The issue isn’t the people. It’s the system.

From my experience, one of the most common onboarding challenges is the classic buddy program. We assign a busy senior rep to pair with a new rep, often intimidated, and hope for success. Usually, all that happens is fifteen minutes of small talk or complaints instead of sharing valuable tribal knowledge.

The issue isn’t the people. It’s the system.

If we want new hires to ramp up faster, we need to gamify the process of extracting tribal knowledge. We should move away from questions like “How are you settling in?” and instead ask “Walk me through how you actually closed that last deal.”

I'm working with three clients right now to develop their sales onboarding programs. Here's a simple idea I’ve been refining: a game that turns buddy time into learning time. Many conversation starter games already exist, so I created...

🃏 The Buddy Deck

You have a deck of cards. Each suit represents a different topic. The goal isn't just to ask questions, but to uncover a story or tactic that would never be found in a handbook.

How it works

The Draw: In the weekly meeting, the new hire selects one card from two different suits.

The Timer: The buddy gets five minutes to answer each question.

The Action: The new hire writes down one golden nugget from the conversation and emails it to the buddy afterward. This reinforces learning and keeps both people honest. Here are some sample questions you might want to include.

Spades: The Dirt (Internal Politics and Process)
How work actually gets done vs what the handbook says.

• Who outside of Sales do I need to befriend to get deals across the line, and how do I do it?
• Which Slack channels are gold, and which ones are noisy?
• What CRM workaround saves you an hour a week?
• What unwritten rule everyone follows but no one says out loud.

Hearts: The Customer (Empathy and Stories)
Understanding the buyer and the market.

• The hardest deal you ever closed and how you saved it.
• A prospect who ghosted you and the red flag you missed.
• The moment in the demo when the buyer’s eyes light up.
• The most common objection and the one sentence that diffuses it.

Clubs: The Tools (Tactical Skills)
The craft of selling.

• Your cold open. Show me how you would start a call with me right now.
• Your highest performing subject line.
• Your favorite discovery question that uncovers the most pain.
• The phrase you use to move from demo to next steps without it feeling weird.

Diamonds: The Lifestyle (Mindset and Career)
Longevity and mental health.

• A time you missed quota and how you bounced back.
• Your first thirty minutes of the day.
• The book, podcast, or newsletter that actually made you better in this industry.
• How you disconnect at the end of the quarter.

🏆 The Win Condition

A digital Bingo card with all topics represented. Every time a new hire completes a card, they mark it off. If they complete a full blackout within sixty days, both the new hire and the buddy get a small reward.