👋 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,

I was planning to continue this week’s newsletter talking about the “outer work” of building teams… 

But I was reading a great book about attachment styles this weekend. It was in the context of romantic partnerships, but I couldn’t help but think about how so much of it can apply to our relationships at work. 

I was also recently chatting with my friend and fellow coach, Cristina, about creating content, and she said something that really stuck with me: that she doesn’t publish anything that’s not “alive in her”. And I really felt that. 

So today I’m switching gears to the “inner work” of building teams so we can talk about secure attachment in the workplace, because that’s what’s feeling alive in me today.

We’ll cover:

• The benefits of secure attachment in the workplace

• How to develop secure attachment with your team

• Also, scroll down to the “Real Talk” section for my recent thoughts on making friends as an adult

P.S. there are a few spots left at the event I’m speaking at next week in NYC. I’ll be sharing my real (vulnerable) story about founder burnout and rebuilding my life in a way that’s felt more in integrity for me.

P.P.S. it’s my birthday today! If you want to make my day, reply and let me know how this newsletter has helped you OR what else you’d like to see from it. Feedback is a gift I value so highly!

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

How to Create Secure Attachment with Your Team

As a boss, is it your responsibility to be a secure attachment figure to your employees?

Traditionalists might argue that no, that’s a step too far in a professional context.

But I would argue that it’s in your best interests to take it upon yourself to do so (and it will feel better for you and your whole company too!).

For many of us, when we think about attachment figures, our minds go to our parents or early caretakers, and whether they enabled us to develop a more secure attachment style, or a more insecure attachment style — i.e. avoidant, anxious or disorganized — in our early years. 

The good thing is, that if we’ve developed a more insecure attachment style, it’s possible to earn secure attachment in our adult years through our relationships with other attachment figures, whether that be a romantic partner, our friends, a mentor or a coach… and I would include a great boss in this category too. 

This weekend I was reading Polysecure by Jessica Fern, which has a very intelligent, accessible explanation of the various attachment styles and how to earn secure attachment in our relationships in adulthood. 

According to her, some of the benefits (intrapersonal & interpersonal) of secure attachment include the bolded words below. I’ve adapted the examples to show how these can be valuable in the workplace. 

INTRAPERSONAL BENEFITS OF SECURE ATTACHMENT AT WORK

• Sense of Safety → Psychological Safety

  • Employees with secure attachment feel safe to express ideas, ask questions, and admit mistakes, which is key for innovation and collaboration.

• Emotional Regulation → Strong Leadership & Crisis Management

  • Securely attached individuals can stay grounded during conflict, pressure, or change, leading with calm, clarity, and empathy.

• Positive Self-Image → Confidence & Initiative

  • A stable sense of self-worth allows for healthy risk-taking, ownership of work, and resilience to constructive feedback.

• Resilience to Rejection → Healthy Detachment from Outcomes

  • Secure professionals bounce back from criticism, rejection, or failure without spiraling into self-doubt or shame.

• Self-Awareness → Better Decision-Making & Boundaries

  • Knowing your needs, limits, and values helps prevent burnout and leads to more aligned career choices.

INTERPERSONAL BENEFITS OF SECURE ATTACHMENT AT WORK

• Trust and Openness → Strong Team Dynamics

  • Securely attached people are more likely to build trust, collaborate effectively, and resolve misunderstandings productively.

• Healthy Boundaries → Sustainable Work Relationships

  • They can say no without guilt, ask for what they need, and avoid over-functioning or martyring themselves.

• Reduced Insecurity → Less Office Politics & Comparison

  • A secure sense of self means less competition, more generosity, and celebrating others' wins.

• Balanced Intimacy & Independence → Empowered Teams

  • They can build close working relationships while maintaining autonomy—great for healthy delegation and distributed leadership.

• Repair & Conflict Resolution → A Culture of Accountability

  • Securely attached employees are more likely to own their impact, listen well, and move toward repair—fostering a high-trust culture.

As a boss, you can see how developing secure attachment with and between your employees can support a foundation of effective communication, emotional intelligence, and collaboration.

So how do we create secure attachment with our direct reports?

HOW TO CREATE SECURE ATTACHMENT

Jessica Fern uses a method called “HEART” which I’ve adapted for a workplace setting.

