I am mentoring 20 people at once

About a month ago I started a program called “Group Mentoring”. Now I have over 20 mentees, in 6 different countries! Crazy, right?

What is group mentoring?

Group mentoring is a series of hour-long online workshops tailored to your career goals. Each group has just 2-4 mentees, ensuring that your mentor has adequate time to spend with you during the session.

Examples of session topics:

  • Interview practice
  • Advanced testing
  • Test automation
  • Career problems
  • Public speaking
  • …and more!

So many mentees, so little time

I’ve been mentoring tech professionals for about 10 years now, both as part of my day job and in my own time. As my reputation in the industry grew, requests for my mentorship grew and it quickly became clear that I couldn’t accommodate everyone. I was forced to limit my free mentoring to 2-3 people at a time, and put hard limits on the time I could spend for each person.

I’m not alone in this. Those of us who regularly speak at tech conferences often do it because we love to share ideas and help others in the industry. Mentoring is a great way to do this, but it’s a massive time commitment. Most of us aren’t paid to give tech talks, and it takes many, many hours to prepare a talk, not to mention the time traveling, giving the talk, and answering follow-up questions. With limited spare time, it can be difficult to add more than one or two mentees to an already busy schedule. At some point, we need to eat!

Ever since I started working for myself, I have more flexible time but this time is expensive. Community commitments like talks and mentoring can be great marketing for my business, but it doesn’t make financial sense for me to invest 50% of my billable time into marketing. I like doing it, but at some point it’s not financially viable anymore.

I also found that when it came to the relationship with my own mentors, I felt bad asking them for too much of their time for free. I’ve found something similar with several people that I’ve mentored too – they don’t feel good about asking me to give up my limited free time to help them out, especially when they know there are others waiting in line. So they just didn’t book in time with me.

I wanted a sustainable mentoring solution. The obvious answer was paid mentoring. I tried this for a while, offering private mentoring sessions for AUD$200 per hour. I had some interest and customers, but overwhelmingly the feedback was that even though the service was valuable, the price was too high for most testers to afford.

So I floated the idea of splitting the costs among several people with similar career goals. This idea was met with a lot of enthusiasm. However, as much as I searched, I could not find an out-of-the-box product to make this happen. So I had to make it myself.

Minimum Viable Product

When somebody signs up for mentoring, I want a few things to happen:

  1. They should get an email telling them what happens next
  2. I should get a record that they are now my mentee
  3. They should start receiving emails about group mentoring sessions
  4. I want to know what their career goals are and what session times work for them

When I first launched the service, this workflow was, quite frankly, a mess. It was 100% manual (woo! startup! MVP!) and between my assistant and myself we were confusing ourselves with emails, spreadsheets, and even more emails.

To make matters more complicated, I had decided that since this is a globally available service, and I didn’t have many mentees (yet!), I should try to accommodate everybody’s schedules. I used a service called Doodle, which asked each attendee to select which times worked for them for the group session. Then it would automatically select the best time available and I would have to manually create an event in Eventzilla. And THEN I would email all the mentees AGAIN to ask them to register for the session. Then they would get sent a Zoom link to attend the session.

So of course, that didn’t work well.

There were way too many steps for mentees to complete in order to register for a session. We all get bombarded with emails and notifications every hour of the day, so no wonder we ignore or forget most of them. It was also a really long, confusing, manual process on my end which was super prone to human error (and oh boy did we error). The first session I ran took two weeks to organise and the Zoom link got sent out to everyone without anyone needing to pay for it. Oops.

Automate all of the things

As much as I was itching to automate the living daylights out of this process by building a platform from the ground up, I resisted this enormous time sink and invested in some tools that could get me SOME of the way there.

First, automate the signup process. Since so much of my workflow revolved around emails, an email sending provider was the obvious solution. MailChimp is pretty excellent for this, and their support crew was super helpful when I asked them for advice on solving this problem.

Five and a half hours of work later, I had a fully automated signup process. Now this happens:

  1. Mentees sign up using a simple form on my website, which adds them to a MailChimp mailing list. It also adds them to two groups – “mentoring” and “not had initial session”.
  2. MailChimp automatically sends them an email telling them how to sign up for their free initial private session, and how to see all of the group sessions.
  3. Every week, MailChimp emails everybody still in the “not had initial session” group with a reminder to book their initial session. I still have to remove folks from this group manually but it’s infrequent.
  4. When mentees book their first initial half hour session using Calendly, I chat to them in person about their career goals and best times for group sessions. It’s also a great chance for me to meet them one on one which I think is important, even for group mentoring.

Next, simplify the group session registration process for mentees. I abandoned the Doodle scheduling madness and now I just collect data based on folks’ general weekly availability and I schedule group sessions based on these times. Mentees can sign up whenever it suits.

  1. All mentees are sent an email about new sessions with a link to the EventZilla event
  2. A mentee registers and pays for a session
  3. The registered mentee automatically receives a confirmation email with the Zoom link for the online session

Too easy.


I’m still finding myself spending several hours a week scheduling events and emails. This is my next automation challenge and it’s pretty tricky. I’ve even looked into using the MailChimp and EventZilla APIs and haven’t been able to plan a complete solution yet. But I will!

I expected the price to be a bigger issue, but many of my mentees are finding that the sessions fit really well into their company’s training budget. I used to run training courses over 2-3 days and it was a hard sell because the cost often required approval from the higher-ups in companies. But sessions under $100 are pretty easy to swing by the boss because it’s less paperwork.

Given the amount of time I still invest in this project, I still have not reached a point where it is financially viable to run it long term. It’s early days, but I am mindful that in order to make this sustainable I will have to work out how to reduce costs and scale further.

Scale, and then scale again

This mentoring service has been more popular than I expected. In 4 weeks I’ve had about a signup per day, and I’ve run 5 successful group mentoring sessions. I have 22 registered mentees, 2 of which are interested in private mentoring too.  I have complete control over my own availability for mentoring and the feedback has been overwhelmingly positive.

It’s really interesting to me that there has been so much interest in this service. There are plenty of mentoring platforms out there, and there are folks doing mentoring for free. I suspect a lot of it is related to my existing reputation as an expert in the field, and many of my mentees have met me in person or seen my talks.

I would like to help other folks in the community with a strong reputation to make mentoring a viable option for them. It will open up opportunities for more folks to access personalised professional guidance from industry leaders.

If you would like to be a mentor

If you are a software testing expert with a strong online following and you are interested in becoming a group mentor yourself, please get in touch! I’d love to chat to you about my future plans for this service and make it work for you.

If you would like me to be your mentor

There’s room for more! Sign up here.


One thought on “I am mentoring 20 people at once

  1. Hey Trish!

    long time follower, but we haven’t formally met.

    I was in a similar situation to you and took a similar path towards group mentoring. wanted to share some leanings through my experience.

    An idea that might help in your journey, you may want to try using trello/google sheets as a way to backlog ideas that mentees want to cover and made available for the mentees to see the topics before the session and allow them to up vote what they want to discuss as a group may have help the sessions be more impactful.

    in regards to your acquisition problem. I use wix for my website and it has some features that takes bookings/payments etc and I’m able to sort out the email campaigns though it as well. I see that you’re using wordpress and i’m sure there are some integrations/plugins you can sort out to help you on that front. I’m not too familiar with wordpress myself, but centralising and automating is key to efficiently(as we know with automation testing!) doing the work that we shouldn’t need to do and allow us to focus on what matters.

    Feel free to reach out if you have any questions or just want to go through thoughts(we’re connected on linkedin). happy to help you do what you do, as I see how much value you’ve bought to many people over the years.

    Ambrose Chea

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