Most organizations are arranged in a pyramid-shaped hierarchy, with large numbers of frontline workers reporting to a smaller group of managers, who in turn report to an even smaller group of directors and VPs, all the way up to a single CEO. Even in organizations that claim to be “flat,” some level of hierarchy is necessary for decision-making and structure.
If we invert this pyramid, it resembles a funnel—managers are often promoted from frontline roles, and senior executives are often selected from middle management. Naturally, developing middle managers into senior leaders is a key priority for organizations seeking sustainable leadership.
While hiring externally for senior leadership roles can bring fresh perspectives and industry expertise, internal development offers key benefits, including deep organizational knowledge, cultural alignment, and employee engagement. Promoting from within signals to employees that the company values their growth and contributions. However, this process is complex and requires strategic investment.
Successful development of middle managers for senior leadership requires two key focus areas: identifying those with the right potential and equipping them with the necessary skills and experience to thrive in executive roles.
Identifying Potential Leaders Among Middle Management
Identifying the right middle managers for senior leadership roles requires a strategic approach beyond just evaluating performance metrics. Strong leadership potential is not solely about hitting key performance indicators (KPIs) but also about demonstrating adaptability, emotional intelligence, and the ability to inspire and lead teams through change.
Assessing Leadership Potential
Organizations must take a broad view of what makes a great leader. As Rachel Hutchisson, CEO of Common Impact, explains, “Beyond the work they and their teams deliver, how do these managers rate when it comes to leading people? Are they good at dealing with ambiguity and helping others do the same? How do they react when a project goes off course?”
Hutchisson stresses the importance of assessing how managers are perceived by their teams and peers. “Are they sought after by others for their opinions? The further up the ladder leaders get, the more they rely on others for their own success.” Consequently, Hutchisson recommends that organizations “look for the potential engagement leaders in your pool, those who see success as a team sport and want to help others be the best.”
The ability to lead through uncertainty and complexity is also a critical factor in identifying future senior leaders. Claire Sears, Manager of Learning Solutions at McLean & Company, notes that leadership development is now the number one organizational priority, surpassing recruitment.
“Today’s leaders must navigate rapidly evolving workplaces, where the external environment is in flux, AI is changing the way work is done, and employees place high value on their relationships with their managers and colleagues,” Sears explains. She emphasizes that focusing on durable leadership skills—such as managing risk, leading through change, and strategic execution—provides a stronger foundation for long-term leadership success.
Looking Beyond Technical Skills
Traditional leadership identification often prioritizes hard skills like operational expertise, financial acumen, and technical proficiency. While these are important, organizations must also consider soft skills, particularly emotional intelligence.
Matt Poepsel, PhD, VP of Talent Optimization at The Predictive Index, highlights the need for organizations to rethink outdated leadership metrics. “To identify and develop effective middle managers, companies need to shift away from outdated leadership metrics that prioritize traits like strength, persuasiveness, or intellect alone,” says Poepsel. “Instead, we must focus on emotional intelligence, coaching ability, and commitment to the well-being of others.”
This shift is especially critical given the increasing reluctance of younger generations to take on traditional management roles due to burnout and stress. Poepsel warns that neglecting people-centered leadership development contributes to a “middle manager crisis,” where many organizations feel uncertain about their leadership pipeline. “The new rules of management require leaders to rehumanize organizations in an increasingly technical world,” he says.
Strategies for Developing Middle Managers for Senior Leadership
Once high-potential middle managers have been identified, organizations must invest in their development through structured learning, mentorship, and real-world leadership experiences.
Tailored Training and Continuous Learning
Middle managers need access to development opportunities that fit into their schedules while providing relevant, actionable knowledge. Marissa Morrison, VP of People at ZipRecruiter, stresses the importance of equipping managers with the right tools at the right time.
“At ZipRecruiter, for example, we developed a People Leader Onboarding Program that includes quarterly virtual training cohorts,” Morrison says. “This equips leaders with resources, tools, and a community of peers so they can learn how to effectively lead teams.”
A one-time leadership seminar is not enough. Morrison highlights the need for ongoing reinforcement and peer learning. “Repetition is key. Reinforcement and real-life application of the knowledge shared in training help keep it top-of-mind for employees. I’ve found success in facilitating check-ins between training sessions, setting up peer-to-peer groups so leaders can use each other as resources, and creating Slack community discussions for post-program conversation,” she explains.
Encouraging Confidence and Leadership Presence
A major challenge for many new leaders is imposter syndrome. Providing a safe environment for learning and peer support can help middle managers build confidence in their leadership abilities. “One of the best ways to foster confidence in rising talent is by providing tailored training that focuses on real-world challenges,” Morrison says. Scenario-based workshops and mentoring from senior leaders provide new managers with validation and guidance.
Hutchisson also emphasizes the importance of visibility and networking in leadership development. “Increased visibility often comes with being a more senior leader. Whether that’s leading a company meeting or representing the organization publicly, leaders need to feel comfortable being with and among people in situations that aren’t always directly about a specific work project,” she says.
Encouraging up-and-coming leaders to participate in cross-functional projects, skills-based volunteerism, and external networking opportunities helps them develop these critical soft skills.
Leveraging AI and Technology for Leadership Development
As work environments become more technology-driven, AI-powered learning solutions can play a crucial role in leadership training. Andrew Scivally, Co-Founder and CEO at ELB Learning, advocates for using AI-driven programs to create personalized leadership development experiences. “AI can analyze skill gaps and learning preferences to create tailored development programs, ensuring efficient skill-building and long-term growth,” he explains. Virtual reality (VR) training has also proven effective in accelerating learning, increasing engagement, and improving knowledge retention.
AI-driven leadership training also helps middle managers prepare for managing remote and hybrid teams, an increasingly important skill. Dr. Cali Morrison, Sr. Director of Workforce Education Strategy at EdAssist by Bright Horizons, emphasizes that organizations must provide structured training in both technical and human-centered leadership skills.
“For instance, our EdAssist partner, eCornell, has a short-term certificate on leading remote teams, which provides not only knowledge on how to build and maintain a high-performing virtual team but also the opportunity for learners to interact in a live, virtual setting to build those skills,” she explains.
Mentorship and Sponsorship
Providing middle managers with mentorship and sponsorship opportunities is essential for their growth. Hutchisson underscores the role of experienced leaders in guiding rising talent. “I can’t say enough about mentorship and sponsorship. Moving into a management role is often the first of many big steps people take in their careers. Make sure your managers have mentors and embrace the practice of sponsorship as much as you can.”
Encouraging senior leaders to actively mentor middle managers can also help ensure a strong leadership pipeline. Pairing emerging leaders with experienced executives provides valuable insights and firsthand exposure to high-level decision-making.
The process of identifying and developing middle managers for senior leadership is a long-term investment that requires strategic focus. Organizations that succeed in this effort will build stronger leadership pipelines, improve retention, and create a culture of internal growth.
By shifting leadership identification criteria to include emotional intelligence and adaptability, providing tailored training and real-world leadership experiences, leveraging technology-driven learning, and fostering mentorship, organizations can ensure their middle managers are prepared for the challenges of senior leadership.
As Morrison of ZipRecruiter puts it, “By investing in the middle today, you’re building the leaders of tomorrow.”
Lin Grensing-Pophal is a Contributing Editor at HR Daily Advisor.