Faculty Essays

10 Things Learned in 10 Years of Fundraising

Written by James Kolakowski on April 9, 2024.

After a decade in fundraising at The Heights School I’ve put together a list of ten personal and organizational ideas which I believe have most contributed to my professional development and which I would now share with any newcomer to the field. Many of these items may be common sense, but they are among the most useful lessons I’ve learned. While gimmicks and quick wins often take the spotlight, the essential aim of educational fundraising is to help build a culture and a community, and this takes time. The more we can take the long view in this work, the better. 

Of course, I’m still working on all of these points and there are many more tips and practices still to learn. Feedback is welcome.


Snail Mail Is Not Dead 

A consistent mailing calendar of around four to six direct mail pieces per year coupled with handwritten thank you notes for gifts received can do wonders for a giving program. Mark the dates for solicitations at the start of the year and stick to them. When the name of the game is building a culture of generosity, regular paper mailings aligned with the school calendar help to keep institutional needs top of mind. Digital communications have their place, but they are not as effective at communicating stability and tone like a hard piece of mail sent at just the right time. 


You Don’t Represent the Organization, You Are the Organization 

Particularly at a time when turnover in our industry is frequent, when it comes to professional growth it can be tempting to hide behind metrics as a means of gauging achievement, but donors are not interested in the success of your portfolio. They are most energized when they see you as an active member of the community who enjoys doing what you do. Make an effort to get out of the office and walk the hallways. Check out a sports game or a band concert. Spend time getting to know the faculty and students. Think less of your day as going to work than of building a culture. This frame of mind says to donors (and yourself) that what you do matters.


Always Have an Answer to “How are Things Going?” 

In Born to Raise, fundraising guru Jerry Panas notes, “the secret to a good impromptu speech is preparation!” Perhaps what most keeps us from starting a new conversation is simply not knowing what to say. For this reason I find it useful to always have three stories in mind: one about a current development project, one about a student interaction, and one about an upcoming school event. This way you can always draw out a substantive conversation while also directing it back to the school. 


Master Scheduling

In many ways, the work of fundraising IS scheduling. Do this well and you’ll always have a job in development. If you’re able to maintain a steady flow of donor meetings you will grow relationships, get better at asking for gifts, develop a more natural cadence, and get better at your job regardless of outcome. In many ways it’s as simple as that. Forty to fifty meetings per year (with just fifteen to twenty of them being to ask for a gift) is a great pace. 


Don’t Just Love Your Donors, Like Them

It’s easy to love your donors, they make your work possible! But do you like them? Could they be included in your friend group? While we’re not necessarily going to develop deep friendships with everyone we meet, cultivating the perspective of liking your donors, not just loving them, can provide the best means to dive deeper into what they find interesting and to listen with greater attention. As in friendship it’s good to be interesting, but it’s better to be interested. 


Don’t be Afraid of “Offending” Anyone

It can be daunting to ask someone for a significant amount of money, but most donors understand that this is your role and the organization they care about is much better off as a result. It is always better to schedule more meetings and to make more and better asks than to shy away from doing so for fear of causing offense. Over time you will become more attune to reading the conversation and to making more sensitive requests. Clearly and politely share what you need, and stop talking.


Practice Discretion

In as much as fundraising is the “gracious art” of helping people realize their noblest aspirations, we are stewards of their ideals. Speaking about your donors flippantly, even internally around the office, is the easiest way to destroy the relationship. Practice sharing only as much about your donors or the organization as is necessary. Fundraisers are rarely benefitted by talking more.


Schedule Meetings With Development Colleagues

I stepped into my role just as two seasoned fundraisers departed. While there was a period of transition, much of my daily activity had to be learned on my own. A few years into the job, still bewildered, I decided to reach out to a colleague and in just a few brief conversations I made years of progress. I felt joy and relief! Little of what we do as fundraisers is new or unique, but a vast amount of practical knowledge is lost due to turnover. Seek out opportunities to “talk shop” with others in your role. You can make remarkable strides in a short period of time.


Write Things Down 

The best fundraisers have a knack for remembering details, but you will forget things over time. Perhaps not month to month, but year to year. Get in the habit of writing things down in a formal way: conversation topics, reminders to follow-up, job changes, funding interests, etc.. Work with your database manager or seek out a reliable means of recording important information. If nothing else, this will be a valuable service to the person who comes after you. 


Process Over Outcome

The health of your organization should always take priority over big wins. A development culture takes time to grow. Don’t rush a gift or a relationship at the expense of the calendar year. While you should always be bold, the right moment will present itself and the gift will be that much more meaningful as a result. 


Connect with me on LinkedIn to continue the conversation.

Additional Reading

Below are a few books I’ve read recently which are worthy of attention:

The Philanthropic Revolution, An Alternative History of American Charity

The Forgotten Foundations of Fundraising: Practical Advice and Contrarian Wisdom for Nonprofit Leaders