All work

Case study · AI-native · Contract lifecycle management

Redline Agent

An AI agent that reviews contracts against a company playbook and drafts the redlines, while people stay in control.

Role
UX designer
Product
AI agent for contract lifecycle management (CLM)
Team
Vinay Kumar, Sandesh Kulkarni, engineering
Platform
Web
Scope
Reviewer + admin experiences
A contract open in the editor with the Redline Agent panel listing flagged clauses by risk Redline Agent panel showing a high-risk payment clause with suggested redlines

Client branding is removed from all screens. Names and figures in the sample contract are demo data.

In 30 seconds

Skim the bold lines and visuals; open "More context" for detail.
Problem
Reviewers redlined contracts from memory, so positions were slow and inconsistent. Admins couldn't govern the playbook.
My role
UX designer for the reviewer and admin experiences, with Vinay Kumar, Sandesh Kulkarni and engineering.
What I did
Interviews and a survey, then a consolidated risk view, explainable suggestions and admin playbook controls.
Result
A first pass that's faster, consistent with policy, and always under the reviewer's control.
~40%faster first-pass review
60%+suggestions accepted
<1 hrto set up a playbook
Projected · Illustrative
00FrameOverview

Redline turns a company's playbook into first-pass redlines people can trust.

Redline Agent is an AI agent inside a contract lifecycle management (CLM) platform. It reviews a contract against the organization's playbook, flags risky or non-standard clauses, and drafts recommended redlines, so legal and business users negotiate faster with less manual effort.

More context

For reviewers, it cuts first-pass review time, keeps redlines consistent with company policy and explains every suggestion. For admins, it gives them a way to define and govern the rules Redline follows, with visibility into how it behaves.

Redline at a glance

Reviewers

  • Faster first passEvery flagged clause is ready when the contract opens.
  • Consistent positionsRedlines follow company policy, not memory.
  • Clear reasoningEach change shows the rule and risk behind it.
  • Final sayAccept, edit or reject every suggestion.
The agent

Redline Agent

One shared playbook drives every review.

  1. 1Admin defines the playbook
  2. 2Agent reviews the contract
  3. 3Agent drafts redlines with reasons
  4. 4Reviewer decides

Admins

  • Playbooks from documentsUpload guidelines and AI extracts the rules.
  • Tunable rulesSet match strictness and risk conditions per clause.
  • GuardrailsChoose which playbooks apply automatically.
  • VisibilitySee which rules the agent used and why.
01FrameProblem framing

Reviewers redlined from memory, and admins couldn't keep guidance consistent.

Reviewers read long contracts clause by clause, compared each one to the playbook by memory, and wrote redlines by hand. The same clause could get a different position depending on who reviewed it.

More context

Admins owned the guidance but it lived in documents. They had no reliable way to keep it current or to know whether anyone followed it.

Problem statement

Contract reviewers need a fast, trustworthy first pass that follows company policy, because manual clause-by-clause review is slow, inconsistent and hard for admins to govern.

How might we · 1

Show reviewers every risky clause up front, instead of making them hunt for it?

How might we · 2

Make each suggested change explain itself, so reviewers can trust or reject it quickly?

How might we · 3

Let admins turn existing legal guidelines into rules the agent follows consistently?

02DiscoverResearch plan

We planned to learn from both sides: playbook authors and playbook users.

Three goals guided the plan: understand how reviews happen today, find where trust in AI suggestions breaks, and learn how playbooks are written and maintained.

One-page research planIllustrative
MethodWhoWhat we wanted to learn
Stakeholder interviewsProduct, legal ops leadsBusiness goals, success criteria, constraints
User interviewsContract managers, sales repsCurrent review steps, workarounds, trust triggers
Admin walkthroughsPlaybook adminsHow guidelines are authored, updated and enforced
Customer surveyExisting CLM customersHow widespread the patterns were
Pattern reviewDesign teamHow AI review tools handle suggestions and control
Week 1Plan & recruit
Week 2Interviews
Week 3Survey in field
Week 4Synthesis
03DiscoverStakeholder and user interviews

Trust, not speed, decides whether reviewers accept an AI redline.

