Learning with Experience, LLC

Our Services &
How We Work

We work with individual leaders, intact teams, and whole departments — from early-stage startups to global Fortune 50 companies. Every engagement is grounded in experiential learning that develops Leadership EQ and builds trust and collaboration across functions.

Jump to: Executive Coaching Team Development Leadership Training Facilitated Dialogue Cross-Functional Program
01
Individual Work

Executive & Leadership
Coaching

1:1 partnership for leaders who are ready to do something about the habits, patterns or blind spots that are limiting their effectiveness, or who want to expand their capacity for a larger leadership role.

We create a space for honest self-reflection, powerful insight, and a drive to action. Engagements are fully customized. Some leaders want to develop greater self-management under pressure; others need help building executive presence, navigating a high-stakes transition, or influencing their cross-functional colleagues.

Leadership EQ Influence Without Authority
Schedule a Consultation
Case Examples
Startup CEO

COO to CEO

A first-time CEO found her authentic leadership voice, made tough decisions with confidence, and successfully negotiated with a demanding board — all while discovering the joy of the role.

Finance SVP

Exerting more influence on executive decisions

A highly valued, long-tenure SVP wanted a stronger voice in shaping the company's future direction. He learned to more effectively navigate uncomfortable conversations with strong personalities, which resulted in commanding even more respect and influence on the team.

Construction VP

From intimidating to inspiring

A high-performing VP's response to pressure was alienating his colleagues. He learned to slow down, manage frustration in real time, and build the working relationships his department actually needed.

02
Team Work

Team
Development

This is not a team-building event. It's a dedicated 6–12 month engagement that adjusts how the team interacts and functions while they do actual work in real time — so it never feels like a detour or disconnected from the business.

We work with two kinds of teams: those rebuilding trust after something has broken down, and solid teams who want to go from good to genuinely high-performing. Both require real commitment. Both deliver results that last.

Our team coaching is grounded in the most rigorously researched frameworks in the field, including Harvard's "Six Team Conditions" and David Kantor's "Structural Dynamics" — as well as Team Coaching International's user-friendly 14 team performance indicators.

Sustainable High Performance Trust & Collaboration
Talk to Us About Team Development
Case Examples
Data Analytics Team

Elevating the team's internal brand

A data analytics team wanted to be seen and utilized as a more strategic partner to other functions across the business. Coaching helped them align around mission-critical priorities and achieve greater cross-departmental influence.

Executive Leadership Team

From conflict to alignment

An executive leadership team was strained by personal conflicts and the bumpy incorporation of a new COO — and their dead-end meetings often led to divisive 1:1 hallway side deals. With live coaching, they engaged in more honest, effective and efficient team sessions that helped them successfully mobilize and navigate existential post-Covid challenges to the business.

Sales vs. Engineering

Passionate but polarizing

An enthusiastic SVP's communication style was alienating teammates in CX and Engineering. During cross-departmental team coaching, he learned to moderate his style and forge a connection with more introverted and analytical team members — in a way that was still true to himself and far more inspiring to them.

I now see with more clarity the impact I have in different contexts. I had no idea I'd been alienating half the team. As a result of the program, my team members belong to a culture they know values who they are and what they have to offer.
Senior Leader
T-Group Program Graduate
03
Training & Workshops

Experiential Leadership
Training

Our workshops are built around engagement, not presentation. Participants don't just learn about communication, negotiation, or Leadership EQ — they practice it, receive feedback, and leave with skills they will use the next day.

a) Leadership EQ & Communication Skills

Custom programs that develop the interpersonal skills leaders need most — feedback, productive conflict, communication across difference, high-stakes conversations, influence without authority, and more. One example: Interpersonal Skills for High-Potential Engineers, a program for technically excellent leaders moving into broader roles.

b) T-Groups for Leaders

T-Groups (or "training groups") are intensive experiential programs rooted in the "Interpersonal Dynamics" curriculum made famous at Stanford, Yale, and Chicago Booth MBA programs. Participants develop self-awareness, candor, trust, and the ability to give and receive feedback in a setting specifically designed to accelerate real learning.

These are among the most powerful Leadership EQ development experiences available — not because of what is taught, but because of what is practiced and felt.

