Unleashing Leadership

Unleashing Your Leadership’s Fundraising Potential

CEOs, Executive Directors, and Presidents play a significant role in an organization's fundraising potential, and fundraising leaders who work with them can, in tandem, take development to a greater level of sophistication and effectiveness.

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Picture of Patrick Gaines

Patrick Gaines

What exactly stands in the way of organizational leaders in fundraising?

How can development leads unlock new possibilities for their higher-ups?

Whether it be time on hand, a leader’s perspective of what will be asked of them in fundraising, or good old-fashioned fear – we urge development leads to work with leadership to address the resources needed to approach (and pass!) these hurdles effectively.

Making Time…

One of the most significant and most complex barriers to an organizational leader’s fundraising success is time. Whether you are the dean of a college, the president of an organization, or the CEO or executive director of a nonprofit, your management and governance duties, along with obligations to boards and committees, take a significant amount of time and energy. While leaders typically delegate much of their day-to-day tasks, they must oversee many additional projects. A productive way for leaders to make time for fundraising is to integrate this work into their other duties. Development is not isolated to its own task but rather a daily practice when done well. This means that when leaders present their organization’s vision to their board and staff, they remind them about their role in the philanthropic ecosystem you continually build together. This expands the amount of time and energy leaders put toward fundraising and will bear fruit when they can dedicate time to making an ask, thanking a donor, or doing discovery or qualification visits.

The phrase “When do I have time to fundraise?” inevitably arises, especially when the chief development officer relays that building relationships takes multiple touchpoints over years.

Creating time to fundraise is linked to effective budgeting – leaders and development leads should work together to understand what additional resources are needed to prime their team for success. Consider people, tools, processes, and associated costs – ask if your investment in each is worth what you are receiving in return. Recognize that just like for-profit businesses, marketing, PR, and communications are essential to fostering general awareness of what your organization does, which primes your donors and prospects for deep and meaningful engagement.

Defining Responsibilities

Lack of clarity around a leader’s role in development and what activities are needed for them to fulfill that role are significant barriers to their fundraising success. When a chief development officer says to their CEO, “You are the number one fundraiser for our organization,” they should also provide them with actionable work to live up to this position.

To be the number one fundraiser for their organization, leaders should take responsibility for setting the tone for a rich, positive culture of philanthropy. This should be top of mind, along with setting the mission and vision of the organization. Leaders should unapologetically champion philanthropy at staff and board meetings, events, and public relations opportunities. Development heads can remind their leaders of this and ask them to introduce themselves at events by describing why philanthropy is essential to their work. Lead fundraisers should emphasize to their higher-ups the importance of embracing and embodying this role to drive everyone in their organization to understand their role in elevating a positive culture of philanthropy.

Nonprofits intentionally establish themselves as tax-free organizations with the knowledge that they will ask the public for support. Leaders can weave this understanding into organizational storytelling to assist in building a positive culture of philanthropy. Individuals, consciously or unconsciously, look to leaders to know how they can contribute to the mission and vision of an organization – and leaders should consistently and earnestly invite others to contribute to the work being done. Explicitly stating, “We are providing a public benefit, and we need the public to support that benefit,” clarifies expectations and needs. 

Development heads should also work with their higher-up to be specific about the number of people or percentage of the organization’s overall donor pool in the leader’s portfolio. To some degree, leaders should focus on larger fundraising opportunities, though relationships should be the deciding factor when determining who the organizational leader is responsible for cultivating. A leader’s responsibility need not hinge on bringing in a certain amount of revenue, as they may be able to foster a fruitful relationship with a few mid-level donors who could make transformational gifts down the road. Depending on your organization’s size, the leader’s portfolio could be anywhere from 15 to 25 individuals, with the development lead supporting a pipeline of new donors and prospects flowing in.

Know Thyself

Leaders should define their fears in fundraising and work with their development leads to understand how they can effectively navigate them together. CEOs take this approach with other areas, such as human resources (by hiring incredible talent acquisition staff to advise on hiring), and fundraising should be no exception.

It is perfectly acceptable to be an organizational leader who prefers not to make a fundraising ask directly. Instead of forcing this work upon the CEO, we recommend a team approach where whoever is most comfortable making the ask does so – likely the staff or volunteer with the best relationship with a donor or prospect. When everyone involved in fundraising knows the role they thrive in, they can build upon these strengths. For example, perhaps you are a leader who can eloquently speak to what makes your organization’s impact unique in your community and world – a valuable asset when building and deepening connections with donors. Leaders can also engage in stewardship and even some discovery work as training and a way to keep the pipeline moving.

No matter who is directly asking for a gift, fear of the word “no” should be investigated.

A leader’s portfolio will hold only those already committed to their organization – no blind or first dates. These donors have an established emotional connection with the organization’s mission, as well as the passion and ability to step up in a bigger way. They’re members of the inside circle – connections with them will be warm and primed by their desire to see your organization succeed.

While some nervousness is expected (I can say from many years as a musician that a bit of stage fright is normal and needed), everyone on the donor relations team should be prepared enough for an in-person ask that they are not fearful of a possible “no.” Roleplaying cannot be underestimated as a way to get comfortable with in-person asks. Again, musicians practice their work over and over before sharing it with the world – and those on the ask team should rehearse their performance as much as needed to approach their donors with confidence. Leaders should ask themselves what they are terrified of and practice navigating that response from a donor when absolutely nothing is at stake. Non-apologetic replies to a “no” along the lines of “thank you for letting me know, that is why they are here,” can move your conversation toward closing a different kind of gift.

