Top Leadership Development Challenges

14 Challenges for Developing Leaders

According to a study done by the Kenan-Flagler Business School, the top challenges for Leadership Development are:

  1. Managing the needs of the multigenerational workforce
  2. Lack of support from senior leadership
  3. Not enough stretch work assignments to provide development opportunities
  4. Identifying high-potentials
  5. Attracting top Talent
  6. Determining future workforce needs
  7. Retaining top talent
  8. Lack of a formal structure
  9. Lack of accountability for the application of new skills and knowledge to the job
  10. Inconsistent buy-in across the organization
  11. Linking leadership development back to the business strategy
  12. Size of budget
  13. Encouraging managers to develop their team
  14. Balancing long-term and short-term business requirements

14. Managing the needs of the multigenerational workforce

According to a recent study by LinkedIn, 89% of talent professionals believe a multigenerational workforce makes organizations more successful [1]. However, working across generations also poses a few challenges. There are differences in communication styles, as well as expectations for organizational hierarchy, personal conduct, and career progression. Employees from different generations also value different things about their employer; some may value reliability or a robust benefits plan, while others value things like socials, retreats, or opportunities for networking and travel. At the end of the day, what is important is that companies are clear about their mission, vision, and values, and that everyone understands and supports the corporate culture while respecting and appreciating one another.

13. Lack of support from senior leadership

One of the most common reasons why talent development plans fail is that they lack the support of managers and senior leaders. In order for any strategic plan to succeed, all parties need to be held accountable, which means accountability must come from the top down. Even if your senior leaders are not involved in the day-to-day execution of your talent development plan, they should be interested, informed, and invested in the process. 

12. Not enough stretch work assignments to provide development opportunities

One of the common misconceptions about talent development is that it has to occur in a classroom-type environment. There are countless programs, courses, conferences, and books that can help individuals grow personally and professionally, but none will be as effective as on-the-job stretch assignments. Stretch assignments give employees the opportunity to put theory into practice. They also help people grow in their knowledge of your company and its operations. No curriculum will be able to provide this kind of organization/role-specific education, not to mention the opportunity for hands-on learning and relationship building. 

11. Identifying high-potentials 

Most leaders understand the importance of investing in high potentials, but organizations often struggle to identify these individuals. For practical tips and tricks, check out SIGMA’s Talent Development Services. You can also download our FREE Talent Development Guide, check out our talent assessments, or read about the 9 box grid, one of the most widely used tools for talent management and selection. 

10. Attracting top Talent

Attracting and retaining talent has become one of the most common strategic priorities across industries and organizations. Nearly every client we speak to highlights the need to be a competitive employer and encourage talented individuals to join (and stay with) their company. This need has been exacerbated by trends like job-hopping, and The Great Resignation. The good news, however, is that talent development itself will help attract top talent. Once you get the ball rolling you will likely notice a positive feedback loop in which your talent development program attracts top talent, which in turn helps you execute and expand the program itself.

9. Determining future workforce needs

Industries and economies are changing rapidly. As a result, many organizations struggle to determine the needs of their future workforce. This struggle is amplified when leadership teams don’t take time for strategic planning and talent development. Determining future workforce needs starts by determining the needs of your own workforce. Understanding the strengths, needs, and goals of your people will help you get a head-start on preparing for the future of the workforce at large. 

8. Retaining top talent

In addition to attracting top talent, organizations struggle to retain top talent. This is usually due to a lack of talent development opportunities. The WorkInstitute’s 2021 Mid-Year Retention Report indicated that the top driver of resignations was “career reasons,” and that 1 in 5 people were quitting their jobs because they had found better opportunities for advancement and professional development elsewhere [2]. What this tells us is that developing talent will help you retain talent. Employees are looking for employers who will invest in them and help them grow in their careers. 

7. Lack of a formal structure 

A proper talent development program is standardized – in other words, it uses the same process, resources, etc. each time it is implemented. This allows talent development to be easily replicated and scaled, not to mention making the entire process more efficient and effective. For this reason, the lack of a formal structure can be a major challenge for organizations looking to develop their talent. In fact, it is one of the top challenges cited by our succession planning webinar participants. If you want to start talent development on the right foot, start by creating a plan; a structure for your development process. 

