Before Day 1
Complete every item on this list before the new hire’s first day. Nothing should be scrambled on Day 1.
- Send welcome email with start date, first-day logistics, and a personal note from the CEO
- Set up all accounts and tools (see the tools setup checklist in Week 1)
- Ship or prepare hardware
- Assign an onboarding buddy (peer, not manager)
- Share pre-reading: company website, recent blog posts, press coverage, key product pages
- Calendar all Week 1 meetings in advance
Week 1: company onboarding
Goal. The new hire understands who we are, what we sell, how we win, and how we work. Owner: CEO / Founder.
| Day | Time | Session | Owner |
|---|---|---|---|
| Day 1 (Mon) | Morning | Tools setup See tools checklist below. Goal: fully set up by end of Day 1. | IT / Ops |
| Day 1 (Mon) | Midday | Team lunch In-person preferred; virtual is great too. Keep it casual and welcoming. | Team |
| Day 1 (Mon) | Afternoon | CEO / founder welcome Mission, vision, origin story, culture, values. Keep it conversational: this sets the tone for everything. | CEO |
| Day 2 (Tue) | Morning | How we work Meeting cadences, communication norms, decision-making principles, performance expectations, feedback culture, OKRs and company goals. | CEO / CoS / Ops |
| Day 2 (Tue) | Midday | Self-directed learning Revisit anything from Days 1–2. Begin applying: set up workflows, start engaging in Slack, review open projects. | New Hire |
| Day 2 (Tue) | Afternoon | Customer deep dive Review real customer stories, case studies, support tickets, and feedback. Understand the customer’s world: their pain points, goals, and why they chose us. | Head of CX |
| Day 3 (Wed) | Morning | GTM positioning ICP, personas, competitive landscape, messaging pillars, how we position vs. alternatives. Share the deck or one-pager they’ll keep. | CEO / Marketing / Sales |
| Day 3 (Wed) | Midday | Self-directed learning Review GTM materials, visit competitor sites, research the market. | New Hire |
| Day 3 (Wed) | Afternoon | High-level sales overview Pipeline stages, deal cycle, key objections, win/loss themes, and how Sales and Marketing work together. | Head of Sales |
| Day 4 (Thu) | Morning | High-level CX overview How we onboard and retain customers, key touchpoints, common issues, escalation paths, and what a great customer experience looks like. | Head of CX |
| Day 4 (Thu) | Midday | Self-directed learning Review CX materials, explore the product from a customer’s perspective. | New Hire |
| Day 4 (Thu) | Afternoon | Product overview Walk through the product end-to-end. What it does, who it’s for, key use cases, the roadmap, and where it’s headed. New hire should leave with login access and a demo to watch. | CPO / CEO |
| Day 5 (Fri) | All day | Open / flex day Catch up, explore, ask questions. Optional: schedule 1:1s with key team members they haven’t met yet. | New Hire |
| Day 5 (Fri) | End of day | Week 1 check-in 30-min debrief. What landed well? What’s still unclear? What are they most excited about? | Manager |
Tools setup checklist
Customize to your stack.
- Email & calendar (Google Workspace / Microsoft 365)
- Password manager
- Slack / team messaging
- Video conferencing (Zoom, Google Meet)
- Project management (Notion, Asana, Linear, Jira)
- HR & payroll platform
- CRM (HubSpot, Salesforce)
- Product / engineering access (if applicable)
Week 2: department onboarding
Goal. The new hire understands their function, their team, their tools, and what success looks like in their role. Owner: Department Head.
For department heads. You own this week entirely. Use the structure below as a guide and fill in the specifics for your team. Deliver your completed Week 2 plan to the new hire by end of Week 1, Day 5.
| Day | Focus area | Notes | Owner |
|---|---|---|---|
| Day 6 (Mon) | Role deep dive | Review job scope, KPIs, 30/60/90 expectations. Walk through current projects and priorities. | Dept Head |
| Day 7 (Tue) | Department tools & processes | Hands-on training on team-specific tools, templates, workflows, and documentation. | Dept Head |
| Day 8 (Wed) | Meet the extended team | 1:1s with direct teammates and key cross-functional partners. | Dept Head |
| Day 9 (Thu) | Immersion in live work | Observe real work in progress: meetings, customer calls, standups, reviews. | Dept Head |
| Day 10 (Fri) | Check-in + first assignment | Assign a small, low-stakes first task. End-of-week debrief with department head. | Dept Head |
Department head checklist
- Prepare role-specific reading list & resources
- Introduce to all key cross-functional stakeholders
- Share team processes and documentation
- Schedule recurring 1:1 with new hire
- Assign onboarding project or starter task
Week 3: shadowing, doing, reinforcing
Goal. The new hire moves from observing to contributing. Key concepts are reinforced through practice. Owner: Manager + Buddy.
Continue sitting in on key meetings, customer calls, and team rituals. Ask questions after, not during.
Take on real tasks with close guidance. Start contributing to live projects at a scope appropriate for their tenure.
Identify the 2–3 most important concepts from Weeks 1–2. Dedicate time to revisiting and deepening understanding.
Mid-week check-in (15–20 min) and an end-of-week review on their first deliverables. Give direct, specific feedback.
