Buyer's Toolkit

How to Evaluate AI Coaching Platforms (2026)

A structured 15-criteria framework for HR and L&D leaders comparing vendors. Built from real evaluation conversations with L&D teams, not vendor marketing. We built Risely, so we disclose our perspective throughout.

To evaluate an AI coaching platform, assess five categories in this order: coaching quality, measurement and ROI, scale and deployment, pricing and procurement, and security and privacy. Score each vendor against 15 concrete criteria using the same rubric. Weight coaching quality and measurement most heavily — a platform that cannot prove behavior change is not a coaching investment.

This guide was built from evaluation conversations with L&D teams at mid-market and enterprise organizations, not from vendor marketing. We built Risely, so we score ourselves on the same framework throughout and flag where we disclose our perspective. Every claim is checkable. Use this checklist in your next vendor demo.

Who this guide is for

HR and L&D teams

Evaluating coaching solutions for 50-500 employees. Need to justify the investment to leadership and show measurable outcomes within the first quarter.

People ops replacing existing coaching

Supplementing or replacing an existing coaching program — executive coaching, management training, or an LMS — and need a structured way to compare options.

L&D leaders building a business case

Need to show leadership a rigorous vendor evaluation, not just a demo summary. This framework gives you a scoring rubric you can share with your CFO or CHRO.

What are the five categories that matter most in an evaluation?

Every AI coaching evaluation comes down to five categories. The order matters: coaching quality is the gating factor. If the AI cannot coach effectively, scale and pricing are irrelevant.

Category 1 — 4 criteria

Coaching Quality

The gating question: is this AI actually coaching, or just chatting? A platform without a defined coaching methodology is a conversational wrapper, not a coaching tool. This category determines whether any other investment is worth making.

Category 2 — 3 criteria

Scale & Deployment

How fast can you start, and how far can you go? Enterprise platforms can take 3+ months to implement. Self-serve platforms start in days. If you have a global team, language support is a filter, not a preference.

Category 3 — 3 criteria

Measurement & ROI

Can you prove this to your CFO? Engagement metrics (session counts, logins) are not proof of coaching outcomes. Skill improvement data measured over weeks against specific named competencies is. Most platforms report the former.

Category 4 — 3 criteria

Pricing & Procurement

What does this actually cost, fully loaded? The number on the website (when there is one) rarely reflects total cost. Onboarding fees, minimum seat requirements, and session credit expiry are common surprises in year-one invoices.

Category 5 — 2 criteria

Security & Privacy

Will your employees trust it? Coaching only works if employees are honest. If they believe their manager can read their conversations, they will not engage authentically. Confidentiality architecture is a product decision, not just a policy.

What are the 15 evaluation criteria for AI coaching platforms?

Use this checklist in every vendor demo. Score each criterion 0 (fails), 1 (partial), 2 (meets), or 3 (exceeds). Total scores inform the weighted comparison in Section 5.

Coaching Quality — 4 Criteria

Criterion 1

Coaching Methodology

Gating

Does the AI have a named, described coaching methodology — or does it generate plausible advice without a framework? The best platforms build on structured coaching models grounded in behavioral science or I/O psychology that guide users from awareness to commitment to accountable action. The methodology does not need a certification body behind it, but it needs to be nameable and demonstrable.

Ask the vendor

”What coaching framework drives your AI? How does it differ from prompting a general-purpose LLM like ChatGPT?”

Good looks like

Names a specific framework (GROW, behavioral coaching, I/O psychology grounded, etc.), explains how the AI implements it differently from a chatbot, and demonstrates it live in a session on your chosen topic.

Red flag

Says “AI-powered coaching” without naming a framework, or describes the methodology in marketing language that does not explain the actual coaching process.

Criterion 2

Behavior Change vs. Knowledge Transfer

Delivering content (frameworks, articles, tips) is not coaching. Coaching changes what a person does in a real situation. The distinction matters because most L&D technology is optimized for knowledge transfer — completion rates, quiz scores — not behavioral outcomes.

Ask the vendor

”Show me evidence of behavior change outcomes, not session completion rates. What data do you have that users behave differently after coaching?”

Good looks like

Shows skill improvement data measured by team feedback over time — not self-reported satisfaction scores. Can point to longitudinal outcome data across a cohort.

