Online Workshop

OW Directives and SAMS Training: Self-Employment: Establishing and Monitoring Eligibility

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About this Online Workshop

Today's business culture requires new demands and considerations with the varied types of contracts/subcontracts/gig contracts and the current state of our work culture in 2020. Caseworkers find it time consuming, clients find it complicated, and while many can speak of its accomplishments the set backs are compounded by achievements that are difficult to make within the current milestone framework. 

This new workshop provides a simpler yet comprehensive self-employment path teaching case workers and clients about quick assessments, reasonable expenses aligned to standard Canada Revenue Agency (CRA) principles and simplicity on workbook goals, setting milestones and developing outcome plans. We have identified gaps and challenges, as well as best practices and strive through training to make self-employment activities a realistic achievement for the clients and for caseworkers to facilitate and support clients within the business world.

By examining the Regulations 134/98 greater flexibility exists in approving self-employment from intake approval, to case management monitoring right through to successful exist strategies to increase CMSM/DSSAB sustainable employment outcomes while improving the quality of life for Ontario Works Participants through reasonable and viable self-employment achievements in gaining higher monthly family income.

Learning Outcomes

This workshop is comprised of 7 Modules based on the following training units: 

  • Module 1 – Defining Self Employment – Directive 5.13
    • Case Study – Uber Driver
    • Case Study – Blended Self Employment
  • Module 2 – Self Employment Readiness Survey
  • Module 3 – Self Assessment Workbook
  • Module 4 – Participant Action Planning
  • Module 5 – Milestone Tracking
  • Module 6 – 60 Week Update
  • Module 7 - Appeals

NOTE: This is an interactive, virtual workshop, which is different from a webinar. Participants will be expected to participate through voice and video, and to engage with each other and the facilitators in large and small group discussions, to learn from each other and practice skill development.

Who Should Attend?

  • Any Ontario Works front-line and management staff

  • Staff whose role requires knowledge of OW directives

Format and Duration

Six, three-hour, and one two-hour, online workshops over two weeks.

Workshop Dates and Registration

All sessions in Eastern Standard Time.

There are currently no upcoming dates scheduled for this workshop. If you would like to enquire about bringing this virtual workshop to your organization or staff, please email


  • Members: $750 + HST

  • Non-Members: $975 + HST

  • Non-Member Education Level 1/2: $780 + HST

Technical Requirements

OMSSA will be hosting this virtual workshop using Zoom, an online, interactive platform that you can join straight from your web browser, or by downloading 'Zoom Client for Meetings' on your computer or tablet

Participants will be expected to join the workshop via both video and audio. Participants should therefore have access to a desktop computer, laptop computer or tablet with:

  • a webcam or built-in camera

  • a built-in microphone or a headphone jack where you can plug in a headset or earphones

We strongly recommend that participants use a headset or earphones with a built-in microphone in order to limit background noise. 

System requirements: Click here for more detailed information on system requirements from Zoom.


Participants must be able to access the SA Extranet site during this training in order to navigate Directives, Legislation and Clearinghouse.

About the Facilitators

Kirby Steinhoff has been in the employment and social services field for over 10 years, starting as a frontline crisis counsellor in a domestic violence shelter transitioning to Ontario Works case management with Norfolk County and is currently employed with Halton Region as an Integrated Case Manager. Kirby has worked as a trainer and policy developer within Halton Region and is considered a subject matter expert and has trained both front-line and supervisory staff on various SAMS modules and directives, while with Halton Region.

Kirby has completed an Undergraduate degree from Western University in Women’s Studies and Feminist Research, a diploma in Human Resources from Fanshawe College and Master of Arts in Labour Studies from McMaster University with research focused on social policy, inclusion and contemporary work. 

David Thomas, social assistance trainer for OMSSA has been involved in the area of policy development and training for over 15 years. He worked for the Region of Durham in policy and research until 2017 and is now an independent consultant supporting municipalities in training, change management policy development, and human services integration. Many of OMSSA's members know David from past years employed by OMSSA as a social assistance trainer and Manager of Consulting and Training. David's networking with our members has continued to build superior working relationships over the decades and David continues to develop and facilitate curriculum for OMSSA. Prior to David's policy and training development he worked several years as a Caseworker and Employment Supervisor throughout the 1980s. David has a degree in Adult Education, a diploma in Social Services and is currently working on his Master's of Education through Athabasca University.