• 25+ Years
  • 7,500+ Coaching hours
  • Former Results Coach, Robbins Research International
  • ICF Member
  • Certified DISC Facilitator
  • English & Spanish

Does this sound like you?

You know what you should be doing. Something keeps getting in the way.

01

You’re succeeding on paper.

But you’re running on autopilot. Saying yes when you mean no, and tired of carrying everything.

02

You know what you should be doing.

And you keep putting it off. You react in moments you later regret, and that has a cost.

03

You want to be taken seriously.

To be heard at work and at home. You want to influence without raising your voice.

04

You’ve read the books.

Done the courses. The habits don’t last. You want a coach who will tell you the truth.

05

Something changed.

A new role, a relationship ending, an empty house. You want to lead this next chapter, not just react to it.

06

You’re doing all of it.

Work, family, health, money. Something always slips. Usually the parts that matter most.

Step 1 · The Leadership Score

Are you leading your life, or is it leading you?

Find out how you lead, where your biggest gap is, and the pattern that might be holding you back.

  • Your leadership archetype: who you are at your best, and under pressure
  • Your top 3 areas of life to focus on
  • Your #1 blind spot, with a tip and a question to work on it
  • Your Leadership Score out of 100
Take the Free Leadership Score

Free · About 25 minutes · Private. Taken by leaders, teams and families.

Example result

72/100

Finding Your Footing

Some areas are on track. Others may be running on autopilot.


How you lead

The Builder, with a pull toward The Visionary. Builders lead by getting things done.

Top 3 focus areas

Energy & healthCareer & moneyLove & connection

Your #1 blind spot

Saying yes when you mean no

What drives you

AchievementConnection

What Clients Say

Real results from real work.

Individual

“Rosa was an important catalyst in this process. When she asked me ‘what might get in the way’ of this dream, that helped me see clearly old patterns of sabotage that I was able to navigate around with a new and different plan of support. So key in the accomplishment of this dream!”

Mat Boggs · Relationship coach and author of Cracking The Man Code

Company

“The most significant transformation I received was reestablishing my work-life balance. Since we started our coaching relationship, I accomplished 50% of my annual goals in just 3 months.”

H.R. · Senior Manager, Deloitte Dubai

“Rosa is full of love and support and calls me out on my own patterns, and that is exactly what I need. She is amazing and I am so fortunate to have her in my corner.”

M.L. · Real Estate Broker and Owner

“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
Rosa Osterling

About Rosa

25 years of real coaching work.

17 years leading sales operations for Robert Kiyosaki’s Rich Dad Education, then selected as a Results Coach for the Tony Robbins organization, one of 29 coaches hired from more than 1,200 applicants. Her coaching draws on Tony Robbins’ strategy tools and the somatic approach of Alyssa Nobriga, founder of the Institute for Coaching Mastery.

Rosa has worked with leaders at Deloitte, Itaú, Direct Wines and Good Apple. She coaches privately, one on one, from anywhere in the world. She built this career while raising two boys on her own.

Leadership is how you live your life. It’s not something you clock out of.

Read Rosa’s full story →

Questions

What people ask first.

Is the Kickstart Session a sales call?

No. You’ll know other options exist, and I’ll email them afterward, but there is no pitch on the call.

Is this therapy?

No. This is forward movement: where you are, where you want to be, and your next move.

Is it confidential?

Yes. In company programs, HR gets a one-page summary of team themes. Never names, and never what you talk about.

I’m not a manager. Is this for me?

Yes. Leadership is how you run your life, with or without a title.

Who is the Leadership Score for?

Anyone 18 or older. Your results are private to you.

How much does it cost?

The Leadership Score is free. First-time clients can book a 30-minute Kickstart Session for 57 USD. The DISC Session is 297 USD and is applied to the yearly coaching package if you continue. Company programs are custom, so let’s talk and I’ll send a proposal.

What happens after I book?

You pick your time right away. You’ll get a confirmation email and a few short questions so we can make the most of our time together.

Coming soon

The 90-Day Success Planner.

You can do it all, just not all at once.

Your calendar syncs. Your apps remind you. Your automations run. And still, the things that matter most drift. Because anything digital is one tap from invisible. You can click away from a notification. You cannot unsee what is written in front of you.

Pen on paper is different. You see it. You own it. No swipe to dismiss, no tab to close. When your hours are on paper, you stop pretending there are more of them than there are.

Rosa built this planner while running her own business, wearing every hat, and still showing up for her kids as a single mother. Because when you are doing all of it, something always starts to slip. Usually the parts of life that matter most. This planner keeps that from happening.

  • Plan your week a week ahead, on paper
  • Know your top 3 priorities for the day and the week
  • Give every task its own block of time
  • See how far you’ve come in 90 days

Built for the ones who are both lion and lioness, strong enough to lead, present enough to live.

Waitlist members get 10% off at launch. By joining you agree to receive occasional emails from Rosa. Unsubscribe anytime.

The 90-Day Success Planner by Rosa Osterling, open weekly spread and black cover with gold lion emblem

Lead Your Life Circle

You lead everyone. Who's leading you?

Free weekly voice notes. Confidential. Doors open December 7.

Learn More →

Let’s Connect

No pitch. No pressure. Just clarity.

Choose your path below and Rosa will have everything she needs to reply with something useful.

Private · ConfidentialRosa responds within 24 hours
Emailrosa@rosaosterling.com