We spoke with legal ops, contract managers, sales reps and admins. Everyone wanted speed, but reviewers only kept a suggestion when they could see where it came from and change it easily.

Affinity mapIllustrative synthesis

Show me why

Wants the rule behind every change
Redoes the review if the source is unclear

Don't make me start over

Prefers tweaking a suggestion to rewriting it
Hates "regenerate" losing good parts

Rounds pile up

Loses track of past concessions
Amendments ignore the parent agreement

Playbooks live in files

Guidance sits in long PDFs
Updates don't reach reviewers

Who changed what

Admins can't see if rules were applied
Need an audit trail for approvals

"If I can't see which rule it used, I'll redo the review myself."

Contract manager · Illustrative

"Our playbook is a long PDF nobody opens mid-review."

Legal ops lead · Illustrative

"By round three I've lost track of what we already gave up."

Sales rep · Illustrative
04DiscoverCustomer survey

The survey got better by getting clearer, not just shorter.

The first draft had 38 questions. We cut it to 14, then found it no longer covered admins or later negotiation rounds, so we rebuilt it to 26.

More context

Reviewer feedback exposed leading wording and AI jargon. We rewrote questions to ask about current behavior, one idea at a time, in the customers' own words.

Survey evolution
How we reworded questionsIllustrative examples
Before

How much time would AI-powered redlining save you?

After

How long does a first review of a standard contract take you today?

Leading → neutral
Before

How useful are LLM-generated clause recommendations?

After

When you change a clause, where does the new wording come from?

Jargon → behavior
Before

Is your playbook hard to use and out of date?

After

When did you last open your team's playbook during a review?

Two questions → one
05DiscoverPersonas

One playbook, two owners: the reviewer applies it, the admin governs it.

Their needs pull in different directions. Reviewers want less work per contract. Admins want more control over every contract. The design had to serve both without one burdening the other.

Persona pairIllustrative
R

The Reviewer

Legal or contract manager
Goals
Clear a backlog of contracts without missing a risky clause.
Frustrations
Re-checking the playbook for every clause; re-reading earlier rounds.
Trust needs
Sees the rule and risk behind each suggestion, and can edit before applying.
Success metric
Time to a complete first-pass review
A

The Playbook admin

Legal ops or CLM administrator
Goals
Keep company positions consistent across every team and region.
Frustrations
Guidelines live in documents; no way to see if they're followed.
Trust needs
Reviews every AI-extracted rule before it goes live; controls auto-apply.
Success metric
Time from guidelines document to live playbook
06DiscoverCurrent-state journey map

Pain peaks at checking the playbook, then again in later rounds.

The lowest points weren't in negotiation itself. They came from looking things up: the playbook during first review, and past decisions during later rounds.

Reviewer journey, todayIllustrative
Stage
Receive contract
Review clauses
Check playbook
Write redlines
Negotiate
Later rounds
Doing
Opens a counterparty draft
Reads every clause in order
Searches a PDF for positions
Types changes and comments
Discusses with the other side
Compares versions by hand
Feeling
Pain points
Unclear priority
Long and repetitive
Lowest pointPositions are hard to find
Inconsistent wording
Can't explain why a change matters
Second lowPast concessions are lost
07DiscoverCompetitive and pattern review

Many tools suggest edits; few explain them or handle later rounds.

We compared categories of tools rather than single products. The gaps clustered around explanation, editing before applying, and continuity across negotiation rounds.

Pattern matrixIllustrative
CapabilityGeneral AI writing assistantsCLM clause librariesAI redline toolsOur opportunity
Grounded in the company playbook
Explains why a change is suggested
All flagged clauses in one view
Edit a suggestion before applying
Amendments and later rounds
Refine by conversation
Admin guardrails and visibility
StrongPartialMissing
08DefineDefine: priorities

We shipped the trust foundations first and left conversation for later.

Each insight became a requirement, then a feature. We plotted them by impact and effort with the PM and engineering, and sequenced releases around the top-left quadrant.

