guide
Retain & Grow Guide
An employer’s playbook for retaining and developing Opportunity Youth.
01
Why retention matters more than ever
Opportunity Youth bring fresh perspectives, untapped potential, and a strong desire to succeed – but too often, they leave jobs not because they want to, but because systems fail to support their long-term success. When they stay, they soar. And when they soar, so does your team.
Retention is not a downstream outcome – it’s a designed experience. One that begins on Day One and builds with intention, inclusion, and a shared sense of purpose.
This guide will help you craft an environment where OY talent not only stays, but thrives.
02
The secret is: ongoing investment
Retention begins where onboarding leaves off – and it relies on your continued willingness to invest in the individual. Opportunity Youth don’t just want a job; they want to grow, feel valued, and be seen as part of something bigger. Your job is to give them reasons to stay.
Extend mentorship beyond onboarding
Mentorship shouldn’t end after the first month. If possible, structure a six- to twelve-month mentorship arc. Formal or informal, regular mentor check-ins build confidence, strengthen learning, and create emotional safety.
- Offer mentor/mentee debriefs quarterly.
- Provide time during work hours for mentorship to happen.
- Encourage reverse mentoring – what might the mentor learn from the mentee?
- Support OY to continue to access external resources that provide mentorship, too.
Growth conversations: Ask, don’t assume
Too often, young workers leave because no one asked them what they wanted next. Make “growth conversations” a regular part of your supervision.
Try this:
- What’s one new thing you’d love to try?
- Where do you see yourself in six months – and how can we help you get there?
- Is there a skill or task you’d like to build confidence in?
Tip: When you make work purposeful with growth visible and attainable, youth are more likely to stay. Retention positively impacts the company and the young employees may later become future managers, trainers or leaders in your organization.
03
Create advancement pathways – even small ones
Career ladders don’t have to be dramatic to be meaningful. Opportunity Youth want to know there’s a future here.
Define advancement
Define what advancement looks like: clearer responsibilities, a raise, or title adjustment.
Link behaviours to progression
Link demonstrated behaviours (reliability, communication, teamwork) to progression.
Set milestones together
Set milestones together. For example: “If you complete X and Y by Month 4, we’ll talk about Z.”
Even if full promotions aren’t immediately possible, micro-advancements (like leading a small project or shadowing in another department) show you’re invested in their trajectory. Have in mind what job the OY might advance to and indicate the path forward.
04
Support learning, inside and out
Learning shouldn’t be left to chance. Equip your OY hire with skill-building opportunities – and make it easy for them to say yes.
Offer paid time for training or upskilling
Reimburse low-cost certification courses or provide internal alternatives
Partner with community organizations for subsidized training programs
Celebrate learning milestones – like completing a first aid course or digital literacy module
Insight: Investing in learning signals trust. And trust builds loyalty.
05
Financial and non-financial benefits: both matter
You don’t need to offer a massive benefits package – but you do need to think carefully about what might make the difference between someone staying or leaving.
Small raises can be a big deal.
Opportunity Youth may live paycheck to paycheck. A $1/hour raise can be more meaningful than a vague “great job.”
Offer clarity on benefits
- Are there savings plan contributions or bonuses?
- Is there support for childcare or transportation?
- Are there wellness days or flex hours?
- Ask your OY what they value and would appreciate; explore what’s possible.
Even occasional free lunches or social activities can build belonging.
06
Design your culture for stickiness
Retention is cultural. People stay where they feel seen, safe, and part of something. Here’s how to make your workplace “sticky” for OY:
Participatory decision-making
Let them weigh in on projects or workplace improvements.
Authentic leadership
Model vulnerability, humility, and curiosity.
Diversity & inclusion training
Normalize conversations about difference and bias.
Equity in advancement
Make sure the pathway upward isn’t reserved for a few.
Try this: Encourage peer recognition programs, team shoutouts, and practices that honour contribution in visible ways.
07
Monitor engagement and belonging
It’s not just about staying – it’s about feeling good while doing so.
Regularly ask:
“What’s working well for you here?”
“Is there anything you’d change if you could?”
“Do you feel like part of the team?”
Reminder: If something’s off, act early. Retention is a relationship, not a transaction.
08
A note to HR and organizational leaders
Stay curious. Stay flexible. Stay committed.
Retention strategies are also about retention of hope, ambition, and belonging. The systems you create now will ripple forward – not just into the life of the young person you’ve hired, but into the culture of your organization for years to come.
Because when you invest in Opportunity Youth with intention, you don’t just keep an employee – you grow a leader.
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Let’s build an inclusive future together
Your leadership can change the trajectory of a young person’s life – and your workplace in the process. Let’s lead with purpose, hire with courage, and grow a future that works for everyone.
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