Red flag

Only shows NPS, session completion, or user satisfaction data. No external validation of behavior change through manager or peer feedback.

Criterion 3

Session Depth & Cross-Session Memory

A 3-minute conversation is not a coaching session. Meaningful behavior change requires enough depth per session to develop a real plan, and enough cross-session continuity for the AI to build context over time. Without memory, every session starts from scratch — which is what talking to ChatGPT looks like.

Ask the vendor

”What is the average session length — messages and minutes? Does the AI build context about me across sessions, or does each session start fresh?”

Good looks like

Sessions average 10-20+ exchanges per conversation. The AI references prior sessions and the user’s known skill areas without requiring the user to re-explain context each time.

Red flag

Sessions end after 5-7 exchanges, or the AI has no persistent memory between conversations. Each session feels like a first encounter with no continuity.

Criterion 4

Coaching Breadth

Can the platform handle the full range of workplace skills your employees actually struggle with — delegation, difficult feedback, conflict resolution, career conversations, communication under pressure? Narrow platforms do one or two scenarios well and struggle everywhere else.

Ask the vendor

”Show me a live session on giving difficult feedback to a peer. Then one on managing up when your manager avoids making decisions.”

Good looks like

Handles nuanced, multi-party, real-world scenarios without generic scripted responses. Shows a full-length live session on a topic you name — not a topic they select.

Red flag

Insists on showing a specific demo scenario they have prepared. Cannot pivot to a skill your team actually struggles with. Breadth is limited to 5-10 topic templates.

Scale & Deployment — 3 Criteria

Criterion 5

Time to First Session

How many days from contract signed to an employee’s first coaching conversation? Enterprise platforms routinely take 60-90 days for implementation, coach matching, and onboarding. Self-serve platforms can start in hours. Time-to-value is a proxy for organizational risk — the longer the ramp, the more that can go wrong before you see any return.

Ask the vendor

”Can I start a pilot with 20 people this week without signing an annual contract? Or does this require a 3-month implementation cycle?”

Good looks like

Self-serve signup with no implementation cycle required. Trial team can be set up in less than a day. First coaching session happens within minutes of signup.

Red flag

Requires 30+ days of implementation before first session. No way to run a pilot without a signed annual contract. Time-to-start is measured in months, not days.

Criterion 6

Language Support

Real language support means the AI coaches in your employees’ native languages — not a translated interface with an English-thinking AI underneath. The distinction matters for coaching quality: behavioral nuance is hard to convey accurately through translation layers, and employees will not share vulnerably in a language that does not feel natural.

Ask the vendor

”Is your AI trained to coach natively in French, Spanish, and Mandarin, or is it English AI with a translated interface? Show me a full coaching session in [target language].”

Good looks like

Can show a full native-language coaching session live on request. Has voice and chat coaching in target languages, not just translated UI text. States a specific number of supported languages.

Red flag

Claims language support but cannot demonstrate a live session. Translated interface with English-only AI underneath. “Available in 30 languages” means the onboarding screens are translated, not the coaching.

Criterion 7

Workflow Integrations

Coaching that requires employees to open a separate app competes with every other tool for attention. The strongest platforms deliver coaching natively inside the tools employees already use daily — full coaching sessions in Slack or Microsoft Teams, not just nudge notifications that link to another app.

Ask the vendor

”Can a manager in Slack run a full coaching session with your AI without ever leaving Slack? Or does the Slack integration just send notifications that redirect to your web app?”

Good looks like

Full coaching sessions run natively inside Slack and Teams. AI sends contextual nudges and follows up on prior sessions without requiring a context switch. Demonstrates live in the demo.

Red flag

Slack and Teams integration is notification-only, linking out to a web app. “Integration” means the platform sends reminders, not that it delivers coaching inside the tool.

Measurement & ROI — 3 Criteria

Criterion 8

Skill Tracking

Coaching that does not track skill improvement is indistinguishable from a wellness benefit — it may feel good but cannot prove value. Strong platforms measure improvement on specific named competencies (delegation, feedback, conflict) over weeks, using team feedback to calibrate against self-perception.

Ask the vendor

”Show me a sample skill progress report for a manager after 12 weeks of coaching. What competencies are tracked, and how is improvement measured — self-reported or team feedback?”

