

XL Legal
Shelley Appleby-Ostroff
Are you a lawyer looking to excel in today’s legal profession? Join host Shelley Appleby-Ostroff, legal talent development consultant and writing coach, as she talks to successful lawyers and leading industry experts who share their knowledge, insights, and advice on topics like: increasing productivity; overcoming perfectionism; developing a personal brand; improving communication skills; building client relationships – and much more.
Episodes
Mentioned books

Dec 1, 2021 • 43min
Breaking Free from Perfection with Simi Botic
Simi Botic shares her wealth of knowledge, wisdom, and advice about breaking free from perfection. Simi’s a corporate lawyer turned holistic health and anti-diet coach, and intuitive eating counsellor, who helps women release their desire to be perfect, and heal their relationships with food and body image. Simi’s also the author of Letting Go of Leo: How I Broke Up with Perfection, a memoir about her own struggles with disordered eating, body image, and perfectionism – and her journey to recovery.
Topics discussed include:
How Simi realized the practice of law wasn’t for her
The ways perfectionism has shown up in her life
How she “broke up with perfection”
Advice for lawyers struggling with the pressure to be perfect
Tips for breaking free from “the prison of perfectionism”
Here are links to the resources Simi mentioned during our discussion, along with a few others:
Intuitive Eating Book and Companion Workbook, by Evelyn Tribole and Elyse Resch
Evelyn Tribole and Elyse Resch’s Website
Christy Harrison’s Food Psych Podcast
The Mindful Self-Compassion Workbook, by Kristen Neff and Christopher Germer
Kristin Neff’s Self-Compassion Website that includes several free guided practices
You can learn more about Simi, her work, and her book here:
Website
Instagram
YouTube
This episode contains 45 minutes of Professionalism Content
You can listen to the episodes here or by subscribing on your favourite podcast apps.
And don’t forget to rate and review the XL Legal Podcast.

Nov 17, 2021 • 45min
Avoiding Malpractice Claims with Ray Leclair
Ray Leclair shares his expertise and practical tips to help lawyers avoid malpractice claims. Ray’s the Vice President, Public Affairs at LAWPRO, the Lawyers’ Professional Indemnity Company. Before joining LAWPRO, Ray worked in-house, practiced with a major national law firm, and ran his own solo practice.
Topics discussed include:
LAWPRO as an innovative liability insurance provider and resource for lawyers
Main reasons why lawyers report malpractice claims
What lawyers can do to avoid malpractice claims
Wire fraud scams targeting law firms and their clients
To access LAWPRO’s wealth of excellent free resources, visit the following LAWPRO sites:
LAWPRO
practicePRO
AvoidAClaim
TitlePLUS
For more information about practicePRO’s upcoming wire fraud program, visit
Avoiding the Wire Fraud Nightmare
This episode contains 45 minutes of Professionalism Content
You can listen to the episodes here or by subscribing on your favourite podcast apps.
And don’t forget to rate and review the XL Legal Podcast.

Nov 3, 2021 • 32min
Creating a Happy and Fulfilling Legal Career with Darlene Tonelli
Darlene Tonelli describes her path to creating a happy and fulfilling legal career, and shares some of the lessons learned along the way. Darlene’s the founder of Inter Alia Law – a very different kind of legal services business. Before founding Inter Alia, Darlene worked in-house at a record label and practiced at a large Bay Street law firm.
Topics discussed include:
Inter Alia Law: the business model, Darlene’s blog, and the Lawyer Life Podcast
Darlene’s career path and how it led to the creation of Inter Alia Law
Differences between practicing in a traditional law firm and working in-house
Why so many lawyers feel stuck in their current jobs
How to get “unstuck”
Advice to lawyers thinking about starting their own firms
To learn more about Inter Alia Law, Darlene’s blog, and the Lawyer Life Podcast, visit Inter Alia Law’s website.
This episode contains 35 minutes of Professionalism Content
You can listen to the episodes here or by subscribing on your favourite podcast apps.
And don’t forget to rate and review the XL Legal Podcast.

