I’d Love to Hear
Your Ideas.
Let’s Connect!

Richard Masters

I’d Love to Hear
Your Ideas.
Let’s Connect!

Richard Masters

I’d Love to Hear
Your Ideas.
Let’s Connect!

Richard Masters

I’d Love to Hear
Your Ideas.
Let’s Connect!

Richard Masters

Designing an AI Co-Pilot for Contract Negotiation

Designing an AI Co-Pilot for Contract Negotiation

Designing an AI Co-Pilot for Contract Negotiation

Enabling faster, evidence-based contract negotiations with AI-powered insights and human control.

Enabling faster, evidence-based contract negotiations with AI-powered insights and human control.

Deal Inbox

Search

⌘K

Asterion Manufacturing

Cargo handling equipment

$50.0m

5% discount offered, conditional on delivery liability and ESG concessions.

STRATEGIC STALEMATE

CrestTech Solutions

Industrial systems

$72.5m

Includes extended warranty and software updates for 3 years.

NEGOTIATING

NexGen Energy

Renewable energy

$88.7m

Volume-based rebate applicable with early payment terms.

NEGOTIATING

Vertex Dynamics

Precision machining tools

$39.3m

Price locked for two years with optional service package.

READY TO SIGN

Blue Horizon Systems

Marine equipment

$64.8m

Delayed payment plan with integrated training sessions offered.

READY TO SIGN

Quantum Robotics

Automated robotics

$53.2m

Custom firmware included; support and maintenance for 5 years.

STRATEGIC PARTNERSHIP

NeuroNet Analytics

AI-driven data interpretation platform

$47.8m

Includes real-time monitoring and quarterly insights reports.

TECHNOLOGY LICENSE

EcoWave Solutions

Renewable energy wave generators

$39.5m

Comprehensive installation and 3-year equipment warranty.

EQUITY STAKE

Asterion Manufacturing

Cargo handling equipment $50.0m · 5-year supply Negotiation · stage 3 of 5

No response by 16:00 returns the deal to Asterion's original terms — $50.0m, no discount.

Deadline today 16:00

4h 12m remaining

Decision recorded and sent

Your counter-offer went to Asterion at 11:48. Your rationale, the evidence you cited and the terms sent are on the deal record and visible to Legal, Finance and ESG without further request.

NEGOTIATION PATH

SAVING

DELIVERY

ESG

RISK

A: Accept supplier package

Take Asterion's terms as offered.

$2.5m

5.0% headline

8 weeks late

costs $0.6–1.5m

Scope 3 removed

breaches 2030 pledge

78

/100

65

B: Counter: trade discount for terms

Offer 2.8%, hold September, keep ESG reporting, add a 24-month warranty.

$2.5m

2.8% below market

On target

September held

Retained

meets commitment

35

/100

65

C: Hold current terms

Decline the trade and close on the terms already aggreed

$0.3m

0.6% admin only

On target

September held

Exceeds

reporting + audit

16

/100

65

Decision Analysis

-$2.0m

-$1.0m

0

$2.0m

$1.0m

+$0.3m

Range −$1.4m to +$1.4m

Option A

Accept supplier package

+$1.4m

Range +$1.2m to +$1.4m

Option B

Counter for terms

+$0.3m

No spread

Option C

Hold current terms

🤖

AI Suggestion: I'd pick B and counter at 2.8% and hold September. Option A's saving is offset by what it gives up - even at its best it only matches Option B. I'd change my mind if Operations prices the eight-week slip below $0.5m.

Hide Analysis

Contract Memory

Where Option B's risk comes from.

35

/100

65

Counter may be refused

+35

Liability cap held at 25%

+0

September held

+0

COUNTER MAY BE REFUSED

2.8% against a 3.1–4.2% market

We ask for less than comparables close at, so there is room. The risk is another round, not a walk-away.

7 of 9 counters pitched below market were accepted within two rounds.

Market benchmark, 24mo ↗

LIABILITY CAP

25% held

Cover stays at $12.5m. Nothing moves onto our balance sheet.

1 of 12 deals that held the cap went to dispute, against 3 of 12 that conceded it.

Past deals §4.2 ↗

DELIVERY DATE

September held

Original date retained, and a damages clause added to enforce it.

Deals carrying damages ran late half as often, and recovered when they did.

Operations review · §8.2 ↗

SELECTED PATH

Accept supplier package

Escalate

Approve

Deal Inbox

Search

⌘K

Asterion Manufacturing

Cargo handling equipment

$50.0m

5% discount offered, conditional on delivery liability and ESG concessions.