Development Leads Can Increase the Confidence of Their Leaders

Statements like “I have confidence in you” remind leaders why they are in their positions. Telling leaders that you see how much they take on (including criticism) and that others have a great deal of trust in them will elevate their readiness to navigate in-person asks with greater comfort.

Alongside the fear of “no” is the misconception that asking for a gift is asking someone to make a sacrifice.

Development leads should coach their leaders to understand that major gift asks are directed at those who play the role of family and close friends.

We have a responsibility to those who care about an organization’s future and to inform them when there is an excellent opportunity to enhance the extraordinary work being done. These conversations often include points like, “We know you believe in us, we are grateful for your commitments so far, and we ask you to lean in again or further or toward something new.” A “no” in these conversations helps get your team closer to knowing the next steps in reaching your development goals.

When we do hear “no,” it is not toward leadership or the organization – but toward the time, amount, or project.

A great tool for establishing the appropriate ask amount is our Donor Engagement Map below, which qualifies prospects and donors based on their affinity and capacity to give. However, often a pivot might need to be made toward an alternative ask, and a development lead can help navigate this either in the moment of a face-to-face meeting or over a period of time. Again, the Donor Engagement Map comes in handy in adjusting the next steps with particular donors.

Donor Engagement Map

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Meet Lauren

Lauren Sisneros

Lauren Sisneros is the founder of LS Consultants, LLC, a consulting firm that provides strategic advising and interim management support to nonprofit and education-focused organizations. A mission-driven leader with over 20 years of experience, Lauren brings a deep commitment to advancing equity across education, workforce development, and public policy.

With a keen understanding of complex systems and a results-oriented approach, Lauren partners with organizations to develop and implement strategies that are both effective and sustainable. Through LS Consultants, she delivers hands-on guidance in program management, board and stakeholder engagement, and leadership transitions, empowering mission-aligned teams to grow, adapt, and create lasting community impact.

Lauren has collaborated with a diverse portfolio of clients, including the Prosperity Denver Fund, Contractor Academy, Education Commission of the States, and Strong Start to Finish. Her work is grounded in a strong foundation of project management, nonprofit leadership, and policy analysis.

She holds a Bachelor’s degree in Business Administration from Colorado State University–Pueblo and a Master’s in Education from Colorado State University Global. Lauren is also a proud graduate of the University of Denver’s Latino Leadership Institute, a fellowship preparing Latino professionals for positions of influence across Colorado, and the Denver Metro Chamber Leadership Foundation’s Leadership Program, an 11-month civic leadership experience.

A Colorado native born and raised in the San Luis Valley, Lauren now lives in Lakewood, Colorado. She is a proud mother of two college students and a devoted grandmother who cherishes time with her family.

Throughout her career, Lauren has remained deeply dedicated to expanding access to opportunity, especially for underserved communities. Her work continues to center on shaping systems that are inclusive, community-driven, and equity-focused.

Meet

Kyle Christensen

Kyle Christensen, M.P.A., is a program leader, facilitator, and trainer with more than 25 years of experience designing and delivering transformative learning experiences that advance leadership, civic engagement, and organizational change. He specializes in designing and evaluating leadership programs, facilitating team and organizational development, and guiding strategic planning processes that align purpose with measurable impact.

As founder of The Connected Leadership Project and consultant with Arrow Performance Group, Kyle partners with organizations such as the State of Colorado, CiviCO, and the University of Denver to design experiential leadership programs that build resilience, connection, and innovation. He also serves as program director for Leadership Veteran, an 8-month leadership initiative advancing the skills of professionals serving veteran communities.

Previously, Kyle directed Colorado State University Douglas County Extension, where he launched Colorado’s first Juntos 4-H program to expand pathways to higher education for Latinx youth and families. He also led the Family Leadership Training Institute of Colorado and has worked with institutions such as Peace Corps (Moldova), NYU Steinhardt, Centrul Educatia 2000+ (Romania), and the Council for Economic Education.

Kyle’s facilitation expertise is rooted in adult learning theory and supported by credentials such as Emergenetics, Strategic Doing, and Technology of Participation. He has led statewide and national trainings, peer learning cohorts, needs assessment processes, and community-centered planning efforts across government, nonprofit, and education sectors.

He holds an M.P.A. from New York University’s Wagner School of Public Service and a graduate certificate in Learning and Development from the University of Denver’s College of Professional Studies.

Kyle believes that the workplace should focus on continuous learning and growth, inclusive engagement, and creating a sense of belonging. “Why wouldn’t we hope for work environments that align with our values and our professional and personal growth aspirations?” He brings curiosity, compassion, and clarity to every engagement, and is most inspired when people find their voice, connect with others, and lead boldly in collective service.

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Jason Pemberton

Jason Pemberton is a multi-award winning facilitator, coach, independent executive board director, and strategist based in Denver, Colorado. Born in USA and raised in New Zealand, his entire career has been dedicated to Not-for-Profit and purpose-led organizations striving for high impact.

A series of catastrophic earthquakes in his home city of Christchurch, New Zealand, launched him into several years of disaster response, which, in turn, launched him into international consulting practice. He has worked in more than a dozen countries supporting companies, networks, and communities navigate through unexpected terrain for mutual benefit.

As a strategist and coach, he is pragmatic, direct, and clear, bringing his sharp mind and depth of thought to the fore whilst supporting groups to identify their own priorities and take charge of their future. His deep governance experience, coupled with professional training in positive psychology and related coaching accreditations, makes him highly effective at supporting teams of leaders and governors to find successful paths forward.

His time now is invested in supporting governance boards and senior leaders to succeed, and coaching technical experts and engineers on how to be skilled leaders of people.