Top 10 Succession Planning Challenges and How to Fix Them

Succession Planning Overview

Succession planning is the practice of preparing employees to fill key roles in the future, ensuring your organization has the right people ready when leadership changes happen. It’s about creating smooth leadership transitions and maintaining business continuity, even when unexpected departures occur. This strategic approach helps organizations maintain stability and stay prepared for change, whether it’s planned retirements or sudden exits. Career advancement becomes more structured and meaningful when employees see clear pathways to growth within the organization. 

Without proper succession planning, companies often find themselves scrambling to fill critical positions, leading to disruption and lost momentum. The public sector faces particularly unique challenges in this area, as agencies must balance competitive hiring practices with regulatory requirements while preparing for significant workforce changes as baby boomers retire. Many organizations discover that reactive hiring approaches cost significantly more than proactive succession planning, both in terms of recruitment expenses and productivity losses during transition periods.

1: Only planning for executive leaders

One of the biggest succession planning challenges organizations face is focusing exclusively on executive positions while ignoring other critical roles. Many companies put all their energy into identifying who will replace the CEO or department heads, but they forget about the specialized roles that keep operations running smoothly. This narrow focus leaves gaps in middle management, technical positions, and other key functions that are just as important for daily operations. Consider the impact when your most experienced budget analyst retires without having trained a replacement, or when your facilities manager who knows every vendor relationship suddenly leaves. The fix is straightforward: include key roles at all levels in your planning process. Start by mapping out which positions would be hardest to replace quickly, regardless of their place on the organizational chart. You might be surprised to find that losing your best project manager or lead technician could be just as disruptive as losing a C-suite executive.

2: Using the same plan for every role

Another common challenge among succession planning challenges is applying a one-size-fits-all approach to very different positions. Every job has unique requirements, skills, and responsibilities, yet many organizations try to use the same template for planning successors across various roles. What works for identifying a future marketing director won’t necessarily work for finding someone to take over complex technical operations. A customer service role requires different interpersonal skills than a research position, and a compliance officer needs different competencies than a creative director.

The solution involves tailoring your approach to match each role’s specific needs. Consider the technical skills required, the relationship-building aspects of the position, and the different pathways someone might take to be ready for that role. A sales leader might need different preparation than a finance manager, so their succession plans should reflect those differences. Think about the learning curve for each position and how long it typically takes someone to become fully effective in that role.

3: Picking just one backup

Relying on a single successor for each critical role creates unnecessary risk and represents one of the most dangerous succession planning challenges. That one person might decide to leave the company, take a different internal role, or simply not be ready when the time comes. They might also get promoted to a different position before the succession opportunity arises, or personal circumstances might change their availability. Putting all your eggs in one basket leaves you vulnerable to the same scrambling you were trying to avoid in the first place. Smart organizations identify multiple potential successors for each key position, creating what’s essentially a bench of candidates at different stages of readiness. This approach gives you options and creates healthy internal competition while also providing valuable development opportunities for more employees. Consider developing candidates across multiple timelines:

• Some candidates might be ready now for immediate succession needs
• Others might need six months of targeted development to reach readiness
• Still others might be longer-term prospects who could be ready in two to three years

Having this range of options means you’re covered regardless of timing and can make the best choice based on the specific circumstances when the succession actually needs to happen.

4: Leaving it all to HR

While HR professionals bring valuable expertise to succession planning, one of the most limiting succession planning challenges occurs when business leaders remain completely hands-off from the process. When managers and department heads don’t participate actively, the plans lose connection to real-world operational needs and day-to-day challenges. HR can facilitate the process and provide structure, but they can’t know every nuance of what makes someone successful in a specific role or team dynamic. They might miss the informal leadership that happens during crises or the relationship-building skills that aren’t obvious in performance reviews.

The fix requires getting managers directly involved in identifying potential successors, assessing readiness, and providing input on development needs. Line managers know their people best and understand the practical requirements of their roles. They see how individuals handle pressure, work with difficult customers, or adapt when priorities change suddenly. They should be partners in the planning process, not passive recipients of HR’s recommendations. This collaboration ensures that succession decisions are based on complete information about both job requirements and candidate capabilities.

5: Letting the plan get outdated

Organizations often treat succession planning as a one-time project rather than an ongoing process, which creates significant succession planning challenges down the road. Business priorities shift, roles evolve, people leave or get promoted, and new talent joins the team. A plan that made perfect sense two years ago might be completely irrelevant today if it hasn’t been maintained and updated. Regular reviews should be built into your planning process, with formal updates at least annually and informal check-ins throughout the year. Consider how various changes might affect your succession plans:

• Changes in strategy, technology, or market conditions that might affect the skills needed in key roles
• How your identified successors are progressing in their development
• Whether new candidates have emerged who should be considered
• Updates to role requirements based on organizational evolution

Think of your succession plan as a living document that grows and changes with your organization.

6: Keeping the plan a secret

Secrecy around succession planning creates one of the most counterproductive succession planning challenges organizations face. When potential successors don’t know they’re being considered for advancement, they can’t prepare effectively or make informed career decisions. Employees who aren’t included in planning may feel overlooked or undervalued, leading to decreased engagement or departure. While you don’t need to share every detail with everyone, transparency about development opportunities and potential career paths benefits both individuals and the organization. Let people know they’re being considered for growth, give them feedback on what they need to work on, and help them understand how they can prepare for future opportunities. This openness helps retain talent and ensures people are actively working toward readiness rather than stumbling into roles unprepared.

