Managers In the Middle

Development opportunities abound for entry- and senior-level employees. But what about those in the middle of their careers?

Most companies Training profiles have strong new hire programs and a wealth of leadership development, but when it comes to mid-level employees, many organizations seem to be scratching their heads. Squeezed between two huge generations, the Millennials and the Baby Boomers, it is not unusual for those in their forties and early fifties— known as Generation Xers—to feel limited in their career opportunities.

To save money, organizations often turn promising roles into lower-level positions, while many Baby Boomers are choosing to stay in the workforce longer, limiting the ability for upward career moves. The challenge is that it is frequently those in a company’s mid-level ranks who carry the heaviest burden, managing entry-level employees, while providing support to senior players. If they don’t see an opportunity for development and growth at your company, what will keep them from going someplace else? Can you afford to lose them?

Earlier Leadership Development

One solution is to offer leadership development that begins at an earlier stage of an employee’s career. At Training Top 125er Haskell, a design, engineering, construction, and professional services firm, opportunities are available to those who are not yet at the top ranks of the company, yet are beyond entry level. The company’s “servant leader” philosophy is advanced early, as an employee just starts climbing the ranks, with Haskell’s multi-level Leadership Series. The program provides three levels of leadership training over three years. Unlike leadership seminars, in which participants are already executives, or close to becoming executives, the Leadership Series has a more heterogeneous group of participants, “comprising team members with different roles, ages, backgrounds, and levels of experience,” says Manager of Learning and Development Arthur Bendolph. In addition to keeping those at the mid-point of their career engaged, the program creates a sense of camaraderie with others who are at the same mid-level point in their career. “Utilizing intensive ‘homework,’ personality and leadership-style assessments, and interactive and thoughtful programming/ projects, the participants become much more self-aware while building their managerial and leadership skills,” Bendolph explains. “As they grow as a cohort, strong bonds form with their peers as they share their challenges and successes over this long-term period. The commitments built with the program have led to better leaders, and ultimately, higher engagement and profitability.”

Aside from building a sense of community with others, Haskell also is careful to foster a sense of team between the generations, so those at different points in their career are able to work with each other, rather than seeing one another as competitors. “We offer multi-generational training courses, along with workshops focused on diversity and inclusion. Strengthening communication and building understanding is key to alleviating the divisions and mistrust that may, or may not, exist in the workforce,” Bendolph explains. “We leverage opportunities for mentoring relationships and job rotations that allow mid-career professionals to oversee those who are working toward licensure,” he notes. “With the Boomer generation, the Generation Xers are able to mentor up with sharing the latest and greatest industry knowledge and technology—which is something they embrace here (as do Generations Y and Z).”

Some companies are rethinking the way they approach mid-level development. At Training Top 125er Jones Lang LaSalle (JLL), a commercial real estate and professional services company, “mid-level development has evolved over the last year,” says Adam Massman, vice president of Learning and Leadership Development. “In 2018, we are launching a new program designed to help the mid-level manager adapt to the rapidly changing workforce, and focusing on driving engagement, inspiring, and getting work from the middle,” he says. “At JLL, we have launched a new employee value proposition called Achieve Your Ambitions. With that, we customize our learning to ensure any employee, no matter the tenure or level, has access to the learning programs and assets relevant to him or her. With that, we stray away from mandatory classes when possible (outside of regulatory and/or client requirements), and focus on quality development plans.”

Value Mid-Level Employees

Appreciating the role mid-level associates play at your company is essential. Training Top 125er Gables Residential has an understanding that, though they may be in the middle of the workforce, mid-level associates are the engine that keeps the company running. “Senior-level associates focus on setting the strategy for the organization, so they rely on their front-line teams to execute and deliver results,” notes Senior Director of Training and Development Rob Rector. “Without these high performers, it would be impossible for us to meet our service and financial targets. Also, since these associates manage the majority of our onsite teams, they are the primary cultivators and maintainers of the company’s culture. Needless to say, this group of leaders makes a significant impact on our ability to drive high levels of associate engagement and retention.”

Rector also says “Gables has fostered a culture where all leaders are encouraged to continuously learn new skills through comprehensive leadership development programs. By regularly evaluating associates’ advancement readiness through a combination of talent reviews, performance appraisals, and self-assessments, we are able to provide customized development opportunities, leveraging both internal and external training resources to give developing leaders exposure to new challenges and assignments. This exposure provides our developing leaders with opportunities to learn transferable skills, implement them with guidance and support, and master them over time.”

Training Top 125er Johns Hopkins Community Physicians offers more than 100 live classroom and e-learning courses directed at developing management and leadership skills for mid-level employees. An annual engagement survey and talent management system are used to orient managers to mid-career development needs. “Our organization participates in an annual employee engagement survey, and our leadership take the results seriously,” says Director of Education Maura McGuire, M.D. “This means there must be ongoing processes for reviewing survey data, impact planning, and educating our teams.”

Course Corrections

Occasionally, an old-fashioned, one-on-one conversation can reveal a mid-level development challenge, notes Piyush Patel, author of “Lead Your Tribe, Love Your Work.” After the successful completion of a demanding project, Patel was surprised to learn of the career dissatisfaction of one of his key team members. It turned out, that as company leader, his own actions unknowingly had led to feelings of a career slump for one of his employees.

“During our first dinner as a team, Dana surprised everyone by stating bluntly: ‘I can’t work for you anymore,”’ Patel recalls. “Once the initial shock wore off, I had an eye-opening chat with Dana that led to a stunning realization: I’d lost my way. I was so focused on increasing our subscribers, and our profits, that I’d forgotten what mattered most—my people. Here I thought everything was going great, but my company was crumbling from the inside,” he remembers. “While I’m not saying you need to have a heart-to-heart to keep your employees around, when someone feels unfulfilled at work, it only leads to anger and frustration. You might think things are great when they’re not. You can throw perks or other surface-level solutions at the issue, but until you can identify the root cause of the problem, the solution will only be a patch.”

