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In investment sales, fundraisers often face what I call the “Problem of Eighteen Months.” New hires have about eighteen months to prove their worth – to establish relationships, secure funds, and meet performance expectations.
But without clear training or guidance, the first months often become a scramble.
I’ve been in the fundraising business for over 2 decades, and I have experienced this 18 month cycle myself and seen it play out with others around me.
In this article, we are going to discuss the problem of 18 months. By the end of this, you’ll know exactly what we are referring to and how to avoid falling into this 18 month cycle with the time tested principles we have codified as The Dakota Way.
The Problem of Eighteen Months is a challenge that many fundraisers don’t realize exists until they’re already deep in it. In investment sales, new fundraising hires are typically expected to prove their value within eighteen months by building a pipeline, establishing key relationships, and raising significant funds. However, most spend the first six months just getting oriented.
By the time they’ve figured out the basics, they’re left with only a year, sometimes less, to deliver measurable results, often against long sales cycles that can stretch from six to thirty-six months. For many, this problem becomes apparent only as leadership’s patience wears thin, leading to missed goals, frustration on both sides, and often, high turnover.
So how do you avoid this 18 month clock? The answer is simple: having a proven structure in place to keep you on track.
When Dakota was founded, I was forced to create a sales process for the hires after me. I developed The Dakota Way – a structured approach to help fundraisers overcome these challenges from day one.
The Dakota Way provides clear guidance, efficient processes, and tools for effective time management to lay a solid foundation for fundraisers to make an impact right from the start.
This approach streamlines each aspect of the fundraising role, allowing new hires to skip the trial-and-error phase and focus immediately on what drives results – getting meetings with qualified prospects. With step-by-step guidance on building a TAM, crafting targeted messaging, and managing follow-ups through a CRM, fundraisers can build a strong pipeline and achieve early successes.
Instead of scrambling to meet goals, fundraisers using The Dakota Way make measurable progress within those critical eighteen months, setting the stage for a successful and lasting career.
With that, let’s get into the four pillars of The Dakota Way.
Sit down with your leadership to define what success looks like in your role. This includes setting clear sales targets, identifying performance metrics, and creating alignment on priorities. If you’re in a one-person team or smaller firm, take the initiative to structure your own expectations.
Regularly measuring against these expectations allows you to track progress, make adjustments, and show tangible results, ensuring you’re on track toward long-term success.
A key element of efficient fundraising is identifying your TAM early. The sooner you know who your target audience is and what they value, the sooner you can start building meaningful relationships with them.
Focus on reaching the right people at the right time, and make sure to diversify your approach to keep your pipeline healthy from the outset.
Your message is your differentiator. In a crowded fundraising landscape, standing out means mastering the art of communication.
Whether through storytelling, data-driven insights, or aligning your message to the core values of your target market, becoming an effective messenger is about delivering a message that resonates deeply with your audience.
Consistent follow-up is essential, and having a CRM-based system keeps you organized and on top of each interaction. By regularly checking in and reinforcing your value, you build trust and keep your prospects engaged.
This process transforms a “maybe” into a “yes” over time, increasing your chances of successful conversions and building a lasting relationship with donors.
At the core of the Dakota Way is the mantra: Focus on What Matters Most.
This guiding principle encourages fundraisers to prioritize efforts that directly contribute to their goals. When challenges arise, this focus allows you to cut through the noise and dedicate time to what drives results, helping you stay grounded and effective despite the pressures of the 18-month timeline.
With the right tools and an intentional approach from day one, fundraisers can break the cycle of short-term stints and high turnover. Implementing the Dakota Way principles not only helps you survive the “Problem of Eighteen Months” but positions you for a fulfilling, long-term career in fundraising.
By focusing on setting expectations, knowing your audience, perfecting your messaging, and following up effectively, you’ll be ready to make an impact that lasts.
Written By: Gui Costin, Founder, CEO
Gui Costin is the Founder and CEO of Dakota.
October 06, 2021
February 18, 2022
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