Retain Your Best People

What You Can Predict

How to Predict

1. Create Employee Mind

Upload past interactions with the employee:

> "Create a mind for Marcus Johnson, Senior Engineer,
using /Documents/employee-interactions/marcus-johnson-1on1s.vtt"

Training: 5-15 minutes

2. Ask Any Question

Assess flight risk:

> "SCENARIO: You've been in your current role for 3 years at the company. You've delivered consistently but haven't been promoted. Workload has increased with recent team departures. Recruiters are messaging you on LinkedIn with interesting opportunities.
QUESTION: How satisfied are you in your current role? Are you considering looking for other opportunities? What would make you stay vs. leave?"

Test feedback approach:

> "SCENARIO: Your manager is scheduling a 1:1 to give you performance feedback. They plan to say: 'You've been missing sprint deadlines consistently and it's impacting the team. We need to see improvement.'
QUESTION: How will you respond to this feedback? How will you feel? What will you do after this conversation?"

Predict reaction to change:

> "SCENARIO: Your company is reorganizing. You're being moved from Engineering Team A (where you've been for 2 years under your current manager) to the new Platform Team under a different manager you haven't worked with. This is being announced next week in an all-hands.
QUESTION: How will you feel about this change? What concerns will you have? How will this impact your decision to stay vs. leave?"

3. Act Proactively

Get predictions. Address concerns before they escalate.

You’ll know:

• How to retain your best people
• How to deliver feedback effectively
• How to navigate changes successfully

Real Examples

> "SCENARIO: You've been a Senior Engineer at the company for 3 years. You've delivered two major projects successfully but haven't been promoted to Staff. Your manager keeps saying 'next cycle' for promotion discussions. Workload has increased 40% after team departures. Recruiters are messaging you weekly with Staff Engineer roles at $40K+ more compensation.
QUESTION: How satisfied are you in your current role? Are you considering looking elsewhere? What would make you stay vs. leave?"

SATISFACTION LEVEL: LOW (high flight risk)
Hidden concerns I have (that I haven't voiced to you):
1. Career Stagnation
   What's happening: Same role for 3 years, no promotion path
   Why I haven't said anything: Don't want to seem pushy
   Impact: Feeling undervalued and stuck
   Risk level: HIGH - actively updating LinkedIn
2. Work-Life Balance Erosion
   What's happening: Expected to work late frequently
   Why I haven't said anything: Team is understaffed
   Impact: Burnout building, family time suffering
   Risk level: HIGH - recruiters reaching out
3. Lack of Recognition
   What's happening: Led 2 major projects, minimal acknowledgment
   Why I haven't said anything: Should be obvious to leadership
   Impact: Feel invisible and unappreciated
   Risk level: MEDIUM - motivation declining
What would make me leave:
- Another company offers senior title
- Recruiter presents better work-life balance
- One more project without recognition
What would make me stay:
- Clear promotion timeline discussion
- Acknowledgment of contributions
- Commitment to work-life boundaries
- Genuine investment in my growth

Common Scenarios

Retention Risk Assessment: Predict current satisfaction and engagement level, unvoiced frustrations building up, what would trigger them to start looking, and what would make them stay long-term. Assess quarterly for high performers and key team members.

Performance Improvement Plans: Predict how they’ll receive performance feedback, what framing will be most effective, underlying issues affecting performance, and which support would help them improve. Test feedback approaches before difficult conversations.

Promotion Discussions: Predict their expectations for promotion timing, how they’ll respond to “not yet”, what development areas they’re aware of, and what timeline would retain them. Navigate promotion conversations transparently and effectively.

Organizational Changes: Predict individual reactions to team restructuring, concerns about new roles or managers, career impact worries, and which employees are at highest flight risk. Test change communication before announcing.

Implementation

> Create an employee mind for Sarah Chen, Product Manager,
using /Documents/employee-1on1s/sarah-chen-2024.vtt

✓ Training employee mind... (~10 min)

> "SCENARIO: Sarah has been a Product Manager for 2.5 years. She's delivered several successful features but hasn't been promoted. She's been given more responsibility recently after a peer left, but her title and compensation haven't changed. Recruiters are reaching out frequently with Senior PM roles.
QUESTION: How satisfied is Sarah in her current role? Is she considering looking elsewhere? What would make her stay vs. leave?"

SATISFACTION LEVEL: MEDIUM (watch closely)
FLIGHT RISK: MODERATE
Current state:
- Frustrated with lack of decision-making authority
- Seeing peers get promoted while she waits
- Open to recruiter conversations
- Will start looking if promotion pushed to next year
What would keep her:
- More project ownership and autonomy
- Clear promotion timeline discussion
- Involvement in strategic decisions

> "SCENARIO: I want to give Sarah ownership of the new product strategy project.
QUESTION: How will she respond?"

POSITIVE. This will significantly improve retention.
"I really appreciate the opportunity. This is exactly the kind of strategic work I've been hoping to do."
Flight risk drops from MODERATE to LOW. Buys you 6-12 months to execute on promotion.

Next Steps