👋 Hi my name is Roslyn, I’m a 2x founder and executive coach. I help purpose-led founders fall in love with building their companies again. Learn about working 1:1 here.

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Hi there,

Hope your long weekend was filled with some fun, rest and relaxation.

I was in Canada visiting my family for a week in nature. It was lovely, and I’m also so happy to be back in New York. I’m low key obsessed with my routine here so it always feels great to come back. Can you relate?

Today we’re continuing to talk about how to build teams with integrity. Last week we spoke about how to hire aligned, high-impact teammates and this week we’ll cover how to onboard for culture and effectiveness. 

We’ll get into:

• Why intentional onboarding is key to long-term success

• How to clarify what your new hire is here to do while grounding in the greater why

• How to integrate your culture and values through the onboarding process

Something new: I added a new section underneath today’s deep dive to share a little more about the behind the scenes of building Within. I share my experience with overcoming fear in order to grow my business. Scroll down to check it out and let me know if you’d like me to keep this section!

Where we go deep on the outer work or the inner work of building a startup.

How to Onboard for Culture and Effectiveness

A guide to setting your team up to thrive, without micromanaging or burning out.

“The best time to plant a tree was 20 years ago. The second best time is now.”

— Chinese Proverb

WHY ONBOARDING MATTERS MORE THAN YOU THINK

Hiring someone new is like planting a seed in your company's soil. If you just toss it in and hope it grows, you’re gambling with your time, energy, and trust.

Effective onboarding isn’t about perfection. It's about intentionally setting someone up to succeed in your unique culture. When done well, it:

• Accelerates productivity

• Reinforces the values you’ve worked so hard to build

• Deepens trust across the team

• Reduces future fires, friction, and founder decision fatigue

The cost of an unclear onboarding process is ambiguity, which, over time, can lead to resentment, rework, and resignation.

Here’s how to onboard intentionally.

3 CORE GOALS

A culture-forward onboarding plan has three core goals:

• Clarify the “what” – What are they here to do, and how will success be measured?

• Model the “how” – How do we communicate, collaborate, make decisions and give feedback around here?

• Anchor the “why” – Why does this role matter? How does it fit into the company’s vision, strategy and goals? Why were they selected for this role? 

We’ll break that down into six practical steps.

1. CREATE A 30-60-90 Plan

Give each new hire a 30-60-90 day success plan that:

• Clearly outlines expectations and deliverables, explains what success looks like and how it will be measured, and ties them back to the broader strategy and company goals

• Is co-created with the hire, not just handed down

• Includes cultural goals (e.g. “facilitate your first team retro” or “give upward feedback at least once”)

• Emphasizes learning before doing

2. NAME THE CULTURE, DON’T JUST ASSUME IT

Clarity is kindness. A great onboarding process names not just the tasks but the tone of your company.

Create a 1-pager or Loom video that answers:

• What behaviors get rewarded here?

• What do we mean when we say things like “ownership” or “done is better than perfect”?

• How do our cultural values show up in practice?

• What does giving and receiving feedback look like in practice?

Use stories to illustrate values. For example:

“One of our values is transparency. That showed up last quarter when our product manager publicly shared what went wrong with a launch, and the team rallied to support rather than blame.”

This makes the culture feel real, not performative.

3. PRIORITIZE RELATIONSHIP-BUILDING

People don’t just join companies. They join teams that are made up of human beings.

Set your new hire up with:

• A “get to know you” tour of cross-functional teammates

• A buddy or onboarding mentor (ideally someone who embodies your values)

• 1:1s with founders or functional leads early and often

Then give them prompts like:

• “What’s something you love doing that we might not know?”

• “What’s your ideal feedback style?”

• “When do you feel most supported at work?”

Bonus: Have new hires fill out a “User Guide” on who they are and how they like to work best with others. Save it where others can find it, have them share parts of it in early intro meetings, and have their manager read through it in detail. 

Building strong relationships are what make radical candor and collaboration possible.

4. NORMALIZE FEEDBACK FROM DAY 1

Don’t wait six months to ask, “How’s it going?” Normalize real-time feedback—both ways—as part of the job, not a special event.

Try this cadence:

• Day 3: “What’s one thing that’s been confusing or unclear so far?”

• Week 2: “What’s one thing you’re proud of? One thing you wish you’d done differently?”

• Week 4: “How could I be a better manager for you?”

Teach your team to use Non-Violent Communication or the Radical Candor framework (Care Personally + Challenge Directly). Also model it yourself. (Here’s my guide for using Non-Violent Communication).

5. REGROUND IN THE WHY

Burnout often stems from disconnection. Help your new hire connect their daily tasks to the bigger mission.

You might:

• Share customer stories or testimonials during onboarding

• Walk through your origin story and what still drives you

• Encourage the new hire to write a short reflection on why they said yes to this role

When you’ve got the right people on the bus and they understand where it’s going, momentum follows.

