Managing from the Middle

The 3 Biggest Challenges Facing Middle Managers—and How to Overcome Them

Middle managers hold one of the most complex roles in any organization. They’re expected to execute strategy, manage teams, develop people, drive results, and keep senior leaders happy—all at once. It’s no wonder many of them feel squeezed in the middle. It's like a game of tug-of-war...but you're the rope.

In my work coaching leaders, I’ve noticed three consistent challenges that show up again and again for managers at this level. If you’re a middle manager—or if you lead them—here’s what you need to know.

1. Managing Up and Down at the Same Time

Middle managers serve two masters: their direct reports and their senior leaders. They’re expected to translate high-level direction from the top into clear, actionable goals—while also advocating for their team’s needs and protecting morale.

• What makes this hard?

  “Leadership wants faster results, but my team is already stretched thin. How do I deliver without burning them out—or looking like I can’t execute?”

• Tips to make it easier:

  • Schedule regular check-ins with your boss to stay aligned on changing priorities. Ask, “What matters most right now?" Be honest when the workload is too much, and partner with your boss to prioritize. Oftentimes, senior leaders don't know how long a particular task will take or how much effort is required, sometimes because they haven't done it before and sometimes because they haven't done it in a long time. Give your boss the benefit of the doubt and manage up to clarify what's important, and what can wait.

  • Help your team connect the dots between strategy and daily tasks. Explain the “why,” not just the “what.” If you don't know why, find out. This piece isn't negotiable if you want your team to give their best effort.

  • Don’t shield your team from leadership or vice versa—be a bridge that brings transparency and empathy in both directions.

2. Driving Change Without Having Full Authority

Middle managers are often tasked with rolling out new initiatives they didn’t help create. They’re accountable for successful adoption but rarely have a say in design or timing.

• What makes this hard:

  “I’m told to roll out a new initiative, but I wasn’t involved in creating it—and my team has serious concerns. How do I champion something I didn’t shape?”

• Tips to lead effectively:

  • Name the reality: “This wasn’t our idea, but we’ll shape how it gets implemented here.” Invite your team into problem-solving mode. Call upon the mission of the team - people often rise to the occasion.

  • Use influence instead of authority—tell stories, show small wins, and connect change to personal or team-level benefits. Influence is a change management activity. You're managing resistance, creating win-wins, creating a burning platform for action-even if it's on a smaller, task-sized scale.

  • Create a feedback loop back to leadership. Sharing what’s working (and what isn’t) positions you as a strategic partner, not just a messenger. Use caution, though - some leaders are more open to constructive feedback than others. If your boss doesn't want to hear it, you may need a new boss. Food for thought.

3. Developing People While Delivering Results

Managers know how important it is to invest in their team—but when you're juggling deadlines, KPIs, and constant pressure to perform, people development often takes a backseat.

• What makes this hard:

  “I want to support my team’s growth, but it feels impossible when every week is a sprint to hit numbers or put out fires.”

• Tips that work in real time:

  • Build development into the work. Use real assignments as coaching moments—delegate with support, not just handoffs. If you find yourself unsure of when and how to delegate, stay tuned for a future post on this topic. In the meantime, consider a brief google search on "situational leadership" for some quick direction.

  • Ask about growth during regular check-ins: “What skill are you working on right now?” This keeps development on the radar. Your team members should be partnering in their own development. You can't care more about it than they do. Call this out and ask them for ideas of how they can grow skills at work.

  • Protect time for strategic thinking—yours and theirs. If everything’s urgent, nothing is meaningful. Block time for future-focused conversations. This is essential. Research has proven that we can't multitask, not really. If you can't plan, you're constantly reacting.

Final Thought

Middle management is not just a stepping stone—it’s a cornerstone. In these roles, leaders shape their leadership identities and create habits they will take with them as they rise through organizations When organizations equip middle managers with tools, space, and support, it strengthens the entire leadership pipeline. If you're in the middle, know this: the work you do matters more than most people will ever see. And if you're leading from the top—invest in the people who hold your organization together.