The Generosity Mindset in Leadership: When Good Intentions Miss the Mark

When I wrote The Generosity Mindset, I focused on helping professional service providers overcome negative mindsets that hold them back, build confidence, and be more effective with their positioning, business development, and pricing.

The principles of The Generosity Mindset® don't stop there. They scale to any level of leadership, from team managers to C-suite executives. The same mindset shifts that help professionals serve better and price more effectively can transform how leaders build loyalty, retain talent, and create thriving cultures.

What The Generosity Mindset Actually Means

At its core, The Generosity Mindset requires three fundamental shifts. First, stop assuming and start asking. What others value is determined by them, not by you. Second, focus outward rather than inward. It's not about what feels generous to you, but what builds trust and value for the other person. Third, generosity that matches real needs creates lasting relationships, deepens trust, and builds loyalty, while misaligned efforts breed skepticism.

These principles work because they force you out of your own head and into genuine service aimed at the needs, hopes, fears, and goals of others. Whether you're pricing a consulting engagement or leading an organization, the same pattern applies: when you focus on what others actually value rather than staying stuck in your own assumptions, both trust and business results improve.

When Leaders Violate Principles of The Generosity Mindset

Research from goBeyondProfit reveals exactly what happens when leaders ignore these principles, and the results are sobering. Despite record-level executive investment in workplace generosity, a quarter of employees who say they "absolutely love their jobs" are actively looking for work elsewhere.

Compensation and culture are always crucial, but the bigger issue here is a generosity misalignment.

The disconnect runs deeper than most leaders realize. Executives are defining generosity through their own lens, focusing on traditional philanthropy like charitable donations and volunteer programs. Meanwhile, their employees define business generosity completely differently: exceptional employee care (35%), values-based company culture (26%), and business operations that genuinely improve lives (22%).

The gap is so wide that 83% of employees don't even consider charitable outreach when they think about business generosity.

This is the exact same pattern I see with professionals who assume clients want lower prices when what they really want is better outcomes. Both executives and individual professionals are giving away the wrong things while the right ones go unaddressed. They're being generous in ways that either they assume employees want, make them feel good, or both. What they are missing is a sharper definition of generosity that actually builds loyalty and trust.

The Costly Consequences

The business impact of this misalignment is severe. When 35% of employees actively pursue jobs at generous companies and 1 in 4 have left jobs because companies didn't display generosity, but leaders can't figure out what generosity actually means to their workforce, you've created a retention crisis disguised as a market problem. Companies aren’t just losing people to higher salaries. They’re losing them because they don’t understand what would truly make employees want to stay.

Even worse, misaligned generosity often breeds skepticism. Only 38% of employees believe their leadership genuinely demonstrates generosity, while 21% perceive their company's generosity efforts as mere virtue signaling. When your employees perceive your good intentions as performance art, you run the risk of actively damaging their trust in your leadership. It's the organizational equivalent of the consultant who over-delivers in ways the client doesn't value, then wonders why they're not seen as indispensable.

I know of a global financial institution that made hiring veterans a high-profile priority. From the outside, it looked like meaningful generosity. This initiative was widely publicized outside the organization.

Employees became cynical when they sensed leadership’s motivation wasn’t centered on serving veterans or honoring their contribution, but on finding employees they believed would be “easier to manage.” When employees detect such hidden motivations, generosity efforts backfire completely.

Applying The Generosity Mindset to Leadership

The solution requires the same mindset shift that transforms individual expert service professionals. Leaders must get out of their own heads about what they think employees should value and start discovering what actually matters to their people. This means listening differently, asking better questions, and investing in what creates genuine trust rather than what creates good press.

Just as professionals find they can serve better and price higher when they embrace The Generosity Mindset, leaders who align their generosity with what employees actually value see remarkable results. Companies where employees feel strongly connected to their mission and purpose are 32% less likely to lose talent.

The parallel isn't coincidental. Whether you're pricing a consulting project or trying to retain your best team members, the same principle applies: true generosity requires understanding what the other person actually values, not what you think they should value. When you get this alignment right, both trust and business results follow.

I encourage you to stop guessing what your team values and start discovering it. Examine how the feedback loop you already have with employees is flawed and not yielding honest responses. Schedule one-on-one conversations and small group meetings and ask directly:

• What does generosity mean to you?

• How does generosity show up in ways that don’t involve charitable giving?

• What community initiatives feel most meaningful to you?

• Which of our efforts feel most genuine?

• What in our community engagement feels performative?

• How can we as a company be more genuine in our efforts at generosity?

Listen to the answers without defending current initiatives. Include employees in decisions about charitable and community initiatives and take their suggestions seriously. Reallocate existing generosity investment toward what they actually told you matters.

Your people will notice the difference, and you may have found one solution to your turnover problem.

Photo by Chanhee Lee on Unsplash

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I'm John, author of The Generosity Mindset. Feel welcome if you'd like to start a conversation on these ideas. If you'd like to read a little more of my work first, you can subscribe to my Sunday morning newsletter here. It's short on sales pitches and heavy on ideas to improve your thinking and your business.