I spent six weeks building a sales onboarding program I was proud of. Twenty-three training modules. Product deep-dives. Demo certification. Pitch practice. Competitive analysis. Market positioning. Everything a new rep could possibly need to know.
We hired four new reps. I put them through the program. They passed every quiz. They aced the certification. They delivered perfect demo presentations to the team.
Then we put them on live calls. They fumbled. They couldn't answer basic objections. They positioned features instead of value. They talked too much and listened too little. After four weeks of intensive training, they were completely unprepared for actual sales conversations.
One of them quit after two months. Two others took six months to hit quota. The fourth is still struggling a year later.
That failure taught me the most important lesson about sales onboarding: You can't train someone to sell. You can only train them to have better conversations.
Why Most Sales Onboarding Fails
The mistake I made—and the mistake I see most PMMs make—is treating sales onboarding like product training.
We build curriculums. We create slides. We test knowledge retention. We measure completion rates. We treat it like school, where the goal is to transfer information from instructor to student.
But selling isn't about knowing information. It's about reading situations and adapting in real-time.
A rep who can recite every product feature but can't tell when a prospect is actually interested versus being polite will lose every deal. A rep who knows the perfect pitch but delivers it to someone who's not ready to hear it will waste everyone's time.
The reps who succeed aren't the ones who memorize the most—they're the ones who learn to read people, ask better questions, and adapt their approach based on what they hear.
My six-week onboarding program taught reps what to say. It didn't teach them when to say it, how to listen for buying signals, or how to pivot when their pitch wasn't landing.
I learned this by watching our best rep onboard a new hire informally. No slides. No modules. Just: "You're going to listen to my next ten calls. Don't say anything. Just listen for what questions I ask and when I ask them."
After ten calls, the new rep shadowed him on five more calls. Then they co-demoed together for a week. By week three, the new rep was running calls solo with the top rep listening in and giving real-time feedback over Slack.
That rep ramped faster than anyone who went through my formal program. Not because he learned more information—because he learned to have better conversations.
What Actually Happens in the First Four Weeks
When I rebuilt our sales onboarding program, I started by asking our top reps: "What did you struggle with most in your first month?"
None of them said "I didn't know enough about the product." Every single one said some version of: "I didn't know what questions to ask" or "I couldn't tell if the prospect was actually interested or just being nice" or "I didn't know how to handle objections in the moment."
The first month of selling is about pattern recognition, not information transfer.
New reps need to learn:
What good discovery sounds like versus interrogation. How to ask questions that reveal priorities without making prospects feel defensive.
What buying signals actually look like versus polite interest. The difference between "this is interesting" and "I need to solve this problem now."
What objections mean versus what they say. When "we don't have budget" means "you haven't shown me enough value" versus "we literally cannot spend money."
What good demos flow like versus feature tours. How to tell a story that connects product capabilities to the prospect's actual problems.
When to push versus when to back off. Reading the room to know if the prospect wants more information or needs space to think.
You can't teach these things in slides. You can only teach them through exposure, practice, and feedback.
Week One: Watch, Don't Talk
My new onboarding program starts with something that feels wasteful: new reps spend the entire first week watching calls without saying a word.
Ten discovery calls. Ten demos. Five objection handling situations. They watch, take notes, and we debrief after each one.
I give them a simple framework to watch for:
What question did the rep ask that changed the conversation? Every good sales call has a moment where the rep asks something that makes the prospect stop and think. Find that question.
When did the prospect's energy shift? Watch for the moment when they lean in, start asking detailed questions, or bring up implementation details. That's a buying signal.
What objection came up and how did the rep respond? Note the exact words the rep used. You'll hear the same objections in your own calls.
What did the rep do that you wouldn't have done? This reveals assumptions to challenge.
One new rep told me: "I thought good discovery meant asking lots of questions. But your top rep only asked four questions in a 30-minute call. He just let the prospect talk and asked follow-up questions based on what he heard."
That insight—learned from observation, not from slides—changed how he approached discovery calls.
Another rep noticed: "The best demos don't show the product first. They start with the prospect's current workflow and then show how the product fits in."
These are things I could have told them in training. But watching it happen in real conversations made it stick in a way lectures never could.
Week Two: Shadow and Debrief
Week two, new reps join live calls as silent observers. They're in the Zoom but camera off, mic muted. They watch their assigned mentor rep run real sales conversations.
After each call, immediate debrief. Not in a formal meeting—in a five-minute Slack huddle or a quick walk.
I train mentor reps to ask three questions:
"What did you notice?" Let the new rep share observations first. This reveals what they're paying attention to.
"What would you have done differently?" This surfaces assumptions and creates teaching moments.
"What question would you ask next if you were me?" This makes them think through next steps, not just observe passively.
One mentor told me about a debrief that changed a new rep's trajectory. After a call where a prospect raised a pricing objection, the mentor asked: "What do you think that objection was really about?"
The new rep said: "They think we're too expensive."
The mentor said: "Listen to the recording again. Right before the pricing objection, what did they say?"
The new rep listened: "They said they're not sure if their team will actually use all the features."
"Right," the mentor said. "The objection wasn't about price. It was about value perception. They don't see themselves using enough of the product to justify the cost. So how would you respond?"
That five-minute debrief taught the new rep more about objection handling than an hour of training ever could.
Week Three: Co-Sell With Safety Net
Week three is where most onboarding programs fail. They either keep reps in training too long (boring them and delaying productivity) or throw them into solo calls too early (setting them up for failure).
The answer is co-selling: new reps run the call, but their mentor is on the line ready to step in if needed.
