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Sylwia Vargas
Sylwia Vargas

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Talk Notes: "Secrets of Successful Mentors" (RailsConf 2021)

What is this post about: As a part of my professional growth, I make time to watch conference talks on Ruby, Rails, JS, React, tech writing, and tech trivia. Previously, I'd just watch them but now I will take and publish notes for future reference. This talk was a part of RailsConf 2021 that I'm participating in at the time of writing.

Talk: 'The Secrets of Successful Mentors' by Doug Bradbury

Prep materials: GitHub Repo

One-paragraph summary: How do the best mentors operate? What makes them so effective? In this workshop, we will explore some counter-intuitive techniques that great mentors use in helping their apprentices learn fast and achieve extraordinary results. Learn how to give just the right learning challenge and just the right time and how to give feedback in a way that will actually be heard!

Impression: I have participated in a number of workshops and talks on mentorship and this was the best by far. I am really impressed by Doug's experience and empathy 💕

Table of contents:


  • Successful mentors mentor because they want to
    • It's important for you to know why you're doing this
  • Successful mentors don't teach, they mentor
    • you're working with their character, not behavior; with their skills, not their knowledge (it's their responsibility to learn);
    • deep-level learning: we are looking for synthesizing what they've learned;
    • the person should be transformed through the time they've spent with you;
Teaching Mentoring
Behavior character
Knowledge Skills
Regurgitate Synthesize
Certify Transform
Group 1-1 Relationship
  • Successful mentors ask more qs than they answer
  • Successful mentors co-learn
    • Experts can actually make poor mentors because they don't remember what it is like to learn
    • Learning happens in relation to what you already know by building a "scaffolding" to what you already know -- experts usually don't have these scaffoldings because they already have a whole structure
    • the best mentor is someone near you, just ahead of you (zone of proximal development)
    • expert-mentors can be a bit intimidating
  • Successful mentors follow the learner
    • the Montessori method of "follow the learner": watch them, present them with the next step, next challenge
    • what is F L O W? It is a perfect balance between relaxation and arousal; if there's too much relaxation, you'll be bored; if there's too much arousal, you'll be anxious; both inhibit learning; ideally, you will be bouncing between a little bit of relaxation and arousal;
    • as a mentor, it's important to find the right challenge, just a little bit more than what the person already knows;
  • Successful mentors replay their reactions (I think that was the phrasing)

    • when we receive critical feedback, our brain may just "shut down" because of the fight-flight-freeze response
    • fight, flight, freeze response narrows your focus and just emphasizes survival
    • how we present what we have to say triggers the defensive reactions - and we usually present feedback as a judgment
    • we want to give people the feedback but the best way to deliver it is to make it not about them but about us
    • use phrases like: "this is how it came across to me", "this is how I saw it"
    • if you replay your reactions, feedback becomes the start of the conversations, not their end

    "Most feedback is much more about the person giving the feedback than the person receiving it"
    "If you don't have anything nice, say something about yourself"

Instead of ... Try ... Because ...
Can I give you some feedback? Here's my reaction. / Tell me about your thought process here. It causes fear, you can't say no, it may sound patronizing (are you implying I can't take feedback?)
Good job! That works for me! I liked what you did there. Tell me how you've arrived at this solution. It's not specific, not helpful. It's rooted in approval and power dynamic (who am I to tell you what is "good"?!)
Here’s what you should do. Have you considered X? / Here's what I'd do (...) - let's talk about it. It's a judgment.
That won’t really work. -,- -,-
You need to improve your communication skills. When you did X, I felt Y. / I'm having a hard time understanding what you're trying to say / Here's where you've lost me Not specific, it's a judgment.
You are slow to complete your work. I feel that you... / I'm concerned that we... Feels too personal. Activates fear and worry. Closes the conversation
You spin your wheels for too long before asking for help. Here's what works for me. If someone is not asking for help, probably it's more about the env, than the individual.
  • Successful mentors look for outcomes
    • what does "success" mean for this person, and in this scenario?
    • the mentee is not a great "vessel" to fill up with our great knowledge
    • we usually a picture of how things should be done and what excellence looks like for us but in this way, the best we can achieve is to build some poor imitation of ourselves but we want to go beyond them
    • instead, look for "excellence outcomes", point them out to the learner, and let them figure out how they got there
    • ask them how they achieved stuff (this feel acknowledging + helps them reflect and recreate what they did)
  • Successful mentors individualize, the pluralize concepts
    • there's nothing like one learning style!!!!
    • it's a mechanism of bias and of putting folks in boxes
    • there are multiple kinds of intelligence, for instance: verbal-linguistic, logical-mathematical, intrapersonal (self), interpersonal (others), musical, visual-spatial, bodily-kinesthetic, naturalist (taxonomy, organization), existential (why?), emotional
    • interconnect different kinds of intelligence!
    • help the learner develop these kinds!
  • Successful mentors define clear learning outcomes
    • THIS IS SO IMPORTANT -- I've seen it first-hand when I was teaching Ruby at a bootcamp
    • Use specific verbs, such as: Name, Memorize, Identify, Do a simple procedure, Recognize, count, define, draw, fund, label, match, quote, recall, recite, order, tell, write, imitate, List, Describe, Classify, Combine, Do algorithms, Report, discuss, illustrate, select, narrate, compute, sequence, outline, separate Analyze, Explain, Integrate, Sequence, Relate, Apply, Compare, Contrast, Argue, Criticize, Relate, Predict, conclude, summarize, review, argue, transfer, make a plan, characterize, differentiate, organize, debate, make a case, construct, review and rewrite, examine, translate, paraphrase, solve a problem Reflect, Theorize, Hypothesize, Create, Imagine, Formulate, Generate Generalize, generate, compose, invent, originate, prove from first principles, make an original case, solve from first principles
    • Build the outcomes with this structure: verb + subject + context, for instance: "List (verb) the three rules of TDD (subject) to a group of apprentices seeing TDD for the first time. (context)", "Contrast (verb) Outside in vs Inside Out TDD (subject) in a blog post targeted at Senior Developers (context)", itd.
  • Successful mentors protect, separate, and leave
    • this is a reference to a Japanese concept of Shu Ha Ri
    • shu (守) "protect": you create a safe env for a person to learn where they can fail (safely) without becoming a failure
    • ha (破) "detach": this is where a person pushes back on the ideas and established ways
    • ri (離) "leave": our hope is that the learner will become able to do more than what we can do, that they grow beyond us; there comes a point in the relationship where they leave this mentorship relationship

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Top comments (3)

gonsie profile image
Elsa Gonsiorowski

Wow, I love this idea of publishing your notes of good talks! Thanks!

Do you know if there was a more specific context around mentoring here? I’ve been in a number of formal mentoring programs, but none of them had targeted learning outcomes. Most of my experience was explicitly for career development.

That said, this talk gives me a lot to think about.

sylwiavargas profile image
Sylwia Vargas

Thank you for your kind words ✨
So I actually asked Doug about informal mentorships (specifically, why they don't work usually) and he responded:

My experience is mostly in formal mentoring relationships, usually as a part of on onboarding or apprenticeship process. Informal relationships suffer when everything else the participants are doing interferes. By definition almost 'Informal" means low on my list of priorities. One thing we have done a One World Coders is that we have a community slack channel that out team watches. We try to help out someone who comes in with a question, but there is not an ongoing relationship.

gonsie profile image
Elsa Gonsiorowski

Makes a lot of sense, especially in the apprenticeship context. Thanks again!