Introducing Toby: How AI Helps Managers Practice the Hardest Parts of Their Job

Overview

Most manager training doesn't work. Managers sit through sessions, take notes, and walk away with a binder full of frameworks they'll never use. The content isn't the problem. The problem is that traditional programs stop at knowledge and never get to practice.

Oxygen's programs are built differently. They're cohort-based, experiential, and designed around live practice, real feedback, and accountability. Managers don't just learn what good delegation looks like. They do it. They rehearse the hard conversation before it happens. They build the muscle memory that turns knowledge into instinct.

Toby, Oxygen's AI course companion, takes that philosophy further. It gives managers a private, always-available way to keep practicing between sessions, on their own time, at their own pace. More reps, more reinforcement, more access to the curriculum, whenever they need it.

What Is Toby?

Toby is an AI tutor built specifically for Oxygen's manager training programs. It's trained on Oxygen's proprietary curriculum, frameworks, and scenarios, not on generic internet content. Toby is designed to be a private, always-available course companion that helps managers practice, prepare, and deepen their learning.

As Nick Herinckx, Co-CEO of Oxygen, puts it: "The main thing that inspired Toby was how hard and awkward it is to practice in front of others. Toby gives you a safe space to practice and refine your skills, 24/7."

Two things kept coming up in conversations with managers going through Oxygen's programs. First, practice is personal. People skills like giving tough feedback or navigating conflict aren't easy to rehearse in front of others. Managers wanted more reps, but they wanted them privately. Second, the learning moments don't wait. Coaching and live sessions are invaluable, but managers often need support in the moment, right before a hard conversation, not three days later.

Toby addresses both. It's available 24/7, it's private, and it's grounded in the same material managers learn in Management Essentials. Instead of giving generic advice, it walks you through exercises so you get to practice in real time.

How Do Managers Use Toby?

Managers in the program use Toby in three main ways:

Rehearsing difficult conversations.

Before a tough feedback session or accountability conversation, managers rehearse with Toby. It creates realistic scenarios customized to your role, your industry, and even your specific strengths and weaknesses. "Toby can create an infinite number of scenarios customized just to you and your industry," Nick says.

Applying frameworks to real situations.

Need to build a role description, draft talking points for a performance review, or structure a delegation plan? Toby walks you through Oxygen's frameworks step by step, turning theory into action. It works like a practice partner that knows your course material and meets you where you are.

Reinforcing learning between sessions.

The cohort experience is built on live interaction and accountability. But the other half of learning is repetition: trying things over and over until they stick. "Humans learn through interacting with others, and there's accountability with it being live," Nick explains. "But the other part of learning is the messy act of trying things over and over. That's where Toby comes in."

What Makes Toby Different from AI Coaching Tools?

There's an important distinction between an AI tutor and an AI coach, and it shapes everything about how Toby was designed.

Generic AI coaching apps are trained on broad business content, built for open-ended Q&A, and designed as standalone tools. They give general advice.

Toby works differently. It's purpose-built as a companion to Oxygen's structured training programs, geared toward scenarios, real-time practice, and immediate feedback grounded in the specific curriculum managers are already learning. "Toby is given directions to not just be a coach, but actually to be a trainer," Nick says. "Instead of telling you something, Toby walks you through an exercise so you get to practice it in real time.

A tutor knows your syllabus, your exercises, and your progress. A coach gives you general guidance. Toby is the tutor.

Does AI Actually Help Managers Build Skills?

The concern with most AI tools in training is that they replace practice with shortcuts. Toby was designed to do the opposite: increase the amount of practice managers get, not reduce it.

Managers aren't using Toby to get quick answers. They're using it to prepare for a one-on-one they're nervous about, revisit a framework they didn't fully absorb in the live session, or work through a delegation exercise one more time before applying it with their team.

The early feedback reflects this. "The two most common things I hear about Toby," Nick shares. "One, I need help learning how to use it best. And two, I use it every day now. I couldn't imagine doing my job without it."

That's the goal: not a tool managers use once, but a companion they rely on as part of their ongoing development.

How Toby Fits into Oxygen's Management Essentials Program

Toby is included for all Management Essentials participants. It's not a separate product or an add-on. It's part of how the program works: live sessions provide accountability and real interaction with other managers, and Toby provides private practice and reinforcement between those sessions.

For organizations evaluating manager training options, Toby is one of the reasons Oxygen's approach produces lasting behavior change. The combination of live cohort-based learning and a private AI tutor means managers get both the human accountability and the repetition they need to build real skills.

Frequently Asked Questions About Toby

What is Toby by Oxygen? Toby is an AI course companion built by Oxygen for its Management Essentials program. It's an AI tutor trained on Oxygen's proprietary manager training curriculum that gives managers a private, 24/7 way to practice skills like giving feedback, holding accountability conversations, and navigating conflict.

Is Toby an AI coach? No. Toby is a tutor and course companion, not a coach. It's trained specifically on Oxygen's curriculum and designed to walk managers through exercises and scenarios, not give generic advice. Oxygen does not position Toby as a standalone AI coaching product.

How is Toby different from ChatGPT? Toby is trained on Oxygen's proprietary frameworks, scenarios, and templates, not on general internet content. It's purpose-built for practice and experiential learning within a structured training program. ChatGPT and similar tools are general-purpose AI assistants that give broad advice without knowledge of a specific curriculum.

Who can use Toby? Toby is currently available to managers enrolled in Oxygen's Management Essentials program. It's part of the cohort experience, not a standalone product.

What can managers do with Toby? Managers use Toby to rehearse difficult conversations, practice giving feedback, build role descriptions, prepare for performance reviews, apply delegation frameworks, and revisit concepts from the program. Toby creates customized scenarios based on the manager's role and industry.

Is Toby available 24/7? Yes. Toby is available anytime, so managers can use it right before a tough conversation, after a live session, or whenever they want to practice.