20th Jan, 2026
The 4 Pillars of Coaching OS
Written By:
Alastair Doig
Guidance, Playbooks, Data, and the Feedback Loop
Executive Summary
A Coaching Operating System (Coaching OS) must do more than record; it must implement performance uplift. It stands on four interdependent pillars: Live Execution Guidance, Automated Playbooks, Objective Performance Data, and The Feedback Loop . Together, these pillars bridge the gap between "knowing what to do" and "doing it" during high-stakes revenue conversations.
Beyond Point Solutions: Why Infrastructure Matters
Most sales tech stacks are a graveyard of "point solutions." You have a CRM for record-keeping, a call recorder for "review", and a set of static PDFs for playbooks.
The problem is that these tools don't talk to each other. Information is siloed, and the "Expertise" of your best sellers remains trapped in their heads. A Coaching Operating System replaces this fragmented approach with a unified architecture.
To be effective, this system must stand on four pillars. If one is missing, the system collapses.
Pillar 1 – Real-time Guidance
Guidance is the "live" component of the OS. It is the ability to share in real time, at the exact moment they need it. This stops the biggest challenge retaining training knowledge and implementing it.
Contextual Triggers: The AI listens to the conversation and recognises "intent" or "keywords". If a prospect mentions a competitor, the system surfaces the best way to handle this instantly.
Behavioural Guardrails: The OS ensures the rep stays within the winning framework. It might prompt a rep to ask about "Budget" if it detects the conversation is moving too quickly toward a proposal.
Reduced Cognitive Load: Reps no longer need to memorise 50-page manuals. The system acts as a "heads-up display", allowing them to focus on building the relationship.
Pillar 2 – Automated Playbooks
Static PDFs in a shared folder are where playbooks go to die. An OS turns these into dynamic, digital "triggers".
Dynamic Interaction: Instead of a 20-page manual, the playbook becomes an interactive "Heads-Up Display" that only appears when relevant.
Ensuring Consistency: Whether a rep is in London or New York, the Automated Playbook ensures they are following the same winning framework for every £10k or £100k deal.
Rapid Deployment: When your market strategy changes, you update the playbook in the OS, and the entire team is "retrained" the moment they start their next call.
Pillar 3 – Objective Performance Data
Rather than relying on a manager’s "gut feel" or a rep's optimistic memory, the OS tracks behaviours executed.
The Autonomous Development Hub: This is where reps take ownership of their growth. The Hub allows sellers to review their own execution data against the "Gold Standard". By surfacing skill gaps automatically, such as missed discovery questions, the system enables reps to course-correct independently without waiting for a 1-to-1.
Objective CRM Accuracy: Because the OS is present during the call, it captures facts in real-time. This eliminates "creative writing" in CRM updates and provides a true picture of pipeline health.
Pillar 4 – The Feedback Loop
The Feedback Loop is what makes the Coaching OS self-evolving. It ensures your organisation learns faster than the competition.
Identify Winning Behaviours: The system correlates Pillar 3 (Data) with win/loss outcomes to see what your top 1% are doing differently.
Global Updates: Once a winning tactic is identified (e.g., a specific way to frame a £-ROI case study), it is pushed back into Pillar 1 (Guidance).
Closing the Loop: This creates a flywheel where the system constantly gets smarter, standardising the "top performer" behaviour across the entire company.
Frequently Asked Questions (FAQ)
Q: Can we implement just one pillar?
A: You can, but you wont solve the problem. Guidance without Data is guesswork. Data without Guidance is just more homework for managers. You need the full loop to see ROI. The current approach is broken, this fixes it.
Q: How does this impact the sales tech budget?
A: A Coaching OS often allows you to consolidate. Because it handles guidance, recording, and CRM data entry, you can replace several overlapping point solutions with one integrated system. The ROI uplift and the cost of inaction ensures investing makes sound financial sense.
Q: Is it difficult to build the "Loop"?
A: Not with Tiller. The system is designed to make the transition from "Data Insight" to "Live Prompt" as simple as clicking a button.
From the Tiller Blog:
Coaching OS vs. Conversation Intelligence: What’s the Difference?
Stop looking backward. Discover why traditional Conversation Intelligence (CI) is a "post-mortem" tool and how a Coaching Operating System provides the "in-flight" guidance needed to actually win deals.
28th Jan, 2026

How to Build an Automated Playbook
Stop guessing which sales tactics work. Learn how a Coaching OS identifies winning patterns from your live calls and automatically updates your playbooks, creating a self-evolving system that gets stronger without manual input.
21/01/2026

Why Sales Leaders Have No Time to Coach
Sales managers are currently trapped in "Inspection Mode"buried in CRM admin and forecasts instead of actually coaching. Discover how a Coaching OS automates the tactical "grunt work" of management, freeing your leaders to move from internal detectives to strategic deal-closers.
21/01/2026




