Cloud Coach Volunteer Resources

Strengthening student motivation to succeed in school and beyond.

Thank you for volunteering with Cloud Coach! With your help, we will reach our mission of serving all 4,000+ ninth-graders in the Minneapolis and St. Paul Public Schools. Throughout the program, you will be having conversations with your mentee to discuss topics including goal-setting, future career options, personal branding, and hobbies and interests. In addition, you will meet your mentee halfway through the program in person for a Cloud Summit.

Keep reading for resources, videos, conversation prompts, and more.

Developed in partnership with Search Institute, the Gateway Prompts are your guide as a mentor. Each week, they’ll walk you through the objective for the week, lead-in questions, and talking points for you to consider adding to make the conversation your own. We hope each will build off the last. The Gateway Prompts are emailed to you each week directly and include a link for you to send a message to your student. Here, you’ll find the full list of Gateway Prompts.

The Gateway Prompts that are emailed to you each week are for the main track, Track 2. This is designed for students in the academic middle.

If your student is an accelerated learner and your conversation gets ahead of the prompt for the week, consider switching to Track 3, designed for students who may benefit with a more in-depth conversation.

If your student is not sending you a message regularly, or if they are sending you messages but don’t seem interested in the Gateway Prompt discussion, consider following Track 1, designed for students who may or may not graduate high school or may just need extra support to develop a relationship.

You can move between the tracks at any time, switching it up as you get to know your student more.

Click the button below for Gateway Prompts to utilize if you haven’t heard from your student.

The Mentor Guide is a written version of the video training that all mentors are expected to watch before connecting with their student. If you’d rather read the information instead of watch it, consider checking out the Mentor Guide which covers program objectives along with the rules, guidelines, and boundaries of the program. Learn more about how it all works, what the Cloud Summit is, and what the next steps are to prepare for your mentoring experience.

Have a question that wasn’t answered by the training video or mentor guide? Check out the Frequently Asked Questions which may help answer your question. We know that every connection with a student is different, and we may not have answered your question here. If you still haven’t gotten the answer you’re looking for, connect with your BestPrep Staff Coordinator who is ready to help with any questions or concerns you may have.

See our library of videos below from Cloud Coach mentors.  They discuss what it is like to be a first-time mentor, how to engage with less engaged students, and how to make the most of this experience!

First-Time Mentor Tips:

Listen to Chad’s biggest piece of
advice to first-time mentors about
student participation.

Hear from Matt about why he finds
the Cloud Coach program so rewarding
and a couple of best practices for
supporting your student.


Engaging Less Engaged Students:

Anne Marie invites you to ask your
student follow-up questions and
to share your authentic experiences.

“We are both learning from one
another.”  Hear from Katherine
about how you can help your
student open up throughout
the weekly exchanges.

Is your student writing really short
responses or you aren’t hearing
from them at all?  Molly shares
some tips to increase engagement!

Listen to Mark’s advice on managing
expectations and showing up for your
student in all circumstances.

Mentoring English Language Learners:

Is English your student’s second,
third, or fourth language? Eloise
shares a few tips to keep your messages
simple and clear.

Caring for Your Student:

Hear from David as he shares
ways to show up as a caring
and impactful mentor with
an emphasis on vulnerability.

“Relationships between caring adults
and young people help students
develop their character strengths.”

Former St. Paul Public Schools
Principal, Theresa Neal, discusses
the importance of student voice and
promoting student strengths.

Kent shares how to help your student
feel seen through effective listening.

Theresa discusses the importance
of staying committed to your student
throughout the program.

Kent shares advice on how to build
your mentorship from the getting
to know you stage to discussing
future aspirations.

Role as a Mentor:

Validating and encouraging your
student’s strengths while helping
them reflect on their current actions
are key aspects of being a mentor.

Kent Pekel from Search Institute
discusses how mentoring can help
develop positive character traits.

General Advice:

Your experience will be different
each year. Hear some of Casey’s
tips like using student friendly
language and meeting your
student where they are at.

“I found that being honest and
really listening to the student has
been very beneficial.” Listen to hear
more about Chrissy’s mentoring experiences!

Interested to hear what the Cloud
Coach program is like? Lisa discusses
her first year as a mentor with a
focus on the weekly messages!

Maureen shares her experience
as a mentor and discussed the
importance of it being a
mutual relationship.

Listen to Eloise as she shares
her top tips for connecting and
engaging with your student each week.

MENTOR Minnesota is a nonprofit that provides support and resources to Minnesota youth mentoring programs. Visit their website for additional information and live trainings on mentoring best practices and how to be the best mentor for your student.

Cloud Coach has had an incredible effect on Minneapolis and St. Paul students lives, and we aim to increase that impact year after year. To view a summary of this year’s program or to learn more about the data results, click the buttons below.


“The danger of a single story,” Chimamanda Ngozi Adichie

“Getting Relationships Right,” Kent Pekel

MENTOR: Black Youth Town Hall

“I’m Mexican. Does that change your assumptions about me?”, Vanessa Vancour

“Rethinking thinking,” Trevor Maber

“My identity is a superpower – not an obstacle,” America Ferrera

“Critical Mentoring – Because Young People Deserve the Best of Us,” Torie Weiston-Serdan



  • Just Mercy by Bryan Stevenson
  • The New Jim Crow: Mass Incarceration in the Age of Colorblindness by Michelle Alexander
  • The Hate U Give by Angie Thomas
  • White Fragility: Why It’s So Hard for White People to Talk About Racism by Robin DiAngelo
  • Black Feminist Thought by Patricia Hill Collins
  • Between the World and Me by Ta-Nehisi Coates
  • Black Like Me by John Howard Griffin
  • A People’s History of the United States by Howard Zinn
  • Me and White Supremacy by Layla F. Saad
  • Why Are All the Black Kids Sitting Together in the Cafeteria? And Other Conversations About Race by Beverley Daniel Tatum