First Conversation Coaching
Workplace Training by The MentorWell
Your company invests in mental health. But when it matters most, your managers don't know what to say.
Employee Assistance Programs. Wellness stipends. Mental health days. You've done the work to show your people you care.
But when someone on your team is struggling, really struggling, the first person they encounter isn't a therapist or an EAP line. It's their manager.
And most managers have never been taught what to do in that moment.
They freeze. They change the subject. They say "let me know if you need anything" and move on. Or they say the wrong thing — and the employee learns it isn't safe to speak up here.
That one moment doesn't just affect one person. Every other employee is watching. Weighing. Deciding whether this is a place where it's safe to be honest — or a place where you keep your head down and your mouth shut.
That's how silence becomes culture.
Start Here: The Workplace Signal Check
Before you think about training, try this.
The Workplace Signal Check is a free, private, 12-question self-audit for managers. It takes five minutes. No one sees your answers but you.
It won't tell you what's wrong with your team. It'll show you what you're noticing, what you're missing, and where one conversation could change everything.
Here are three of the twelve questions:
When you ask how they're doing, what do you get back?
Do you know if they're dealing with something outside of work?
If they were struggling, do you believe they'd come to you?
If you paused on any of those, that's not a problem. That's a starting point.
[Take the Workplace Signal Check →]
What The First Conversation Is
The First Conversation is a practical training program that teaches managers and leaders two things most of them were never given the tools to do:
Recognise when someone is struggling. Not the obvious signs. The subtle ones. The slow withdrawal. The shift in energy. The employee who's still performing but has gone quiet. The one who's suddenly always "fine."
Respond without making it worse. What to say. What not to say. How to open a door without kicking it down. How to follow up without overstepping. How to hold space for someone without trying to fix them.
This isn't therapy. It's not clinical. It's a leadership skill — and one that directly affects whether your people stay, speak up, or shut down.
Who This Is For
This isn't for every company. It's for the ones who want to be better, need to be better, and are building a culture of trust, support, and compassion.
Business owners who've built something they care about and want their people to feel that — not just read it on a careers page.
HR and People & Culture leaders who know their mental health benefits are only as good as the managers delivering on that promise day to day.
Companies that already invest in their people and want to make sure that investment holds up in the moments that actually define their culture.
The Program
Three guided sessions, delivered virtually. One hour each, lunch-and-learn format. Built for real managers with real teams — not a lecture hall.
Session 1: Signal
How to read what most people miss. The subtle behavioural shifts that tell you someone is struggling — before it becomes a crisis, a leave request, or a resignation letter. What silence actually looks like in a workplace. Why your best employees are often the ones hiding the most.
Session 2: Response
The anatomy of the first conversation. What to say when you notice something. What to never say. How to be direct without being intrusive. How to make it clear you see them — without making it about you. Real scenarios. Guided practice. No role-playing exercises that make everyone uncomfortable.
Session 3: Follow-Through
The conversation doesn't end when the meeting does. How to follow up without hovering. How to create ongoing psychological safety on your team. How to normalise check-ins so they don't feel like interventions. What to do when someone needs more support than you can give — and how to bridge them to it.
All sessions are recorded for ongoing access and onboarding of future managers.
1-on-1 Manager Coaching
Some conversations can't wait for a training session.
For managers navigating real situations in real time — an employee who just disclosed something difficult, a team member whose performance has changed, a moment where the wrong words could break trust — we offer private, confidential coaching.
This isn't general leadership development. It's a skilled coach helping you prepare for or debrief a specific conversation that matters.
Single session: $250/hour
Four-session block: $900 — for managers who want ongoing support as they build this skill with their team.
Investment
The First Conversation Program Three 60-minute virtual sessions for up to 25 managers. All sessions recorded with ongoing access.
$5,000
Additional managers beyond 25: $150 per seat.
Program + Coaching Bundle Everything above, plus two hours of private 1-on-1 coaching for managers who are already navigating a situation.
$5,400
The Business Case
This isn't just about being a good employer. It's about protecting what you've built.
Turnover is expensive. Replacing an employee costs 50% to 200% of their annual salary. Many departures trace back to a moment where someone felt unseen or unsupported — and decided this wasn't the place for them.
Presenteeism is invisible. An employee who's struggling but silent isn't gone. They're just not there. Productivity drops. Engagement drops. And it spreads to the people around them.
Your culture is defined in hard moments. Not in your values statement. Not on your website. In the moment a manager sits across from someone who's falling apart — what happens next is what your culture actually is.
Psychological safety drives performance. Teams where people feel safe to speak up outperform teams where they don't. That's not philosophy. That's data.
Why The MentorWell
The MentorWell was founded by Chris Coulter, a parent, mental health advocate, and someone who learned the cost of silence firsthand.
The same patterns that break families break workplaces. People who are struggling go quiet. The people around them see what they want to see. And by the time anyone says something, it's often too late, not always in the worst way, but in ways that cost you trust, talent, and culture that took years to build.
The First Conversation exists because earlier is always better than too late. In a home. And in a workplace.
What This Isn't
This is not crisis intervention training. It's not a substitute for therapy or clinical support. It's not about turning managers into counsellors.
It's about equipping the people closest to your employees with the awareness and the skill to notice sooner, respond better, and create the kind of environment where people don't have to hit rock bottom before someone asks if they're okay.
“The managers who retain great people aren't the ones who notice problems. They're the ones who notice people”
Next Step
Book a free 15-minute call with The MentorWell to find out if The First Conversation is right for your team.
No pressure. No pitch. Just a conversation about whether your managers have the tools they need for the conversations they're already avoiding.
The First Conversation is delivered by trained facilitators on behalf of The MentorWell. Available for virtual delivery across Canada.
Not sure where to start? Take the Workplace Signal Check, it takes five minutes and it'll show you exactly where the gaps are.
