Welcome to Leadership Lessons from the Field.

In this space, I share the advancement and leadership strategies that I have learned throughout my career in philanthropy, educational leadership, and nonprofit management. These lessons reflect my own personal story, the challenges that I have faced, and the opportunities that have led to growth.

These entries are not one-size-fits-all solutions, rather they are thoughts and ideas for strategies that will allow you to overcome obstacles and move forward in your professional goals, advancement practices, and strengthen your organization.

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My hope is that these lessons will give you perspective, cultivate a greater understanding of yourself and those around you, and encourage you to continue learning throughout your journey.

I welcome your feedback, ideas, and collaborations.

Carolyn P. Woolf

Leadership Lessons

Leadership requires that we ask ourselves, “Am I willing to grow?”

— Carolyn Woolf

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Cultivating a Healthy Perspective on Leadership

An individual’s perspective on leadership guides the way in which they interact with stakeholders, affects how they make decisions, and shapes their views of themselves and their organization. Cultivating a healthy perspective on what makes a leader effective is fundamental to allowing your organization to benefit and grow from the strengths and skills of your team.

Understanding Motivation

Throughout my career, I have led countless planning meetings or debriefings to help determine what could go, or what went, “wrong,” and how we could guard against common pitfalls such as lack of clarity, defensiveness, and making assumptions. These meetings have addressed a range of issues, including donor solicitations, employee and parent conflicts, directors’ plans having been rejected by their team--you name it. These meetings became an opportunity to help educate, guide, and support a greater institutional awareness of the various motivations of the stakeholders involved. Acknowledging, understanding, and accounting for motivations is an essential step in crafting effective strategic action and will result in greater organizational alignment and interpersonal success.

Understanding Your Leadership Style and Thriving

This journey started at a point of professional frustration, where I felt powerless and at odds with my workplace and continued to a place of great joy, agency, and capacity in my career. This blog post outlines this progression and addresses how I was able to understand my personal leadership style, cultivate my strengths, and act with confidence as the leader that I am.

“This blog shares my journey from a point of professional frustration and feelings of powerlessness in the workplace to finding great joy, agency, and capacity in my career.”
— Carolyn Woolf, Finding Your Leadership Style

Development Best Practices

Personalization and due diligence is critical in producing a quality work product.

— Carolyn Woolf

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Fundraising Volunteer Engagement & Management

Effective volunteer management requires a strategic communication and engagement plan for all levels of interest, skill, and time commitment. Creating pathways for volunteers to feel meaningfully involved and appreciated is key to building a successful volunteer program.

Preparing for Major Donor Solicitation

Not being prepared for a fundraising meeting is a mistake you should only make once. I remember the embarrassment and panic that struck when during one of my first fundraising meetings the prospect asked for a more granular breakdown of costs than I was prepared for. What was a warm lead turned cold the second I fumbled through my papers and had to admit that I didn’t know. Their response was kind, but they clearly lost confidence in our organization and in me.

Starting a Major Gift Program

The major gift pipeline has two primary entry points. The first is to upgrade existing donors through appropriate involvement and cultivation. The second is to identify high net-worth individuals through peer associations and networks and attempt to ignite an interest in the organization and form a linkage.

The Major Gift Pipeline, Part 1

Major gifts fundraising is a process based on the premise that it takes time to prepare donors and ask them for a major gift. It can take 6-18 months from when a major gift prospect is identified and then finally solicited for a donation. During this time, the prospect transitions through various stages in the major gift process. Common stages include identification, qualification, cultivation, solicitation, and stewardship. In Part 1 of this post, I will outline the key elements of identifying and qualifying major donors.

The Major Gift Pipeline, Part 2

Cultivating major donors is equal parts art and science. It is the process by which we build stronger and deeper relationships with current donors and prospects while simultaneously testing our assumptions regarding the prospect’s linkage, ability, and interest. While the goal of this stage is to build an authentic and natural feeling connection with the prospect, the major gift officer, must also be disciplined to create and document a cultivation plan for each prospect.

The Major Gift Pipeline, Part 3

Stewardship is the process of acknowledgment, recognition, and donor involvement that follows after an individual has made a major gift. Effective stewardship should (1) further establish the donor’s positive feelings about their gift and (2) strengthen their relationship with the organization.

Defining a Major Gift for Your Organization

A major gift to your organization will depend upon a number of factors. A donation of $10,000 may be considered a major gift to one organization, and an annual gift to another. The key to understanding what makes a donation a “major gift,” is in the process of solicitation. The solicitations for major gifts differ significantly from the solicitation process of smaller donations.

“ I have often spoken to organizations that claim that they have a successful major donor program because they have received a major gift. However, securing a large donation does not mean that an organization has a successful major donor program. I have often seen organizations over-leverage their confidence based on a single gift and squander the opportunity and relationship that the gift represented.

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— Carolyn Woolf, Growing a Major Gift Program