Keep your best people. Grow your leaders. Without hiring a coach.

Your own in-house performance coach for every employee, from frontline to executive. One trusted coach, private sessions, and a quarterly team summary for HR.

  • Every employee starts with DISC
  • Private coaching anyone can book
  • A quarterly team summary for HR, never personal details
Book a 15-Minute Call

No commitment. Custom proposal within 48 hours.

Can’t find a time that works? Email rosa@rosaosterling.com with 3 dates and Rosa will confirm within 48 hours.

“Rosa is a patient encourager with great insights as to how and why we react as we do.”
S.H., Head of Wine Planning and Operations, Direct Wines

Trusted by leaders at Deloitte, Itaú, Direct Wines and Good Apple

Rosa Osterling, leadership coachFor Companies & HR
  • 25+ Years
  • 7,500+ Coaching hours
  • Former Results Coach, Robbins Research International
  • ICF Member
  • Certified DISC Facilitator
  • English & Spanish

Sound familiar?

This is for you if…

01

Your best people were promoted for technical skill, not for leading people.

They know the work. Leading the team is a different skill entirely.

02

Good people are leaving, and you can’t say exactly why.

Exit interviews give you answers that don’t quite add up.

03

You invest in training and the results fade within weeks.

The habits don’t stick and the behaviour doesn’t change.

04

HR is stretched across culture, retention and development.

There isn’t enough bandwidth to develop every leader individually.

05

Difficult conversations get avoided.

Accountability is inconsistent. Team meetings feel like status updates, not decisions.

06

You have a strong team on paper.

The problem is communication, alignment and how people show up under pressure.

If your company has even one of these, let’s talk.

Book a 15-Minute Call

The 30-Day Leadership Kickoff

See the difference in your leaders in 30 days.

Start small. See the results. Then decide.

For up to 5 leaders on your team:

  • A 15-minute kickoff call to meet me and see how it works
  • A DISC Session: their DISC assessment, plus life, business and career clarity
  • Two 45-minute one-on-one coaching sessions
  • The Leadership Score at the start and again at day 30, so you can see the growth in numbers (optional)

For your HR leader:

  • A 30-minute one-on-one session with me, because the people who support everyone need support too
  • A one-page Before and After Report at the end: team averages, growth and themes, never names or personal details

Available in English or Spanish.

Everything is confidential. Your leaders get support. You get clear insight, and numbers you can show.

My promise: if your leaders don’t feel the Kickoff was worth it, I’ll coach one more leader free.

If you continue with a yearly partnership within 30 days, the full Kickoff investment is applied to your first year.

Rosa will respond within 24 hours.

Free during our pilot

Try the Leadership Score with your team. Free.

The Leadership Score is my own coaching tool, and it's new. Right now I'm running a pilot with a small number of companies, and I'd love yours to be one of them.

Here's how it works:

  • You get a private link for your team.
  • Your people take the Leadership Score on their own. Their results are private to them.
  • When 5 or more have finished, you get a one-page Team Snapshot: where your team feels stuck, what's draining them and how many are thinking about leaving. Anonymous totals only. Never names, never personal answers.

In return, I ask for one thing: your feedback, so I can make it even better.

It's not a test. No one passes or fails. It's a way for your people to look deeper, and for you to see what's really going on.

Free for pilot companies.

Join the Pilot

The In-House Coach Partnership

Your own performance coach. Without the hire.

Your people want to grow. They want to hit bigger goals, lead better and stop running on empty. And someone on your team is sitting on a problem they won’t bring to their manager or to HR. By the time you hear about it, it’s a resignation.

The In-House Coach Partnership gives every person on your team a private, trusted coach to grow with, and a safe place to bring what’s really going on.

How it works

1. Everyone starts with DISC.

Each person completes a DISC Session and keeps their report, so your whole team speaks the same language.

2. Anyone can book.

From frontline to executive, people who opt in book private coaching sessions with the same trusted coach.

3. HR stays informed, never intrusive.

Each quarter you get a one-page summary of what’s coming up across the team, with Rosa’s suggestions. Never names. Never personal details.

