Beyond “Difficult” Bosses: The Reality Check You Didn’t Know You Needed

What Does Your Boss Think of You?

You might have plenty of opinions about your boss—who doesn’t? But have you ever stopped to wonder what your boss actually thinks about you? If not, it’s time for a serious reality check. Your perception of your own performance means little if the decision-makers don’t see it the same way.

What Executives Actually Want

Back in February 2022, we hosted an exclusive happy hour and dinner for C-level executives—Directors of Development (DODs), VPs, and other decision-makers—where the conversation turned to employee relations. After much discussion, our group reached a consensus about the top challenges they face with their teams. These six critical areas (Forbes) stood out:

1. The ability to communicate and empathize with individuals from diverse backgrounds
2. Follow-through and completion of tasks
3. Attention to detail
4. A genuine desire to learn the trade and grow in the current role, instead of obsessing over the next promotion
5. Picking up the phone instead of hiding behind emails and text messages
6. The use of handwritten or at least personalized notes and letters

These may sound like simple expectations, but here’s the kicker: Most employees believe they are already excelling in these areas, while executives strongly disagree.

So, before you assume you’re knocking it out of the park, take a moment to reflect. If you focus on improving these six key areas, you’ll make significant progress—not just in how your boss perceives you, but in your long-term career trajectory.

Reframing the “Difficult Boss” Narrative

When workplace challenges arise with leadership, our default response often involves labeling bosses as “difficult” or “unpredictable.” However, this perspective may be limiting our professional growth and success.

What constitutes a “difficult” leader is remarkably subjective. Take our nation’s presidents as an example. President Donald Trump’s direct, business-oriented leadership approach has been described as refreshingly decisive by supporters (Havard Business Review) and unnecessarily confrontational by critics. Contrast this with President Jimmy Carter, often remembered for his gentle demeanor and collaborative style (Leadership Now), yet some historians argue his consensus-building approach sometimes lacked the assertiveness needed during critical moments.

Neither style is inherently right or wrong—they’re simply different approaches to leadership that resonate differently with various individuals and situations.

The Spectrum of Leadership Styles

Every leader brings a unique combination of strengths and challenges. A boss who maintains exacting standards might seem demanding when you’re under pressure but may be exactly what the organization needs during critical projects. The executive who wants daily updates isn’t necessarily micromanaging—they may be accountable to stakeholders requiring frequent communication.

Rather than categorizing bosses as “difficult” or “easy,” consider viewing leadership styles as existing on a spectrum, with each style offering different advantages in different contexts.

Navigating Dynamic Leadership Styles

Generally, you know the type of situation. One minute, your boss seems like your biggest advocate, and the next, they appear to be creating obstacles. They might change your assignments, keep you guessing, or occasionally criticize you in front of colleagues. Sound familiar?

If your boss is simply demanding but respectful, you can likely find a way to adapt. However, if their behavior feels erratic or even toxic, you’ll need a strategy to protect your well-being and career.

Steps to Take on Your Own

• Stay calm. If your boss has frequent shifts in approach, remember that their behavior is often a reflection of their own pressures, not your performance.
• Be strategic with timing. Identify when they are most approachable. Maybe they’re more relaxed after lunch or on days without management meetings.
• Take short breaks. Step away when you feel overwhelmed. A quick walk, meditation, or even a deep breath can help reset your mindset.
• Document everything. If clarity seems to vary day-to-day, create a paper trail. Confirm discussions in email and keep records of major decisions.
• Consult HR or a mentor. If the situation escalates, seek advice from HR or a trusted colleague—but be discreet.
• Explore your options. Even if you’re not ready to leave, updating your resume and networking can give you leverage and confidence.
• Stay positive. No matter what, keep your attitude in check. A positive outlook will keep you from becoming part of the problem.

Steps to Take with Your Leader

• Identify patterns. Does your boss get more stressed before deadlines? Do they expect immediate responses to emails? If you can anticipate stress triggers, you can better manage them.
• Clarify expectations. Instead of guessing, ask direct questions about priorities and performance standards.
• Focus on the message, not the tone. Even if feedback is delivered in a style different from your preference, extract the useful parts and recognize different communication styles.
• Validate their concerns. Recognize their pressure points. A little empathy can go a long way.
• Show appreciation. Every leader has strengths. Expressing gratitude for their guidance or opportunities can create a more positive dynamic.