Ask: “What’s one thing you wish you’d learned sooner?” Use the answer to improve this template.
Week 4: independent work with support
Goal. The new hire is operating independently, contributing meaningfully, and building confidence. Owner: New Hire.
Manage tasks and projects independently. Raise blockers proactively; don’t wait for a 1:1.
Lean on your onboarding buddy and teammates. Ask questions freely: Week 4 is still early days.
Recurring 1:1s continue. Manager shifts from active coaching to available-on-demand.
By end of Week 4, the new hire should have completed or be mid-delivery on a meaningful piece of work.
End-of-Week-4 check-in agenda.
- Review Week 4 deliverables and quality
- Revisit 30/60/90 plan: are we on track?
- What went well in onboarding? What would you change?
- What do you need to be successful in Month 2?
CEO note. This is a good moment to reconnect personally. A short message or 15-minute call from the founder at the end of Week 4 is a low-cost way to reinforce the relationship, support retention and culture-building, and signal that leadership is paying attention.
Onboarding success metrics
Track these after each new hire so you can improve the onboarding program over time.
Time to first contribution
Date of first meaningful deliverable.
Week 1 satisfaction
Short survey (1–5) at end of Week 1.
30-day retention & engagement
Manager assessment + new hire self-rating.
Onboarding feedback
Structured debrief at end of Week 4.
Ramp time to full productivity
Define per role; track against baseline.
Customization guidance
For CEOs & founders. This is a living template. Customize each section to reflect your company’s current stage, tools, and culture. Department heads should own Week 2 entirely: give them this template and a deadline before the new hire’s start date.
The CEO will likely own more of Weeks 1 and 2. That’s okay: lean into it. Direct attention from leadership is something larger companies can’t easily match.
Replace in-person touchpoints with high-quality video calls. Over-communicate and over-schedule in Week 1.
After every new hire, debrief with them and update this doc. Onboarding programs improve over dozens of iterations.
Add, remove, and reshape to fit your company’s stage, culture, and role type.
At 90 days, a new hire knows enough to have real opinions, but hasn’t been around long enough to rationalize things away.
The 90-day founder conversation
Goal. Get an honest read on onboarding, culture, promises made versus kept, and what only fresh eyes can see. Owner: CEO / Founder.
Why this conversation matters. A new hire at that point still remembers what surprised them, what disappointed them, and what exceeded their expectations. That window closes fast, so schedule the conversation while it’s open.
Onboarding retrospective
| Question | What you’re really listening for |
|---|---|
| “Looking back, what did we over-explain, and what did we under-explain?” | Where the onboarding mismatched reality. Signs of noise vs. genuine gaps. |
| “What took you longest to figure out that nobody told you?” | Undocumented tribal knowledge. Hidden friction. What the next hire needs earlier. |
| “Was there anything in Week 1 that felt like a waste of time?” | Meetings that don’t land. Sessions that are too early. What to cut or reorder. |
| “What would have made your first 30 days meaningfully better?” | Specific, actionable improvements. Take notes and act on them rather than deflecting. |
Culture & reality check
| Question | What you’re really listening for |
|---|---|
| “How would you describe our culture to a friend considering joining?” | The lived version of culture, not the pitch version. Are they saying what you hoped? |
| “Is there anything about how we work that surprised you, positively or negatively?” | Drift between stated values and actual norms. Positive surprises matter too. |
| “Do you feel like people here say what they actually think?” | Psychological safety signal. A hesitant answer is more informative than a yes. |
| “Is there anything we say we value that you haven’t seen us actually live?” | A hard question, and a revealing one. Ask it directly rather than softening it. |
Promises made vs. kept
| Question | What you’re really listening for |
|---|---|
| “What did we tell you about this role during hiring that hasn’t matched reality?” | Recruiting promises vs. lived experience. Scope, growth, autonomy, team quality. |
| “Has the role turned out to be what you expected? What’s different?” | Misalignment in scope or focus. Early signal of engagement risk. |
| “Is there anything you feel we should have told you before you joined?” | The things candidates can’t see until they’re inside. Useful input for future hiring. |
Fresh eyes: what only they can see
| Question | What you’re really listening for |
|---|---|
| “What’s something we do that you find genuinely odd, but everyone here seems to accept?” | Normalised dysfunction. Legacy habits that no one has questioned. High-value signal. |
| “If you were building this company from scratch, what’s one thing you’d do differently?” | Process, structure, tooling, communication. Treat as strategic input, not complaint. |
| “Where do you see us leaving opportunity on the table?” | GTM gaps, product blind spots, team dynamics. Outside perspective has outsized value. |
| “What do you know now that you wish you’d known on Day 1?” | A strong question for improving the next onboarding. Ask it last. |
How to run this conversation. Do this 1:1, just you and the employee, with no manager in the room. Keep it off the record in tone. Lead with curiosity, not defensiveness. If something stings, say “thank you, that’s useful” and mean it. Close by telling them one specific thing you’re going to act on.
Founder commitments
- Write down 1–3 specific changes you’ll make based on this conversation
- Update this onboarding template with anything that should change
- Follow up with the employee in 2 weeks on any commitments you made
- Share relevant insights with department heads (remove attribution if needed)