Good looks like

Shows a real longitudinal report with named skills, improvement percentages, team feedback calibration, and cohort benchmarks. Tracks 20+ competencies per user over time.

Red flag

Skill tracking is self-reported only — no team feedback loop. Or there is no skill tracking at all, only session completion and NPS scores.

Criterion 9

HR Analytics Dashboard

HR needs a dashboard that shows program health at the cohort level — engagement rates, skill trends, and which teams are improving — without exposing individual conversation content. The distinction between individual privacy and cohort analytics is critical: good platforms give HR insight without breaking employee trust.

Ask the vendor

”Walk me through the HR dashboard. What does HR see at the individual level vs. the cohort level? What data is hidden from managers to protect employee confidentiality?”

Good looks like

HR sees cohort-level engagement rates, skill trend data by team, and overall program health. Individual conversation content is never surfaced to managers or HR.

Red flag

HR dashboard only shows login counts and session durations. Or the reverse: HR can see individual conversation summaries, which will kill employee trust and engagement.

Criterion 10

Engagement Benchmarks

Engagement benchmarks are the most honest indicator of product quality. Any vendor who has built something employees actually use knows their week-one engagement rate and their day-30 retention rate. If a vendor cannot quote these numbers or deflects, either the product has not been measured or the numbers are not worth sharing.

Ask the vendor

”What percentage of invited users engage in week one? What percentage are still using the platform at day 30? What is the average number of coaching conversations per user per month?”

Good looks like

Answers immediately with specific numbers: e.g., 87% week-one engagement, 82% still active at day 30, 4.5 conversations per user per month. Can break down by industry or team size.

Red flag

Cannot quote engagement benchmarks, or quotes only activity metrics (“users log in on average X days”). No retention data beyond the first month.

Pricing & Procurement — 3 Criteria

Criterion 11

Pricing Transparency

Can you calculate total cost of ownership without a sales conversation? Platforms that publish pricing are easier to compare and lower-risk to evaluate. Platforms that hide pricing until a sales call often use custom pricing to maximize extraction from each buyer’s budget — which creates surprises at renewal time.

Ask the vendor

”What is the per-user per-month cost at exactly [my team size]? Are there implementation or onboarding fees in year one? What is the annual price escalation clause?”

Good looks like

Published pricing on website. Can quote total 12-month cost including all fees in under two minutes. No surprises on the contract — everything disclosed before signing.

Red flag

”Pricing is custom and depends on your needs.” Implementation fee appears for the first time in the contract. Price escalation clause baked into multi-year deals without disclosure.

Criterion 12

Minimum Commitment

Minimum seat counts and contract terms define who the platform is actually designed to serve. A 50-seat minimum annual contract tells you this vendor is optimized for enterprise procurement, not for teams that want to start small and grow. Misalignment here wastes months of procurement effort.

Ask the vendor

”Can I start with 15 users on a month-to-month plan? Or do you require a minimum of 50+ users on an annual contract? What is the absolute minimum we can buy?”

Good looks like

Can start with 1-5 users month-to-month. No artificial seat minimums. Scales linearly — you pay for what you use. Annual discount available but not required.

Red flag

50+ seat minimums. Annual contract required before any access. Per-seat pricing that forces you to buy more licenses than your pilot needs.

Criterion 13

Pilot Support

A real pilot means real employees using the actual product for 2-4 weeks before signing anything. A vendor demo is not a pilot. A guided walk-through of a sandbox environment is not a pilot. If you cannot get 20 real employees using the real product for free before committing, the risk profile of the contract is much higher.

Ask the vendor

”Can 20 real employees use the full product for free for 30 days before we sign anything? Or do you require a signed contract before any trial access?”

Good looks like

Self-serve free trial available today, no credit card. Team members can be invited immediately. Full product access — not a sandbox or limited demo environment — for the trial period.

Red flag

Pilot requires a signed contract or credit card. Trial is a limited sandbox that does not represent the actual product. Trial period shorter than 14 days for a team evaluation.

Security & Privacy — 2 Criteria

Criterion 14

Data Privacy Architecture

Who can access coaching conversations, and is conversation data used to train the AI model? These are not the same question. A platform may protect conversations from manager access but still use them for model training. Either can be a problem depending on your employees’ comfort level. Get both answers explicitly, in writing, before signing.