What your people work on

  • Hitting goals and KPIs
  • Peak performance and next-level growth
  • Communication and difficult conversations
  • Stress, overwhelm and work-life harmony
  • Confidence, influence and leading others

What changes for your company

  • Your people grow faster, and it shows in their results
  • Problems get handled before they become resignations
  • Managers get their time back, because they stop being coach, therapist and referee
  • Your high performers stay
  • A benefit that helps you hire and keep great people

What your HR leader gets

  • A 30-minute session with Rosa every month, because the people who support everyone need support too
  • The Leadership Score every quarter for each participant, with a Before and After Report so you can track your team’s growth all year
  • Available in English or Spanish

A partnership, not a new hire

You don’t need to post a job, run interviews or add a salary and benefits. Rosa becomes your in-house coach on contract: part of your team’s week, outside your chain of command, and flexible as you grow. Monthly partnership or longer-term contract, starting this month.

Why this works when training doesn’t

Training fades in a week. Coaching apps give you a different stranger every time. EAP is for crisis, not performance. This is one trusted coach who knows your people and your culture, and is outside your chain of command, so people tell the truth.

Rosa partners with a limited number of companies at a time.

Book a 15-Minute Call

No commitment. You’ll get a custom proposal within 48 hours.

Case Studies

Real people. Real change.

S.H., Head of Wine Planning and Operations, Direct Wines

“A steadier, less anxious approach.”

I feel I am more composed and better prepared for one on one sessions. I feel more empowered to allow my reports to work with greater independence.

“More likely to take challenges in my stride rather than let them blow up.”

J.O., Senior Director of Propositions and Innovation, Direct Wines

“A trusted thought partner while navigating a growing team.”

I’ve grown more comfortable delegating and setting clear expectations. Coaching has also helped me lead through change with steadiness, even as my responsibilities have continued to expand.

“Coaching is an incredibly valuable investment in your leadership and growth.”

V.B., Senior Media Planner, Good Apple

“I feel more confident after each call.”

I am able to take the tools you taught me and apply them not only in my career when leading my team, but also within my personal life as well.

“It has helped me be kinder to myself and overall more confident as well.”

“Working with you has unlocked so many breakthroughs, revelations, and realizations that have shed light on the limiting beliefs, habits and ways of thinking that have held me back from achieving my greatest potential.”

A.B. · Media Supervisor, Good Apple

“Rosa is a patient encourager with great insights as to how and why we react as we do.”

S.H. · Head of Wine Planning and Operations, Direct Wines

“The most significant transformation I received was re-setting my balance between personal and professional life. Since starting our coaching relationship I achieved 50% of my annual goals within just 3 months.”

H.R. · Senior Manager, Deloitte Dubai
Book a 15-Minute Call

How It Works

A clear process from first call to measurable change.

1

Book a 15-Minute Call

A short call. We look at your people, your goals, and where leadership is stalling.

2

Find the gaps

Together we identify which skills and behaviours need attention: communication, accountability, decision-making or presence.

3

Get your proposal

Within 48 hours, Rosa sends a proposal: who is involved, what the sessions cover, and what success looks like.

4

Measure and expand

Quarterly summaries along the way. See what’s changing, then decide whether to expand, add group trainings, workshops or speaking.

Book a 15-Minute Call

Every program is built around your company. Works for small businesses and large teams.

Other Ways to Work Together

Other ways to work together.

1:1 Private Coaching

Leadership Coaching for Individuals

Private, one-on-one sessions for anyone on your team, from new hires and individual contributors to managers, directors and executives. Each engagement starts with a DISC assessment to understand how they communicate and lead under pressure.

  • Private one-on-one sessions
  • DISC behavioral assessment included
  • Communication and presence
  • Accountability and decision-making
  • Available in English or Spanish

Group Programs

Leadership Development & Team Workshops

Structured programs for leadership cohorts, teams at any level, and groups where consistent habits need to be built across the organization, not just for one person at a time.

  • Group DISC facilitation
  • Leadership workshops and training
  • Communication and influence
  • Handling difficult conversations
  • On-site or virtual

Speaking

Leadership Keynotes & Workshops

Rosa speaks on leadership, DISC behavioral styles, and what it means to lead your life with intention. Practical, direct and grounded in 25+ years of coaching experience.