6. Lack of accountability for the application of new skills and knowledge to the job

Talent development requires accountability. Leaders need to hold candidates accountable to their development goals, and organizations need to hold leaders accountable to their commitment to develop talent. Methods of accountability can also be highly motivating because they tend to break goals down into smaller steps that measure short-term, rather than long-term progress. This gives candidates a sense of accomplishment and gives leaders an early sense of ROI (return on their investment).

5. Inconsistent buy-in across the organization 

Lack of buy-in can seriously hamper strategic planning. When leaders do not buy-in to a plan, the plan inevitably does not get implemented. When followers do not buy-in to a plan, implementation becomes seriously restricted. There is another, perhaps even greater challenge when buy-in is inconsistent though. In addition to hampering progress, inconsistent buy-in can be a source of conflict and strife within/across teams. Make sure that everyone is on board before you begin your talent development process. 

4. Linking leadership development back to the business strategy 

Proper talent development requires a significant investment of time, HR, and money. This investment should only be made if it furthers the organization’s mission and vision. Therefore, one of the most important parts of talent development is taking time to link it back to the business strategy. If this is not done up-front, it can become a major challenge in the long-run. 

3. Size of budget 

Talent development can get expensive – especially if you’re buying into books, courses, modules, and other methods of education and training. But it doesn’t have to be this way. One of the most effective ways to develop talent is through on-the-job learning, stretch assignments, and internal coaching. It might take some time, but those are all resources you already have! 

2. Encouraging managers to develop their team 

Apart from being cost-effective, internal coaching (i.e., having managers develop their team) is also one of the most effective ways to develop talent in general. Whether your organization has a large talent development budget, or small, we recommend calling your leaders to develop other leaders. To learn more, check out our guide, Great Leaders Develop Others and learn how you can start developing talent with the people you have today. 

1. Balancing long-term and short-term business requirements 

Most leaders understand the importance of strategic planning, they just can’t find time to sit down and plan when there are so many immediate matters pressing for their attention. These short-term, urgent, and seemingly important matters constitute what we call “the whirlwind.” The whirlwind is what leaves you looking at your to-do list for the day and wondering how it’s already 4 o’clock in the afternoon and you haven’t checked any of the boxes. It’s the emails, meetings, or other unexpected questions, conflicts, and demands that arise during regular day-to-day operations.  

In order to find time for strategic planning, you will have to carve it out. If you don’t set that time aside in advance, it will get filled with other things. That being said, you are not left entirely to your own devices – SIGMA can help! Our talent development services can provide the structure, accountability, and resources you need to get the ball rolling and accomplish the goals you set. This can help you save time, allowing you to be present for short-term business requirements, while also making progress on long-term goals for your team. 

Make a Change

This is an interesting (though not terribly surprising) list that may seem overwhelming for those of you looking to build better leaders in your organization. The good news is that the challenges listed above are not mutually exclusive. Focusing on addressing just one of the challenges above (if chosen strategically) can have a ripple effect and serve to alleviate several of the leadership development challenges you face. For example, consider the impact of how senior leadership support (#13) would have on things like budget (#3) and encouraging managers to develop their team (#2).

Combat Leadership Development Challenges with SIGMA

Looking for help with your leadership development challenges? SIGMA offers a range of science-based leadership assessments that can help you combat these challenges. Contact us for more information on how we help our clients build better leaders, or explore our leadership assessments below.

[1] Anderson, B.M. (February 12, 2020). A Guide for the Ages: What You Need to Know to Attract a Multigenerational Workforce. LinkedIn Talent Blog. Retrieved from  

[2] WorkInstitute. (2021). 2021 Mid-Year Retention Report. Reasons for Leaving Shift as Open Jobs Skyrocket. WorkInstitute. Retrieved from chrome-extension://efaidnbmnnnibpcajpcglclefindmkaj/  

About the Author

Glen Harrison

Vice President

Glen oversees SIGMA’s sales and marketing activities. As a skilled presenter and trainer, he has designed and delivered engaging and entertaining workshops and webinars to help leaders and HR professionals enhance their understanding of how our products and services can be used to realize potential within their organizations.