Key Challenges in CEO Succession Planning – Addressing Talent Gaps
and Strategic Misalignment

By Richard Waddell

Succession planning for CEOs and boards of directors is critical to establish smooth leadership transitions and long-term business success. Yet, many organisations fail to prioritise this essential process. Without a robust succession strategy, the sudden departure of key leaders can leave companies vulnerable, threatening strategic initiatives, investor confidence, and employee morale. Effective succession planning mitigates these risks by preparing for leadership continuity.

From working with boards, CEOs and their leadership teams, the Boyden team has recently seen several common challenges related to CEO succession planning and leadership transition:

  1. Talent Shortages and Skills Gaps in Executive Leadership

    One of the most significant challenges businesses face is the ongoing talent shortage, particularly at a senior leadership level. The skills, behaviours and experience required for leadership roles - such as digital literacy (artificial intelligence, automation, data literacy, digital transformation, ethics), strategic thinking, and change management - are in high demand but short supply. Many CEOs report that, while they see individuals with potential below their executive team, they often lack the breadth of experience to step into their senior roles in the short term.

    The rapid pace of technological change and growing importance of ESG (Environmental, Social, and Governance) factors further complicate the leadership profile required for executive roles. This highlights the need for proactive leadership development and succession management strategies that address the evolving skills gap in executive leadership.
  2. Overcoming Proactivity Challenges in Leadership Succession Planning

    Many organisations lack a proactive approach to succession planning. Rather than treating it as an ongoing, strategic initiative run by the board and executive committee, succession planning is often addressed only when a key leader is preparing to leave or when there is an unforeseen departure. This reactive mindset limits the time and resources available to prepare potential internal successors and identify external talent, resulting in rushed decisions and ill-prepared leaders.
  1. Aligning the Board and Executive Team for Effective Succession Planning

    Succession planning requires close alignment between the board of directors and executive team. However, miscommunication and differing priorities often lead to ineffective planning. For example, while the board Chair may prioritise long-term leadership continuity, the CEO might be more focused on short-term performance, leading to a disagreement over the necessary leadership capabilities for a successor. We have seen this play out in practice, leading to long-term damage to the Chair/CEO relationship.

    For successful succession management, the board governance framework must promote open dialogue between the Chair and the CEO to ensure that the leadership transition process is seamless and aligned with the company’s long-term goals.
  2. Navigating Cultural and Regulatory Complexities in Succession Planning

    In many geographies, especially where corporate governance is strictly regulated, boards face additional challenges when planning for executive leadership transitions. For example, the UK Corporate Governance Code mandates that companies regularly review their leadership needs, yet many fail to integrate these reviews into practical succession plans. Additionally, cultural factors such as a reluctance to discuss leadership changes or an over-reliance on long-standing senior executives, can hinder honest conversations about future leadership needs.
     

Practical Steps to Build a Robust Succession Plan

Despite these challenges, CEOs and boards can take practical steps to build and strengthen their succession plans:

  1. Develop a Succession-Ready Culture

    Creating a succession-ready culture is essential for long-term success. Organisations must prioritise leadership development by fostering open discussions about career aspirations, development needs, and future leadership opportunities. Facilitate regular discussions about succession at all leadership levels, but especially with your executive team and board – normalise this conversation. Hold individuals in the business, as well as HR, accountable for leading the development and evolution of succession plans. This encourages them to think more broadly about the business beyond their own team and function. Help your leaders to understand that discussing succession is not about immediate replacement but about building the long-term health and sustainability of the organisation and their careers. By making succession an ongoing conversation, businesses can certify they are prepared for future transitions.
  1. Embed Succession Planning into the Strategic Agenda

    Rather than treating succession planning as a one-off task, make it an integral part of your company’s strategic agenda. At board level, succession should be a dynamic, ongoing process. Regularly review potential successors at least annually, considering both internal and external candidates (market mapping is valuable here), and align leadership development efforts with your company’s evolving strategic goals.
  2. Invest in Leadership Development

    One of the most effective ways to mitigate talent shortages is by investing in leadership development. Identify high-potential employees early and provide them with the resources, mentorship, and experiences necessary to prepare them for senior roles well-ahead of time. This strengthens your succession management process and establishes continuity in leadership transitions. Rotational programs, stretch assignments, live projects, reverse mentoring, and leadership coaching can all play a role in developing well-rounded leaders who are ready to take on greater responsibilities when the time comes. For younger generations, these development opportunities are typically seen as an expectation rather than a special opportunity. If your competitors offer them and you don’t, you risk losing your best talent.  
  3. Engage in Transparent and Honest Dialogue

    Effective succession planning relies on open communication between the board, CEO, and senior leaders. This is especially important when the business is going through a significant change, for example a family business bringing in external investment to accelerate growth. Additionally, seek regular feedback from potential successors and benchmark them to gauge their readiness and willingness to step into senior roles (potential is a ‘state’ not a ‘trait’ and can change over time).  Transparency about future plans and leadership transitions ensures better preparation and avoids disruptions caused by unexpected departures.
  4. Leverage External Expertise

    Encourage your board to seek external advice. Independent experts can provide valuable insights into industry trends, competitor practices, regulatory requirements and best practices in CEO succession planning. External perspectives provide context and insight to help improve the quality of your talent management decisions and de-risk the business of succession.
     

Conclusion

Succession planning is a complex but essential aspect of the growth strategy for CEOs and boards, regardless of size, industry or maturity. By managing talent shortages, adopting a proactive approach, and fostering a succession-ready culture, you can build a robust pipeline of future leaders whilst engaging and retaining them. The right approach to succession planning guarantees leadership continuity, drives long-term success, and strengthens your company’s resilience to take on unforeseen challenges

At Boyden, succession planning is a core area of expertise for the Boyden team. We specialise in developing and maintaining executive succession plans, ensuring leadership continuity and business resilience.

Contact us to learn how our leadership consulting services can help your business navigate succession planning.

About the Author
This website uses cookies to ensure you get the best experience on our website. Learn more