[difficult people] - 19. The Art of Managing Up
Dealing with Difficult People
The View from the Middle: A Story About Managing Up
Lisa stared at the email from her boss, Marcus, feeling that familiar knot in her stomach. Another last-minute project, another impossible deadline. Below it was an angry message from her team member, Jake, about being overwhelmed. Stuck between a demanding boss and a frustrated team, Lisa felt like a human sandwich.
She remembered her first months as a project manager, trying to shield her team from Marcus's constant pivots while simultaneously trying to meet his expectations. It wasn't working. Jake was close to burning out, Marcus was growing impatient with missed deadlines, and Lisa was losing sleep trying to keep it all together.
The turning point came after a particularly rough project review. Instead of just nodding along to Marcus's criticism, Lisa tried something different. "Could we spend fifteen minutes understanding your priorities for the next quarter?" she asked. "I want to make sure our team's efforts align with what matters most."
That simple question changed everything. Over coffee, Lisa learned that Marcus was under pressure from the executive team to innovate while cutting costs. His scattered requests weren't random – they were reactions to his own challenges. Understanding this context helped Lisa see opportunities she'd missed before.
She began scheduling brief weekly check-ins with Marcus, always coming prepared with solutions instead of just problems. When new requests came in, she'd help Marcus understand their impact on existing priorities, offering realistic trade-offs instead of just saying no.
The effect on her team was remarkable. With better insight into Marcus's world, Lisa could explain the "why" behind changing priorities. She could advocate for her team more effectively because she understood what mattered to leadership. Even Jake started to see the bigger picture, making him more adaptable to changes.
Key Strategies That Made the Difference:
Build Understanding
Learn your boss's pressures and priorities
Understand their communication style
Identify what success looks like from their perspective
Communicate Strategically
Bring solutions, not just problems
Frame issues in terms of business impact
Keep updates brief and relevant
Manage Expectations Both Ways
Be realistic about timelines
Offer options instead of obstacles
Explain impacts before they occur
Create Information Flow
Regular brief check-ins
Proactive status updates
Early warning of potential issues
Daily Practices:
Start of Day:
Review priorities against leadership goals
Anticipate potential challenges
Plan strategic communications
During Interactions:
Listen for underlying concerns
Document key decisions and rationale
Connect team efforts to larger objectives
End of Day:
Prepare brief updates on critical items
Plan next day's priorities
Note any needed follow-up
Remember:
Managing up isn't about manipulation – it's about creating understanding that benefits everyone. When you bridge the gap between leadership's vision and your team's reality, you create an environment where everyone can succeed.
The most effective middle managers aren't just good at directing their teams; they're skilled at managing up to create the conditions their teams need to thrive. As Lisa learned, sometimes the key to solving problems at your level is understanding the challenges above you.
What one step could you take tomorrow to better understand and align with your manager's priorities?