The demo went well. The buyer nodded through the ROI slide. Your rep asked every discovery question in the playbook. Two weeks later the deal is “pushed to next quarter” and nobody can say exactly why.
Our founder saw this pattern for years while leading sales enablement. The reps knew the product. They knew the methodology. They still lost deals they should have won, and the reason was almost never the product. It was the conversation.
On October 14 she sat down with David Bush, President of BDR.ai, on his podcast, Turn More Conversations Into Customers: AI Coaching for Modern Sales Teams, to talk about exactly this. Here is what they covered, and what she would tell any sales leader heading into 2027 planning.
The Buyer Felt Misunderstood
Picture two buyers on the same call. One is technical. She wants details, case studies, and a clear view of how the thing actually works. The other is a VP who cares about one question: what does this do to my team’s number, and how painful is the rollout?
Your rep gives both of them the same pitch. The technical buyer hears fluff. The VP hears noise. Neither says anything. Trust just quietly drains out of the call.
Now add a CFO focused on cost and an end user who dreads learning another tool. Each one needs something different, and your rep has to connect all of it to one business case. That is the real job. Most coaching never touches it.
More Meetings Will Not Fix This
Most sales orgs spend far more on getting the meeting than on preparing the rep to win it. Data, sequences, SDR headcount, automation. Then the meeting starts and the rep is on their own.
That imbalance creates a familiar dashboard: meetings up, stage conversion flat. If that is your dashboard, the pipeline is not the problem.
Timing makes it worse. Feedback that arrives after the deal is lost might help the next call. It cannot save this one. Reps use coaching when they can apply it right away to a deal they care about.
The Skills That Matter More Now, Not Less
When David asked which human skills matter most as AI gets better, our founder’s first answer was empathy. Not the soft version. The business version: understanding the buyer’s pain, priorities, decision criteria, and personal definition of success.
David shared a lesson he learned from Brian Tracy years ago: ask questions skillfully and listen carefully. Most reps ask a prepared question and then wait for their turn to ask the next one. The better move is to hear what deserves a second, third, or fourth question.
Coaching Before, During, and After the Call
This is where Influence Coaching changes the math.
- Before the call: a short buyer brief built from public data and past interactions. Dextego uses Big 5 and DISC profiles to show how this person likes to receive information, what likely motivates them, and which objections to expect. For a high stakes call, the rep role plays against an AI version of that buyer first.
- During the call: a timely prompt when it matters. What does success look like for you? What happens if you do nothing? What is driving the timeline? Not a teleprompter. A nudge at the moment the outcome can still change.
- After the call: notes, a drafted follow up, new objections flagged, and the playbook updated. The feedback loop runs every week instead of waiting for the next training day.
What This Looks Like in Practice
Our founder’s own routine takes about ten minutes for an important call. Five minutes to read a daily brief: who she is meeting, what to know, one thing to do, one thing to avoid. Five more minutes to rehearse the hardest part of the conversation. After the call, the follow up is drafted for her to review. On Fridays she looks at the new objections from the week.
David raised a fair concern: AI can bury you in information. The answer is short outputs built around one decision. Give the rep what changes their next move. Automate everything else.
Where to Start
Pick the stage where deals stall most. Pull ten calls that did not advance. Find the two behaviors that show up again and again. Coach those two things for 90 days, and measure stage conversion before and after.
You already did the hard work of getting the meeting. The opportunity is helping your reps win the conversations you have already paid for.
Watch the full conversation on David’s podcast: Turn More Conversations Into Customers: AI Coaching for Modern Sales Teams.
Learn more about Dextego, Influence Coaching for sales teams, at dextego.com. Explore AI powered prospecting and business development with David Bush at BDR.ai.
Frequently Asked Questions
Why do sales teams lose deals they were close to winning?
Usually because the buyer felt misunderstood. The rep gave the wrong kind of information for how that buyer makes decisions, or missed a stakeholder’s concern, and trust faded even though the product was a good fit.
What is Influence Coaching for sales teams?
Coaching that helps reps adapt to each buyer before, during and after the call: a buyer brief built from Big 5 and DISC profiles, role play against an AI version of the buyer, and prompts during the live call. Dextego provides it.
How should sales leaders start fixing stalled deals?
Pick the stage where deals stall most, review ten calls that did not advance, find the two behaviors that repeat, and coach those for 90 days while tracking stage conversion.