Kristin's 1-on-1 Communication Guidance
Context
After receiving the high-level transition plan from Quan, Kristin will hold 1-on-1 conversations with Paula and Carmee to discuss the upcoming team restructure.
Key principles:
- Supportive, not directive — Listen first, explain second
- Address concerns proactively — Acknowledge uncertainty and provide clarity
- Frame as opportunity — Not "taking away" but "evolving toward strengths"
- Establish ongoing support — This is the first conversation, not the only one
1-on-1 with Paula
Goals
- Discuss maternity leave timeline and policy
- Clarify design handoff to Carmee
- Explore return-to-work options (part-time social media?)
- Ensure she feels supported and valued
Conversation Flow
Opening (5 min)
"Hey Paula — thanks for making time. I wanted to talk through the upcoming transition with your maternity leave and make sure you feel supported through it. How are you feeling about everything right now?"
Listen first. Let her share concerns, excitement, uncertainty.
Maternity Leave Policy (10 min)
"We've drafted a maternity leave policy that we hope works for you. Here's what we're offering:"
Key points to cover:
- Leave duration: [X weeks] paid leave (aligned with CA law + company support)
- Benefits continuation: Health insurance, etc. remain active
- Job protection: Guaranteed return to equivalent role
- Flexibility: Part-time or full-time return options
Ask:
"Does this feel supportive? Is there anything we should adjust to make this work better for you?"
Design Handoff (10 min)
"While you're on leave, Carmee will be taking over design responsibilities. We want to make sure your work is in good hands and that the transition is smooth."
Key points:
- Carmee is being onboarded with daily structure + Jedi Council support
- We'll schedule handoff sessions with you before you leave
- You're not being "replaced" — we're ensuring continuity
- When you return, we can discuss what role makes sense (design? social media? both?)
Ask:
"What would make you feel confident about this handoff? What does Carmee need to know from you?"
Return-to-Work Options (10 min)
"We know you might want flexibility when you return. We're open to part-time, async work — especially for social media, which you've been great at."
Options to discuss:
- Full-time return (design + social media)
- Part-time return (social media only, flexible hours)
- Consultant/contractor basis (async, project-based)
- Take time to decide (no pressure now)
Ask:
"What sounds most appealing to you? We don't need to decide today, but I want you to know the options."
Closing (5 min)
"We really value what you bring to the team, and we want this transition to work for you. Let's stay in close touch as things get closer."
Action items:
- Schedule handoff sessions with Carmee (before leave)
- Finalize maternity leave policy (any adjustments?)
- Check in again in [2 weeks / 1 month] as leave approaches
Emotional tone:
- Supportive, warm, appreciative
- Acknowledge uncertainty ("This is a big transition")
- Emphasize flexibility ("We'll figure this out together")
1-on-1 with Carmee
Goals
- Explain the new design responsibilities
- Address concerns about workload and capacity
- Introduce support structure (Jedi Council, daily onboarding, pathway automation)
- Frame as opportunity for growth
Conversation Flow
Opening (5 min)
"Hey Carmee — I wanted to talk through an exciting opportunity that's coming up. With Paula's maternity leave, we're thinking about your role evolving to include design work. How does that sound to you?"
Listen for:
- Excitement vs. anxiety
- Confidence vs. overwhelm
- Current workload concerns
The Opportunity (10 min)
"We've seen your work on pathways, sales support, and customer communication — you're really strong at understanding what people need and translating it into action. We think those skills translate well to design."
Key points:
- Paula will train you before she leaves
- This is additive, not a complete role change
- You'll have structured daily onboarding (small wins, not overwhelming)
- Jedi Council (Quan, Charlie, Steve, me) will support you twice a week
Frame positively:
"This is a chance to grow your skills and take on more creative work. We wouldn't ask if we didn't think you could do this."
Ask:
"What excites you about this? What worries you?"
Addressing Workload Concerns (15 min)
"I know you're already handling a lot with pathway coordination. Here's the plan to make sure you're not overloaded:"
Key mitigation:
- Pathway automation (Minnie will automate classification, eligibility, quotes)
- Expected time savings: 10-18 hrs/week
- This frees you up for design work
- Structured onboarding (daily 30-60 min tasks, not overwhelming)
- Gradual ramp (small projects first, then bigger ones)
- Support system (Jedi Council, Charlie for design feedback, Paula for handoff)
Ask:
"Does this feel manageable? What would make you feel more confident about taking this on?"
Support Structure (10 min)
"You won't be doing this alone. Here's the support system:"
Jedi Council meetings:
- When: Tuesdays and Thursdays, 1 hour
- Who: Quan, Charlie, Steve, me
- Purpose: Check in on progress, answer questions, remove blockers, celebrate wins
Daily onboarding plan:
- Small, achievable tasks each day (30-60 min)
- Clear success criteria
- Build momentum and confidence
- You'll always know who to ask for help
Pathway automation:
- Minnie (AI assistant) will handle routine tasks
- You focus on judgment calls and design learning
- Expected to free 10-18 hrs/week
Ask:
"Does this support structure feel solid? What else would help?"