7: Thinking that good performers can do any job

High performers in their current roles don’t automatically make good candidates for every other position, yet this assumption creates recurring succession planning challenges. Success in sales doesn’t guarantee success in sales management, and being an excellent individual contributor doesn’t mean someone will thrive in a team leadership role. Different positions require different skill sets, temperaments, and interests. 

The solution involves assessing people for future fit rather than just rewarding past performance. Look at the specific competencies required for the target role and evaluate candidates against those requirements. Consider providing stretch assignments or temporary leadership opportunities to see how people handle different responsibilities. Some of your best current performers might not want the responsibilities that come with certain advanced roles, and that’s perfectly fine. Focus on finding people who both can and want to do the job well.

8: Avoiding tough conversations

Many succession planning challenges stem from organizations avoiding difficult but necessary conversations about career timelines, retirement plans, and leadership transitions. When there’s no open dialogue about when current leaders might step back or move on, it’s impossible to plan effectively for succession. These conversations can feel awkward, but avoiding them creates much bigger problems when changes happen suddenly. The fix involves building regular, honest discussions into your management practices. Create multiple touchpoints for these important conversations:

• Talk with key employees about their long-term career goals and timeline
• Discuss retirement planning with senior staff members before it becomes urgent
• Have frank conversations about performance issues that might affect succession readiness
• Address any concerns about role changes or additional responsibilities

These discussions should happen early and often, not just when someone is about to leave. Create a culture where talking about career progression and transitions feels natural rather than threatening.

9: Letting bias influence decisions

Unconscious bias can significantly impact succession planning decisions, creating one of the most persistent succession planning challenges organizations face. When selection criteria aren’t clear or consistently applied, personal preferences and assumptions can drive choices rather than objective qualifications. This leads to qualified candidates being overlooked and to potentially unfair advancement decisions. 

Implementing clear, documented selection criteria helps address this challenge by creating consistent standards for evaluating potential successors. Define the specific skills, experiences, and competencies required for each role, then use these criteria to assess all candidates fairly. Consider using structured evaluation processes and multiple perspectives to reduce individual bias. Regular training on unconscious bias can help decision-makers recognize their own tendencies and make more objective choices. The goal is ensuring that the best candidates are identified based on their ability to succeed in the role, not on who they know or how similar they are to current leaders.

10: Not writing things down clearly

Verbal agreements and informal understandings about succession create significant succession planning challenges when key information gets lost or misremembered. Without clear documentation, there’s no accountability for following through on development commitments or succession decisions. When people leave or change roles, important context and agreements disappear with them. 

The solution requires documenting all aspects of your succession planning process clearly and consistently. Write down who the potential successors are for each role, what development they need, who’s responsible for providing it, and when progress will be reviewed. Document the criteria used for selection decisions and track progress over time. Keep records of development conversations and commitments made to individuals. This documentation creates accountability, ensures continuity when staff changes occur, and provides a clear reference point for making decisions. It also helps demonstrate fairness and transparency in your succession planning process.

Looking Beyond Leadership Titles

Many succession strategies focus exclusively on traditional leadership roles, but this narrow approach misses other critical areas that affect organizational continuity. While preparing the next CEO or department head is important, organizations need to think more broadly about what happens when key people leave. The relationships with major clients or vendors that one person has built over years, the institutional knowledge about how certain processes really work, and the cultural values that guide daily decisions all need attention in succession planning. Sometimes the person who knows how to navigate a critical software system or who has the best rapport with your biggest client isn’t in a traditional leadership role, but their departure could still create significant disruption.

CPS HR’s approach recognizes five distinct areas that require succession planning:

• Management succession – focuses on developing operational capabilities and day-to-day decision-making skills that keep the organization running smoothly
• Ownership succession – addresses who will be responsible for strategic direction and long-term organizational health, ensuring continuity in vision and accountability
• Relationship succession – ensures that critical external connections don’t disappear when individuals leave, protecting valuable partnerships and client connections
• Cultural succession – preserves the values and working style that make the organization effective, maintaining the behaviors and attitudes that drive success
• Leadership succession – prepares people to guide and inspire others through change and challenge, developing the emotional intelligence and vision needed to motivate teams

This broader model helps protect continuity across all these dimensions, not just the obvious leadership positions on the organizational chart.

Build Stability Through Better Planning

The challenges of succession planning can feel overwhelming, but addressing them systematically makes the process much more manageable and effective. By expanding your focus beyond just executive roles, customizing plans for different positions, identifying multiple candidates, involving managers directly, and maintaining current documentation, you create a foundation for organizational stability. Regular communication, fair selection processes, and honest conversations about career progression turn succession planning from a dreaded administrative task into a valuable tool for employee development and organizational strength. Remember that succession planning is not about predicting the future perfectly, but about being prepared for various possibilities and having options when change occurs.

Working with experienced professionals can help you navigate these succession planning challenges more effectively and build systems that work for your specific organizational needs. CPS HR offers specialized succession planning services that address all five levels of organizational continuity, helping you create stability through better planning. Connect with a professional today to start building the leadership pipeline your organization needs for long-term success.