Course Corrections

Sometimes when challenges are discovered among mid-level employees, detective work is needed to identify the source. At Training Top 125er LaSalle Network, a national staffing, recruiting, and culture firm, it isn’t enough to know that a mid-career employee is unfulfilled. It’s important to see if the company can fix the employee’s dissatisfaction, says Chief Human Resources Officer Sirmara Campbell. “Dig into why they’re feeling unfulfilled. Is it the role, the industry, the company, or the manager? If it is the role, what have they asked for as of late? What other projects have they volunteered for? What ideas have they brought to you? What have they done on their own to be more fulfilled? If the answer is nothing, then they’re not ready for a more senior position, which some managers think could solve the problem. Employees need to take ownership of their careers.”

Sadly, the answer isn’t always more development, but removing the mid-level employee from the team, if he or she is proving a distraction, or damaging group morale. “A negative Nancy is detrimental because of the negative ripple effect she causes, especially on a small team or in a small organization. However, on the flip side, in an organization that lacks transparency, the employee may be going through something personal, but doesn’t feel comfortable sharing it with her manager. If you notice a change in behavior, have a candid conversation about how the employee is coming off; it may be more than what it seems at the surface level,” says Campbell. “Someone who is bored may need new challenges, and to be given more work, more autonomy, more responsibility. That said, someone who is disengaged isn’t necessarily bored. It means he or she has pulled back from the company, the team, the work, whatever, and isn’t giving it his or her all anymore. It could be because of a manager or a peer or the project he or she is working on. That employee needs to decide whether he or she wants to reengage or not.”

Creating individualized employee development plans, rather than having the manager dictate the development to the employee, also can help avoid the mid-level blues, says Lee Caraher, author of “The Boomerang Principle.” “We work with employees for their own development program, to help them articulate to us what it is they want to do in their career. And then we work with each person over his or her tenure with us to help achieve what he or she wants to achieve within the structures of our work. So it is all about internal promotion from within,” she says, noting that her firm, Double Forte, is generous about sponsoring employees to participate in outside learning opportunities. “At our firm, everybody has a generous education allowance, and we send people to conferences at least once a year,” she says. “We expect people to be learning and to be out there in the world, learning new things, bringing new skills back to the firm, because that is what is going to keep them—and, therefore, the firm—relevant in the marketplace. It plays a big role in keeping our high performers in the firm.”

Sometimes it’s simply important to acknowledge that mid-level employees have distinct training needs. At Training Top 125er Morrison Healthcare, a Compass One Healthcare Company, individualized, custom programming caters to these employees’ needs. “It is important to help mid-career employees see their own development needs,” says Director of Learning & Development Catherine Cape. “To address this, we have assessment tools to help identify gaps, and we have a performance management process built for development feedback. Coaching is key.”

Cape says the company also keeps close tabs on its employees’ development progress, which helps avoid mid-career slumps. “Our performance management process encourages check-ins outside of the actual review where the manager shares her or his assessment of the employee’s needs, and has a discussion about how to bridge development gaps.”

Another course correction is encouraging mid-level leaders to take fulfillment in building their own teams and mentoring others. They might not have reached the top themselves, but there’s no reason they can’t share what they have learned so far, says Lisa Sinclair, Global Portfolio manager and senior faculty at the Center for Creative Leadership (CCL). “The key for mid-level leaders is to learn how to delegate (and feel comfortable doing so more often), and to reinvest that time in developing their team. Great mid-level leaders recognize they don’t have to be the experts,” she says. “Instead, they mine their team for future leaders, cultivate and develop those individuals, and finally sponsor them by putting them on project teams or special assignments that provide opportunities for growth and visibility. It’s crucial for mid-level leaders to begin seeing the organization as a whole, rather than as multiple parts. ‘How can I better align the work of my function to the broader organizational strategy?’ and ‘In what ways can I improve collaboration with my peers to share information and explore ways to gain efficiencies?’ are two questions proven mid-level leaders ask themselves.”

The solution also can come down to tapping into work that aligns with an employee’s greatest interests. Amanda Beers, vice president of Learning and Development for The Learning Experience, says it’s worth the time to be proactive and help mid-career employees do work that is meaningful to them, rather than wait for a development problem to arise. “The biggest challenge is helping them harness their passion. At times, people are in a position where they may not be most passionate, but because of experience or tenure, they tend not to explore or entertain the thought of pursuing anything different,” she says. “The first step is working with them to align them to their passion, and then we can work to create a development plan that helps them continue to grow within the company in an area they truly love.”


  • Create leadership programs for multiple levels in the company, so those in the middle of their career are developed for further advancement, and see future opportunities in your organization.
  • Encourage mid-career employees to write development plans with their managers, so their assignments and long-term plan is as much their own as their manager’s.
  • Employee engagement surveys targeted to mid-career employees can be complemented by informal heart-to-heart conversations between manager and mid-level employee, in which the employee shares the frustrations of his or her job, as well as aspirations.
  • Dig into the dissatisfaction of a mid-career employee, and be honest with yourself and the company if the problem appears to be the employee’s manager or company culture.
  • Help mid-level employees devote at least part of their time to work that’s meaningful to them—“passion projects” that may spur innovation and growth for the company.
Lorri Freifeld
Lorri Freifeld is the editor/publisher of Training magazine. She writes on a number of topics, including talent management, training technology, and leadership development. She spearheads two awards programs: the Training APEX Awards and Emerging Training Leaders. A writer/editor for the last 30 years, she has held editing positions at a variety of publications and holds a Master’s degree in journalism from New York University.