Do’s and Don’ts of Gray Sky Prospecting

Nonprofits across the country are facing an unprecedented level of uncertainty, with challenges ranging from funding instability to increased demand for services. In these "gray sky" times—periods of crisis or uncertainty that significantly impact nonprofit operations—organizations must navigate shifting donor behavior, economic pressures, and unexpected changes in legislation.

For-profit companies that sell to nonprofits must tread carefully—offering real value while respecting the mission and urgency these organizations are experiencing. However, some companies engage in "ambulance chasing," a term borrowed from the legal field that refers to predatory tactics where businesses take advantage of vulnerable situations for financial gain.

How can you navigate these difficult waters without being exploitative? Here’s a practical guide outlining the do’s and don’ts of prospecting nonprofits during times of crisis.

The Do’s: How to Sell to Nonprofits the Right Way

1. Do Your Homework

Nonprofits are not a monolith, and every organization has its unique challenges. Before reaching out, research the nonprofit’s financial health, mission focus, and any recent changes that may impact its operations. Check their website, social media, CEO blog posts, and press releases to gain a deeper understanding of their current priorities.

2. Lead with Empathy and Value

Nonprofits are staffed by passionate professionals dedicated to making a difference. Approach your conversations with genuine care and concern for their mission. Instead of a hard sales pitch, frame your outreach as a way to help solve their most pressing problems.

3. Offer Specific, Immediate Solutions

Be clear on how your product or service can provide real, tangible benefits in the short term. If you can help a nonprofit save staff time, reduce costs, or adapt to changing donor behavior, make that the focal point of your conversation. Generic claims like “we’ll help you raise more money” won’t cut it—give specific examples and success metrics.

4. Use Personal Outreach Instead of Mass Emails

During times of crisis, nonprofit leaders are overwhelmed. They don’t have time for impersonal email blasts or vague sales pitches. Instead, reach out with a personalized email, a direct LinkedIn message, or even a text, referencing specific challenges the nonprofit is facing and how you can help.

5. Acknowledge the Crisis, But Stay Respectful

If a nonprofit is facing financial hardship, recognize the reality of their situation. Instead of a standard sales approach, frame your outreach with understanding:

“I saw that your funding was recently impacted by [specific event]. I wanted to see if there’s a way we can support your team through this transition.”

This shows awareness without being exploitative.

6. Offer Low-Risk or No-Cost Entry Points

If possible, offer a free trial, an early adopter program, or a reduced-rate pilot that lets nonprofits experience the benefits of your service without a large upfront commitment. This builds trust and allows them to see real impact before making a financial decision.

7. Help Nonprofits Adapt to Changing Donor Behavior

Many nonprofits struggle to anticipate shifts in donor behavior, especially during economic uncertainty. If you have data on changing trends—such as increased engagement in digital giving or a shift towards grassroots fundraising—share it. Providing valuable insights strengthens your position as a trusted partner rather than just another vendor.

The Don’ts: What to Avoid When Prospecting Nonprofits

1. Don’t “Ambulance Chase”

In the legal world, ambulance chasing refers to predatory lawyers looking to take advantage of vulnerable people in crisis. In nonprofit sales, it means aggressively pushing products during moments of extreme distress. If your approach comes across as opportunistic rather than supportive, you will lose credibility and damage relationships.

2. Don’t Rely on Generic, Automated Emails

Nonprofit professionals can easily spot a templated email that’s been sent to hundreds of other organizations. If your message is impersonal or lacks relevance to their current situation, it will be ignored—or worse, create a negative impression of your company.

3. Don’t Waste Their Time with Vague Pitches

Nonprofit leaders don’t have time for a 45-minute call that’s just a fishing expedition. Avoid emails like:

“We’d love to hear about your challenges and explore ways to help.”

Instead, bring a clear proposal to the table:

“Given [specific challenge], we have a solution that can help in [specific way]. We’d love to walk you through it—would a quick 15-minute call work?”

4. Don’t Assume Fundraising is Their Only Concern

Not every nonprofit needs immediate fundraising help. Some may be overwhelmed with demand, struggling with staffing cuts, or navigating legislative threats. Be sure your outreach aligns with their actual needs instead of making assumptions.

5. Don’t Ignore Relationship Building

If you’ve never engaged with a nonprofit before, don’t expect an immediate sale. Take time to build relationships by engaging on LinkedIn, attending nonprofit industry events, and contributing to discussions in meaningful ways before making a pitch.

6. Don’t Overpromise

Be realistic about what your solution can do. Nonprofits are often skeptical of “miracle solutions.” If you claim to help them raise more money, show them how. If you promise efficiency gains, provide case studies or data that back it up.

7. Don’t Use Clickbait or Empty Marketing Gimmicks

Titling your webinar or white paper with a crisis-related hook, only to present generic content, is a surefire way to lose trust. If you’re offering thought leadership, make sure it genuinely adds value and isn’t just a sales funnel disguised as content.

Final Thoughts: Selling to Nonprofits with Integrity

Nonprofits are in a challenging position, and the last thing they need is a sales pitch from someone who doesn’t understand their reality. If you want to successfully sell to and support nonprofits during gray sky times, lead with empathy, do your research, and offer solutions that genuinely help.

If you’re in nonprofit sales and want to discuss best practices further, connect with us at Constant Method or reach out on LinkedIn. Let’s work together to support the organizations making a difference.