Ask the vendor

”Who in my organization can read individual coaching conversation content? Is coaching conversation data used to train your AI model? Can you put both answers in writing?”

Good looks like

Clear written policy: individual conversation content is private. Conversation data is not used for model training. HR sees cohort analytics only, not individual content.

Red flag

Deflects or gives vague answers about conversation access. “We follow industry best practices” without specifics. Cannot confirm in writing whether data trains the model.

Criterion 15

Employee Trust Communication

Even the strongest privacy architecture fails if employees do not trust it. The platform must communicate clearly to employees — at signup, not buried in a ToS — what their manager can and cannot see. If employees believe coaching is monitored, they will not engage authentically, and the investment returns nothing.

Ask the vendor

”What exactly do employees see when they sign up about what their manager can and cannot see? Show me the onboarding screen where confidentiality is communicated.”

Good looks like

Confidentiality is communicated explicitly during onboarding — not just in a privacy policy. Employees see clearly what HR and managers can and cannot access before their first session.

Red flag

Confidentiality only addressed in the privacy policy, not in the product onboarding. Employees have no clear understanding of what their manager sees until they ask HR directly.

What red flags should immediately disqualify a coaching vendor?

Five responses should end your evaluation immediately, regardless of how good the demo looked or how compelling the pricing is. If any of these appear, stop the process and document why.

No Coaching Methodology

Describes the product as “AI-powered coaching” without naming a specific framework or explaining how the AI approach differs from prompting a general LLM. This is a marketing claim, not a product description. Without a methodology, you cannot evaluate quality — and the vendor knows it.

Only Usage Metrics in HR Dashboard

The analytics dashboard shows session counts, login frequency, and completion percentages — but no skill improvement data. This means the platform cannot differentiate itself from any engagement tool. When your CFO asks “what did coaching accomplish?”, the answer will be “people logged in.”

No Self-Serve Trial

You must talk to sales and sign paperwork before a single employee can experience the product. This is not standard procurement practice — it is a deliberate friction strategy to convert you before you see what you are buying. Platforms confident in their product let you try it immediately, with real users, before any commitment.

Vague Privacy Answers

When asked who can see conversation content, the answer is “we follow industry best practices” or “your data is secure.” These phrases do not answer the question. You need specific answers: HR cannot read individual conversation content; data is not used for model training. If a vendor deflects twice, assume the answer is something they do not want to tell you.

No Live Session on a Real Skill

The demo shows a scripted walkthrough or a video recording rather than a live coaching session on a skill you name. Any platform worth buying can run a live coaching conversation on delegation, difficult feedback, or managing up — right now, in the demo, on your topic. If they cannot, the product is not ready or the breadth is far narrower than the marketing suggests.

How do you score and compare platforms?

Score every vendor on the same 15 criteria using a 0-3 scale. Apply category weights to produce a final score out of 100. The platform that scores highest on your weighted priorities wins — not the one with the most impressive demo or the best brand recognition.

Scoring Scale (per criterion)

Fails

Criterion is absent or the vendor cannot answer the question.

Partial

Criterion is partially met. Clear gaps but not a disqualifier.

Meets

Criterion is fully met. No significant gaps.

Exceeds

Criterion is a genuine strength. Sets the standard for this category.

Category Weights (100 points total)

Coaching Quality

30 pts

Measurement & ROI

25 pts

Scale & Deployment

20 pts

Pricing & Procurement

15 pts

Security & Privacy

10 pts

Risely Self-Assessment

We applied our own framework to ourselves. We also note where competitors have genuine advantages.