STRATEGIC STALEMATE

CrestTech Solutions

Industrial systems

$72.5m

Includes extended warranty and software updates for 3 years.

NEGOTIATING

NexGen Energy

Renewable energy

$88.7m

Volume-based rebate applicable with early payment terms.

NEGOTIATING

Vertex Dynamics

Precision machining tools

$39.3m

Price locked for two years with optional service package.

READY TO SIGN

Blue Horizon Systems

Marine equipment

$64.8m

Delayed payment plan with integrated training sessions offered.

READY TO SIGN

Quantum Robotics

Automated robotics

$53.2m

Custom firmware included; support and maintenance for 5 years.

STRATEGIC PARTNERSHIP

NeuroNet Analytics

AI-driven data interpretation platform

$47.8m

Includes real-time monitoring and quarterly insights reports.

TECHNOLOGY LICENSE

EcoWave Solutions

Renewable energy wave generators

$39.5m

Comprehensive installation and 3-year equipment warranty.

EQUITY STAKE

Asterion Manufacturing

Cargo handling equipment $50.0m · 5-year supply Negotiation · stage 3 of 5

No response by 16:00 returns the deal to Asterion's original terms — $50.0m, no discount.

Deadline today 16:00

4h 12m remaining

Decision recorded and sent

Your counter-offer went to Asterion at 11:48. Your rationale, the evidence you cited and the terms sent are on the deal record and visible to Legal, Finance and ESG without further request.

NEGOTIATION PATH

SAVING

DELIVERY

ESG

RISK

A: Accept supplier package

Take Asterion's terms as offered.

$2.5m

5.0% headline

8 weeks late

costs $0.6–1.5m

Scope 3 removed

breaches 2030 pledge

78

/100

65

B: Counter: trade discount for terms

Offer 2.8%, hold September, keep ESG reporting, add a 24-month warranty.

$2.5m

2.8% below market

On target

September held

Retained

meets commitment

35

/100

65

C: Hold current terms

Decline the trade and close on the terms already aggreed

$0.3m

0.6% admin only

On target

September held

Exceeds

reporting + audit

16

/100

65

Decision Analysis

-$2.0m

-$1.0m

0

$2.0m

$1.0m

+$0.3m

Range −$1.4m to +$1.4m

Option A

Accept supplier package

+$1.4m

Range +$1.2m to +$1.4m

Option B

Counter for terms

+$0.3m

No spread

Option C

Hold current terms

🤖

AI Suggestion: I'd pick B and counter at 2.8% and hold September. Option A's saving is offset by what it gives up - even at its best it only matches Option B. I'd change my mind if Operations prices the eight-week slip below $0.5m.

Hide Analysis

Contract Memory

Where Option B's risk comes from.

35

/100

65

Counter may be refused

+35

Liability cap held at 25%

+0

September held

+0

COUNTER MAY BE REFUSED

2.8% against a 3.1–4.2% market

We ask for less than comparables close at, so there is room. The risk is another round, not a walk-away.

7 of 9 counters pitched below market were accepted within two rounds.

Market benchmark, 24mo ↗

LIABILITY CAP

25% held

Cover stays at $12.5m. Nothing moves onto our balance sheet.

1 of 12 deals that held the cap went to dispute, against 3 of 12 that conceded it.

Past deals §4.2 ↗

DELIVERY DATE

September held

Original date retained, and a damages clause added to enforce it.

Deals carrying damages ran late half as often, and recovered when they did.

Operations review · §8.2 ↗

SELECTED PATH

Accept supplier package

Escalate

Approve

Deal Inbox

Search

⌘K

Asterion Manufacturing

Cargo handling equipment

$50.0m

5% discount offered, conditional on delivery liability and ESG concessions.

STRATEGIC STALEMATE

CrestTech Solutions

Industrial systems

$72.5m

Includes extended warranty and software updates for 3 years.

NEGOTIATING

NexGen Energy

Renewable energy

$88.7m

Volume-based rebate applicable with early payment terms.

NEGOTIATING

Vertex Dynamics

Precision machining tools

$39.3m

Price locked for two years with optional service package.

READY TO SIGN

Blue Horizon Systems

Marine equipment

$64.8m

Delayed payment plan with integrated training sessions offered.

READY TO SIGN

Quantum Robotics

Automated robotics

$53.2m

Custom firmware included; support and maintenance for 5 years.

