together understands the nuanced challenges and opportunities tied to executive roles. By prioritizing mentorship as a core facet of executive onboarding, Together is forging a new path in leadership success, ensuring that executives don't just adapt but thrive.

Tailored mentor-mentee pairing: Every executive is unique, bringing a blend of skills, experiences, and aspirations to the table. Together’s advanced algorithms recognize this diversity and pair executives with mentors who complement and challenge them. This bespoke matching ensures that mentorship is not a generic exercise but a deeply personalized experience.

Accelerated learning curve: Time is of the essence in leadership roles. With the right mentor, executives can sidestep common pitfalls, understand organizational dynamics faster, and start contributing meaningfully in a shorter span. Together, by enabling such impactful mentorship, drastically reduces the time executives take to become pivotal players.

Expert insights: While data and reports provide a wealth of knowledge, there are certain insights only experience can offer. Through Together, mentors, with their years of expertise, help new leaders decode these unwritten nuances. This ensures that executives don't just understand the 'what' and 'how' but also the 'why' behind company dynamics and industry trends.

Building relationships: Beyond the formal hierarchies and organizational charts lie the intricate web of relationships that truly drive an organization. Mentorship relationships cultivated through Together serves as the gateway to this hidden framework, allowing executives to foster deeper connections, engender trust, and lay the foundation for collaborative success.

Leadership development: Leadership isn't just about decision-making; it's about influencing, inspiring, and innovating. Through consistent feedback, challenging discussions, and exposure to varied perspectives, mentorship via Together hones these softer yet pivotal facets of leadership. The platform thus doesn't just onboard executives but crafts leaders who drive transformation.

Monitoring and progress: Mentorship isn't a one-off event; it's a journey. Together recognizes this and offers tools for continuous assessment. Whether it's tracking the progress of the executive, gauging the effectiveness of the mentorship, or identifying areas for improvement, Together ensures that the mentorship journey is not just impactful but also evolving, setting both the mentor and mentee up for sustained success.

Executive onboarding is a continuous process

Executive onboarding stands out as a critical juncture in an executive's journey. It is not merely about familiarizing oneself with the organization's mechanics but about immersing in its culture, aligning with its vision, and laying the groundwork for transformative leadership. Mentorship amplifies the effectiveness of this process, bridging gaps, and accelerating adaptation. It’s not just about a smooth transition; it's about ensuring that every transition is the beginning of a legacy of success.

And Together emerges as more than just a tool – it's a companion. A companion that recognizes the intricacies of leadership, values the importance of mentorship, and strives to ensure every executive meets and exceeds their potential. As we move forward in a world that values agility, adaptability, and authenticity, executive onboarding and mentorship become paramount.

Leadership isn't about reaching the top; it's about elevating everyone with you.

Don't leave the success of your executive transitions to chance. Harness the power of structured onboarding and impactful mentorship with Together

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