A Step-By-Step Guide To Designing Your Startup’s First Manager Training Program
Most managers at startups get promoted on a Friday and are leading a team by - oh wait, they’ve been informally leading a team for 3 months leading up to their actual promotion? Not surprised…
Any of these other manager pitfalls sound familiar?
- Still doing IC work while trying to manage (often unavoidable in startup life, but there are ways to ease the frustration)
- Pushing a strong IC into a management role, only to find out they have little - if any - interest in or affinity for people leadership
- No clue how to handle feedback, 1:1s, or tough convos
- Reporting to a founder who’s already maxed out
- Zero tools, playbooks, or support systems
Easy solution: hire externally. Might be the right call, but if not done thoughtfully you run the risk of alienating existing folks and ending up with someone who panics at startup chaos (hi, ambiguous asks 👋).
Our point? Leadership is hard. Leadership at a startup? Oh boy…
The good news? You don’t need a 12-week course or a $50K manager training program. You just need a plan.
This is your no-fluff, founder-friendly guide on: what to teach, when to teach it, and how to keep it light but impactful.
Steps to Designing Manager Training
Step 1: Define What “Good Management” Looks Like
Chart & Carry take: What it takes to be a good manager should be tied to real, measurable behaviors. Move from vague language like “Managers should be having 1:1s” to something more clear and definitive like “Weekly 1:1:s aren’t optional - they’re a core part of your job as a manager”
The same goes for things like giving feedback, coaching, and facilitating team growth.
Step 2: Leadership Training Begins Before the Promotion
The #1 thing you can do at your org to develop good future managers is to show them what good managers look like. I’ll say it again in case you weren’t paying attention: The #1 thing you can do at your org to develop good future managers is to show them what good managers look like. Ie, monkey see, monkey do. Lead by example.
Beyond that, here are some lightweight, startup-friendly ways to prep future managers:
- Give stretch moments: lead a project, onboard someone, run a retro.
- Start a "manager-curious" channel: share prompts, AMAs, and leadership best practices.
- Drop in micro-resources on people leadership: a Loom, a Slack screenshot, a Notion doc.
🔍 The goal: help folks see what managing actually looks like before they sign up.
Step 3: Figure Out Training Goals
Great managers are often both emotionally intelligence and buttoned up when it comes to day-to-day operations. And in startups, it’s common to train for one while not giving TLC to the other.
Bake in training goals and content that teaches both sides of the coin:
- Leadership/EQ skills: giving (and receiving) feedback, coaching, translating founder vision to team goals, navigating conflict, building trust, etc
- Execution/operations skills: facilitating meetings, onboarding logistics, using project management tools, PTO approvals, performance reviews, tracking work, etc
Step 4: Leverage Internal Community
- Create a Slack channel just for managers
- Host recurring “Manager Roundtables" - monthly at a minimum, more frequent if possible
- Tap into asynchronous learning opportunities (Notion, Loom, etc)
- Share quick resources (articles, podcasts, prompts)
Chart & Carry take: Put the onus on managers to create this sense of community. Instead of “HR” hosting your monthly roundtables (which, let’s be honest, can be hit or miss..), have a rotating schedule of manager facilitators to own each session
Step 5: Tie it Together Asynchronously via a Manager Toolkit
Create a lightweight, easily updatable Notion page, Confluence space, or Google Doc to give folks the resources they need.
Things you might want to include:
- Templates for 1:1s, growth plans, etc
- Comms drafts for handling underperformance, terminations, etc
- Best practices on running team meetings, motivating folks, etc
- Checklists for new hire onboarding, offboarding, etc
- And more…you get the jist!
Step 6: Review, Iterate, and Scale
- Run a quick manager pulse check 30-90 days into your enablement program: What’s working? What’s missing?
- Iterate. Keep the stuff that’s working, ditch what’s not.
- As you grow, evolve the content and keep it up-to-date (ie, this is not a set it and forget it exercise).
- Be proactive about identifying poor leaders. Build skip-level check-ins into your process. Don't wait until after half a team resigns to ask yourself “Is this manager leading well?”.
🗓 Sample Manager Training Timeline
This isn’t a full-fledged training guide, just a sample cadence to get the brain juices flowin’.
Week 1: Set the Stage
- Kick off with a live intro or short Loom of “What We Expect from Managers”
- Drop a link to your Manager Toolkit (Notion/Google Doc/Etc)
Week 2: Async Learning Starts
- Have them walk through the Manager Toolkit
- Get them to put a template into action (1:1 template, feedback framework, etc.)
- Bonus: Light self-assessment or reflection form
Week 3: First Roundtable
- 60-min live or async session with all managers
- Topics: General (what’s working, what’s hard, peer advice) or tailored (topic-specific)
- Bonus: Co-create shared manager norms
Weeks 4–6: Keep It Rollin’
- Weekly nudge: One micro-topic + tool (e.g. goals, team meetings, burnout)
- Add tools/templates to your manager space as needed.
Month 2+: Sustain & Evolve
- Keep monthly roundtables
- Add manager buddies or peer shadows
- Run a pulse survey at 90 days to check in and improve
What Founders Can Do to Support
You don’t need an HR team of 10. As a founder (or People person), your role is to:
- Give feedback, ask for feedback, repeat
- Normalize the learning curve (nobody’s great on day one)
- Make space for managers to talk to each other
- Provide a few tools: enough to be helpful, not overwhelming
And if you really want to be helpful: model the behavior. Show your managers what good leadership looks like. Do the 1:1s. Share your thought process. Ask for feedback on how you manage.