STRATEGIC PARTNERSHIP

NeuroNet Analytics

AI-driven data interpretation platform

$47.8m

Includes real-time monitoring and quarterly insights reports.

TECHNOLOGY LICENSE

EcoWave Solutions

Renewable energy wave generators

$39.5m

Comprehensive installation and 3-year equipment warranty.

EQUITY STAKE

Asterion Manufacturing

Cargo handling equipment $50.0m · 5-year supply Negotiation · stage 3 of 5

No response by 16:00 returns the deal to Asterion's original terms — $50.0m, no discount.

Deadline today 16:00

4h 12m remaining

Decision recorded and sent

Your counter-offer went to Asterion at 11:48. Your rationale, the evidence you cited and the terms sent are on the deal record and visible to Legal, Finance and ESG without further request.

NEGOTIATION PATH

SAVING

DELIVERY

ESG

RISK

A: Accept supplier package

Take Asterion's terms as offered.

$2.5m

5.0% headline

8 weeks late

costs $0.6–1.5m

Scope 3 removed

breaches 2030 pledge

78

/100

65

B: Counter: trade discount for terms

Offer 2.8%, hold September, keep ESG reporting, add a 24-month warranty.

$2.5m

2.8% below market

On target

September held

Retained

meets commitment

35

/100

65

C: Hold current terms

Decline the trade and close on the terms already aggreed

$0.3m

0.6% admin only

On target

September held

Exceeds

reporting + audit

16

/100

65

Decision Analysis

-$2.0m

-$1.0m

0

$2.0m

$1.0m

+$0.3m

Range −$1.4m to +$1.4m

Option A

Accept supplier package

+$1.4m

Range +$1.2m to +$1.4m

Option B

Counter for terms

+$0.3m

No spread

Option C

Hold current terms

🤖

AI Suggestion: I'd pick B and counter at 2.8% and hold September. Option A's saving is offset by what it gives up - even at its best it only matches Option B. I'd change my mind if Operations prices the eight-week slip below $0.5m.

Hide Analysis

Contract Memory

Where Option B's risk comes from.

35

/100

65

Counter may be refused

+35

Liability cap held at 25%

+0

September held

+0

COUNTER MAY BE REFUSED

2.8% against a 3.1–4.2% market

We ask for less than comparables close at, so there is room. The risk is another round, not a walk-away.

7 of 9 counters pitched below market were accepted within two rounds.

Market benchmark, 24mo ↗

LIABILITY CAP

25% held

Cover stays at $12.5m. Nothing moves onto our balance sheet.

1 of 12 deals that held the cap went to dispute, against 3 of 12 that conceded it.

Past deals §4.2 ↗

DELIVERY DATE

September held

Original date retained, and a damages clause added to enforce it.

Deals carrying damages ran late half as often, and recovered when they did.

Operations review · §8.2 ↗

SELECTED PATH

Accept supplier package

Escalate

Approve

Project Result

31%

31%

31%

Reduction in time to close offers

82%

82%

82%

AI recommendation acceptance rate

71

71

71

SUS Score

Problem Statement

Contract negotiations relied on memory and judgement, producing inconsistent terms and poorly documented decisions.

Under time pressure, negotiators conceded liability and ESG protections or accepted discounts without checking comparable deals.

The goal: an AI co-pilot that uses past deals to recommend a defensible position, explains its reasoning and hands control back when needed.

Requirements Gathering

Discovery with procurement, legal and category managers identified three requirements:

REQUIREMENT

Visible reasoning

Show comparable deals and assumptions so negotiators can assess the recommendation and Legal can sign off.

REQUIREMENT

Clear Lines of Authority

Define what AI can agree to and when it must pause for human review.

REQUIREMENT

Auditability

Record the evidence, assumptions and rationale behind each position for audit and training.

Research: start with the stalled deal

I spoke with procurement and negotiation leads, Legal and Finance, and category and operations stakeholders. Rather than asking which AI features they wanted, I asked them to walk through their last stalled deal: who needed convincing, what evidence was missing, what they needed before signing and where AI should never act alone. The recurring need was a shared decision record that connected commercial terms, delivery, liability and ESG to the people authorised to make the call.

Using AI to accelerate discovery

Lovable turned early ideas into working prototypes in days, giving stakeholders something concrete to challenge.Maze tested whether users understood the AI’s task and sources, could review and amend its output, and saved time without losing confidence or control.The focus was trust: recommendations had to be understandable, controllable and accountable.

