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

Reader love: “Quickly becoming one of my favorite reads!”

Hi there,

How was your weekend? 

I thought I was going to catch up on work this weekend but pivoted to spending some quality time reconnecting with my partner. 

We’ve both been a little wrapped up in our own work and lives lately so we decided to dedicate our weekend to reconnecting. We had some deep conversations about our relationship, a date night — dinner and dancing in NYC, went for walks around the neighborhood, cuddled on the couch, and cooked together (okay, he cooked for me). 

We feel about 10x more connected than we did going in. Seriously.

If you’ve been disconnected in your romantic partnership, or any important relationship (friend, co-founder, or even yourself!), I highly recommend dedicating a weekend to intentional reconnection. I promise the goodness will spill into other areas of your life (even work!).

Today we’re getting into a topic that’s pretty challenging for most first-time founders (and honestly all founders!) — navigating performance issues and letting people go. 

In today’s newsletter we’ll cover:

• Structures for feedback and hard conversations 

• Setting expectations and putting someone on a PIP

• How to let someone go

BTW, I’m thinking of interrupting some of our startup programming to drop in the occasional newsletter about living meaningfully OUTSIDE of building our startups, with topics like: health & wellness, creativity & self-expression, love, relationships & friendships. Because I believe in order to be great founders, we need to invest in the other areas of our life too.

Let me know if you’re up for that below.

Thank you! Now let’s dive in.

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

Performance Issues & Letting People Go

As a founder and leader, few things feel heavier than when someone isn’t meeting expectations. 

This is something I personally struggled with as a first-time founder.

My inner people-pleaser sometimes stopped me from giving people the direct and honest feedback they needed to meet and exceed expectations. Or, at least give them the heads up they weren’t on the right track before it was too late, leading to surprise when it did come time to put them on a performance improvement plan (PIP) or let them go.

Then trying to course-correct, I would sometimes come across too harsh in those conversations.

Sometimes I would struggle to take radical ownership, looking at where I went wrong — whether it was hiring the wrong person, having unrealistic expectations or not giving enough direct feedback — instead choosing to blame the person.

Other times, I would be way too hard on myself, beating myself up for not navigating these things “properly”. When, as a first time as a founder, I was bound to get stuff wrong.

Can you relate? 

So today I want to share my steps for successfully navigating performance issues and letting people go.

Because how you show up in these moments can define your culture more than how you handle success. 

STEP 1: START WITH RADICAL OWNERSHIP

Before jumping to judgment, pause and ask:

• How have I contributed to this situation?

• Have I been clear about expectations and success metrics?

• Have I provided the right support, context, and feedback?

• Have I addressed issues early—or avoided them?

• Did I hire the right person for this role?

This isn’t about blame—it’s about reclaiming your agency and modeling integrity.

STEP 2: GIVE FEEDBACK EARLY, CLEARLY & KINDLY

Avoiding hard feedback doesn’t protect people—it erodes trust.

Structure feedback using the SBIS format:

• Situation: What happened / what’s the context

• Behavior: What they did

• Impact: How it affected the team/business

• Suggestion: What to do differently

“In Monday’s planning meeting (Situation), you cut off your teammate multiple times (Behavior), which made it hard to build trust in the group (Impact). I’d love to see you actively listen and create more space next time (Suggestion).”

Remember: you’re critiquing the behavior, not the person.

If you have a hard time giving direct, caring feedback, read Radical Candor.

STEP 3: CLARIFY EXPECTATIONS & TRACK PROGRESS

When performance concerns persist:

1. Document clear expectations—what good looks like (make it measurable)

2. Agree on a timeline for improvement—often 30–60 days

3. Check in regularly—weekly is ideal

4. Continue to support—offer coaching, remove roadblocks, and name progress honestly

If it’s unclear whose “fault” it is—yours, theirs, or the system’s—assume shared responsibility. But be specific and rigorous in defining what success must look like.

STEP 4: USE STRUCTURES FOR HARD CONVERSATIONS

You’re not just managing output—you’re communicating with a human being.

Use Nonviolent Communication (NVC) to bring grounded presence:

• Observation: “Here’s what I’m noticing…” (State the objective facts, without any judgments.)

• Feeling: “I feel concerned because…” (Use this list of feelings.)

• Need: “I need to trust this role is fulfilling X outcomes…” (Use this list of needs.)

• Request: “Can we align on what needs to change in the next 30 days?”

Add: “Here’s my responsibility in this, and my commitment moving forward…”

This opens the door to partnership, not punishment.

If you want to learn about NVC more in depth, read the book or check out my summary.