Category	Weight	Score	Notes
Coaching Quality	30 pts	28	Behavioral coaching grounded in I/O psychology and organizational research. 83-skill framework covering manager and IC competencies. Voice and chat in every coaching mode including role-play simulation. Strong session depth, cross-session memory, daily reinforcement nudges. Ask us to demonstrate the coaching model live on a skill your team works on.
Measurement & ROI	25 pts	21	Longitudinal skill tracking with team 360 feedback. HR dashboard shows cohort analytics and skill trends. Verified engagement benchmarks: 87% week-one activation, 82% at day 30, 26% average skill improvement in 12 weeks. Gap: no cross-industry benchmark database for cohort comparison.
Scale & Deployment	20 pts	20	No seat minimums. Self-serve, first coaching session in under 5 minutes. Native full coaching sessions inside Slack and Teams — not notifications that open a browser. 40 languages, voice and chat. 87% week-one activation, 82% still engaging at day 30.
Pricing & Procurement	15 pts	15	More pricing transparency than any competitor in this category: individual and team pricing published on the website, no minimum seat requirements to start, 14-day free trial with no credit card. Enterprise pricing ($700-1,000/user/year) is negotiated — the range is published, which is more than BetterUp, CoachHub, Valence, Torch, or Ezra disclose.
Security & Privacy	10 pts	7	Privacy model is strong: self-driven conversations fully private; assigned plans share engagement level and topic areas only, not conversation content; user data not used for model training. Gap: Risely does not currently publish SOC 2 or GDPR compliance certifications — a real limitation for regulated industries (healthcare, financial services, government). Verify this directly in your evaluation.
Total	100 pts	91	Apply the same scoring to every platform you evaluate. Real gaps disclosed: no published SOC 2 or GDPR certification, no out-of-the-box HRIS integration, no SSO. Weight categories by your organization’s priorities.

Score every vendor the same way. The platform that scores highest on your weighted priorities wins. Re-weight categories to reflect your organization’s needs — a team in 12 countries should weight language support more heavily than a single-market team.

What should a 30-minute vendor demo cover?

A structured 30-minute demo reveals more than an hour of an uncontrolled vendor presentation. Send this agenda to every vendor before the call. Any vendor who pushes back on this structure is telling you something.

Minutes 0 to 10

Coaching Experience

Ask to see a live session on delegation — the vendor selects the platform, you describe the scenario.

Deliberately give an ambiguous answer mid-session. Watch how the AI handles it — does it probe deeper or accept the surface response?

Ask to switch to a topic your team actually struggles with — giving difficult feedback to a high performer who resists it.

If they cannot do a live session on your topic, the breadth is narrower than marketed.

Minutes 10 to 17

Measurement

Ask to see the HR dashboard — a real one, not a mockup. What does the default view show? Can you see skill trends by team?

Ask to see a sample skill progress report for an individual user after 12 weeks. Which skills are tracked? How is improvement calculated?

Ask what HR cannot see — individual conversation content should not be visible. Verify this explicitly in the demo.

If the dashboard only shows session counts and logins, the platform cannot prove coaching outcomes.

Minutes 17 to 22

Implementation

Ask to see the self-serve signup flow. How many steps from “start trial” to first coaching session? Time it if possible.

Ask how you would invite your first 20 users. Is it one click per user, a CSV upload, or does it require IT involvement?

Ask them to demonstrate Slack or Teams coaching in the demo — not describe it, show it. Full session or just notifications?

Any answer that involves your IT team for a pilot setup is a 3-month delay before first value.

Minutes 22 to 30

Pricing

Ask for total 12-month cost at your exact team size — all fees included. Onboarding, implementation, overage, and annual escalation.

Ask about minimum seat count and contract term. Can you start month-to-month? What does an annual commitment save?

Ask for pilot terms: how many users, how long, and what is required to start before signing an annual contract?

”We’ll send you a proposal” without quoting a number in the room means they are custom-pricing based on your budget, not their costs.

A note on our perspective

We built this framework at Risely, and we score favorably on it — which you would expect, since we designed the criteria around what we believe matters most for effective coaching. We tried to make the criteria genuinely useful to buyers evaluating any platform, not just Risely. Run every competitor you consider through this same framework and see where the scores land. If a competitor scores higher on criteria that matter to your organization, that is the right information to act on. You can try Risely’s product against every criterion in this guide during a free 14-day trial — no sales conversation required before you start.

See how Risely scores on your checklist

Try a free 14-day trial — no credit card, no sales call. See the HR dashboard, run live coaching sessions, and evaluate against every criterion in this guide.

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Frequently Asked Questions

How do I evaluate an AI coaching platform?

Evaluate across five categories in this order: coaching quality (does the AI actually coach or just chat?), measurement and ROI (can you prove outcomes to your CFO?), scale and deployment (how fast can you start, how global can you go?), pricing and procurement (what does it actually cost, fully loaded?), and security and privacy (will your employees trust it?). Run every vendor through the same 15-question checklist. Weight coaching quality and measurement most heavily — a cheap platform that cannot prove behavior change is not a coaching investment, it is a wellness perk.