Impact / effortIllustrative placement
Quick winsBig betsFill-insLater Effort →Impact → 1 2 3 4 5 6 7
  1. 1
    Consolidated multi-clause view
    Quick win: one place to triage risk
  2. 2
    Admin playbook controls
    Quick win: makes every suggestion governable
  3. 3
    Draft recommendations
    Core value, medium-high effort
  4. 4
    Subsequent Document Negotiation
    Big bet for repeat rounds
  5. 5
    Parent Agreement Context
    Low effort once rounds were modeled
  6. 6
    Historical Precedents
    Builds trust with past decisions
  7. 7
    Conversational Redline
    High effort; planned after the core
09DefineFlows and information architecture

Admins and reviewers never meet, except through the playbook.

Admin work lives in settings; reviewer work lives in the document. The playbook is the only shared object, so its structure (contract type, intent, rules, risk conditions) became the backbone of both experiences.

End-to-end flow
Admin path · Settings
  1. Open Solutions setupChoose Redline Agent
  2. Upload guidelinesPDF, DOCX or TXT
  3. AI extracts rulesClauses detected
  4. Review and refineStrictness, risk levels
  5. Publish playbookSet auto-apply
Shared playbookContract type · intent · rules · risk conditions
Reviewer path · Document
  1. Open the contractIn the editor
  2. Run Redline AgentFrom the AI assistant
  3. Triage flagged clausesRanked by risk
  4. Accept, edit or rejectWith reasons shown
  5. Later roundsRe-run with context
10DesignExploration and wireframes

We moved from one clause at a time to every flagged clause up front.

The first concept walked reviewers through clauses in sequence. It felt guided, but reviewers couldn't see the overall risk of a contract until the end, and couldn't choose where to start.

Option A vs Option BRecreated wireframes

A · Sequential

Not chosen

B · Consolidated

Chosen

Why B

  • Reviewers see the contract's overall risk the moment analysis ends.
  • They triage by risk and start where it matters, not where the document starts.
  • Progress ("0/13 actioned") stays visible across sessions.
  • The sequential view survives inside each clause, as Previous / Next.
11DesignFinal design · Reviewer experience

Every flagged clause is ranked, explained and one click from a decision.

Redline lives in the full-document panel next to the contract. Reviewers start it from the AI assistant, keep working while it runs, then get every flagged clause ranked by risk with a drafted redline and the reasoning behind it.

Try the working prototypes

Run the agent on a sample contract as a reviewer, or set up playbooks and rules as an admin.

Password protected. Email me at ramprasadp1304@gmail.com for access. Best on a laptop or desktop screen.
Reviewer flow · real screensOpen prototype →
Contract with the Redline panel listing 13 clause rules with risk-colored status dots 1 2 3 4
  1. Overall risk scoreOne chip summarizes the contract's risk before any reading.
  2. Every flagged clause at onceStatus dots show risk; "0/13 actioned" tracks progress.
  3. Missing clausesThe ? marks playbook clauses the contract doesn't include at all.
  4. Values in contextKey terms like days and dates are highlighted inline in the document.
12DesignFinal design · Amendments and later rounds

Later rounds keep their history in view: parent terms and past precedents.

Amendments now show a Parent Agreement Context block, so reviewers judge a change against what was already signed. Subsequent Review groups clauses by what changed since the last round. Historical Precedents synthesizes how similar clauses were settled before.

Amendment context + precedentsContext and grouping mocks illustrative
Parent agreement context Amendment 2
Payment terms Medium
Parent MSA
Net 30 days, no processing fee
This amendment
Net 60 days, 3% processing fee
Playbook
Net 30–45 days; fees not accepted
Governing law Low
Parent MSA
Unchanged by this amendment
Subsequent review Round 3
Changed since round 23
Payment terms
Notice provisions
Termination
New this round1
Audit rights
Accepted earlier9
Collapsed by default
Historical Precedents card: a redline synthesized from 5 references with highlighted values
13DesignFinal design · Conversational Redline

Reviewers refine a redline by asking, not by rewriting it.

Sometimes a suggestion is nearly right. Instead of editing legal text by hand, reviewers ask the assistant to adjust it ("make this less strict") or explain it ("why this change?"), and see the document update beside the chat.