STEP 5: CONSIDER A PERFORMANCE IMPROVEMENT PLAN (PIP)

If performance isn’t improving:

• Clearly outline 2–3 core expectations

• Define success criteria (make them measurable) and timeframe (usually 30–60 days)

• Offer weekly check-ins, written feedback, and opportunities to course-correct

• Communicate what happens if expectations aren’t met (e.g., role transition or exit)

A PIP isn’t a punishment—it’s a structure for clarity and a final opportunity for mutual alignment.

STEP 6: WHEN IT’S TIME TO LET SOMEONE GO

If there’s still misalignment after honest effort: Letting someone go can be an act of respect. If the role or environment isn’t a fit for them, letting them go with compassion for their situation can set them free to find something more aligned. 

However, don’t expect people will necessarily see it that way. Getting fired can bring up heavy emotions for people – they may feel upset, scared, ashamed, angry, etc. Prepare to hold space for those emotions with compassion, while simultaneously holding your decision with firmness.

Do it:

• Promptly, once the decision is clear

• Privately, with dignity and clarity

• Respectfully, without blaming or dragging it out

What to say:

“This is hard. We’ve worked together on these areas, and I appreciate the effort you’ve made. And at this point, the role requires things that aren't the right fit right now. I want to thank you for what you’ve contributed.”

Be clear, kind, and confident. Don’t over explain, project guilt or waver on the decision.

LEGAL & OPS SAFEGUARDS

• Document everything: feedback, check-ins, written expectations

• Consult HR or legal counsel (especially before termination)

• Provide final pay (including vacation payout if applicable), severance (if applicable), benefits info and what happens with equity/stock options (if applicable)

• Ensure access removal and handover are handled cleanly

Don’t skip this. Even in early-stage teams, legal basics matter.

COMMUNICATING TO THE TEAM

When someone leaves, the silence is louder than you think.

• Be honest, without oversharing: “They’re no longer with the company.”

• Affirm their contribution: “We’re grateful for the work they did to help us get to this stage.”

• Share what happens next: “We’re in the process of redistributing X or hiring for Y.”

This models a culture of transparency, not gossip or fear.

FINAL THOUGHTS

Handling performance issues with courage and compassion is one of the hardest and most scary parts of leadership.

When you show up with clarity, care, and responsibility, you give your team the gift of trust—even when the outcome is hard.

And hey, I want to just acknowledge that this is a topic that can be much more complicated in practice than is fully reflected in the steps I’ve listed above. 

It’s normal for these situations to trigger all kinds of emotions in you—like guilt, anger, shame, fear—and all kinds of behaviors—like blame, procrastination, being overly harsh, or too indirect in communication. 

If you’d like support on navigating these challenges and the complicated emotions that come with them, you can book a chat with me to talk about coaching.

I shared the story of my founder burnout, healing journey and creating a life that feels aligned, with the wonderful Sana Sana Social community this week. It feels vulnerable to say this but I’m so happy with how it went—it was received with such warmth.

Many people came up afterward to share how moved they were and how much it resonated with them. Even my husband —who, as a content production expert, always has notes—was floored by my speaking skills (and had zero feedback, which is unheard of!). 🥹 

This means a lot to me because public speaking has traditionally made me QUITE nervous—pounding heart, shaky voice, memories of times I’ve frozen up on stage.

Here’s what people don’t see behind the scenes:

• The time spent writing and refining a speech that was straight from my heart, and practicing the delivery till it felt natural

• The Parts Work (IFS) I’ve done to understand the scared parts of me that sound the alarm when I stand on stage

• The nervous system regulation I’ve done to teach my body how to access safety from my environment.

• The Toastmasters meetings I’ve been attending to help me get comfortable in front of a crowd.

• The inner work I’ve been doing to allow myself to be seen in the wholeness of who I am, including the parts that feel scary to show.

Interestingly, nearly every question I got afterward was about the most personal part of my talk—which isn’t surprising. The vulnerable, imperfect, scary parts are always what connect us most. They’re often what people most need to hear.

It’s a reminder to me (and maybe to you, too): The parts we hide are usually the ones that make us most relatable, most human, most magnetic. If you’ve been keeping parts of yourself in the shadows, I encourage you to experiment with letting them be seen. Because authenticity is magnetism.

Also, I’m currently building out The Within Resource Library — a database of all of the recommendations I’ve made in this newsletter and that I regularly make to my clients —be it podcasts, books, newsletters, templates, exercisese, courses or practitioners to work with.

Have a great recommendation to share with this community? Reply to this email and let me know, and I’ll make sure to send the resource library your way when it’s complete.

Thank you so much!

• 1:1 Coaching: I want to help you fall in love with building your company again. Want to explore what that looks like? Book a free coaching consultation.

• 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 so much for being here.

With love,
Roslyn 💚