AI Object!: Using AI in Objection Handling and Sales Training with Andrew Leshak

Objection handling is one of the hardest skills to master in sales. Andrew Leshak, a sales enablement expert who has worked with companies at Sapient Industries and founded Samme, built exactly that, and it’s only getting smarter.

In his conversation with Rachel Kreis, Landbot’s Director of Sales, Andrew broke down how AI is transforming sales training and objection handling — and why the future of sales enablement is more human, not less.

Watch the full interview below or keep reading for the key insights.

Watch the Full Interview

Chapter 1: Why Traditional Sales Training Falls Short

Traditional sales training has a fundamental problem: it’s episodic. Reps get trained, then go back to their desks, and most of what they learned fades within days. The gap between training and real-world application is enormous.

Andrew has spent years studying this gap. His core insight: sales skills are built through repetition and feedback, not through watching presentations or sitting in workshops. You can’t learn to ride a bike by watching someone else do it.

The challenge is that giving every rep personalized, high-quality repetitions at scale is incredibly resource-intensive. Managers can only do so many role-plays. Senior reps can only coach so many junior colleagues. This is exactly where AI changes the equation.

Chapter 2: What AI-Powered Sales Training Actually Looks Like

AI sales training tools can now simulate realistic customer conversations, play the role of a skeptical prospect, and provide immediate, specific feedback on how a rep handled each objection. This creates the repetition loop that traditional training lacks.

Andrew described the ideal AI training scenario: a rep practices handling a pricing objection, gets feedback on what worked and what didn’t, tries it again with a slightly different angle, and iterates until the response becomes natural. All of this happens without taking up a manager’s time.

The best tools also adapt to the rep’s level. Early-stage reps need to build basic frameworks; experienced reps need to sharpen edge cases and unusual objections. A good AI training system recognizes where each rep is and adjusts accordingly.

Chapter 3: The Most Common Objections — and How to Handle Them

Andrew walked through the objection categories that sales teams struggle with most:

• Price objections: Often a signal that value hasn’t been established. The fix isn’t to discount — it’s to reframe value more concretely.
• Timing objections: “Not right now” often means “I don’t see urgency.” The response needs to surface the cost of inaction.
• Competitor comparisons: Reps who panic and start listing features lose. The better move is to understand what specifically the competitor appears to offer and address the underlying need.
• Internal approval objections: These are really about risk. Help the prospect articulate the business case internally, and you become an ally rather than a vendor.

For each category, AI training can expose reps to dozens of variations, building pattern recognition that’s hard to develop from real calls alone.

Chapter 4: Why Human Coaching Still Matters

Andrew was careful to emphasize that AI doesn’t replace human coaching — it amplifies it. The best training programs use AI for volume and consistency, then use human coaches for nuance and emotional intelligence.

AI can tell a rep that their answer to a pricing objection lacked specificity. A human coach can hear the uncertainty in their voice and help them find their authentic version of the response. Both are valuable; neither is sufficient alone.

The teams that will win are those that use AI to handle the repetition layer, freeing up coaches to focus on higher-order development: confidence, presence, strategic thinking.

Chapter 5: Building a Culture of Continuous Improvement

The biggest shift Andrew has observed in high-performing sales teams isn’t a specific technique — it’s a mindset shift toward continuous improvement. Top reps review their calls, seek feedback proactively, and treat every lost deal as a learning opportunity.

AI makes this culture easier to build because it removes the friction of getting feedback. Instead of waiting for a manager to review a call, a rep can practice the same scenario immediately after a tough call and try a different approach.

Over time, this creates compounding improvement. Reps who practice consistently don’t just get better at objection handling — they develop a fundamentally different relationship with difficulty in sales.

Key Takeaways

• Traditional sales training fails because it lacks repetition and real-time feedback loops
• AI training tools enable reps to practice objection handling at scale, without requiring manager time
• The best approach combines AI for volume with human coaching for nuance and emotional intelligence
• Price, timing, competitor, and approval objections each require distinct frameworks
• Teams that build a culture of continuous improvement through AI-assisted practice develop lasting competitive advantages