Oct 20, 2021 • 38min
Modern Training for Lawyers and Law Students with Aaron Baer
Lawyer/entrepreneur Aaron Baer talks about the two innovative legal training companies he recently co-founded – 4L Academy and Build Your Book Academy. Aaron’s currently a partner and director of training and development at the Montreal-based digital law firm Renno & Co.
Topics discussed include:
Aaron’s journey from lawyer to lawyer/entrepreneur
How Aaron’s experiences as a law student and junior lawyer inspired the creation of 4L Academy and Build Your Book Academy
What’s missing from traditional law school and law firm training
4L and Build Your Book’s practical, engaging, and modern training approach
The connection between legal training and mental health
To learn more about Aaron’s training companies and programs, visit 4L Academy and Build Your Book.
This episode contains 35 minutes of Professionalism Content
You can listen to the episodes here or by subscribing on your favourite podcast apps.
And don’t forget to rate and review the XL Legal Podcast.

Oct 6, 2021 • 42min
Career Alternatives for Lawyers with Hindi Greenberg
Hindi Greenberg – a recognized expert on career counselling and outplacement for lawyers – shares her wealth of knowledge about lawyer career satisfaction and alternatives. Hindi’s the founder and president of the career consulting firm Lawyers in Transition, author of The Lawyer’s Career Change Handbook, and former practicing lawyer.
Topics discussed include:
Why so many lawyers are unhappy at work
Advice to lawyers considering a career change
Career alternatives for lawyers (both inside and outside of law)
Common challenges lawyers experience when switching careers
What new lawyers should think about – and look for – when choosing their first job
For more information about Hindi and her work, visit her website – Lawyers in Transition – and make sure to check out her list of 101 Things You Can Do With a Law Degree.
This episode contains 40 minutes of Professionalism Content
You can listen to the episodes here or by subscribing on your favourite podcast apps.
And don’t forget to rate and review the XL Legal Podcast.

Sep 22, 2021 • 43min
What a Partner Looks for in an Articling Student with Mary Paterson
Mary Paterson – a litigation partner at Osler, Hoskin & Harcourt LLP in Toronto – discusses what she looks for when working with an articling student.
Topics discussed include:
The articling program at Osler
What the firm expects from its articling students
Traits of a successful articling student
How articling students can prove their value to the firm
The importance of finding balance and maintaining intellectual curiosity
Common mistakes articling students make and what to do when they happen
This episode contains 40 minutes of Professionalism Content
You can listen to the episodes here or by subscribing on your favourite podcast apps.
And don’t forget to rate and review the XL Legal Podcast.

Sep 8, 2021 • 41min
Avoiding Common Appellate Advocacy Mistakes with Eugene Meehan,Q.C.
Eugene Meehan,Q.C. shares his expertise about appellate advocacy. Eugene’s the founding partner of the boutique law firm, Supreme Advocacy LLP, where he specializes in appellate advocacy and agency work.
Topics discussed include:
Differences between trial and appellate advocacy
Preparing and presenting an oral argument
Common factum writing mistakes
Factum writing tips
Eugene kindly wrote a companion paper for this episode entitled “Ten Ways to Lose at the Court of Appeal or Supreme Court of Canada”. To request a free copy of the paper, email me at info@exellegal.com or Eugene at emeehan@supremeadvocacy.ca
For more information about Eugene and his work, visit the Supreme Advocacy LLP website
This episode contains 40 minutes of Professionalism Content
You can listen to the episodes here or by subscribing on your favourite podcast apps.
And don’t forget to rate and review the XL Legal Podcast.

Jun 9, 2021 • 1min
Summer Break Announcement
After 30 episodes, I’ve decided to take a break for the summer. In the meantime, you might want to check out an earlier episode. All 30 are still available and accredited by the Law Society of Ontario for Professionalism Content.
Wishing you a happy and healthy summer.
I look forward to reconnecting with you in September.
You can listen to the episodes here or by subscribing on your favourite podcast apps.
And don’t forget to rate and review the XL Legal Podcast.

May 26, 2021 • 51min
Finding Your First Job as a Lawyer with Paulette Nnorom
Paulette Nnorom shares her expertise about finding your first job as a lawyer. Paulette’s a lawyer, coach, and certified career and résumé strategist. She’s also the founder and principal coach at hireback.ca – an online coaching program created specifically to help articling students and LPP candidates in Ontario find their first job as a lawyer.
Topics discussed include:
Developing a focused job search strategy
Networking during the pandemic
Tapping into the hidden job market
Preparing personal marketing material
To learn more about Paulette and her work, visit https://21stcenturylawyer.ca/coaching/ and https://www.hireback.ca/
This episode contains 50 minutes of Professionalism Content
You can listen to the episodes here or by subscribing on your favourite podcast apps.And don’t forget to rate and review the XL Legal Podcast.

May 11, 2021 • 48min