Conversation + documentIllustrative
I've drafted a redline for Payment terms based on your Enterprise MSA playbook.
Make this less strict.
Done. I kept your 30-day term but replaced the removed fee with late interest, which your playbook allows.Rule used: Payment terms · Moderate match
Why this change?
Your playbook rejects processing fees, and the counterparty's 60-day term is outside the 30–45 day range.
Show the playbook ruleMake it stricterUndo
Ask about this clause…

3. Payment Terms and Conditions

Customer shall pay all undisputed invoices within 60 30 days of invoice receipt. A processing fee of 3% shall be added to all payments to cover administrative costs. Late payments shall incur interest of 1.5% per month from the due date. Payment amounts shall be as specified in the applicable Statement of Work.

Updated from chat2 edits · Accept or reject in the panel
14DesignFinal design · Admin experience

Admins turn a guidelines document into reviewed rules in three steps.

Admins manage Redline from Solutions setup. Playbooks and rules live in separate libraries, and a guided flow lets AI draft a playbook from an uploaded document, with the admin reviewing every rule before it goes live.

Admin console · real screensOpen prototype →
Playbooks library with cards showing contract type, intent, number of rules, auto apply toggle and description 1 2 3 4
  1. AI playbook generationA banner explains the three-step flow and starts it in one click.
  2. Auto-apply guardrailAdmins decide which playbooks run without a reviewer choosing them.
  3. Traceable sourcePlaybooks created from a document link back to it.
  4. Out-of-the-box vs customShipped playbooks are labeled so admins know what they own.
15ValidateValidation

Testing pushed rationale higher and made editing impossible to miss.

Six participants completed three tasks: triage a contract's flagged clauses, apply or adjust a suggested redline, and create a playbook from a guidelines document.

FindingsIllustrative · 6 participants, 3 tasks
FindingSeverityChange made
Reviewers looked for why a clause was flagged before reading the fixHighMoved risk and rule above the suggestion
"Accept all" felt unsafe on high-risk clausesHighHigh-risk clauses need a per-clause decision
Editing a suggestion wasn't discoverableMediumClause library alternates with one-click Apply
Admins didn't understand match percentagesMediumNamed ranges with a recommended default
Reviewers lost their place after minimizing analysisLowResume at the first unactioned clause
BeforeSuggestion text first; risk reason hidden in a tooltip.
AfterRisk chip and clause library first; redline below.
BeforeMatch threshold set as a 0–100 slider.
AfterFlexible, Moderate (recommended) or Strict.
BeforeSpinner with no detail during analysis.
AfterNamed steps, rule count and Minimize.
16DeliverHandoff and design system

Built on PDS, with every state specified before engineering asked.

Everything used existing PDS components and rules: sentence case buttons, Title Case labels, "New" instead of "Add" or "Create", and brand blue #0170ef. Edge cases and states were documented alongside the screens.

Spec sheet

Components used

Side panelTabsRisk chipClause list itemStepperSegmented controlToggleAccordionInline diffBanner

PDS writing rules

New playbookRerun redline#0170EF
Button: New rule
Button: Create Rule
Label: Contract Type
Label: contract type

States

AnalyzingNamed steps, rule count
PartialResults shown as rules finish
Nothing flaggedConfirms the playbook that ran
Missing clause? icon with playbook text to insert
Failed runReason + Rerun redline
Interaction note for engineeringWhen the reviewer selects Minimize during analysis, collapse the panel to a progress chip. On completion, notify, then reopen the panel at the first high-risk unactioned clause. Never move the document scroll position without user action.
17DeliverOutcomes and learnings

Projected: faster first reviews, steadier positions and quicker playbook setup.

These are targets set with the product team, not measured results. They'll be replaced with live data as usage grows.

Expected impactProjected · Illustrative
~40%

Less time on a first-pass review

60%+

Suggestions accepted as-is or with small edits

<1 hr

From guidelines document to live playbook

What I'd do differently
  1. Bring admins in earlierThe playbook shapes everything; admin research should start on day one, not after reviewer flows.
  2. Measure trust from launchTrack edit-before-accept and override rates, not just time saved.
  3. Prototype conversation soonerTesting chat with real clauses early would have sharpened what it should and shouldn't change.