Embedded Coaching...A Startup Secret Weapon? (Alita Watson)

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Alita Watson is a transformational leader and pioneer in the world of embedded coaching. She joined Sonder, a unicorn startup when they were 150 people to become a full-time coach to everyone in the organization. 6 years later, they had scaled to 2,500 people globally and she had conducted over 15,000 coaching sessions across the company.

She now works with leaders and companies to implement the transformative model of embedded coaching to help companies successfully scale.  In this conversation, we explored what embedded coaching is and how it might just be the next big thing in leadership.

Most companies treat coaching like emergency medicine. Someone's struggling; performance is slipping or there's a leadership crisis so you bring in an expensive external coach. They parachute in for a few sessions, maybe things improve, and then they disappear until the next fire. What if there was a different way?

In this conversation, we talk about how instead of bringing coaches in from the outside for crisis intervention, you place a coach directly inside your organization. Embedded coaching flips the entire model. They work with everyone from the C-suite to customer-facing employees. They become woven into the cultural fabric, responding to real-time challenges as they emerge.

The model works because it meets people where they actually are, when they actually need help, using frameworks simple enough that everyone can practice them daily. It scales because it's built on proven systems, not on one person being extraordinary.

This episode is sponsored by my book Conscious Accomplishment - How to Use Personal Achievement for Spiritual Growth.

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This episode is great for:

• Founders and CEOs of fast-growing companies who sense their scaling challenges are more about people dynamics than processes

• HR leaders looking to innovate beyond traditional coaching models

• Leaders managing teams for the first time who are getting triggered by what management reveals

• Anyone who takes work conflicts home with them

• Coaches interested in the embedded model

• People exhausted by workplace drama who want practical frameworks to communicate without breaking connection

• Conscious leaders who view their business as a spiritual practice

Ideas that really stuck out to me:

1. Embedded coaching serves all layers of the organization and adapts as it evolves. This means coaching everyone from the C-suite down to customer-facing employees. It means working closely with HR to respond to feedback and engagement surveys. It means helping leaders see where they can up-level and improve communication. After Alita has been doing this for a period of time, embedded coaches become cultural ambassadors who weave the company's language, values, and principles into actual practice. Culture stops being just words on the wall and becomes how people actually collaborate, deal with conflict, and work together.

2. The workplace becomes a way to do inner work when things get hard. This is what transforms the HR function from bureaucracy into something that actually serves the people in the organization. As Alita describes it, embedded coaching is "a way for them to do their inner work in the workplace when things get hard." Instead of suffering through difficult dynamics or taking problems home, people have real-time support to work with what's being activated. The coach isn't there once a quarter. They're embedded in the ecosystem, available when you actually need help.

3. Relational intelligence becomes the foundation that everything else is built on. Esther Perel's insight that "relational intelligence is the new bottom line" points to the ability to both be in connection AND stay in connection. Being in connection means being open, curious, aware, and wanting to go deeper with the humans you work with. Staying in connection is the hard part: when there's collapse, conflict, or you just don't like someone, how do you lean in and reveal your true experience instead of withdrawing, shutting down, or rallying others? This single capacity determines how much people engage, how creative they can get, how innovative and collaborative they can be.

4. Most workplace suffering comes from not being able to say what's true. Alita has watched this pattern play out thousands of times: people withhold what's bothering them, internalize it, ruminate endlessly, war game scenarios in their heads, then go home and dump it on their partners. The issue sits in the background of every interaction, festering. Learning to simply name what's coming up in the moment eliminates this entire cycle. The breakthrough is to be able to name what's happening.

5. Five simple sentence stems transform how people communicate. Alita teaches people to express anything using: I notice, I imagine, I feel, I'm curious, and I need. These let you reveal what's happening for you while staying on your side of the street, instead of making assumptions or statements like you are, you should, it always, or it never. You simply name what's coming up, for example, “I notice what you just said has me feel really frustrated,” and then stop. The other person isn't defensive because you're revealing your experience, not attacking them.

6. Separating observation from evaluation is where magic happens. What do you actually see with your senses versus what meaning are you making from it? When you can break these apart, everything changes because the other person is having a completely different reaction, feeling, and curiosity. You're not arguing about what happened but about your different interpretations. One person's initiative is another person's overstepping boundaries in the same situation, two totally different planets.

7. Startups become accelerators that reveal your patterns. When Alita herself joined a startup after years of teaching this work, she got humbled fast. Her judge came out, her impatience flared, all her old patterns smacked her across the face. But instead of resisting it, she recognized what she'd been teaching: these little pods we put ourselves in, these ecosystems, really are accelerators, and it's super uncomfortable. They show you who you are, how you're showing up, what old strategies you're using. The workplace becomes a spiritual practice if you're willing to see it that way.

8. The model scales because it's built on systems and processes. After years of implementing embedded coaching across organizations, Alita has built proven systems and processes that make this model work over and over again. She's not just coaching individuals anymore but training other coaches how to integrate into organizations effectively. Her goal is to meet organizations where they are, find them the right coach, and make sure it's integrated well. The transformation isn't dependent on her being special—it's a replicable model with proven frameworks.

I stumbled onto Alita's work through a mutual connection and immediately thought: "Wait, this exists? Why isn't everyone doing this?"

What struck me most about Alita was her refreshing directness. She's done the inner work herself and teaches from lived experience rather than theory. As a leader who can't tolerate things left unsaid, she had to learn these communication tools for her own survival. Now she's on a mission to bring them into organizations where the cost of poor communication shows up in everything from innovation to retention.

There's nothing idealized about Alita's approach. She teaches people how to stay present with discomfort, name what's actually happening, and remain engaged instead of checking out. These are powerful skills for modern organizations.

This conversation reminded me that businesses are collections of humans trying to coordinate toward shared goals. When those humans don't know how to navigate their own triggers, communicate their actual needs, or stay curious when someone rubs them the wrong way, everything else suffers.

You can have the best strategy in the world, but if people can't work together, you're screwed.

I hope you enjoy this conversation!

- Scott

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Recommended Resources:

• About Alita Watson

• Learn More About Her Work

• Alma Leadership

• Alita’s Substack Page: My Dear Leaders

Episode Transcript

• Alita Watson Full Transcript

Show Notes

• 00:00 - How Alita Watson Built the Embedded Coaching Movement

• 13:40 - Unlocking Relational Intelligence Inside Organizations

• 19:31 - What Coaching Reveals When Growth Means Letting Go

• 23:12 - How Coaches Navigate the Dilemma of Trust Privacy and Truth

• 27:41 - Why Embedding Coach Early Is the Key to Scalable Culture

• 30:02 - How Internal Coaching Is Breaking the Stigma and Finally Working

• 33:01 - Why Startups Are the Pressure Cookers That Accelerate Leadership Growth

• 36:27 - Alita’s Tools for Speaking the Unspeakable and Having Real Conversations