Tips for Starting, Leading a Volunteer-Based Tutor/Mentor Program

I led a volunteer-based tutor, mentor and learning programs serving 2nd to 6th grade youth in Chicago from 1975 to 1992.

Based on what I had learned from my networking with other programs in Chicago, and my 17 years working in retail advertising for the Montgomery Ward corporation, I formed the Tutor/Mentor Connection (T/MC) in 1993 to collect and share information that anyone can use to build personal and/organizational strategies that reach more k-12 youth living in high poverty areas and help them stay in school, stay safer in non-school hours, expand their network of adult support, and move toward graduation, advanced education and to jobs and careers.  

As we formed the T/MC in 1993 we were also launching a new volunteer-based tutor/mentor program aimed at helping kids who aged out of the first program after 6th grade have continued support all the way through high school. I led that until 2011.

I'm still connected to former student and volunteers from the programs I led, and now I see them posting photos showing their own kids finishing high school and college. That was the goal.

In 2011 I formed the Tutor/Mentor Institute, LLC to help keep the T/MC in Chicago and help the ideas spread to other cities with high concentrations of persistent poverty.  I still lead both. 

Note the use of maps in my essays. I focus on actions that need to be repeated over and over for many years in many places of Chicago and other cities. Such actions would lead to high-quality, mentor rich programs operating in every neighborhood with high concentrations of poverty. The information I share was intended to be used by our own volunteers, students, staff, leaders and donors at Cabrini Connections, the program we lead.

It's also intended to be used by others in the for-profit world, education, and the for-profit world. In fact, if leaders in business, religion, health care and universities adopt this leadership strategy, employees can form tutor/mentor support teams using the ideas we share.

As we enter a new school year staff and volunteers at tutor/mentor programs throughout Chicago and the rest of the country are beginning to plan 2025-26 events.

I'm sure that somewhere, meetings are being held where someone is asking "what roles are we looking to fill on the year-end dinner committee or volunteer recruitment committee?"

Since the programs I led aimed to empower many teams of volunteers and students to support different activities and events throughout the year, I thought I'd share some ideas that I've learned over my 35 years of leading a volunteer-based tutor/mentor program.

I'm not going to write a long blog article, instead I encourage you to open this "Steps to Start a Program" pdf and use it as a guide in forming teams that want to have an impact.



Then review this "Operating Principles" pdf which focuses on good planning. I show two pages from that essay below.



This page of the "Operating Principles" pdf focuses on types of talents that need to be part of an effective committee.

Do you have someone who can be the project manager for your committee? Or someone who is an effective communicator? Perhaps the most important role is that of a "recruiter" who can find people with these talents and bring them onto a committee or a board.

This Tutor/Mentor essay shows how volunteers from the business community can help expand learning opportunities in organized tutor/mentor programs.  

This Total Quality Mentoring visual essay shows the same ideas, but in a different format. 

I hope these planning guides help you identify the skills and talents your volunteers might contribute to one or more of the projects your planning for the coming school year.

If you're with a business or a university and can form teams of volunteers, your team can help every tutor/mentor program in Chicago and other cities by the way it mobilizes resources and points them to individual organizations.  You can use the ideas from this volunteer recruitment visual essay.

If you find these ideas useful please connect with me on LinkedIn, BlueSky, Twitter, Mastodon, Facebook, or Instagram. (see links here). 

Use your own media to help share the ideas and others that you'll find in dozens of articles on this blog.

I depend on a small group of donors to continue doing this work. If you can help please visit this page and send a contribution.

Lessons Learned from Leading Tutor/Mentor Program for 35 Years

When I started leading a volunteer based tutor/mentor program in Chicago in 1975 I held a full-time retail advertising job and the program already had an enrollment of 100 pairs of elementary school age kids and workplace volunteers to begin the school year.

With so little time available to lead the program I had to learn to recruit volunteers to help me and delegate roles for them to take.  Over time I learned that many volunteers often over-commit, and for various reasons could not complete the project assigned. Often this led to them disappearing from the program instead of asking for help.

Thus I learned that I needed to follow up, and help volunteers succeed. The result was that volunteers became more committed to the program and often took greater roles in the future.

However, I also learned one more thing. As the leader of the program my vision and commitment was usually greater than that of most volunteers. Because of my constant learning from other programs I often saw opportunities that others did not see. Thus, I had to LEAD. I had to share my visions in ways that volunteers might want to give their time and talent to make those visions a reality.

This led to me coining the formula of "R&D+F&L=Success".  

I applied what I learned as the tutoring program grew from 100 pairs to 440 kids and 550 volunteers by June 1992.

Here's a photo showing the leadership committee supporting the 1976-77 program.

Here's a photo showing the leadership team for the 1991-92 program, which had converted to a non profit structure at the start of the 1990-91 school year.

Click on each photo to enlarge. Look at the difference in the number of people involved and the organizational structure between 1976 and 1991-2.

Between 1975 and 1981 I had to recruit a new team of leaders ever spring, with just a few carry-overs from the previous year. We had no paid staff  until 1979 when we were able to hire a student from Moody Bible Institute for 10-15 hours a week.

In 1981 we began to change how the committee was organized and recruit leaders for different functional roles. By this time the program size was nearly 200 and more and more volunteers were coming from companies beyond Montgomery Ward (Partly due to downsizing and closing of the MW catalog business.  As volunteers went to different companies they continued to tutor, and often began bringing co-workers).

You can see in the second leadership group photos that some volunteers served as formal representatives of the companies they worked at. I used an Excel spreadsheet to record volunteer enrollment and listed the companies they worked at, occupation, and number of years they volunteered. Thus, as I saw groups of five or more from the same company, I began to reach out to veteran volunteers and asked them to become a mentor to co-worker volunteers and a contact point for reaching into the company for donations (we were not a non profit, but still needed food and snack donations, and gifts for the annual Christmas party).

This structure took time to develop. It took more than 15 years. The program was already 10 years old when I became its third leader. At the end of the 1989-90 school  year, as we begin creating a non-profit structure, the program already had 300 pairs of kids and volunteers meeting weekly. It still only had a paid staff of three part time college students who worked a total of less than 30 hours a week. 

Thus it was a 25 year journey to developing this volunteer leadership structure. The R&D+F&L=Success strategy really worked.   I created a concept map to visualize this growth.

Growth of Tutoring Program - 1965-1992 - map

In this section of the Tutor/Mentor Institute, LLC site  you can find three PDF essays that share my experiences and can help you start and grow a volunteer based tutor/mentor program in Chicago or elsewhere.  While these and all of the resources I share are free, I'm available for a small consulting and/or retainer fee, to help you understand and apply these ideas.

I created the Tutor/Mentor Connection in 1993  (and Tutor/Mentor Institute, LLC in 2011) as we were starting a new program to serve 7th to 12th grade youth who aged out of the first program. The T/MC's vision was to help high quality programs grow in all poverty areas of Chicago. Thus, my goal is that city and business leaders reach out to me for the experiences and ideas I share, and that they provide funds needed for me to collect, organize and share this information.

So far I'm not having a lot of success at this.

If you value the experiences and ideas I've been sharing please consider a contribution to help me continue to do this. Use the PayPal button or mailing address on this page.