Confessions of a Development Director: I Can’t Keep a Development Job Longer Than Two Years

advice confessions of a development director fundraising two year development phenomenon Nov 29, 2021

Confessions of a Development Director: I Can’t Keep a Development Job Longer Than Two Years


In this series, entitled “Confessions of a Development Director,” I share with you emails between real-life development directors and me about the struggles they don’t want their boss to know they have. My email inbox is a safe place where fundraising professionals can ask the questions they need to without shame or judgment AND get the answers. If you would like to make a confession and/or ask a question – email [email protected]. Identities are, as always, confidential.


The Confession: 

I read your post where you described the two-year lifespan of certain development directors. I can’t get that out of my head. I’m with my fourth nonprofit, this is year eight, and I find myself browsing job boards. What do I do to break through and stay? 

- Jeremy (Springfield, IL)


Kevin’s Response:

Thanks for your email. I’d love to talk you through breaking the Two Year Development Phenomenon™ and keeping your job as a development director. We can make a plan for staying at one place through many years of improved fundraising. Let me just ask a clarifying question: if you had to self-diagnose your most significant obstacle to success, what would it be?


Development Director:

I’m embarrassed to say, but I don’t ask for money. I hide behind my email. I don’t even like making phone calls and definitely don’t want to meet with people to do even a low-pressure ask. In my eight years as a development director, I’ve only asked a handful of people directly. When I look at the goals for the development position - increasing annual giving by 10% year over year, improving donor relations, etc., it seems like such a good gig for the pay. It seems like a no-brainer, but inevitably I end up feeling like I need to change careers, and I get depressed and down on myself. Please help! I want to learn and improve. 


Kevin’s Response: 

Eight years of repeating the same two-year schedule has given you some good perspective. You cannot hold down a development position for an extended period of time without making some asks. Do not hide behind your desk, your email, or even your phone, and expect to be a successful fundraiser. If fundraising is about relationships and communication, in-person or at the very least, Zoom interactions are essential. The good news is learning to ask in a way that you are comfortable with is a skill that you can learn and develop. I will give you six mindset shifts to help with improving your asks. 

But first, let me expound upon relationships and communication and the keys to the Two Year Development Phenomenon™. 

It takes two years to establish and/or turn around a development program; this applies to a consultant or an employee such as a development director. 

  • Relationships: First, you need to establish trust and relationships with donors, and only time, meetings, following up, maintaining consistent touchpoints, etc., can do that. 
  • Communication: You need two cycles to establish a communication system. The first year is trial and error, learning, mistakes, and determining what worked and what did not. The second-year is solidifying the approach and executing consistently. 

You should see some success with your different/new/updated efforts, but it will inevitably be inconsistent (hit-or-miss). You also may have early success or identify low-hanging fruit, but predictable systemic fundraising success and building a development process takes two annual cycles.

You are very “normal” - Development Directors average only two years in one position. You have good instincts feeling in your gut that you question whether you are missing something after two years. If you were doing well, you should be hitting your stride at two years and confident in your plan to consistently. From your answer, it seems to me you may be lacking on the relationship side of the equation, but you may be behind on your communications as well. I did not get enough details. That leads me to my #1 solution to avoid two-year development director burnout… a development plan!

Why a development plan helps development directors stay at an organization longer than two years:

  • Strategy Up Front: Great development plans are based on strategies that actually work. I see many development plans, and most that I see are very focused on the tactics (“how to execute”) with little strategy (“why we are doing these things”). If you share your strategies upfront in a plan, you can have confidence that the tactics are working you into a place where you will succeed.
  • Measures of Success: I know that “development goals” are often constantly moving targets. I have agreed to development roles with clearly defined goals, only to have them changed over and over again until I was no longer working on what I was hired to do. How can you make progress if you are constantly changing your target? Having a written development plan makes changing the measures of success less likely. It also clearly defines what the measures are and how they are to be understood. Does “net-new donors” mean totally new relationships, or are they first-time gifts regardless of whether that person was in the database? What about lapsed donors who you bring back, are those net-new gifts or not? 
  • Board/Leadership Buy-In: Development Directors or Executive Directors charged with fundraising are almost always accountable to a board. When you have a written development plan, the board votes and agrees to pursue a specific approach to development; they are then bought-in and can help you reach your goal - which means they want it to work as much as you do - this changes the relationship. The board no longer needs to look speculatively at you; rather, you simply report on your progress. 
  • Accountability: Many of us development folks are talkers, socializers, and people pleasers. We want to be a part of everything, which causes us to be pulled in many directions and overcommit. Having a development plan keeps our efforts focused and limited to what is possible. If we choose to get involved in other areas, that’s on us, but for the most important things, we have built-in accountability for ourselves - ensuring we are making progress on our key indicators. If others try to pull us into projects and events that we cannot afford to do, we now have a clear reason to say, “not right now; cannot afford to take my focus away from XYZ.” 
  • Plan A, B, and C: I talk to development directors and executive directors all the time. Many believe they are on the chopping block if they miss their goal (and some are let go that easily). However, when you have a plan, and that plan does not work, it is not the same as you failing. A good development plan will include systematic assessments of efforts, so you do not go too long without meeting the goals. Also, and perhaps more importantly, a good plan includes backup plans for what you will do when (inevitably) things change and something does not work. If you experience no failure, you are not innovating. 

An excellent start to a development plan is my free Fundraising Framework which you can download here.


Six Mindset Shifts for Being Comfortable Asking for Support

  1. You are not asking for a gift; you are inviting people to be superheroes and impact makers. 

  2. Giving to your organization is NOT for everyone, so do not take it personally when someone says “no” or “not at this time.” 

  3. Focus on WHY the donor would want to support you and work on finding a personal reason for them to support you, so when you talk to them, you can show them how the impact might feel for them and how it would help the donor fulfill something important to them.

  4. If you set up an ask and the potential donor knows it is an ask, you are way more likely to get a gift and will not face much rejection. You would face most rejection in donors not taking the appointment, not during the in-person face-to-face discussion.

  5. If you do not have anything to talk to the donor about, spend most of the time asking them about themselves and learning something you can use later to relate. A discovery call, although not an ask today, is a future ask in the making. 

  6. The “advice model” - soliciting feedback and advice from potential donors on internal decisions, brings about strong buy-in from the donors or prospective donors and makes them sticky for future appeals.