Tools Used

We mapped mandates and escalation, prototyped negotiation paths and examined how users accessed evidence. AI accelerated exploration; people judged the results.

Miro

Stakeholder collaboration, early concepts and user flows.

Easy to collaborate

Non-visual

Perfect for user-flow diagrams

Figma

Reusable components, interactive prototypes and developer handoff.

Component-based architecture

Design and Prototyping

Easy developer handoffs

Google Analytics

Track user behaviour and performance to inform design decisions.

Comprehensive user tracking

Bespoke trend tracking

Integration with Power BI

Claude AI

Explore concepts, refine interactions and accelerate content design.

UX/UI Ideation and exploration

Design feedback and refinement

Faster content and interaction design

Shareable decision records

PROCUREMENT + LEGAL

Capture terms, clauses, alternatives and approval rationale in one shareable record so Legal, Finance and ESG can review the same evidence.

Explainable recommendations

PROCUREMENT LEAD

Show evidence, assumptions, uncertainty and what would change the recommendation. Make countering and escalating as clear as approving.

Comparable contract context

CATEGORY MANAGER

Show supplier, category, scope, value and timing so category managers can judge whether a precedent is relevant.

Historical deal benchmarks

COMMERCIAL ANALYST

Include comparison periods, sample sizes and deal conditions. Expose uncertainty when benchmarks are sparse or outdated.

Decisions under time pressure

SENIOR BUYER

Keep deadlines, trade-offs and mandate limits together, with clear actions to approve, counter or escalate.

Clause-level evidence

LEGAL REVIEWER

Break risk down by liability, delivery, warranty, discount and ESG. Link each contribution to a clause or precedent for Legal to inspect.

Illustrative waterfall: a $2.5m headline saving falls to $0.25m after delivery, liability and ESG consequences.

01 / A discount can hide a worse deal

INTERVIEW LEARNING / COMMERCIAL TRADE-OFFS

Interview learning: a 5% saving can be consumed by late delivery, weaker liability protection and lost ESG reporting. Design response: show the net consequences of every option together, with ranges and assumptions beside the recommendation. The figures above illustrate the trade-off; they are not measured project results.

Stakeholder map connecting Sarah in Procurement with Legal, Finance, Operations, ESG and the supplier.

02 / Six perspectives, one decision

INTERVIEW LEARNING / STAKEHOLDER ALIGNMENT

Interview learning: negotiation touched Procurement, Legal, Finance, Operations, ESG and the supplier, while one negotiator had to move it forward. Design response: answer those stakeholders’ questions in a single workspace and retain the terms, evidence and rationale as one shareable decision record.

Illustrative four-hour negotiation timeline: orient, resume, interrogate and record, from alert to deadline.

03 / Four hours to make a defensible call

INTERVIEW LEARNING / DECISIONS UNDER PRESSURE

Interview learning: buyers could have only four hours to move a negotiation forward, with time spent consulting other teams. Design response: support a ten-second first read, keep the deal state stable when users return, expose assumptions and missing evidence, and record both the decision and its rationale.

Personas

Sarah Chen is a composite persona built from conversations with procurement, legal, finance, category and operations stakeholders. Her job is to move a stalled negotiation forward without trading away delivery, liability or ESG protections. A four-hour decision window made the challenge concrete: she needed comparable terms, visible assumptions and a clear route to approve, counter or escalate. Legal and Finance needed the same evidence and a record of why each concession was made. That synthesis changed the brief from “ask AI a question” to “make a defensible decision within your mandate”.

Logic Map

I mapped what happens when AI reaches its mandate: show the breached boundary, supporting evidence and options to approve, counter or escalate.

The flow also records who decided, what evidence they used and why, then adds the outcome to Contract Memory.

Wireframes and iteration

I used wireframes to test the decision model before refining the interface. Customer interviews established the constraints; qualitative feedback showed where comparison, evidence and control still broke down. The iterations below connect those findings to the direction we chose.

Schematic comparison of a sequential AI conversation and a decision workspace with simultaneous options, evidence and controls.

Iteration 01 / Conversation or decision workspace?

CUSTOMER FEEDBACK / COMPARISON AND CONTROL

Interviews showed that buyers had to balance savings, delivery, liability and ESG within a short decision window. I tested a conversational thread against a prepared decision workspace. Feedback exposed the thread’s memory burden: users had to hold one option in mind while reading the next, repeat questions about ESG and scroll back to find actions. The workspace gave the comparison a stable home and made approve, counter and escalate easier to find.