Feedback & Communication Experiential T-Groups
Discuss a Program
Case Example
High-Potential Engineers Program

Building the human skills to match the technical ones

A recurring program developed for technically excellent engineers transitioning into broader leadership roles. Participants work through real interpersonal dynamics — how they communicate under pressure, how they give and receive feedback, and how their default patterns affect the people around them.

About T-Groups

Why they work

T-Groups create a "here and now" learning environment — participants practice with each other in real time, receiving immediate feedback on their actual impact. The result is the kind of change that doesn't happen in a lecture hall or from a book.

I'm less flustered by emotions, just days after the workshop, because I'm better able to express myself and listen with genuine curiosity. That's a lot of progress for 2.5 days.
Program Participant — Leadership EQ Weekend
Learning with Jana is a profound and powerful experience. She creates safety by modeling and setting norms that allow people to share honestly without fear. Jana is one of the most skillful facilitators I know.
Tish Robinson, PhD
Faculty, Hitotsubashi University of Business
04
Facilitation

Facilitated
Dialogue

Sometimes a team needs a structured space to have a specific conversation they haven't been able to have on their own. We design and facilitate those sessions — bringing the skill and neutrality to make hard conversations productive.

Align Around a Critical Task

For teams that need to clarify priorities, resolve a strategic impasse, or make a high-stakes decision together. We create the structure that lets the real thinking happen.

Navigate the Elephant in the Room

For teams where an unaddressed dynamic — a conflict, a breakdown in trust, or a long-avoided conversation — is getting in the way of performance and relationships.

Peer Wisdom and Support

Tap into peer connections with genuine accountability and candor. Includes executive women's gatherings inspired by Jana's work with Stanford GSB's Alumnae Circles, CHIEF, and her women's professional coaching network.

Team Offsites Strategic Dialogue Peer Advisory Women's Circles
Let's Talk
Case Examples
20-Person Engineering Team

Overnight transformation

A team needed to surface a high-stakes conversation about troubling lags and omissions in their communication. Result: an immediate increase in honest and proactive information-sharing, starting the very next day.

Co-Founder Pair

Rebuilding a partnership under pressure

A CEO and CTO's working relationship had fractured under the pressure of early-stage growth. Through facilitated coaching, they repaired trust and developed the tools to navigate their Series A and B, a global pandemic, and tightening investor conditions — together.

CMO Women's Leadership Circle

Finding her voice at the table

The only woman on an executive team needed to establish greater influence with a CEO who wasn't influenced by her style. Peer group coaching helped her develop a strategy — and the confidence to show up differently.

As a direct result of the 2-hour workshop, we showed up with greater transparency and information sharing, starting the very next day. It was an overnight transformation! That alone was worth the money.
Startup Co-Founder
Flagship Program

Cross-Functional Collaboration
& Negotiation

Our newest keystone program is distinctive because it develops all three of the capacities in an integrated manner: it builds Leadership EQ, it strengthens team effectiveness, and it directly solves the cross-functional communication and negotiation challenges that slow organizations down.

When departments don't communicate or negotiate effectively, projects stall — sometimes for years. This workshop uses real work scenarios so the change happens in the room, not just in theory.

1
Build and strengthen 1:1 cross-functional relationships
2
Practice listening and asking more effective questions
3
Connect individuals and the group to the shared "why"
4
Practice 3-step advocacy and conduct real negotiations
5
Distinguish between expectations and clear agreements
6
Surface cross-functional needs, dependencies and requests

"In 30 minutes we fixed something that's been plaguing us for 2 years." —Commercial Real Estate SVP

Participant Ratings

Overall usefulness — 10-point scale (36 respondents)

C-Suite & VP 8.4 /10
Managers & Directors 8.5 /10
Breakout sessions on Inquiry, Advocacy & Negotiation received a median score of 9.0 /10 from C-Suite, VPs, Managers and Directors.

Custom Programs Available

Can be as large as a 2–3 day all-hands transformative event to smaller skill-development modules, either in person or over Zoom.

Bring This to Your Team →

Not sure where to start?
Let's have a conversation.

Schedule a Consultation

jana@learningwithexperience.com  ·  (650) 291-1065

© 2026 Learning with Experience, LLC. All rights reserved. Chicagoland  ·  San Francisco Bay Area