During this discussion, we explored leveraging AI with young people and as professionals. Mike Geddes (Teaching and Learning Manager) and Jessye Herrell (Director of Youth & Community Development Programs) from The Knowledge House, shared how they've been using AI in their work. Nine organizations in the Network joined the conversation, sharing perspectives and resources from their own programs.

Here’s what we heard: 

Resources from Mike and Jessye 

• Google Notebook LM 

• Playlab.AI

• MIT RAISE (Day of AI)

• Napkin 

• Brisk Teaching

AI Use with Young People 

Uses

• Distill learner profile insights to plan program activities 

• Generate podcasts covering key class topics for review/retention 

• Create a chatbot for students to locate handbook policies 

• Identify standards alignment in lessons 

• Studybot to help with science homework (built by a student!)

• Training students to be good prompters to build critical thinking

Questions and Challenges

• How can AI make learning more accessible, especially for students with disabilities? 

• How do we teach students to think critically about AI tools, including understanding bias, limitations, and ethical use?

• Protecting student data

• Preventing over-reliance on AI (ex: students typing a prompt and accepting the first “good enough” answer)

• Environmental impact of AI tools 

• Who is designing these tools and what are their intentions?

• How could or should AI be used in roles like counseling and advising?

• Whether AI is something that will be "done to us" or something we actively choose to shape

• Students don’t know how to prompt well (even with Google). How do we build this foundational skill?

AI Use as Professionals

Uses

• Using AI as a research and “thought partner” to support internal work and student-facing activities

• Generating meeting agendas and summaries

• Writing support

• Professional development - prompt engineering to improve efficiency

• Starting small - "Walk before you run" to better understand how AI functions and patterns

• Being transparent about when AI is being used 

Challenges 

• Accuracy 

• Figuring out when to use AI vs. when to not (ex: perfectionism, feeling like it’s “making me stupid,” or losing writing skills)

• AI messaging and communication can feel fragmented or generic 

• Tension between improving efficiency and ballooning workloads

During this discussion, we explored the challenges and opportunities of working on intergenerational teams and shared approaches to improving collaboration and innovation across different generations. Yalenis Cruz, Senior Deputy Director of Learning and Development in the Youth Division at Children’s Aid, and Chelsea Williams, Founder & CEO of Reimagine Talent, shared insights from the professional development series they created at Children’s Aid focused on leading intergenerational teams. Participants also shared perspectives and resources from their own programs. 

Here’s what we heard: 

The Value of Intergenerational Teams

• Nonprofits are one of few sectors that may have five generations working side by side

• Understanding generational perspectives can allow us to better service youth and families

• Learning is a two-way street - older generations can also benefit from the leadership and innovation of younger staff

• Gen Z is reshaping workplace norms around work-life balance, professionalism, inclusion, and feedback

• Many orgs are hiring from within their communities and alumni of programs are often drawn to orgs based on positive experiences and mission alignment 

• Focusing on generational dynamics can help address broader sector issues like staff burnout, retention, and mission-first culture

Challenges

• Definitions of “professionalism” vary across generations (ex: attire, communication style, boundaries, etc.)

• Work/life balance expectations differ across generations with younger staff valuing wellness more openly

• Leadership gaps often show up in middle management, with managers feeling underprepared to navigate challenging conversations

• Inadequate skill-building and scaffolding can hinder long-term staff development

• Some younger staff members excel at technical skills but need support with soft skills (time management, attendance, communication, etc.)

• Gen Z staff turnover and engagement is an increasing concern 

• Research shows that post-COVID learning gaps have led to a decrease in critical thinking/problem solving, systems-thinking, and interpersonal skills 

Strategies

• Strengthen onboarding systems with clear expectation-setting, behavior modeling, and early onboarding surveys to surface and address concerns 

• Create space for new staff to connect and build peer networks early

• Develop learning paths focused on roles, including self-paced learning/training

• Ensure every staff member has a professional development plan focused on skill and competency growth

• Incorporate intentional coaching structures: peer-to-peer, reverse mentoring, and traditional mentoring

• Use observation cycles to provide consistent feedback and use peer learning spaces to reflect on lessons learned

• Provide scripts and rehearsal opportunities to practice communication skills 

• Translate core organizational values into what it looks like in practice 

Resources from Reimagine Talent

• Leading Across Generations: Building, Engaging, and Retaining a Multi-Generational Team

• What Employers Need to Know about Gen Z: Insights and Strategies to Support the Next-Gen Workforce

• Coaching for Career: Infusing Future-Proof Skills into the Gen Z Workforce

During this discussion, we explored creating high-quality internship opportunities for young people with Trequan Bekka, Director of Career Connections at Good Shepherd Services. Ten organizations from this Network joined together to discuss creating and managing programs, partnering with worksites, and supporting student skill development. Participants also shared perspectives and resources from their own programs.

