Session 2 · High-Impact Coaching & the Coaching Cadence. From a one-off review to a rhythm that compounds.
Picking up where we left off
Last week you took on three reps. How did they go?
1You recorded an SSSS roleplay setup with your team.
2You applied the REKS framework to one direct report.
3You completed the pre-work for today.
Quick round: one thing that worked, or one thing that did not.
Introduction
The power of the missing tenth of a second.
Michael Phelps did not win by a body length. He won by the length of a fingernail, the result of a thousand tiny, reviewed, corrected strokes.
Not rare, massive breakthroughsConsistent, incremental progressThe extra stroke
Module 3
Game Tape. Skills Coaching.
The fastest way to improve a skill is to watch it, name the one gap, and drill it. Just like the tape.
What every interview told us
Coaching has been about results, not development.
→Past training lost momentum after 2 to 3 weeks.
→Coaching defaults to "where are my deals?", a lagging indicator.
→Stickiness beyond launch is the number one ask.
So today is built around the things that actually stick: a repeatable way to coach skills, and a cadence to keep it alive.
Before we watch, let's frame it
How are we using call coaching today?
Micro-skills
Are we coaching one specific skill, or reviewing the whole call at once?
Group vs 1:1
What belongs in a team review, and what belongs in a private conversation?
Do's & don'ts
What sets the team up to feel safe, not exposed?
AI before & after
How could AI prep the call review, and follow up after it?
Watch together
Two real FCTG calls. Watch like a coach, not a critic.
As you watch: where does discovery stop? What is the one micro-skill you would drill first?
The AI Coaching Edge
"Take a dozen, twenty transcripts from their calls, drop them into an approved LLM, and ask: based on SPICED, what is this person good at and where is there room for advancement? In about thirty minutes you have huge insights."
Antoine, WbD facilitator · live Managing for Impact session
For your coaching: the pattern you would spend a month noticing is already sitting in your call data. AI surfaces it in half an hour, so you walk into the 1:1 with a hypothesis, not a hunch. You are about to build exactly this prompt.
From the room
"A roleplay with the chatbot is a completely different experience than verbalizing it. But the powerful thing is seeing the transcript. It is very eye-opening to see what you actually say."
Dan Smith · live Managing for Impact session
And it works in a real deal: Steve Bracchi (FCM AU) rehearsed a tough fee-increase conversation in Claude Enterprise, good cop and bad cop. "It covered perspectives my colleague and I were not thinking of, and gave us the confidence to push through." The real meeting went the way they had practiced.
Build 1 of 2 · in Claude · groups of 3 to 4
Build a call-coaching analyzer you keep.
1In groups of 3 to 4. One person shares their screen and opens Claude (app or browser), new chat.
2Paste the prompt on the right. Read it together first, the group owns it.
3Add a call: use the sample on the next slide, or paste a real Gong transcript if someone has one handy.
4Iterate as a group: change one instruction, run it again, see what improves. The discussion is the learning.
Mixed access is fine. Claude Enterprise keeps the transcript in your tenant, ideal for real calls. On personal Claude, use the sample call only.
Paste into Claude
You are an expert sales coach trained in the Winning by Design SPICED framework (Situation, Pain, Impact, Critical Event, Decision) and the REKS development model (Results, Effort, Knowledge, Skills).
I will paste a transcript of one of my reps on a customer call. Coach it for development, not deal inspection.
Return, in this order:
1. SPICED scorecard. For each of S, P, I, CE, D give a score from 1 to 5 and quote one line from the call as evidence, or say it was missing.
2. The single biggest skill gap, named as one practiceable micro skill (for example, "ask a layered follow up before moving on"), not a vague trait. Show me where you see it.
3. Two coaching points: one thing the rep did well that I should reinforce, and the one thing to work on. Use exact quotes.
4. A 90 second RingRing roleplay to drill that micro skill, using the SSSS framework: the Skill, the Scene, the Scenario, and the Start.
5. One open coaching question I can ask so the rep discovers the gap themselves, instead of me telling them.
Here is the transcript:
[paste your call transcript here, or use the sample call on the next slide]
Sample call · paste after the prompt
No recording handy? Use this one.
Sample transcript · Corporate Traveller
Rep (Jordan): Hi Sarah, thanks for making the time. I know we said 30 minutes, does that still work?
Sarah (Head of Procurement, multinational): Yes, that is fine.
Jordan: Great. So I wanted to walk you through our corporate travel platform today and show you how we can save your team money.
Sarah: Okay.
Jordan: We have a really strong online booking tool, 24 by 7 support, and our reporting dashboards are best in class. Clients your size love the duty of care features.
Sarah: We do have some concerns about traveller safety, yes.
Jordan: Perfect. Our duty of care is excellent, we can track every traveller in real time. Should I set up a demo with your wider team?
Sarah: Maybe. We are quite happy with our current provider, to be honest. It would take a strong case to move.
Jordan: Totally understand. I think once you see the demo you will be impressed. How about next Tuesday?
Sarah: Let me check with the team and come back to you.