Schematic reconstruction of three workspace iterations: charts first, reasoning first, then all options above analysis with evidence and actions close at hand.

Iteration 02 / Why we chose this direction

DESIGN RESPONSE / EVIDENCE, AUTHORITY AND ACTION

The early workspace still put charts before the reasoning and clipped the third option. A revised version improved explanation but left the evidence cramped. The chosen direction kept all three negotiation paths visible above the analysis, with consistent terms, consequences and risk against the authority limit. Customer needs drove the detail: a stable deal inbox supported interruptions; option-specific evidence made recommendations defensible; and a fixed evidence set with annotations avoided hiding findings that challenged the preferred option. The rationale and final action stayed on the deal record.

Designing the Interface

The interface combines comparable terms, visible uncertainty and supporting evidence. Sarah can approve, counter or escalate, with her rationale retained on the deal record.

UI DESIGN

Comparing negotiation paths

Side-by-side options help users assess alternatives instead of over-trusting the AI’s first answer.

Identical cards and field order give each path equal weight. Risk appears last to support the final comparison.

UI DESIGN

AI Suggestion and analysis

Ranges on a common scale expose uncertainty and show whether one option clearly outperforms another.

The chart shows the trade-off; the explanation states why the AI recommends a path.

UI DESIGN

Compare your deals

Users need evidence to verify an AI recommendation.

An always-visible comparable-deals panel keeps evidence beside the conclusion and reduces context switching.

Behavioural analysis: evidence at the decision

Heatmaps show interaction around negotiation choices, supporting evidence and final actions. They reinforce the need to keep terms, rationale and consequences together. Heatmaps show where users interact; feedback helps explain why.

MEASURE

System Usability Score

The System Usability Scale (SUS) is a quick and reliable tool for measuring the usability of a system or product through a 10-item questionnaire that provides a single score reflecting users' overall satisfaction and ease of use.

MEASURE

SUS Distribution

Reviewing the decision

DECISION REVIEW HEATMAP

The review dialog has dense click clusters around the option selectors and bottom confirmation controls, with lighter activity across the terms. The concentration is strongest where users choose and confirm a negotiation path.

Inspecting the AI’s reasoning

RECOMMENDATION HEATMAP

Clicks are spread across the recommendation text, but concentrate most heavily on the bottom action controls. The explanation receives interaction alongside the controls for responding to it.

Comparing negotiation paths

WORKSPACE HEATMAP

In the main workspace, clicks cluster on the deal list, negotiation-path selectors and final action buttons. The strongest hotspots mark deal selection and decision-making, with lighter activity across the analysis.

Checking comparable deals

EVIDENCE PANEL HEATMAP

The open comparable-deals panel shows click clusters across its benchmark cards and details. Strong hotspots remain on the final action buttons, showing interaction with both the supporting evidence and decision controls.

Across the four heatmaps, click concentration shifts from selecting a deal and negotiation path to reviewing recommendations and comparable evidence. Final action controls attract the strongest clusters. These patterns show where interaction happens; they do not establish whether users understood the content.

“Easy to manoeuvre and clear overviews”

"Looks great."

Go-to-market: trust before scale

Position the boundary clearly, validate a controlled pilot and support the first live negotiation.

01 / POSITION

A pause is control

Reframe escalation as AI Control Mode: an agreed authority boundary has been reached. Sell evidence-led negotiation with human control, rather than an AI that claims to decide everything.

02 / VALIDATE

Pilot before expansion

Start with roughly 10% of live negotiations and compare against the existing process. Agree gates for closing speed, overrides, usability and review workload before expanding availability.

03 / ENABLE

Make the first deal work

Proposed enablement: guide the first live deal, confirm authority limits and share its record with Legal and Finance. Review activation, repeat use, overrides and escalations weekly; pause expansion if quality suffers.

Outcomes, learning and next steps

The results were encouraging. The next test is whether faster decisions hold up over time.

01 / REPORTED RESULTS

Speed and confidence

31% faster offer closing. 82% recommendation acceptance. SUS 71. These signals support usability and speed; acceptance alone does not prove a better commercial outcome.

02 / DESIGN LEARNING

Test the decision model first

A paper comparison could have exposed the conversation’s memory burden sooner. Test whether people can compare, inspect evidence and act within their mandate before investing in visual polish.

03 / NEXT EVALUATION

Follow decision quality

Track repeat use, overrides, disputes, review workload and realised commercial outcomes. Feed the learning into Contract Memory and explore a portfolio view without hiding individual authority limits.

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