Training the class of 2026: Leadership lessons from the front lines of sales

Each morning, our team gathers for a stand-up coaching session — 20 minutes of practical, tactical sales training pulled from real conversations and the lessons from the day before. It’s the most important meeting for the team. It’s the most important meeting in the company. It’s all about the fundamentals of sales and communication.

The class of 2026 enters the workforce at a moment when the conversation is dominated by AI. Large language models and other automation tools are reshaping workflows across every industry and every company, and that includes real estate. Yet, according to Randstad, in 2026, sales associate is the most in-demand job in Canada. That’s because the ability to communicate, build trust, strengthen relationships and convert a conversation into opportunities are skills that can’t be automated or completed by an AI agent. But this is also a skillset that almost no one is teaching.

I lead a team of 75 people in Toronto, but this advice applies to those with direct report teams of any size, from two to 200. Our sales team takes thousands of calls every day. The work is relentless and extremely human. And that’s by design.

Yet when a new hire joins the team, a pattern emerges. These under-30-year-olds arrive smart, eager and generally exceptional in a lot of ways. Yet they’re often almost entirely unprepared for the realities of professional communication. This isn’t because they don’t have the potential to be great at it. It’s because they haven’t been taught the fundamentals: eye contact, active listening, using insight to probe beyond the script, and, importantly, handling rejection without spiralling. These are all teachable skills, but they aren’t being taught in classrooms.

For the workforce of tomorrow, micro-coaching beats traditional onboarding

In most places, onboarding is a week of training, a binder of scripts and then you’re on your own. At a previous employer, new hires went through a training session and within two hours they were on the phone doing scripts. For a generation that’s learned primarily through screens and texts, this is not setting them up for success. The difference between telling them what to say, and them learning how to say it (with conviction, curiosity and, importantly, genuine warmth) is enormous.

What works to effectively teach the practice of sales are morning standups and micro-coaching. Instead of thinking of training as a fire-and-forget process that’s started and finished the first week (or first day!) that a new hire begins, it’s reframed as a continual part of the everyday process of doing the job.

Our morning stand-up meetings are not one person climbing up on a table and orating pep talks. They are tactical debriefs. For example, yesterday a team member fumbled a conversation because they rushed past an objection. Today we broke down exactly what happened, then brainstormed what they could have done differently, and how an actively curious question is a better response to doubt. Tomorrow they will apply this coaching live, and the day after we will refine it again in our stand-up. That cycle — teach, apply, refine, repeat — is what actually builds competence.

Teaching the skills AI can’t replace

For clarity: I am not anti-AI. My team uses AI tools all the time: to role-play client conversations before going live, to assess buying intent and to assist in the research of local market data for follow-up emails. Yet the moment a homeowner asks, “Why should I sell now?” is an inherently human conversation. The doubt in their voice, the personal context behind the question and, most importantly, the trust required to take action are things no algorithm can match. This isn’t a theory, it’s a tactical reality.

So, I train for competencies that sit on the other side of technology:

• Resilience after a difficult stretch of calls.
• Discipline to lead with curiosity rather than pitch.
• The ability to read a conversation and know when to push and when to listen.

These have, in the past, been dismissed as “soft skills,” but they are the hardest skills in business, and they are the skills that separate the essential salespeople from those who fall by the wayside. And just like a sports team that practises as much as it plays, it makes sense to always be training these skills.

And even if the employees being trained don’t stay in sales specifically, these skills serve them well in almost every job function and beyond, to true entrepreneurship. Complex decision making, resilience, persuasion and relationship building make you better wherever you go.

Bridging the execution gap

Back to guiding and training the next generation of workers. They are motivated and have excellent ideas. The challenge for them, and for those training them, is the gap between those good ideas and disciplined execution.

They know relationship building is important. They can articulate why follow-up matters. The daily grind of actually doing it — picking up the phone and making 200–300 calls each day, sending personalized messages to each prospect spoken to, and maintaining energy and, essentially, authenticity — that’s where almost everybody stalls at first. It’s leadership’s job to close the gap.

This isn’t done through slogans and aphorisms, but structure, repetition, accountability measures and a coaching culture that treats sales like what it is: a performance discipline.

The frontline leader’s responsibility

So, if you lead a sales team (in any industry that depends on human persuasion and relationship building), the class of 2026 is your responsibility. It isn’t HR’s. It doesn’t fall on some learning management system. Yours. These new hires will absolutely exceed your expectations, but only if you invest the time to teach them what school didn’t and have the patience to maintain that training as a daily practice. This means seeing your team both as a complete unit and as individual members who need unique help to level up their confidence and execution.

These skills are often seen as basic and foundational skills, and they are often overlooked by employers because they are considered a bare minimum. But since they are rarely taught, you get otherwise exceptional workers who start without them, and those that have them are clearly distinguished from the rest. The leaders who recognize that, and who build the practice of coaching into their daily workflow, are the leaders whose teams will outperform the AI-enabled market.

The future of work isn’t less human. It’s more human.

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