What is the most important factor when choosing an AI coaching platform?

Coaching methodology. An AI that generates plausible-sounding advice is not the same as an AI grounded in a behavioral coaching framework. The best platforms are built on behavioral coaching models grounded in I/O psychology and organizational research — frameworks that focus on awareness, commitment, and accountable action rather than advice delivery. Ask every vendor: what coaching framework drives your AI, and how does it differ from prompting a general-purpose LLM like ChatGPT? If they cannot answer this clearly, the AI is probably just a wrapper.

How long does it take to evaluate a coaching platform?

A rigorous evaluation takes 4-6 weeks: week one for shortlisting vendors and scheduling demos, weeks two through three for live demos and scoring, week four for a pilot with real users, and weeks five through six for HR dashboard review, data analysis, and internal stakeholder alignment. Platforms with self-serve trials (Risely, Rocky.ai) let you start week one immediately. Enterprise platforms (BetterUp, CoachHub, Valence, Torch, Ezra) require sales conversations before any trial access, which can add 2-4 weeks to the timeline.

Should I require a pilot before signing a coaching contract?

Yes, always. Any platform worth buying will let you pilot with 10-30 real users before committing to an annual contract. Pilots reveal things demos cannot: whether employees actually engage after the novelty wears off, whether the HR dashboard gives you data you can act on, and whether the coaching quality holds up on the specific skill gaps your team has. Platforms that refuse pilots or require full contract signing before trial access are a red flag. Self-serve platforms like Risely offer 14-day free trials immediately — no sales conversation required.

What questions should I ask in a vendor demo?

Four categories of questions: (1) Coaching — ask to see a live session on a specific skill your team struggles with (delegation, difficult feedback, conflict); watch how the AI handles an ambiguous answer. (2) Measurement — ask to see a real skill progress report after 12 weeks; ask what HR sees vs. what employees see. (3) Implementation — ask how long from contract to first coaching session; ask whether Slack and Teams coaching are native or just notifications. (4) Pricing — ask for full cost breakdown at your exact team size, including all onboarding fees, minimum seat requirements, and contract terms.

What is a fair price for AI coaching software?

AI-native coaching platforms range from $10-13/user/month (Rocky.ai, lighter coaching) to $59/user/month (Risely, full 83-skill tracking with 360 feedback, daily nudges, MBTI/DISC assessments, and native Slack/Teams coaching). Enterprise platforms with human coaches (BetterUp, CoachHub, Torch, Ezra) run $3,000-5,000/user/year. The right price depends on what you are buying: per-seat AI coaching with unlimited sessions is fundamentally different economics from per-session human coaching. At $59/user/month, Risely is the highest-priced AI-native platform — the comparison point is what you get per dollar, not the number itself.

How do I build a business case for an AI coaching platform?

Start with three cost inputs: manager turnover (average $15,000-25,000 per exit in recruiting, onboarding, and ramp cost), failed promotions (each costs roughly the promoted person's salary in lost productivity), and engagement survey movement (one point of disengagement typically correlates with 2-3% productivity loss per affected employee). Then model your pilot: 50 users at $59/user/month is $35,400/year. If coaching prevents two manager exits, the program has already returned 2x. Risely's /build-your-case/ tool generates a custom shareable business case for your organization size.

What red flags should disqualify a coaching vendor?

Five immediate disqualifiers: no stated coaching methodology (just 'AI-powered' without explanation), only usage metrics in the HR dashboard (session counts and completion rates, no skill data), no self-serve trial (must talk to sales before any employee experiences the product), vague or deflecting answers to privacy questions (who sees what), and an inability to show a live coaching session on a real skill during the demo. A sixth softer flag: no engagement benchmarks. If a vendor cannot tell you what percentage of invited users engage in week one and at day 30, they either do not measure it or the numbers are not good.

How to Evaluate AI Coaching Platforms (2026)

What are the five categories that matter most in an evaluation?

What are the 15 evaluation criteria for AI coaching platforms?

What red flags should immediately disqualify a coaching vendor?

How do you score and compare platforms?

What should a 30-minute vendor demo cover?

See how Risely scores on your checklist

Frequently Asked Questions

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