Organization Presentation

Running a Mentoring Program

Use the what?
Credit: Flickr / mendhak

As part of our Technically Speaking Anniversary, we ran a mentoring program. If you’d told me a year ago that we would be running a mentoring program as part of this I would have been shocked, because we had explicitly gone in this direction of scaling up the mentoring we did, and moving away from 1:1. But it was clear from the emails we get, and the tweets we see, and the questions asked in our webinars that, especially for people who have never got on stage before, sometimes what people really need is a bit of 1:1 help.

That being said, a lot of mentoring programs fail. They fail publicly, by going nowhere. And they fail silently, e.g. women report being over-mentored and under-sponsored. Mentoring gets offered as this panacea, like you just get a mentor and everything will be fine. This is completely wrong. Getting a mentor is the least of it (I wrote a bit about why).

The way we tried to deal with that was simple: Expectations. Expectations. Expectations.


A note first on how we found out mentors – we reached out to people with varying degrees of speaking experience, mostly who we knew. We deliberately did not ask the “usual suspects” commonly found in any mentoring program that has some aspect of “diversity”. We also did not publish the names of our mentors, but encouraged them to share what they were comfortable with.

The main reason for this was that we wanted people to focus on what topics they wanted help from rather than who might help them.

First, we set expectations with our mentors.

  • Sessions would be 1-hour.
  • Asking for preparation is encouraged.
  • No obligation for follow up.
  • We asked for minimum 2 and maximum 4 (it’s a lot easier to ask for 2-4 hours of someone’s time than to ask them to enter into an indefinite relationship with a stranger).

Initial email to mentors:

Thank you so much for agreeing to be a mentor as part of our anniversary celebration! We super appreciate it.

We want this to be the most efficient use of your time possible. Please feel free to ask your mentee to do some preparation, and highlight what aspects you are most comfortable helping with.

We’ve set expectations as one 1-hour mentoring session. If you want to follow up that’s great! But there is no expectation that you will do more than one session for each person.

We still have some slots available so if you want to share the anniversary with your network and mention that you are mentoring that would be awesome!

Finally – we’d love to send you a Technically Speaking tshirt as a thank you. If you pick out what you want and let us know an address, we will get one sent your way. If you’d prefer something else, we’d love to buy you a book! Some of my recent faves: Gravitas, Hot Seat, Slack, Women Don’t Ask, Why Not Me, or let me know if there’s anything you’ve been meaning to buy. I need to know whether you’d prefer a Kindle version or a Real Book (and if so what address to send it to).

Thanks again!



Most importantly, we set expectations with mentees.

These two things were helpful to us in assigning mentors. They also encouraged people to think and be concrete about what they wanted to achieve.

Email to mentees:

Hi! Thanks for taking part in the Technically Speaking Anniversary!

You’re receiving this email because you signed up to get a 1 hour mentoring session. Following this email will be another connecting you to your mentor. Meanwhile here are some guidelines we’d like you to keep in mind.

  • Remember your mentor is giving up their time to help you! Be respectful of their time:
    • Show up on time.
    • Follow up with a thank you note if their advice helped (e.g. when you get a CfP acceptance).
  • Please reply to the intro email with some background on you and your speaking goals. Try to be as succinct as possible.
  • If your mentor asks you to do some preparation, please make sure it’s done well in advance of your call.
  • You will get the most out of mentoring if you have concrete questions and specific things you want to work on. E.g.
    • Turning an outline into a good abstract.
    • Putting together an outline for a talk about <specific subject>.
    • Choosing what to talk about from a range of topics.

We still have some slots available so if you want to share the anniversary with your network and mention that you are taking part that would be awesome!



We matched people based on their experience and goals, and the expertise of the mentors. Some were really clear and obvious matches, and others less so. We also considered timezones, but chose what seemed like a better mentor-mentee pair rather than convenience. E.g. Someone focused on giving their first talk would be paired with a mentor who had become a regular conference speaker relatively recently. Someone who was thinking about how to get paid to speak would get one of our most experienced mentors. We also tried to connect people who worked on similar platforms where possible, especially when the mentee was thinking about things like branching out to international events.

Intro email:

<Mentee, mentor is>

<Mentor, mentee> participated in our anniversary and suggested that they would most like to work on <XXX>

<Mentor> please respond to this email with some times you have available and your communication preferences.

<Mentee> please respond to this email with a short explanation of your speaking experiences and what you want to work on.



(Notice again we are clarifying expectations: Mentee will accomodate the mentor’s availability, and be clear in what they are hoping to achieve).

A Note on Thank Yous

In the initial mentor email we offered to send all mentors a small gift. Firstly, being able to do that kind of thing is part of why we started having sponsorship for the newsletter. But also this is circular – if money goes through whatever it is you run, some of that should be allocated to thank people who volunteer to help you.

Secondly, it’s amazing to me how many programs that rely on volunteer effort come across as entitled to and unappreciative of those volunteers. If people are giving up their time to help you, that needs to be appreciated. The time to do that needs to be factored in to the overhead of the program. We (with a little help) opted to surprise and delight people where possible (this part is ongoing).


  • Running a mentoring program is a lot of work.
  • … especially if you do work as an organiser that makes life easier for mentors: e.g. getting people’s goals out of them.
  • Expectations are important. We needed to be clear about them in even more places – e.g.what does a good goal look like?
  • Template emails help a lot.
  • Having a collaborator that keeps you honest is gold. E.g. Chiu-Ki and I both reviewed people’s goals and requests and pushed each other to do the right thing by our mentors rather than the easy thing for us.


We basically have no idea who subscribes to our newsletter. We estimate >50% women, in part because a lot of people think it’s for women even though it’s for everyone – we just consider women as first class consumers of the content.

We more mentoring requests from Europe than expected, so more mentors based in Europe would have been really helpful.

We also had about >25% of mentoring requests from men. This was initially surprising to me, but actually I think makes sense – there are so many “mentoring” programs (of dubious effectiveness) for women, but Technically Speaking is for everyone because everyone is afraid of public speaking.


One way to support what we do is sponsor Technically Speaking. Sponsoring an issue is currently 250 USD, webinars start at 500 USD.

And if you haven’t already… why not subscribe?

One reply on “Running a Mentoring Program”

Comments are closed.