The Executive's 90-Day Guide to ChatGPT Enterprise

Why This Matters Now

Your competitors are already using it. McKinsey estimates generative AI could add $4.4 trillion annually to the global economy. The question isn't whether to adopt—it's how fast you can move.

This guide gives you a practical 90-day roadmap.

Week 1-2: Executive Immersion

Before rolling out to your organization, you need hands-on experience.

Your First Tasks

1. Sign up for ChatGPT Plus ($20/month) to experience the consumer product
2. Use it daily for real work tasks:
   • Draft emails and memos
   • Summarize lengthy reports
   • Brainstorm strategic options
   • Prepare meeting talking points
3. Document what works and what doesn't

Key Insight

You can't lead an AI transformation without personal fluency. Executives who skip this step make poor deployment decisions.

Week 3-4: Enterprise Evaluation

Contact OpenAI Enterprise Sales

ChatGPT Enterprise offers:

• SOC 2 compliance
• Data not used for training
• Admin controls and SSO
• Higher rate limits
• Advanced analytics

Questions to Ask

• What's the pricing model for our employee count?
• How does data handling comply with our industry regulations?
• What admin controls are available?
• Can we customize for our specific use cases?

Internal Stakeholder Alignment

Brief these leaders:

• CTO/CIO: Technical integration requirements
• CISO: Security and compliance review
• Legal: Terms of service and liability
• HR: Training and change management
• CFO: Budget and ROI expectations

Week 5-6: Pilot Design

Select 2-3 Pilot Groups

Choose departments where:

• Tasks involve significant writing/analysis
• Staff are relatively tech-savvy
• Results are measurable
• Leadership is supportive

Good candidates: Marketing, Legal, HR, Strategy

Define Success Metrics

Before launching, establish:

• Time saved per employee per week
• Quality assessments (blind comparisons)
• Employee satisfaction scores
• Specific task completion rates

Create Usage Guidelines

Document clear policies:

• What data can be input (never confidential client info initially)
• Review requirements for AI-generated content
• Disclosure rules (when to reveal AI assistance)
• Escalation paths for concerns

Week 7-10: Pilot Execution

Launch with Training

Don't just give access—provide:

• 2-hour hands-on workshop
• Prompt engineering basics
• Department-specific use cases
• Office hours for questions

Gather Feedback Weekly

Short surveys asking:

• What tasks are you using it for?
• What's working well?
• What's frustrating?
• What do you wish it could do?

Iterate Rapidly

Adjust guidelines and training based on feedback. Common early issues:

• Outputs too generic (need better prompts)
• Compliance concerns (need clearer boundaries)
• Uneven adoption (need peer champions)

Week 11-12: Measure and Decide

Quantify Results

Compare pilot groups to control groups:

• Productivity metrics
• Quality assessments
• Employee satisfaction
• Cost per task

Build the Business Case

Create an executive summary covering:

• Pilot results with specific numbers
• Projected organization-wide impact
• Implementation costs and timeline
• Risk mitigation approach

Make the Go/No-Go Decision

With data in hand, decide:

• Full deployment
• Expanded pilot
• Pause for more evaluation

Beyond 90 Days: Scaling Up

If proceeding to full deployment:

Phase 1 (Months 4-6): Department Rollout

• Prioritize high-impact departments
• Train department champions
• Build prompt libraries for common tasks

Phase 2 (Months 7-9): Organization-Wide

• All employees with appropriate access
• Advanced training for power users
• Integration with existing workflows

Phase 3 (Months 10-12): Optimization

• Custom GPTs for specific functions
• API integrations with internal systems
• Advanced analytics and ROI tracking

Common Pitfalls to Avoid

Moving too slowly: Competitors aren't waiting Moving too fast: Skipping security review creates risk Insufficient training: Untrained users get poor results No clear guidelines: Ambiguity creates compliance issues Ignoring change management: Technology without adoption is waste

The Bottom Line

ChatGPT Enterprise can transform how your organization works—but only with thoughtful deployment. This 90-day roadmap gets you from curiosity to capability with measurable results.

Start your executive immersion this week. Your future self will thank you.