Lessons Learned from Founding a Remote Mentorship Program: Mentor Everywhere

For years when I was living in Italy, I found it very difficult to find mentors. Since I was leading an organization about networking amongst women in tech (the Girl Geek Dinners in Italy), I naturally fell into the role of a mentor, but lacked one of my own.

A few years ago I decided that I couldn’t fight the mentor pull any longer and wanted to actually dedicate some time in an official program. I volunteered and was matched but the mentee never followed through. This was disappointing and such a waste of time that I took to Twitter and Facebook to get some leads on mentoring. I received several requests to be mentored and I thoroughly enjoyed interacting with them.

The next opportunity I received to mentor was for a women’s organization which had global participants, but the mentorship was based in San Francisco. Since I work remotely (and travel often), I couldn’t predict where I would be for a six-week block and had to pass on that opportunity, which was a shame.

And then, Mentor Everywhere.

Screen Shot 2018-05-15 at 4.35.36 PM.png

With a few of my female colleagues at Automattic we came up with the idea to have a remote mentoring program, organized the program, and launched it! We wanted to make mentorship itself a distributed opportunity and bring a remote philosophy to mentorship instead of traditional programs which were very focused on co-location of mentor and mentee.

We initially hoped to have around 30 people participate in the first cohort and we ended up with 100, with many more on the waitlist. We took specified preferences into account and manually matched every participant in the program. Not all of those matches ended up being stellar matches, and not all experiences were life-changing for those people, but it proved something: people don’t need to be in the same place physically to make mentorship work. They need an opportunity to connect.

I took charge in figuring out the program content, length, and cadence, and created the checkpoints and materials we’d collect from participants during the program to gauge progress. Check out our Resources page where we share it all online.

A brief overview of Mentor Everywhere: a mentorship program with a duration of 6 months, starting with a mentoring goals document filled out by the pair, monthly interactions remotely (encouraged, not enforced), and mid-program and end-of-program surveys sent back to the organizing team.

There has been a second cohort of Mentor Everywhere since it launched (I was out on leave), and there may be other cohorts in the future (check the website), but I was excited by the results!

Below are some stats I shared internally about the first cohort and wanted to share here so others can see and learn from our experience, as we’ve had some requests to duplicate the remote mentoring program elsewhere.

Questions? Leave them in the comments!

Mentor Everywhere – Cohort #1

Applicants by the Numbers

  • 79 mentees and 55 mentors applied for the program. Automatticians (my colleagues) accounted for ~40% of all mentors since we shared the initiative organically through our networks and with some partner organizations.
  • 60% of mentee applicants worked full-time, and the large majority had 1-5 years experience.

Mentees’ work experience:

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Here are the types of expertise our mentees wanted – engineering, management/leadership, and design led the way:

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Our mentor applicants had some impressive job experience, though we could have had more mentors with >15 years experience:

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  • This program encouraged a lot of new mentors and mentees – 79% of mentees, and 42% of mentors had never participated in a mentoring program.
  • We did 100% organic/unpaid promotion of the program. While we didn’t specifically aim to serve underrepresented or impacted groups with the mentoring program, we did reach out to many organizations to help spread the word for applicants, including: Tech Ladies, Women Who Code, Support Driven, LGTBQ in Tech, Unicorns in Tech, and more.
  • The large majority of applicants were in the U.S., making it slightly harder to accommodate matches in Europe, and matches in APAC nearly impossible.

Cohort #1

We initially planned to match 20 pairs of mentors-mentees in the program. However, we received an overwhelming response to our call for applications and ended up accepting 50 pairs (100 participants) into cohort #1. 39 pairs (78 participants) completed the program. Mentees dropped out of the program at a rate of 9:2 compared to mentors.

