Before diving into our third face-to-face session tomorrow at SMLS, I thought it might be important to re-center myself in my how might we question while amending my previous post. So here goes:
Design Thinking Challenge: How might we help alumni discover ways to give back that align with their financial capacity while helping them see how their contributions directly support the transformative experiences that shaped their HTS education? Excellent, yes! Still want to run with this as my question.
Your Vision
Create a personalized, historically-grounded giving experience that:
- Honors alumni’s past experiences and contributions to HTS
- Provides transparency through personalized updates and class-based crowdfunding dashboards
- Empowers alumni as giving ambassadors within their peer networks
- Scales as technology (Almabase/Graduway) becomes available
Some of this is years away, but yes! As encouraged by other Cohort peers, I will give my how might we question a big runway to evolve and develop with the needs of our community and my capacity to deliver this program.
Phase 1: Foundation (December 2025 – January 2026)
Experiment A: Pilot Case for Support Story
Goal: Build the complete narrative for ONE case for support (e.g., Debate Program, Arts Initiative, etc.)
Deliverables:
- Historical timeline: Where this program came from, key milestones, why it’s important
- Giving menu: Multiple entry points, but also complete cost and endowment models
- Impact promise ex: “Your $500 gift will [specific outcome]”
- Personalization template: How you’ll communicate back to donors about their specific impact
Success Metric: One fully-developed giving category ready to launch
Have changed this to fit better with internal team goals and current projects!
Experiment B: Identify Giving Ambassadors
Goal: Identify 3-5 alumni influencers who are passionate about this category and willing to champion it
Approach:
- Look for alumni who: participated in/benefited from this program, have given before, are active in alumni networks
- Reach out personally: “We’re re-imagining how alumni give back. Would you help us tell this story?”
- Invite them to a brief call to share their experience and get their input on the giving strategy
- Position them as “founding ambassadors” for this initiative
Success Metric: 3-5 committed ambassadors who understand the vision
Absolutely! These people have been identified.
Phase 2: Pilot Launch (February 2026) – TBD
Experiment C: Ambassador-Led Peer Outreach
Goal: Test whether peer influence + compelling narrative drives giving
Approach:
- Provide ambassadors with: the giving story, talking points, personalized email templates
- Ambassadors reach out to 3-5 peers in their class/network with the story
- Track: How many people they reach, conversion rate, average gift size
- Gather feedback: What resonated? What questions came up?
Success Metric: 10%+ of contacted alumni engage; at least 3-5 gifts received
Experiment D: Personalized Impact Communication
Goal: Test your personalized update model
Approach:
- For each gift received, create a personalized thank-you that includes: how their gift will be used, connection to HTS history, invitation to see impact (campus visit, video update in 3 months)
- Send first impact update at 3-month mark showing real outcomes
Success Metric: Donors feel seen and connected; they’re willing to give again
Phase 3: Refine & Scale (March – April 2026) – TBD
- Analyze what worked: Which ambassadors were most effective? Which giving amounts resonated? What stories moved people?
- Refine the narrative and process based on feedback
- Plan Phase 2: Expand to second giving category OR expand ambassador network
- Prepare for dashboard integration when technology arrives
- Document lessons learned for your exit ticket/blog post
Key Principles Throughout
- Yes, and approach: Build on what alumni already care about; don’t replace it
- Transparency first: Always show where money goes and who benefits
- Legacy honored: Every ask acknowledges the past while inviting future impact
- Multiple entry points: Different giving levels for different capacities
- Peer power: Ambassadors are your most credible messengers
Quick Wins to Start This Week
- Choose your pilot giving category
- Gather historical materials (photos, stories, alumni testimonials from that program)
- Identify your first 3 potential ambassadors
- Draft one personalized thank-you email template
The quick wins are done – next is about building this sustainably and slowly.
You’ve got this! 🚀
Wow – there is a lot of work and thought in here, Colin! I keep coming back to your idea of story – what story to Alum want to share, how can they tell that story in a meaningful way to them..and how to they keep that story going through the pilot phase 2? Crescent has a good story-telling for alumni through their Past and Present if you’re looking for some examples. Looking forward to hearing more!
Thanks Jeff! Yes, we have many Crescent connections and I get handed an issue of Past and Present often. They are definitely setting the bar high in terms of alum storytelling! Optimistic to achieve new heights in the same realm at HTS in the near future. Excited to see how your project keeps developing too!
Colin, this “take 2” is really strong. Your How Might We question feels human and clear, and I love how you’ve built a phased plan that matches your capacity while still giving the work a long runway. The historically grounded, personalized giving experience is a real point of difference, and Phase 1 is spot on, one excellent giving category will give you something concrete to test and then reuse. For our session tomorrow, I’m curious, if you could optimize for only one outcome in the February pilot, would it be first time giving, repeat giving, or alumni engagement and advocacy even when someone can’t give yet?
– Gareth
Thanks Gareth for your reflection on my action plan and “how might we” more generally! To answer your question going forward, I hope our pilot of the category of the giving menu/catalogue will produce first time donors first and foremost. I need to start people moving down our donor pipeline. Those that have donated before are an easier sell and I can push them in different ways. And those that only have capacity to be donors of their time and expertise, I have other ways for them to reach out and plug-in to our programming and academic teams. But you’ve made me think about adding a section on the giving page that speaks to being the notion that “giving” takes non-financial forms too and to “reach out to [email protected] if this aligns more with your current capacity”, for example. Thanks so much!