We talked with a dozen middle managers who work for insurance carriers, brokers and other industry organizations. Here are some edited comments.

How do you handle situations where you feel your team lacks the necessary resources or support to meet management’s expectations?

• “I’ll share with management that we don’t have the resources to meet their expectations. I’ll do it as early on in the process as possible so we can work on a solve together.”

• “Transparency and open communication are key in managing expectations of upper management. I communicate progress, milestones and challenges or roadblocks our team may be facing to get a project completed.”

What strategies do you use to keep your team’s morale high, especially when there are pressures from upper management?

• “Pep talks and looking for additional time off I can give back if they’ve been working nights or weekends. Verbal affirmation that they’re doing a great job.”

• “I focus on clear communication, recognition and support. I ensure everyone understands our goals and their roles, celebrate achievements regularly (both with my team and senior leadership), and provide consistent feedback.”

• “I give them my full support and trust that we can get the job done. Recognition and rewards are key to keep them motivated. I include them in meetings with upper management, when appropriate, to ensure they’re getting the face time and recognition from leadership.”

• “I take the time to celebrate successes, no matter how small. This reinforces a positive environment and a sense of accomplishment. I encourage professional development, which usually inspires and motivates the team. I show genuine concern for teammates’ well-being and maintain a psychologically safe environment where we can talk candidly about any issues that arise.”

Can you describe a situation where you had to mediate a conflict between your team and upper management? How did you handle it?

• “Sometimes there is misalignment on the methods [and] expected outcome of a project. Usually, I’ll own my role in not fully communicating what needs to be done.”

If you could change one aspect of your relationship with senior management or your team, what would it be and why?

• “More autonomy to make decisions and final creative calls.”

• “Implement short, regular, skip-level meetings that are prioritized—not cancelled or frequently rescheduled. These meetings, held once a quarter for even just a 15-minute coffee chat, can be so transformative. This simple yet powerful dialogue can bridge gaps, foster stronger connections, and enhance overall understanding and collaboration.”

• “I’d like senior management to better understand the day-to-day tasks and responsibilities that our team is responsible for. A lot of what they do is necessary but sometimes not always ‘visible’ work to management.”

• “The structure of our organization doesn’t leave much authority to middle managers. I wish we were given more direct authority and clearer defined areas of what they could do to support their employees. There is also a lack of sharing information beyond senior leadership and lack of transparency, which leaves some middle managers without full context to be able to better support the organizational goals.”

What challenges, if any, do you face managing newer Gen Z employees?

• “Balancing their expectations for work/life balance (which I admire) and expected outcomes. Adjusting to their more casual conversation style in the workplace. Coaching and giving feedback, in general, and making sure extra care is taken in how to share lessons with them.”

• “Building a strong network is crucial for getting things done, solving problems and even advancing one’s own career. However, Gen Z employees often seem more hesitant to initiate informal networking opportunities, such as setting up coffee chats or lunches to get to know colleagues. This hesitation can lead to delays in building valuable connections that are essential for professional growth and collaboration. I’ve even built this out as a formal development opportunity for a few Gen Z employees. Their goal will be to schedule three coffee chats with people from X department this quarter.”

How do you cope with the stress and pressures of being the intermediary between senior management and your team?

• “Internalize it all and harbor resentment! Haha. But in all seriousness, it’s more so taking a step back and having perspective and seeing every moment as a growth opportunity.”

• “I prioritize clear communication, foster transparency as much as possible, manage expectations and maintain a supportive environment. I seek feedback and support from peers and focus on solutions that help to bridge any gaps between senior management and the team.”

• “Drink lots of wine, LOL!”

Reported by Peter van Aartrijk and Warren Wright