How to Help Middle Managers Succeed

Middle managers are often pulled in different directions by their superiors and subordinates. Neglect them at your peril.

By Kathryn Tyler Jun 1, 2016

​Todd Summers, who manages a team of five employees and five contractors for Southwest Airlines in Dallas, admits that he struggles with delegation. “I am a doer,” he says. “I want to help my team with the execution of a project.”

That worked well when he managed a smaller group—but now that he is overseeing 10 people, not so much. “I have to force myself to step back and remember I’m here to coach my people through the work,” he says.

 Summers isn’t new to managing employees—he has held several supervisory positions throughout his career, including the three years he has spent in a managerial capacity at Southwest. But fortunately, even with this experience, his company recognizes that, as a manager, his development should never end.

That’s why he and 30 of his fellow supervisors took part in a three-week training program last fall in which they learned management skills from senior leaders while living and dining together in a Dallas hotel.

Aside from the practical workplace applications, this kind of training “builds long-lasting relationships with the other people in class. I can reach out to those people with questions,” he says.

Southwest has received numerous awards and accolades for its program, which supports new and experienced managers. And the HR team deserves much of the credit for recognizing the pressures middle managers face—as well as the vital importance of helping them develop in their roles.

“The front-line supervisors are in the trenches with the tactical work. The directors spend their time casting a vision. When you’re in the middle, you have to do both. That is a challenge,” says Greg Muccio, a senior manager in Southwest’s People Department.

While managing people has never been easy, these days it may be harder than ever. “The pace of change is accelerating,” says Bruce Tulgan, CEO of RainmakerThinking Inc., a training and consulting firm in New Haven, Conn., and author of The 27 Challenges Managers Face (Jossey-Bass, 2014). “Work that used to take weeks takes moments. Relationships that would have been nearly impossible due to geography are now taken for granted. Everybody is under more pressure to run lean and flexible.” 

When middle managers are neglected, “high-performers leave their jobs,” Tulgan says. “Small problems that should have been solved with ease get worse … . And deals with vendors and customers sour.”

‘Middle managers don’t always get to see the big picture.’

Managers also have an enormous impact on employee retention and engagement. Recent Gallup data found that less than one-third of employees are engaged in their work—which is perhaps not surprising considering that only 35 percent of managers themselves are engaged and that only 1 in 10 of them have the requisite skills to do their jobs. According to the Society for Human Resource Management’s 2015 Employee Job Satisfaction and Engagement research report, 58 percent of employees rate their relationship with their immediate supervisor as “very important,” but only 40 percent say they are “very satisfied” with that relationship.

“Remember the old adage: People don’t leave a job because of the work, they leave a job because of the management,” says Melinda Stallings, SHRM-SCP, CEO of Melinda Stallings International, a consultancy in Baton Rouge, La.

Feeling the Crunch

“Middle managers are the translators of the organization’s strategy and implementation,” says Jim Harter, chief scientist of workplace management and well-being for Gallup. That’s important considering that, from the executive team to the front line, the understanding of and passion for an organization’s mission drops by nearly 50 percent, according to HMuccioarter.

Senior leaders set the strategy, and managers are the ones who make it happen—or at least they’re supposed to. But their workloads have increased dramatically over the past decade.“The average middle manager has 50 percent more direct reports than 10 years ago and spends about 15 percent less time with each of them,” says Brian Kropp, HR practice leader for CEB Inc., a consulting company in Arlington, Va.

Managers are feeling the strain. They have the highest rates of anxiety and depression of any worker group, according to a 2015 study of nearly 22,000 full-time workers by researchers at Columbia University’s Mailman School of Public Health. 

“While in middle management, I experienced some of the greatest challenges in my career,” says Travis Andreas, a business manager for the Kern County Assessor-Recorder’s Office in Bakersfield, Calif. “In middle management, you serve as a liaison and face all of the individual problems, where upper management only gets the consolidated version.”

Middle managers are often frustrated by trying to meet the needs of both their superiors and subordinates, while feeling as though their own needs are ignored and their efforts underappreciated. They often see themselves as caught in an endless cycle of tedious work with a meager, inequitable salary and no promotion opportunities in sight. 

Targeted Training

Fortunately, HR professionals can help prevent manager burnout by training for skills gaps, facilitating coaching and building personal relationships.

While online education can provide on-demand assistance, most leadership training is best delivered in person because of its focus on communication, says Barbara Moy, SHRM-CP, manager of people and culture at CaseWare International Inc., an accounting and auditing software company based in Toronto. CaseWare provides two-hour communication workshops for all employees. More than half of the company’s middle managers, both new and veteran, attended a recent training session on how to communicate without getting defensive.

“This workshop required that employees role-play,” Moy says. “This is key to putting a theory into practice.”

To decrease costs, Moy is creative with her training budget. 

Look to organizational psychology departments at state universities for Ph.D. students or adjunct faculty who would be interested in spearheading such workshops,” she suggests. “The fee is minimal, and you have an expert as the facilitator.” 

The added advantage of in-person training is that it creates an informal support network. 

“When managers are in a room with their peers, they realize they are not alone. They make friends who understand,” she says.Endicott

Since CaseWare started providing the communications training, “the number of meetings where I coach middle managers on personnel problems has decreased.”

One Southwest Airlines training program called “Next Level Leadership” covers change management, strategic thinking, talent management and developing people. Middle managers meet each month for a full day over the course of three months. 