Resources from Tre

• LTW Research Findings: Internships At Their Best

• Resources for Internship Coordinators 

• Pathways to Work-Based Learning

Here’s what we heard: 

Approaches for Creating and Managing Internship Programs 

Participants discussed the challenge of ensuring that interns gain value through structured processes and meaningful mentorship.

Tools: Program Self-Reflection and Checklist for Internship Coordinators

• Align tasks and skills with students’ career interests 

• Assess student readiness and provide tiered pathways to work-based learning to ensure successful placements

• Assess employer readiness and ensure they understand the program’s purpose and population 

• Develop systems using tools like Slack for communication, Salesforce for managing data and notetaking, Asana for managing tasks, and Google Classroom as a central hub for internship resources and documents

• Provide compensation, credentials, or work experience that provide access to other opportunities

• Establish clear onboarding and offboarding systems 

• Check in on skill development and provide mentorship and reflection opportunities 

• Have staff dedicated to helping students with issues that arise (financial, mental health, attendance, etc.)  

Approaches for Partnering with Worksites

Participants discussed the challenge of individualizing experiences as programs expand, as well as mismatches between student skills and site expectations, especially when worksites seek interns to manage the workload rather than to support their learning.

Tool: Employer Site Assessment Form 

• Leverage personal relationships and communities to identify potential worksites 

• Engage with small businesses in person to build relationships 

• Listen for employer concerns and discuss strategies for addressing student challenges

• Consider where students live and offer remote opportunities 

• Maintain a strong understanding of student strengths, interests, and goals

• Listen to employers to identify the technical and interpersonal skills they value

• Avoid forcing partnerships solely to meet quotas and prioritize successful experiences over numbers

Approaches for Supporting Student Skill Development 

Participants discussed the challenges of virtual versus in-person experiences, teaching professional communication, limited staff capacity for supporting many students, and students struggling to balance work responsibilities with their academics and personal lives.

Tool: Skills Progress Form

• Provide networking events and career readiness workshops to allow students opportunities to practice skills 

• Debrief work experiences and connect experiences to students' values and hopes for the future ( Ex: What do you like about your managers? What do you like about your co-workers?  How does this fit into your school plan?) 

• Have conversations about communicating effectively and building a “brand”

• Help students connect transferable skills to employment opportunities and facilitate goal-setting conversations 

• Introduce students to effective ways to use tools like calendars and project management systems 

• Host themed monthly meetings and small group check-ins for reflection (Ex: February - relationships,  November - how to show thanks and gratitude)

• Celebrate the wins and discuss “why” it was a win and “how” they contributed to that win 

During this discussion, we explored sustaining student and staff well-being. Melissa Hunte, Social Work Manager, shared insights from her experience managing Social Work interns and implementing the Social Emotional Learning Curriculum at “I Have a Dream” Foundation.  Our discussion centered on our Future9 definition of Well-Being: nurturing identity, building affirming life practices, enhancing cultural intelligence, and connecting to the natural world. Participants also shared perspectives and resources from their own programs.

Here’s what we heard: 

Challenge #1: Prioritizing Well-Being in Student Programming

Participants discussed that student well-being is often deprioritized in favor of skill development. Limited funding and a lack of resources also contribute to stress.

Approaches Shared:

• Implementing SEL surveys with affirmatively framed questions, similar to the Future 9 framework

• Incorporating identity exploration in student programming

• Shifting the focus from solely outcome-based values to also recognizing students' inherent worth (acknowledging their existence, who they are, and what makes them special)

• Listening with empathy

• Building partnerships with local MSW programs to bring in interns who can support staff in driving well-being 

• Offering wellness programs that provide both emotional and career-related support

• Staffing with relationships in mind - assign students with who they build trust with and supporting student-facing staff with resources and training 

• Checking in consistently and frequently which increases student engagement and retention

• Gently pushing students’ barriers as a necessity for them to grow -  understanding the difference between empowerment and enabling

• Engaging families through check-ins and parent workshops to support student well-being at home

Challenge #2: Balancing Work and Life

Participants discussed the challenge of maintaining a healthy balance between work and personal life, particularly in spaces where there is cultural pressure to work as hard as possible. 

