Coaching & Training
Coaching grounded in the work your team does.
I've coached hundreds of salespeople and managers. We work on real 1:1s, deals, and customer conversations so new skills show up where they matter.
When it fits
When skills aren't carrying into the work
- Managers use 1:1s to collect updates but struggle to develop sellers.
- Deal reviews end with a forecast instead of a better plan for the buyer.
- Sellers need help with discovery, account strategy, or complex deals.
- Training and onboarding happen, but the skills fade once people return to the job.
What the work covers
Develop the skills the work demands
The audience and skills follow the constraint we identify together.
Manager coaching
Practice 1:1s, deal coaching, and specific feedback that helps sellers improve without taking over their work.
Leader development
Help sales leaders coach their managers, set clear expectations, and follow through on development.
Seller coaching
Work through discovery, account strategy, and complex opportunities using the team's actual customers and deals.
Training and onboarding
Build focused sessions, practice, and follow-up around the skills new or existing team members need on the job.
How it works
Practice, feedback, and reinforcement
Step 01
Observe
Look at real meetings, conversations, and deals to understand what people do today.
Step 02
Focus
Choose the few behaviors that matter most and agree on what good looks like.
Step 03
Practice
Coach on live work, with preparation before and specific feedback afterward.
Step 04
Reinforce
Put the new practices into 1:1s, deal reviews, and onboarding so managers can sustain them.
Measurement
What shows coaching is taking hold
We agree on the behaviors and leading indicators to watch, then look for them in real sales work.
- Managers use the agreed coaching practices in real 1:1s and deal reviews.
- Sellers demonstrate the targeted skills in customer conversations and opportunities.
- New practices continue after training and appear in weekly routines.
- Relevant indicators, such as deal progression or ramp time, are reviewed over a useful period.
How it connects
Connected capabilities, scoped to the problem.
Sales Strategy sets direction. Sales Leadership establishes the management structure. Coaching & Training develops the skills people use in that structure. AI can support preparation where it helps.
Common questions
Questions about coaching & training.
Who is the sales coaching for?
Coaching can focus on frontline managers, sales leaders, or sellers. We choose the audience and skills after looking at the live meetings, deals, and customer conversations where the work needs to improve.
How do you keep sales training from fading?
Training includes practice on real work and specific feedback, then reinforcement in 1:1s, deal reviews, and onboarding. Managers continue to use the practices after a session ends.
Work with Kevin
Tell me what needs to change in sales.
Share what you're building, rebuilding, or struggling to execute. I'll read your note personally and reply by email.