When I was at Carta, we spent $100k+ on a training everybody forgot about.
For a few weeks after, people were eating, sleeping, and breathing the concepts.
Then a month later, my VP of Sales brought me into his office and asked:
“Why isn’t anyone using the training anymore!?”
Here’s why:
Reps forget your 72-hour SKO training when you don’t reinforce it every single week.
Mark Kosoglow led Outreach from $0-250M+ ARR and he learned very quickly how to lead trainings that actually stick.
So today we’ll cover Mark’s complete step-by-step training process:
- Determine how much training your team can handle
- Use the 20/80 Rule to make the training stick
- Run a training that doesn’t suck
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Step 1: Determine How Much Training Your Team Can Handle

Managers often times overwhelm their teams with trainings and they end up not remembering any of it.
So start by determining how much training your team can handle with the Rep Assessment Matrix above:
- How much Cognitive Load does it require? How mentally taxing is it to learn?
- What Capability do you want your reps at? How good does the rep need to get?
- Plot your Topics. You get 16 points max. This prevents you from overloading the team.
So if you’re completely overhauling your discovery methodology… don’t do a million other things.
Step 2: Use the 20/80 Rule to Make the Training Stick
If you lead a training and then never reinforce any of the concepts, your reps will forget it.
So follow the 20/80 rule: 20% Training -> 80% Reinforcement. Example for discovery:

Remember that reps are already strapped for time, so don’t add any additional meetings to reinforce trainings.
You should already be operating with these 4 rhythms that are perfect for reinforcement:
- Team Meetings: Great for reinforcing prospecting numbers, roleplays, or quick metrics reviews
- Deal Reviews: Great for reinforcing deal process (multithreading, driving timeline, negotiation)
- 1:1s: Great for any skill at the team or individual level (discovery call reviews, cold call roleplays)
- Bi-Weekly Skill Building: Great for any skill at the team level (more discovery call reviews, cold call roleplays)
Step 3: Run a Training That Doesn’t Suck
If your training is a 90 minute monologue run, consider it a complete waste of time.
That’s a one way ticket to your reps retaining absolutely nothing.
Instead, use Mark’s “Show, Don’t Tell” framework to keep your reps from falling asleep.
Here’s an example cold call training he actually led:
- Lay out the framework: Opener, provocative question, green turkey, 3 strikes & out.
- Break down each step (with examples): Deep dive each step above with talk tracks.
- Reps make it their own: Have them write down their opener to match their personality.
- Reps roleplay: Go into roleplays of their scripts.
Teach the concepts then make reps literally do it live 3, 4, 5 times.
Lastly, try to get the top managers or reps to run the training while enablement supports.
They’re far more likely to stay engaged when they see the #1 rep leading from the front.
And that’s a wrap, folks!
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