Setting Expectations (5 min)
"We don't expect perfection on day one. This is a learning process, and we'll adjust as we go."
Key points:
- Mistakes are okay (that's how you learn)
- Feedback loops are frequent (Charlie reviews, Jedi Council checks in)
- We'll track progress and adjust if it's too much
- You can always flag concerns early
Ask:
"What would success look like for you in the first 30 days?"
Closing (5 min)
"I'm excited for you, and I think this is going to be great. Let's start with the daily onboarding plan and check in twice a week. Sound good?"
Action items:
- Review daily onboarding document (once it's ready)
- Schedule first Jedi Council meeting (Tuesday)
- Schedule handoff sessions with Paula (before her leave)
- Start pathway automation rollout (Minnie takes over routine tasks)
Emotional tone:
- Encouraging, confident in her abilities
- Acknowledge nervousness is normal ("It's okay to feel overwhelmed at first")
- Emphasize support ("You're not alone in this")
- Frame as growth opportunity ("This is a big step for your career")
After Both 1-on-1s
Kristin's Follow-Up Actions
Share feedback with Quan:
- How did Paula react? Any concerns?
- How did Carmee react? Confidence level?
- Any adjustments needed to the plans?
Schedule handoff sessions:
- Paula → Carmee design training (before maternity leave)
- Calendar these now (don't wait)
Coordinate with Jedi Council:
- Share Carmee's concerns/questions
- Prep for first Tue/Thu meeting
- Ensure everyone knows their role in supporting her
Check in regularly:
- Paula: Every 2 weeks as leave approaches
- Carmee: Weekly (in addition to Tue/Thu Council meetings)
Red Flags to Watch For
Paula:
- Feeling undervalued or "replaced"
- Unclear on return-to-work options
- Stressing about design handoff quality
Carmee:
- Overwhelmed before even starting
- Not confident in her ability to do design
- Current workload not actually decreasing (pathway automation not working)
If red flags appear: Loop in Quan immediately, adjust plans before problems escalate.
Key Messaging to Emphasize
For Paula:
- "You're valued, and we want this to work for you."
- "This is about continuity, not replacement."
- "We're flexible about what your return looks like."
For Carmee:
- "We believe in your ability to do this."
- "You have a strong support system."
- "We'll adjust if it's too much — speak up early."
For Both:
- "This is a team effort, and we're all adapting together."
- "Communication is key — let us know what's working and what's not."
- "We're committed to making this transition smooth for everyone."
Timeline Summary
This Week:
- Kristin receives transition plan from Quan
- Kristin holds 1-on-1s with Paula and Carmee
- Jedi Council schedules first meeting with Carmee (Tuesday)
Next 2 Weeks:
- Paula begins handoff sessions with Carmee
- Carmee starts daily onboarding plan
- Pathway automation rolls out (Minnie takes over routine tasks)
Week 3-4:
- Carmee takes on first small design projects
- Paula finalizes handoff materials
- Team evaluates: Is Carmee's workload manageable?
Month 2+:
- Paula goes on maternity leave
- Carmee fully owns design responsibilities
- Jedi Council continues Tue/Thu support until Carmee feels confident
Questions Kristin Should Be Ready to Answer
From Paula:
- "How long is my maternity leave?" → [X weeks, paid, with flexibility]
- "Will I have a job when I come back?" → Yes, guaranteed
- "What if I want to work part-time?" → That's an option we can explore
- "Who will do my work while I'm gone?" → Carmee, with training and support
From Carmee:
- "Do I have to do this?" → It's a growth opportunity, but we'll adjust if needed
- "What if I'm not good at design?" → You'll have training, feedback, and support
- "Will my pathway work decrease?" → Yes, automation will free 10-18 hrs/week
- "What if I'm overwhelmed?" → Speak up early, we'll adjust the plan
Success Criteria
1-on-1s were successful if:
- ✅ Paula feels supported and clear on the plan
- ✅ Carmee feels excited (or at least willing) and supported
- ✅ Both understand the timeline and next steps
- ✅ Concerns are surfaced (not hidden) and addressed
- ✅ Kristin has clear action items to follow up on
1-on-1s need follow-up if:
- ❌ Paula feels anxious or undervalued
- ❌ Carmee feels overwhelmed or not confident
- ❌ Unclear on timeline, support, or expectations
- ❌ Red flags appeared and weren't resolved
Kristin's Mindset Going In
You're not delivering bad news. You're facilitating a transition that benefits everyone:
- Paula gets maternity leave + flexible return options
- Carmee gets growth opportunity + structured support
- Charlie gets freed from admin to focus on brand strategy
- Team gets stronger through role alignment
Your role: Be the bridge. Listen, clarify, support, adjust as needed.
Remember: This is the first conversation, not the only one. You'll check in regularly, and plans can adjust based on feedback.
You've got this. 💪