AI-based Coaching at the Intersection of Technology and Humanity

It wouldn’t be a 2025 strategy meeting if someone didn’t ask “how can AI help with (fill in the blank).”

It seems like every day brings advances in conversational AI that promise to change selling as we know it. From territory analysis, to automated outbound engagement bots through contract redlining and forecasting, I can’t think of a sales skill that doesn’t have some AI vendor claiming to transform it.

But one of the first places that I see companies starting their AI journey is in the real-time coaching of sellers.

With a PhD in Communication, I’ve always viewed sales through a social scientist’s lens. Group decision making and persuasion are processes governed by rules that have been studied for years – and sellers can get great results if they understand what those rules are That’s why I’ve gravitated as a leader towards sales playbooks that focus on clear methodologies. Sandler, or Challenger, or MEDIC – all offer a prescribed set of questions to ask or conversations a seller needs to have with their prospect to deliver a predictable result:

• Customer goes quiet on you? Send a “breaking up” email, and they’ll come right back.
• Think your deal is going to be approved next Tuesday? Not if you haven’t spoken directly to the economic buyer about their personal win.
• Want to maximize your negotiated price? Throw out a high anchor that customers will work back from.

For years, these rules have been largely handed down through word of mouth – in classroom-based training and ridealongs with sellers and managers.

But my experiences as a sales leader was that there was never enough time to coach every seller as much as I’d like. Yes, I could schedule trips to be out in the field with my team – but at best, I was only going to go on a handful of calls with each seller in a given year.

As call recording and transcribing tools get married with AI systems, we suddenly have the ability to “ride along” on literally every call our sellers make – and provide automated feedback on how to handle objections or move the deal forward as soon as the call is over (if not in real-time).

That undoubtedly has the potential to really develop sellers quicker and further than ever before. But it can come as a shock to some of our best performers – senior sellers who have worked remotely with limited supervision for some time, and haven’t had that level of oversight, measurement, and word-level coaching since their days in a BDR bullpen decades ago.

And if we suddenly introduce it to them without any context – it can feel like management no longer trusts these talented sellers, or have developed into some unpleasant big-brother organization they don’t want to be a part of. Without a great cultural rollout of these new ways of working, the introduction of these tools can drive some of the best talent away to other companies.

At the end of the day, our sellers are human beings, who are paid to build interpersonal relationships with other human beings – and we need to remember their humanity as we start using AI to change their work environment.  With this in mind, here are four important suggestions:

• Prioritize Transparency and Explain the “Why”: Before flipping the switch on any AI coaching tool, clearly communicate the purpose behind its introduction. Explain how it’s designed to support and develop them, not just monitor or micromanage. Frame it as a way to augment their skills, provide insights they might miss, and ultimately help them achieve greater success and earning potential. Address concerns about data privacy and usage head-on.
• Blend AI Insights with Human-Led Coaching: AI can be incredibly effective at identifying patterns, adherence to methodology, and specific coaching moments in a vast number of calls. However, this data is most powerful when used as a foundation for human-to-human coaching. Managers should use AI-generated insights to inform more targeted and impactful coaching conversations, focusing on the nuances, emotional intelligence, and strategic thinking that AI might not fully grasp. The AI can flag an issue; the manager can help explore the why and co-create solutions.
• Empower Sellers with Control and Personalization: Where possible, give sellers some agency over how AI coaching is implemented. This could involve allowing them to opt-in to certain features, customize the type of feedback they receive, or focus the AI on specific areas they want to develop. For senior sellers, position it as a tool for refining their already excellent skills or for mentoring junior team members by analyzing their own successful calls as models.
• Focus on Developmental Feedback, Not Just Critiques: The rollout of AI coaching should emphasize growth and learning. Ensure the feedback provided is constructive, actionable, and balanced. Highlight what sellers are doing well, in addition to areas for improvement. Avoid using AI data punitively, especially during the initial adoption phase. The goal is to build confidence and competence, not to create an environment of fear or constant judgment.

The promise of AI-powered coaching in sales is undeniably attractive, offering scalability and insights beyond what we are capable of without it. However, the path to realizing this potential is paved with careful consideration for the human element. By prioritizing transparency, integrating AI insights with empathetic human guidance, empowering sellers, and fostering a culture of development rather than surveillance, organizations can successfully navigate coaching at the intersection of technology and humanity. Ultimately, the goal is not to replace the skill of selling (or sellers themselves) with algorithms, but to elevate it, creating a sales team that is both highly effective and deeply engaged – leveraging the best of what both artificial and human intelligence have to offer.

For more tactical, practical advice and on this and other topics for the modern CRO, please see my bestselling book: The CRO’s Guide to Winning in Private Equity