Jordan: Sounds good, I will send some times. Thanks Sarah.
Share-out
What did Claude catch that you would act on?
Each group: the one micro-skill you would drill, and the RingRing you would run.
Five minutes
Break.
Grab a coffee. Back in five for the part that makes all of this stick: cadence.
Module 4
The Coaching Cadence.
A single great review changes one call. A rhythm changes a career. This is how coaching becomes a habit, not an event.
The navigation log that built predictable performance
Every week1:1 plus skills practice. Newer reps weekly, veterans every other week.
MonthlyPattern review across calls, stage health, a skip-level conversation.
Quarter endBusiness review, growth plan, recalibrate the whole cadence.
Sources: Andy Grove, High Output Management (weekly 1:1s are the highest-leverage thing a manager does, run as the rep's meeting, roughly half a day per report). Sales-coaching research: a 30-minute 1:1 split 10 minutes deal, 10 skill or roleplay, 10 goals; reps who get 3+ hours of coaching a month hit quota about 7 points higher. Keep coaching and pipeline review in separate slots.
From the room
"We do roleplays every single Friday. My team knows they need a written formal excuse to miss one. We have done it for eight years. They are sacrilege."
Courtney Van Schalkwyk · Corporate Traveller, Sales Lead Asia
This is a cadence that stuck. Not because it was mandated, because it became "just what we do." When the rhythm is sacred, the fear leaves the room and the practice compounds. Eight years of Fridays is how you build a coaching culture.
The AI Coaching Edge
"Do a REKS analysis the night before the 1:1. Walk in with a hypothesis, spend the meeting coaching, not analyzing."
Antoine, WbD facilitator · live Managing for Impact session
For your cadence: AI is what makes a demanding cadence survivable. It preps the call review, summarizes the patterns, and can even play the buyer for a roleplay. You can also build a "manager agent" that gives feedback the way you do, so a rep can practice receiving your feedback before the live session.
Build 2 of 2 · in Claude · groups of 3 to 4
Build your team's coaching cadence.
1Same groups. One person shares screen, opens Claude, new chat.
2Paste the prompt. Claude will interview you one question at a time, answer for a real team.
3It builds a daily / weekly / monthly / quarterly cadence tuned to your motion, plus the one change to start now.
4Pressure-test it as a group: is it realistic? Where would it break? Refine and rerun.
Goal: each of you leaves with a cadence you could put on your calendar Monday, built on the rhythm you already have, not a brand new set of meetings.
Paste into Claude
You are an expert sales leadership coach trained in the Winning by Design coaching cadence model. Help me design a realistic coaching cadence for my team that I can start next week, built on the rhythm I already have rather than new meetings.
Ask me these questions one at a time, wait for each answer, then build the plan:
1. What kind of team do I lead: corporate and strategic, retail and transactional, or groups and multi stakeholder, and how many people?
2. What is our sales motion and the main result metric?
3. How much time can I realistically protect for coaching each week?
4. What is already on our calendar (1 to 1s, team meetings, pipeline reviews)?
5. What is the single biggest coaching gap on my team right now?
Then produce:
A. A cadence table with Daily, Weekly, Monthly, and Quarterly rows. For each: the activity, its REKS focus (Results, Effort, Knowledge, or Skills), and what good looks like. Modify what I already do, do not just add meetings.
B. The one change I should implement immediately.
C. A 90 day "try this with me" framing I can use to sell the change to my team.
D. For each recurring slot, one way I could use Claude to assist (call review, summary, role play partner, pattern analysis).
Share-out
Three questions, one answer each.
1Your cadence design in one line.
2The biggest gap in how you coach today.
3The one change you will implement immediately.
Wrap up
One system, three moving parts.
SESSION 1
REKS
Diagnose: is it a result, effort, knowledge, or skill gap?
TODAY · SKILLS
Game tape + AI
Find the gap in the call data, drill it with a roleplay.
TODAY · CADENCE
The rhythm
Repeat it weekly so the improvement compounds.
Diagnose with REKS. Develop with game tape and roleplay. Sustain with a cadence. That is managing for impact.
Before we meet again
Your three reps for the week.
1Run the call-coaching analyzer on one real rep's call.
2Implement the one cadence change you committed to today.
3Come back ready to share what worked, or what did not.
Both prompts are yours to keep. Save them today.
Winning by Design™
Thank you.
Please take 60 seconds for the survey, your feedback shapes the next session. [ facilitator: drop your survey link in the chat ]
Winning by Design™ · Proprietary & Confidential, Do not distribute
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Facilitator Script00:00Mirroring to a projector? Press P for Speaker View so the room only sees the slide.
Speaker View, opens notes + timer in a separate window for a mirrored room
O
Overview, jump to any slide (when running long)
T
Start / show the session timer
B
Black the screen for an open discussion
F
Fullscreen
?
This help
Projecting to a room? Set your display to Extend (not Mirror), put the slides on the projector, and press P here to keep your script + timer on your laptop only. Running a live build? Drop each prompt into the chat so every breakout group can paste it.