Not all Mentorship Is Created Equal: On a Mission to Solve the Age-Old Problem

Most people wouldn't argue with the finding of Inc. Magazine (2017) that “70% of mentored startups and businesses survive more than 5 years, which is double the rate of non-mentored businesses in the US.” However, the "who," the "how" and the "when" of effective business mentorship is a lot less clear.

When our nonprofit, Startup Tucson, launched the Women in Tech Fellowship earlier this year, our staff and fellows interviewed dozens of women in STEM and entrepreneurs to try to understand their most pressing needs. Universally, one of the biggest needs interviewees stated was "mentorship"; however, when we pressed a little deeper on exactly what they wanted out of the mentorship, who their ideal mentor would be, or their past mentorship experiences, the folks we spoke to were a little less sure.

The struggle of mentorship is certainly not limited only to this group. In our experience working with hundreds of entrepreneurs a year, we have discovered that early stage founders know they need help, but they are not exactly sure what they need help with. Even if an entrepreneur knows exactly what they need help with, accessing the right person who can help them with that question becomes a whole new problem. "Who can I trust?" and "How do I ask?" are constant questions that arise. Some entrepreneurs we spoke with told us horror stories of mentors taking advantage of them, bullying them into a paid service, or degrading them.

Our job is to create transparency, structure, and accountability. Under these conditions -- and only under these conditions -- can the magic alchemy of mentorship truly flourish.

And entrepreneurs are not the only ones who struggle -- mentors themselves often feel unclear on how to engage with founders and sometimes leave these interactions feeling burned out. Typically mentor programs receive many mentors expressing interest in being involved, but when their experience isn't positive or they aren’t effectively used, these programs see very high churn rates.

As ecosystem builders, mentorship can be a gordian knot. It is one thing if all of your mentors are highly paid contractors, but it is quite another if your organization depends on mentors to volunteer their time and to help broaden the services that your organization can provide. Our organization is a nonprofit, providing low-cost or free services to entrepreneurs. We have a staff of four yet engage with over 15,000 entrepreneurs a year through events and actively work with approximately 300 founders intensively from month to month. It would be impossible for us to complete our mission without the generosity of mentors and subject matter experts who volunteer their time and expertise for our early-stage companies. Luckily, we live in a community with many experts who are retired and looking to give back to young companies as a service and have always had a steady flow of mentors interested in getting involved. However, we previously lacked a systematic process for vetting and connecting them to our entrepreneurs in meaningful ways so we were not always able to take full advantage of the incredible wealth of knowledge.

Our status-quo felt scatter-shot and overwhelming. We were constantly trying to stay organized with excel sheets and CRMS, but we felt like there had to be a better way.

About a year ago, Startup Tucson set out to try to address the major problems we saw in the status-quo of mentorship. Our goal was to create clear structures and systems that would be transparent, systematic, and satisfying for both the entrepreneur AND the mentor.

To do this, we knew we needed input from stakeholders from both sides. Luckily, our Startup Tucson Advisory Committee is stacked with both world-class mentors and high-performing, entrepreneurs. We convened a diverse sub-committee to help us re-build our mentorship approach from the ground up.

What we discovered in this process is that we needed a CONSTELLATION approach that included:

  • Open-ended time to explore "help me find out what I don't know" type queries. This is a job for paid staff as we discovered this is not something a lot of high-level mentors enjoy doing!

  • Single-interaction opportunities around specific tactical questions. Great for those folks who are super skilled in an area, but not necessarily founders or generalists. Also a good spot to plug in folks who don't have the time or soft-skills for relationship-based mentoring.

  • Time-boxed intensive experiences around a single challenging project. This solves a major problem of burn-out. Mentors get the most satisfaction out of seeing a success, but are worried about bleeding boundaries. This provides structure (and an end date!). If the mentorship pairing is a success they are welcomed to continue, but there is a built in way to wrap up the commitment gracefully.

  • A roster of highly specialized experts "on-demand" for industry-specific questions. One challenge we have had is how to use those folks with highly-specific skills and interests. By setting the expectations that we will only contact them with a qualified lead (could be only 1 time a year) we keep them involved, but not burned out.

Additionally, we knew that for the entire structure to be successful we would require:

  • Clear definitions: "Mentors" was too big a bucket. We needed to clarify expectations and roles; in our case we chose to distinguish between MENTORS and ADVISORS and EXPERTS. The term mentor being reserved for only the individuals who complete our mentor training program.

  • Guardrails: For more intensive mentoring experiences where a greater potential exists for A) harm to the entrepreneur and B) burn out for the mentor, we would need guardrails to ensure the mentors were trained properly and the entrepreneurs were ready and committed to the experience.

  • In order to be considered a Startup Tucson mentor, you must complete our mentor-training program and agree to our terms and conditions.

  • In order to participate in our more intensive programs as an entrepreneur, you must complete our Startup Fundamentals Series or be a confirmed scaling venture. If sessions are missed without communication, you can be dismissed from the program.

  • The program has a small fee to ensure buy-in but still remain accessible.

  • Diversity. The lack of diversity of the mentor-pool was a critical issue that could no longer be shrugged away. (Our continued effort to address this gap will be tackled in a forthcoming blog, so stay tuned!)

  • Feedback: Ongoing feedback processes to capture successes, problem-solve challenges, and respond to bad actors

Part of the great challenge with mentorship is that on one hand it is very predictable (ie. most companies have similar problems) but on the other hand it is highly personal and individual; a successful mentor-mentee relationship must have personal chemistry. The “magic” element of mentoring is hard to predict. For example, you may assume that a certain “tough-love” mentor might not be a good fit for a certain inexperienced entrepreneur and then it turns out that is exactly what they are looking for!

As an entrepreneurial support organization our job is to create transparency, structure, and accountability. Under these conditions -- and only under these conditions -- can the magic alchemy of mentorship truly flourish. Build a platform that engenders confidence and trust, then step out of the way and let the mentor and mentee run.


If you are an entrepreneur looking to learn more about our mentoring services, click here.

If you are a mentor, looking to engage click here.

If you are an entrepreneurial organization looking for support in building out your mentoring programs, contact


About the Author

Dre Thompson

Dre Thompson is the Executive VP at Startup Tucson and the Festival Director of TENWEST Impact Festival. She is delighted everyday that she has landed her dream job which brings together her diverse background in community development, research and education, startup businesses, and also creative entrepreneurship. Her passion is to build a more beautiful, more innovative, and more equitable community where all people have the opportunity, resources, and support to build their own dream jobs too.  ​

In the Tucson community, Dre serves on the Women's Foundation of Southern Arizona Advisory Committee, the Pima Community College Business Advisory Committee, and the Tucson Innovation Partnership. She has previously served as the Governance Chair on the Board of Tucson Young Professionals and has served on the Talent Attraction and Retention Taskforce at the Tucson Metro Chamber.

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