Adaptability as a Professional Strength

Rather than expecting leaders to conform to our preferred style, developing adaptability becomes a career-defining skill. When we encounter leadership approaches that challenge us, we have an opportunity to expand our professional toolkit.

At the end of the day, you have two choices: Find a way to work effectively with your leader, or find a new opportunity. Either way, understanding the diversity of leadership styles gives you an edge in navigating your career.

Why This Matters for Fundraisers

If you work in major gifts or planned giving, managing relationships isn’t just about donors—it’s also about internal diplomacy. Your ability to navigate various leadership styles—whether with your boss, your colleagues, or your board members—can directly impact your success in fundraising.

Think about it: If your boss doesn’t see you as a strategic, high-value team member, why would they put you in front of their top donors? If you don’t communicate effectively with leadership, how can you expect to close transformative gifts?

Mastering these internal dynamics isn’t just about career advancement—it’s about becoming a better fundraiser. That’s where the Major Gifts Boot Camp comes in.

This program teaches you how to:

• Build stronger relationships with leadership and donors
• Communicate more persuasively
• Increase your confidence in high-stakes conversations
• Develop strategies that ensure your boss sees you as an indispensable asset

If you’re in planned giving, the Planned Giving Boot Camp for Major Gifts Officers is an essential addition to your skill set. It will help you understand the nuances of legacy giving, making you even more valuable to your organization.

The Career Advantage of Leadership Fluency

Professionals who can work effectively with diverse leadership styles have a distinct career advantage. They become organizational translators, capable of bridging communication gaps and navigating complex workplace dynamics.

Rather than hoping for an “easy” boss, perhaps our career development is better served by becoming the type of professional who can thrive under any leadership style—recognizing that each approach offers valuable lessons for our professional growth.

The Bigger Picture: Your Role in Philanthropy

Understanding how you are perceived within your organization isn’t just a career move—it’s a leadership move. As a fundraiser, your work extends beyond raising money; you’re shaping your institution’s future. That’s why it’s critical to stay informed, sharpen your skills, and build your personal brand within the sector.

For deeper insights into philanthropy, leadership, and industry trends, explore Philanthropy.org—a hub of thought leadership, best practices, and professional development for fundraisers and nonprofit professionals.

And if you’re looking for tools to elevate your planned giving efforts, PlannedGiving.com provides the resources you need to engage donors more effectively and grow your nonprofit’s endowment.

Strengthen Your Influence in Major Gifts

Your success in major gifts and planned giving isn’t just about donor relations—it’s about how you position yourself within your own organization. The better your leadership team perceives you, the more opportunities you’ll have to lead, close bigger gifts, and make a lasting impact.

Invest in yourself. Take the time to refine your communication, build stronger internal relationships, and expand your fundraising knowledge. Whether it’s through the Major Gifts Boot Camp or the Planned Giving Boot Camp, the next step in your career starts with you.

Moving Beyond Labels

When we shift our perspective from labeling bosses as “difficult” to recognizing the diversity of leadership styles, we open ourselves to greater professional growth. Specific behaviors that challenge us—whether from a direct communicator like Trump or a consensus-builder like Carter—become learning opportunities rather than obstacles.

Instead of saying, “My boss is difficult,” try articulating specific behaviors: “My manager prefers more detailed reports than I’m accustomed to providing.” This shift makes challenges concrete and addressable rather than personal and fixed.

Your leadership team is watching—what do you want them to see? A professional who can adapt to different leadership styles and excel regardless of the approach, or someone who thrives only under certain conditions?

The most successful professionals aren’t those who find “easy” bosses—they’re the ones who develop the versatility to succeed with any leader. And in the process, they often discover that what initially seemed like a challenging leadership style was actually the catalyst for their most significant professional growth.

What leadership styles have you encountered in your career, and how have they shaped your development? The leader you initially found most challenging might ultimately be the one who contributed most to your success.