Approaches Shared:

• Checking in with other staff:  How are you? How are you taking care of yourself? 

• Establishing clear boundaries between work and personal life (“work from home” and not "home from work”) and clear boundaries between coworkers and friends 

• Taking intentional breaks, such as outdoor walks, to create mental separation from work 

• Management modeling sustainable work habits and supporting staff in prioritizing tasks and deprioritizing non-urgent work when needed

• Measuring and recognizing all achievements even if target goals aren’t met

• Focusing on time for community building - building trust between staff and managers

• Strengthening trust through transparency and open communication

• Normalizing the use of therapy and personal well-being practices

Resources Shared 

• Future 9 Framework - Sustaining Well-Being

• CASEL Framework

• OppNet Youth Mental Health Resource Guide

• Degrees NYC: Student-Ready Schools and Campuses Report

• Self-Care Assessment for Staff

• Youth Communication Webinars

• Helping Migrant & Immigrant Youth Feel Valued (February 19, 2 PM)

• Helping Youth Manage Stress & Anxiety (March 3, 2 PM)

• Supporting Transgender Youth in Uncertain Times (April 9, 2 PM)

During this discussion, we explored strategies and challenges for engaging alumni. Sam Kahn, Alumni Engagement Manager at Futures and Options, shared insights and resources from his experience managing a program of 17,000 alumni, which he built from scratch to address growing student needs. Participants also shared perspectives and resources from their own programs.

Here’s what we heard: 

Challenge #1: Maintaining Accurate Alumni Data 

Participants discussed that alumni often change emails and phone numbers, making it difficult to maintain accurate records. Self-reported data often becomes outdated and tracking data can be time-consuming. 

Strategies:

• Collect personal (non-school) emails, phone numbers, and social media handles during the application process and request updated contact information when alumni leave HS 

• Use data platforms/CRM tools like Salesforce, Monday, and Form Assembly to collect and manage alumni records

• Conduct regular outreach calls or surveys to verify/collect updated information 

• Incentivize alumni surveys to track data and get updates 

• Use LinkedIn groups or connections to track career updates

Challenge #2: Consistent Alumni Outreach 

Participants discussed that, even with accurate data, maintaining regular communication is challenging due to staff capacity, especially for larger networks. 

Strategies:

• Use social media, like LinkedIn, Discord, Instagram, and WhatsApp for alumni groups, job and internship postings, newsletters, and sharing information

• Leverage tools like Calendly (scheduling and reminders for appointments and events),  Mailchimp (email marketing), Modern Campus (mass texting), and Yet Another Mail Merge for outreach

• Use design tools like Canva to create visually appealing content and boost engagement 

Challenge #3: Sustaining Program Engagement

Participants discussed that alumni don’t always understand the value of programming or feel connected if they lack direct relationships with current staff. Dedicated staff and high-quality offerings are critical to sustaining engagement.

Strategies:

• One-on-one conversations are a big lift, but necessary for relationship-building

• Offer resources that provide value to alumni like networking events, internships and job referrals, scholarships, and career pipelines

• Develop mentorship programs or fellowships to connect alumni with field experts 

• Incorporate networking and relationship-building as key skills for students to develop in programming

• Offer low-commitment opportunities and community-building events for alumni to connect with peers and current students 

• Pair older and younger alumni based on career interests, identities, and other common factors

• Build career resource hubs that include templates for resumes, cover letters, and post-grad planning

• Leverage alumni newsletters to hare opportunities and updates through alumni newsletters

• Create private alumni groups on Facebook, LinkedIn, or Instagram for updates, check-ins, and networking

• Have staff who have direct relationships make alumni calls 

Additional Resources from Sam:

• The Ultimate Guide to Navigating the New Landscape of Alumni Engagement

• Elements of Effective Practice for Mentoring

• Analysis of Alumni Engagement at CBOs

• 1-1 Advising Template