  • ~80% of respondents said it was a good match at the mid-program and end-of-program surveys. ~10% said it was a neutral match, and ~10% it was not a good match.
  • 80-87% of respondents said they made good progress towards their mentoring goals at the mid-program and end-of-program surveys.
  • 92% of respondents would recommend others participate in this program as a mentee, though only 82% said they would participate again as a mentor.
  • We asked about program length and 82% of respondents said 6 months felt like the right amount of time.
  • Most pairs interacted between once and twice a month (the program recommended once a month), with some pairs interacting as frequently as once a week, and others unfortunately missing meetings or dropping out completely.
  • Participants were divided on how much structure and flexibility they wanted. Many of the mentors wanted more resources, more prompts for interactions, and in general more guidance & structure while many of the participants appreciated the flexibility in meeting frequency. It’s clear we can provide way more resources while giving the pairs the ability to decide frequency and interaction method on their own.

What We Learned Creating the Program

  • Mentees will always, always, always say yes to something free. These same mentees will also be the first people to flake, which is extremely disappointing to both the organizing team and their mentors. Asking more from mentees in terms of demonstrating a commitment in wanting to be a part of the program, most likely in the form of more screening questions which will require thoughtful answers, could help this. 9 mentees dropped out vs. 2 mentors.
  • Mentors are the scarce resource and you’ll want to spend most of the promotion and networking time identifying and courting for their participation. It would be great to have more mentors with >15 years experience and they can be hard to find due to the unorthodox nature of the program being promoted mainly online.
  • Mentors also have the largest burden of the program and some of them felt we could have given more guidance and/or their mentees weren’t focused enough. They also wanted more interaction / support amongst themselves, something we saw in our internal Slack channel but didn’t make a similar space available to all mentors.
  • Between application and acceptance into the program, you need to get another buy-in from participants before assigning pairs. You’ll want another step of confirmation of interest in the program after the application and before assigning them to pairs, a sort of ‘pre-approved’ process asking them to reconfirm their interest to reduce the number of dropouts. Of course, if the turnaround is quick on matching (like 1-2 weeks) you might not need this, but many applicants had signed up weeks to months before.
  • You have to continue to remind mentors/mentees that we can help them if their match disappears. On several occasions following a survey or email sent, the organizing team reached out to a match to check on participation and ultimately terminated participation if there was no response, which helped end frustration for those still participating.
  • You have to send out a few more reminders about meeting frequency and the resources available to both mentors and mentees. We were striving not to be too intrusive a regular cadence of communication is helpful, and you can plan those touchpoints out before.
  • Offer preferences carefully. Given the nature of it being a volunteer program, it’s quite difficult to ensure you can meet demand of sometimes very specific requests (i.e., like gender or specific expertise or other, etc.) Narrowing the focus on timezone and expertise ended up being the most important factors for the program & matching.
  • We manually paired the mentors/mentees, which took several hours of our time, so be prepared. Narrowing the personalization of the ‘request’ / preferences can speed that up (per above).

Some Tips for Effective Mentor – Mentee Interactions

The success of the Mentor Everywhere program relied on interactive participation and collaboration by both the mentee and the mentor.

In addition to the resources we shared with them, we asked the two to decide on the details of their mentor partnership during the initial session and build upon it throughout the working relationship.

Some of the questions we asked them to discuss and agree upon in the first session are below. Perhaps they can be useful for you with your own mentorship:

  1. What are 1-2 specific area(s) or concern(s) you want to address during your mentor relationship?
  2. What would you like to gain from your mentor/mentee relationship?

Complete the following sentences –

  • In 6 months, I want the following to be true:
  • In order to achieve the above, I will set the following goals:
    • Primary Goal 1:
    • Primary Goal 2:
    • Primary Goal 3:

Thanks to all who participated!

Sharing Mentoring Program Resources

The Mentor Everywhere site should be online for quite some time, but I’ve also made some of the documents and forms we used in the program available in this Google Drive, including the mentoring goals document, check-ins, program survey, and signup forms as well as our Resources and Code of Conduct pages.

2 replies »

  1. Very interesting programs and good report!
    I think that the mentoring methodology fits well in a lot of different situations, and I’m a sort of “Mentoring evangelist” (I took a speech about Mentoring just recently in wcbri) 😉
    Hoping to meet you somewhere around (maybe Belgrade?) for talking in person. Ciao 🙂

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Director of Product Marketing @ HubSpot. Early hire @ Automattic / WordPress.com. Founder World Nutella Day. MBA Alumni Advisory Board @ Santa Clara University.

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