H – Here (Being Present)

At work: You’re grounded and attentive. You stay mentally present in meetings, during 1:1s, and in moments of tension or celebration. You don’t check out or avoid.

Why it matters: Presence builds trust and signals to others that they matter—especially during high-stakes or vulnerable moments.

E – Expressed Delight (Letting Others Feel Seen and Celebrated)

At work: You express genuine appreciation, curiosity, and delight in your teammates —not just for what they do, but for who they are. You notice and name their strengths, quirks, values, and growth. You make it clear that they matter as full humans, not just performers.

Why it matters: When people feel truly known—not just evaluated—they feel safer, more motivated, and more connected to their work and team. Expressing delight in this way affirms their belonging and amplifies their unique contribution.

A – Attuned (Being Understood)

At work: You actively tune in to and mirror others’s emotions—picking up on verbal and nonverbal cues, asking thoughtful questions, and adapting your style based on their needs or emotions.

Why it matters: Attunement supports psychological safety, helps people feel understood, and allows for more empathetic leadership.

R – Rituals and Routines (Creating Consistency)

At work: You implement predictable systems—like weekly team check-ins, retros, or Slack rituals—that build rhythm and reliability into your culture.

Why it matters: Consistency creates safety. When people know what to expect, they feel more secure, supported, and able to focus on doing great work.

T – Turning Toward in Conflict (Repairing and Reconnecting)

At work: Instead of avoiding or escalating conflict, you turn toward it with curiosity and care. You’re willing to name ruptures, take accountability, and co-create repair.

Why it matters: Strong teams don’t avoid conflict—they use it to make the relationship even stronger. Turning toward hard conversations strengthens connection, trust, and resilience.

Using the HEART method at work helps build secure, connected, high-trust teams where people feel safe to show up as their full selves and thrive.

Culture starts from the top. If you, as the founder, cultivate an experience of secure attachment with your direct reports, that models to them how they can create secure attachment with their own direct reports and peers and it eventually becomes engrained in the company culture.

Prompts for your own reflection.

1. Reflect on the bosses you’ve had in your career. Which ones did you feel a secure attachment with? An insecure attachment with? How did this affect your performance and wellbeing at work?

2. Which aspects of the HEART method are you already practicing with your team?

3. Which aspects of the HEART method would you like to add? How will you add them?

Thoughts on living meaningfully outside of work.

On the topic of secure adult attachments… I wrote an article on How to Make Friends in Adulthood a few months ago. At the time, I was feeling a bit lonely. Because I’ve gone through a lot of personal transformation in the last couple of years, a lot of my friendships and communities in my life weren’t fully fitting anymore. And so I was deeply craving more aligned friendships.

In my article, I wrote about what holds us back from making friends and how we can intentionally call in aligned friendships and community.

Three months later, I’ve been feeling so much more content on the friendship front and hopeful about the community I’m building around me. Sitting down to set intentions about how I wanted to feel and what I wanted to do with friends really helped me more actively call in what was missing.

I just got back from a weekend in the Hamptons with two relatively new friends and I left the weekend feeling incredibly energized, seen and connected. 

We talked about everything from business strategy, personal finance and personal branding to sober curiosity, core wounds and navigating dating and relationships.

We went for walks, kayaking, swimming at the beach, cooked meals, went out for dinner, and toured the towns. It was a relaxed, dynamic kind of fun where I felt I could relax, be present and be appreciated for the person I’m becoming.

It’s wild how taking some time to get clarity on what you’re calling in can so quickly manifest. 

So, if you, like me, are wanting to call in more aligned friendships, try these 3 steps:

• Get clear on how you want to feel in your friendships and what kind of activities you want to do with friends.

• Make space for more aligned friendships by investing less in the ones that don’t fit (this takes getting honest with yourself).

• Put yourself out there and show up authentically (whether online on IRL). You can’t attract the people that are aligned if you aren’t willing to be seen as the real you.

• For more tips, you can read the full article here. 

And if you want to check out a community of growth-minded people next week in NYC, grab your ticket to this event next Wednesday. More details below.

• You’re invited! Join me at Sana Sana Social’s July 30th gathering where I’ll be giving a talk on burnout, bravery and living in alignment.

• 1:1 Coaching: I help founders fall in love with building their companies again. If that sounds like something you need, 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 your presence and feedback.

With love,
Roslyn 💚