Here's how we structure it:
Before the call: 10-minute prep. Mentor and new rep review the prospect's info and decide who's asking which questions. New rep owns discovery, mentor owns demo.
During the call: New rep leads. Mentor stays muted unless the new rep gets stuck or misses something critical. Then mentor steps in smoothly: "Great question—can I add some context here?"
After the call: Immediate feedback. What went well, what to adjust, what to try next time.
The safety net is critical. New reps are terrified of screwing up in front of prospects. Knowing their mentor is there to save them if they get stuck lets them take risks and try things.
I watched one new rep completely blank when a prospect asked about security compliance. She froze for three seconds—an eternity on a live call. Her mentor jumped in: "Great question. We're SOC 2 Type II certified and I can walk you through our compliance framework. But first, can you tell me which specific compliance requirements you need to meet?"
After the call, the mentor told her: "You'll get asked that question on 30% of calls. Here's how to answer it." They practiced the response three times. She never froze on that question again.
Week Four: Solo Calls With Review
By week four, new reps are running calls solo. But the learning doesn't stop.
Every rep records all their calls (we use Gong). Each week, they pick two calls to review with their mentor:
One call that went well to identify what's working and should be repeated.
One call that went poorly to identify what to adjust.
The mentor doesn't watch every call—that doesn't scale. But reviewing two calls per week creates a continuous feedback loop.
I also have new reps do self-review first. Before meeting with their mentor, they watch their own calls and answer:
What did I do that moved the deal forward?
What did I miss or should have done differently?
What question should I have asked that I didn't?
This self-awareness is what separates reps who plateau from reps who keep improving.
One rep reviewed a call where she lost a deal and realized: "I spent 15 minutes explaining features the prospect never asked about. I didn't ask if they had budget or timeline. I didn't even confirm if the problem I was solving was their actual priority."
She didn't need her mentor to tell her that—she saw it herself when she watched the recording. Her mentor just helped her practice better discovery questions for next time.
The Training That Actually Matters
You'll notice my four-week program has very little formal training. No product deep-dives. No slide decks about market positioning. No quizzes on feature lists.
That's intentional. Formal training has its place, but not in the first four weeks.
Here's what I do include:
Two hours on the customer: Who they are, what problems they have, what they've tried before. This comes from customer interviews, not product marketing decks.
One hour on the pitch: The 30-second version, the 5-minute version, the 30-minute version. Practiced out loud, not read from slides.
One hour on objection handling: The five objections every rep will face, with scripted responses practiced in role-play.
One hour on demo flow: The story structure of a good demo, with live examples from top reps.
One hour on discovery questions: The 10 questions every discovery call should include, with examples of good follow-ups.
That's it. Five hours of formal training across four weeks. The other 35 hours are spent watching calls, doing calls, and debriefing calls.
This feels uncomfortably light to most PMMs. We're trained to build comprehensive curriculums. Five hours feels insufficient.
But I've tested both approaches. Reps who go through five hours of focused training plus 35 hours of call practice ramp faster and hit quota sooner than reps who go through 40 hours of formal training.
The learning happens in the calls, not in the classroom.
The Metrics That Actually Predict Success
Most onboarding programs measure completion rates and quiz scores. Those metrics are worthless.
A rep who scores 100% on a product knowledge quiz but can't handle objections in live calls is not ready to sell.
The metrics I track for new reps:
Calls completed in first 30 days: Target is 50. If a rep isn't doing 2-3 calls per day, they're not getting enough practice.
Discovery questions asked per call: Target is 8-10. If they're asking fewer, they're pitching too early.
Demo-to-close ratio: Track from day one. Top reps close 20-25% of demos. New reps start around 10% and should be climbing.
Objection handling confidence: Mentor-rated after each co-sell call. Are they getting more comfortable handling objections or still freezing?
Self-awareness in reviews: When they review their own calls, can they identify what went wrong? This predicts long-term improvement.
These metrics tell me if a rep is actually learning to sell, not just memorizing information.
What I Got Wrong the First Time
My first onboarding program failed because I optimized for my comfort, not for rep success.
Building training modules felt productive. I could show stakeholders the curriculum I'd built. I could measure completion rates. I could demonstrate that I was being thorough.
But none of that helped reps sell.
The program that works—heavy on call practice, light on formal training—feels uncomfortably unstructured. It's harder to measure. It's harder to show progress on a Gantt chart. It requires mentor reps to invest time in coaching instead of just pointing new hires to training materials.
But it produces reps who can actually sell.
The shift I had to make: stop treating onboarding like a curriculum to complete and start treating it like an apprenticeship to practice.
Sales is a craft, not a subject. You don't learn it from lectures. You learn it from watching masters, practicing under supervision, and getting real-time feedback.
The Uncomfortable Truth About Sales Onboarding
Most sales onboarding programs fail because they're designed to make PMMs look good, not to make reps successful.
We build comprehensive programs because we want to demonstrate our expertise. We create formal certifications because we want measurable outcomes. We test product knowledge because it's easier to test than sales judgment.
But none of that correlates with quota attainment.
The reps who hit quota fastest aren't the ones who know the most about the product. They're the ones who learned to read prospects, ask better questions, and adapt in real-time.
You can't teach that in slides. You can only create the conditions for them to learn it through practice.
That means less formal training and more call practice. Less testing and more coaching. Less curriculum and more apprenticeship.
It's uncomfortable because it's hard to measure and hard to scale. But it works.
The choice is simple: build an onboarding program that makes you look good, or build one that makes reps successful.
I tried both. Only one actually works.