  • Keynote presentations
  • Interactive workshops
  • DISC for teams and groups
  • In-person or virtual, in English or Spanish

Separate from Coaching · Monthly Retainer

Leadership & Talent Advisory

This is not coaching for your people. It is Rosa on your side, as your advisor. For HR leaders and founders who want a senior partner to think with, build with, and consult any time.

  • Advise on talent, culture and leadership strategy
  • Design and deliver training for your teams
  • Consult on any leadership or people challenge
  • Help attract and retain top talent
  • Works alongside your HR team, not instead of it

Because I’m outside your organization, people say what’s really going on. The conversations that matter most, about performance, frustration, blind spots and gaps, happen when there is no risk in saying what is true.

Book a 15-Minute Call

Questions

What HR leaders and business owners ask first.

Will our people actually use it?

Yes. Every person starts with a DISC Session, so they meet Rosa first. Booking is private and simple, and nobody has to go through their manager.

How do we see the impact?

Each quarter, people fill out a short check-in about their growth, and you get a one-page team summary of themes with Rosa’s suggestions. You see what’s changing across the team without ever seeing private conversations.

How much does it cost?

Every partnership is built around your team size and goals. Book a 15-Minute Call and you’ll get a custom proposal within 48 hours.

Is this confidential?

Yes. What people share in coaching stays between them and Rosa. HR gets a one-page quarterly summary of team themes. Never names, never personal details.

How is this different from training?

Training fades in a week. Coaching builds habits over months, one person at a time, with the same trusted coach.

Do you work with small businesses?

Yes. Every partnership is built around your company, from small businesses to large teams.

How long does a program run?

A monthly partnership or a longer-term contract. We decide what fits after our call.

How quickly can we start?

You’ll get a custom proposal within 48 hours of our call, and we can start this month.

Do you offer DISC for teams?

Yes. Every person starts with a DISC Session and keeps their report, and group DISC Sessions are available for teams.

Does coaching guarantee my people will stay?

No coach can promise that. What coaching does is help your people make clear, grounded decisions instead of emotional ones. Most people recommit and grow. If someone realizes the role isn’t the right fit, they leave on good terms, and that’s better for your team too. Coaching supports clear decision-making. It does not guarantee that any employee will stay with the company.

Two tools. One clear picture.

Everything you need to know your team.

Rosa’s own coaching tool. New, and free during our pilot.

The Leadership Score

What it shows

Where your leaders are leading and where they’re not, across 8 areas of life. Their leadership archetype. Their blind spots. Their Leadership Score out of 100.

Take the Free Leadership Score →

A widely used, research-based behavioral assessment.

DISC

What it shows

How someone is wired: how they behave, how they communicate with others, and their blind spots. Every partnership starts here so your whole team speaks the same language.

Book a DISC Session for your team →

Choose what fits your team.

Start with the free Leadership Score to see where your team is. Add DISC for a deeper behavioral picture. Use both when you want to know your people inside and out before the first coaching session.

Neither is a test. No one passes or fails. They’re a way to look more closely at what’s really going on.

Free Tools

Start here before we talk.

Not ready to call yet? These will show you what leadership development could look like for your team.

Rosa's own coaching tool. New, and free during our pilot.

Leadership Score

What it shows

Where your leaders are strong, where they have gaps, and what may be holding them back. About 25 minutes. Free and private.

Take the Assessment →

A widely used, research-based behavioral assessment.

DISC for Teams

What it shows

How you’re wired: how you behave, how you communicate with others, and your blind spots. Every partnership with Rosa starts here, so your whole team speaks the same language.

Book a DISC Session →

15-Minute Call

See if this fits your team.

A short call with no commitment. You share what is happening with your people, Rosa listens and asks a few questions, and you leave with a clear picture of what is possible.

Book a Free Call →

Let’s Talk

Tell me about your team.

The fastest way to start is a 15-Minute Call. You’ll get a custom proposal within 48 hours. No commitment.

Book a 15-Minute Call

Can’t find a time that works? Email rosa@rosaosterling.com with 3 dates and Rosa will confirm within 48 hours.

Emailrosa@rosaosterling.com

Prefer to write? Send a note.

Book a 15-Minute Call