6. DON’T JUST SET & FORGET, ITERATE

Onboarding is a living system. Revisit it every time you hire someone new.

Ask:

• What worked?

• Where did we lose clarity?

• What did this hire need that we didn’t anticipate?

And don’t forget to check in around emotional onboarding, too. New team members often carry imposter syndrome, performance anxiety, or fear of disappointing you. Create space to name and normalize that.

FOUNDER REFLECTION

You are no longer just a doer, you are a culture creator and keeper.

Your job is to make the invisible visible: the assumptions, rhythms, rituals, and expectations that make your company tick.

This doesn’t mean scripting every move. But it does mean choosing to lead with intention instead of default.

Managing through ambiguity is the job.

Intentional onboarding helps your team manage through that ambiguity with confidence, connection, and clarity.

TL;DR: YOUR CULTURE-FIRST ONBOARDING TEMPLATE

WITHIN RESOURCES

If you’re a founder who’s onboarding team members, I created these resources just for you:

• User Guide: This is a template you can have new hires fill it out for sharing with others and referring to when introducing themselves/explaining how they work best.

• Guide to Non-Violent Communication: This is a step-by-step guide on how to use Non-Violent Communication in order to express observations, feelings and requests with grace and compassion.

READ

• Non-Violent Communication: And if you want to go even deeper on Non-Violent Communication you can read the whole book. It’s great for work and it’s also incredibly effective in personal relationships too (I use it in my marriage every week!).

• Radical Candor: I will probably recommend this book many times throughout our “Building Teams” newsletters. It’s a classic on how and why to give direct and honest feedback in an empathetic way (and so much more on the topic of managing). IMO it’s a must-read for first-time and seasoned founders alike.

ON FACING YOUR FEARS

Hi! I’m creating a new section here where I share a little more vulnerably about what’s on my mind with building Within these days. 

For those of you that are new here, Within is a personal development platform that helps founders fall in love with building their companies again. Through coaching, content, and community, I support founders with both the outer work (strategy and execution) and the inner work (mindset and emotional wellbeing), so they can scale their impact without burning out.

I started Within last fall after burning out from my previous startup, The GIST. That experience set me on a deep healing journey—rediscovering who I am, how I want to work, and how I want to serve the world. That’s what led me here.

Lately, I’ve been reflecting on what’s needed to take Within to the next level—and what’s been blocking me. And I realized one of my biggest blocks is a fear of being fully seen. Seen not just for my gifts and greatness, but also for my flaws, mistakes, and shadows. I’ve been afraid of being seen as someone who doesn’t have it all figured out. Who sometimes gets it wrong. Who is far from perfect.

Most of my clients today have come through referrals or in-person events where I’ve shared my story. Naturally, I’ve concluded that putting myself in more of these rooms will help grow my business, not stifle it.

But that visibility—hosting events and workshops, speaking publicly—also activates a deep fear in my nervous system. It feels at odds with my instinct to protect myself. And for a while, that fear left me stuck.

Until recently.

Because when I got honest with myself, I realized that growth requires moving through this fear. So I’ve decided to be scared and do it anyway.

Next week, I’m launching my first online group coaching cohort. The week after that, I’ll be speaking publicly for the first time in a while (details to come if you’re in NYC!). I’m proud of myself for taking the risk of being seen—even if I fumble or do an "okay" job at first. I’m trying to treat it as practice, not perfection.

What’s helped me move forward is the healing work I’ve been doing: IFS, EMDR, and nervous system work. Each modality is helping me process old wounds and access more safety internally. And with that, more courage.

If you’re stuck in a similar place, here’s what I suggest:

1. Get clear on why it matters. Why is facing this fear aligned with your goals, values, and the life you want to live? What’s at stake if you don’t?

2. Create safety in your nervous system. Offer reassurance to the parts of you that want to stay hidden. Use regulation tools. Seek support from a therapist or coach if needed.

3. Take micro steps to build self-trust. If public speaking feels big, start smaller: try a Toastmasters meeting or speak to a small, supportive group. Alternate between building safety and taking action to grow your capacity over time.

Bob Proctor says “faith and fear both demand you believe in something you cannot see”. The choice is yours.

P.S. if you like this section please reply and LMK if I should keep writing it!

• 1:1 Coaching: If you’d like a partner in navigating the growth edge of team building, overcoming fears, or building a startup in general, you can book a free coaching consultation.

• Ask a Founder Coach: Got a question about team building? Drop it here and I may answer it in a future newsletter.

• Let’s be friends: If you want to see more of the BTS of building Within and receive more tips and ideas on building with integrity, connect with me on LinkedIn and Instagram.

• Finally, tell me how you liked this newsletter. I read every piece of feedback.

Thanks for being here! It means the world to me.

With love,
Roslyn 💚