One of the most popular segments of that program includes a senior leader discussing current company initiatives.

“Middle managers don’t always get to see the big picture,” says Bonnie Endicott, director of people for Southwest. “It helps them to better understand how their projects fit into the company as a whole and translate strategic initiatives for their teams.”

If HR professionals create a strong succession planning program, manager training can begin before employees step into new roles. “HR needs to give employees critical experiences before they are promoted,” says Stefanie Mockler, a consultant for Vantage Leadership Consulting in Chicago. 

Facilitate Coaching

Coaching is another way to help new managers learn and grow. They can be matched with executives, other managers or outside coaches. Each kind of relationship has its advantages.

Coaching by executives. “Training that produces the most significant impact is one-on-one training with upper management,” Andreas asserts. “This type of training should review the objective expectations of the middle manager, examples of above-standard work, examples of substandard work and where the middle manager should focus. Middle managers should have tangible references to the expectations so they know to what level they are performing.”

One way to encourage leaders to offer coaching is to include it as a criterion on their performance evaluations—which is what Southwest Airlines does. “We expect our leaders to have consistent one-on-one conversations with their team members about their work and personal lives,” Endicott says.

And there’s no reason coaches can’t come from a different department. “HR could identify people who want to be coaches and those who want to be coached to create two pools” from which to pair individuals, Stallings says. 

Matching could also be more informal. “It can be as simple as a brown-bag luncheon with a speaker who talks about strategy or conflict, and then giving them the opportunity to network with one another,” Stallings says.

Peer coaching. “Have luncheons with employees of similar-level roles and have an expert facilitate a conversation,” says Russ Elliot, founder of the Conscious Culture Group, a consulting company in Santa Cruz, Calif. “Use the talent knowledge of the group to address their struggles. It increases their skill sets and collaboration, as well as bonding between people in similar roles.” 

RussHR also can help middle managers network internally. “Knowing others in different parts of the company can help remove obstacles for my team because I can reach out to someone and get information I need,” Muccio says. “HR can help facilitate those relationships with breakfasts, lunch-and-learn sessions or happy hours. They can bring folks together intentionally in a speed-dating format to help managers learn about different parts of the company.” 

Outside professional coaching. An external coach can provide unbiased advice and a sense of safety. “Managers can be uncomfortable with internal coaches and won’t open up if they fear the information they reveal may be used differently than they intended,” Elliot says.

Employee assistance programs (EAPs) can be a resource as well. At CaseWare, employees can get management consultation through the EAP. “My managers are able to contact a 24-hour service to aid them in being effective managers,” Moy says. “I want them to know there is always help.” 

Providing that extra support can make all the difference. “Managers need someone they can ask that tough question or [get] advice [from] on a challenge,” Stallings says. “They need someone they know they can call or send an e-mail [to] and that person will respond.” 

Build Relationships

HR professionals must take time to build relationships with middle managers that are based on credibility and trust. The best way to do that is to execute every HR function with the utmost care.

“As an HR department, you need to demonstrate great competency on the basics,” Elliot says. “Benefits and compensation must go seamlessly. Recruiting is the most visible thing HR does. Those basics must go really well to develop a level of credibility. If those things aren’t done well, managers can’t get past that. They think, ‘If HR can’t handle administrative things well, why should I trust them with more-difficult things?’ 

Staffing is of particular importance. “Be diligent in hiring the right people, not only for your organization as a whole, but for that manager and team so they fit in well,” Muccio says. When you’ve got the right people on board, many other things will fall into place, he maintains.

It’s also crucial to be present. “Be engaged with middle managers on a regular basis,” Stallings advises. The more familiar managers are with you, the more confident they will be about bringing you tough problems.

“Consistently be visible in front of middle managers and communicate that you are partners,” Mockler adds. 

That could be as simple as mixing up your daily routine. “To make sure I am visible and available to everyone, I literally take a different path every time I go to a meeting, break room or the bathroom,” Muccio says. “When I have coffee in the morning, I intentionally walk around and talk to people.”

Understanding what managers do is just as critical. “Immerse yourself in their daily business,” Endicott says. If you want them to think of you when they need support, “you need to prove you can talk their talk and understand where they are coming from.” 


‘To make sure I am visible and available to everyone, I literally take a different path every time I go to a meeting ... ’

The business partner model, in which HR professionals are embedded in different departments to provide day-to-day guidance, can also help foster strong relationships. At Southwest Airlines, practitioners “are there to help with talent development, answer questions, deal with performance issues, any HR issue,” Endicott explains. “They have relationships with those leaders and understand the priorities of that department.”

Middle managers at Southwest such as Summers praise this structure. “Our HR business partners are our best friends,” he says. “We know we aren’t alone in dealing with challenges.”

For example, when his employee’s significant other died one weekend, Summers was able to text his HR contact to discuss what they needed to do to take care of both the worker and the work.

That support means a lot, since middle managers believe they have one of the hardest jobs in the company—pulled from above and below. While they rarely get the glory that senior leaders do (and are often easy targets for blame), they play a key role in implementing an organization’s strategy and generating enthusiasm among employees to see it through. Indeed, they are the heart and soul of most organizations, and HR can play a pivotal role in ensuring that they get the support and recognition they need before they are stretched too thin. 

Kathryn Tyler is a freelance writer and former HR generalist and trainer in Wixom, Mich.

Illustration by Pete Ryan for HR Magazine.