Grounded Product Leadership for When the Stakes Get Higher

Grounded Product Leadership for When the Stakes Get Higher

Offered by Diana L.

Executive Leadership & Product Coach | x-Amazon, Box, Iterable, Apollo

Berkeley Executive Coaching Institute (BECI) Logo

Studied at Berkeley Executive Coaching Institute (BECI)

Iterable Logo

Worked at Iterable

Package Description:

The Ground Product Leader who wins as the stakes get higher. I coach builders as the stakes get higher. Grounded. Clear. Intentional. You've mastered the climb to get here. But you've reached an inflection point, and the skills that got you this far, the grit, the constant execution, the shipping, are not the ones that carry you through what's next. Where you're headed asks for a version of you that hasn't fully emerged yet. In a world racing toward AI automation, your humanity is your edge. Your discernment, empathy, presence, and imagination are uniquely yours, and they are the building blocks of the leadership that will set you apart. At this altitude you don't need someone to tell you what to do. You need a creative think-tank partner and a steady sounding board who has sat in the product leader's seat, sees the patterns you can't, and is in it with you. This is not a fixed curriculum. In our discovery session we shape what serves you: pure coaching, a mix of coaching and advisory, or work grounded in product craft and the Catalyst Framework™ when you want more rigor. You set the direction. I bring two decades of product leadership to the other side of the table. I'm in the arena with: The Founder building a product org from scratch. The Leader betting on themselves for the first time. The Director owning double the scope without a playbook. The VP leading leaders, where the politics got louder and the product got harder to protect. The PM moving from shipping to people leadership, or navigating their most complex challenge yet. The Woman in Tech, across orgs and levels, ready to claim her narrative and rise boldly into her next chapter. I'm especially drawn to the underestimated. If you've spent your career in rooms that weren't built for you, your difference is not a deficit. It is the thing that makes your leadership un-copyable. We anchor into your own power so you can meet this moment on your own terms. What's included: * Gallup CliftonStrengths assessment plus a dedicated session to root your growth in the data of your own natural strengths and translate them into a leadership style that finally feels like yours * 6 coaching sessions where you bring what is most pressing, a product strategy call, a stakeholder dynamic, a team you are leading, an AI-first bet you are weighing, and think it through with a partner who understands the work and can ground it in product craft when you want it * 2 async document reviews. Send your strategy doc, PRD, deck, or narrative for my async review. * 2 follow-up 30-minute sessions to discuss feedback and how to sharpen the next draft. You'll leave with a clearer leadership identity, sharper instincts, and artifacts that finally reflect how good you actually are. Kind enough to tell you the truth. Tough enough to walk through it with you. Grounded in 20+ years scaling enterprise B2B SaaS.


What you'll get from this package

Your full Gallup CliftonStrengths report, a personalized profile you keep and return to, decoded into how it shows up in the way you lead

A leadership style that finally feels like yours, rooted in your natural strengths rather than the grind that got you here

Real progress on the highest-stakes calls you're carrying right now thought through with a partner who has sat in the seat

Sharper instincts for the decisions that define the next level, and the clarity to know what this chapter actually requires of you

A clearer read on the patterns you couldn't see alone, and the steadiness to lead through them instead of reacting to them

Two of your real artifacts (a strategy doc, PRD, or narrative) sharpened based on constructive feedback from someone who has been there and is in your corner.


Additional details

Coaching delivered via live sessions.

I coach the way I led product for twenty years: kind enough to tell you the truth, tough enough to walk through it with you. You won't get advice from the sidelines. You'll get a partner who has sat in the seat, sees the patterns you can't, and asks the questions that create clarity instead of handing you answers. Full presence and real candor in the same room. I start with your strengths, not your gaps. As a Gallup CliftonStrengths and BECI-certified coach who scaled product at Amazon, Box, Iterable, and Apollo, I build from what's already powerful in you, because the leader this next chapter needs is made from your real talents, not someone else's playbook. You set the direction every session. I hold the human work and the product work at once, because at this level they were never separate.

Refund Policy

Services included:

Conflict Resolution

Ethical Leadership

Problem Solving

Emotional Intelligence

Coaching and Mentoring

Time Management

Innovation and Creativity

AI Strategy

Team AI Upskilling


More packages from Diana

Custom hourly · $400/hr

Get help with Conflict Resolution, Ethical Leadership, and .

View all of Diana’s categories


Diana L.

Offered by Diana L.

Joined March 2026

Executive Leadership & Product Coach | x-Amazon, Box, Iterable, Apollo

I don’t coach from the sidelines. I coach from the seat. With 20+ years leading product teams at Amazon, Box, Iterable, and Apollo.io, I’ve lived through the hypergrowth, the AI shifts, and high-stakes executive decisioning. I’m a UC Berkeley (BECI) Certified Executive Coach and a Gallup Certified CliftonStrengths Coach, but my real methodology was forged while building organizations from $42M to $225M+ ARR. My Philosophy: Kind but Tough. Most leaders think they have to choose between empathy and accountability. That is a myth that kills performance. I help you integrate a Radical Heart with a Relentless Edge. Kindness is the clarity to tell the truth when everything is chaos. Toughness is the conviction to hold the standard for the outcomes that matter. The Approach: I don’t deal in leadership platitudes. Using Gallup Strengths-based frameworks, we decode how you are specifically wired to lead so you can stop chasing an archetype and start operating from your Irreplaceable Human Edge: Discernment, Empathy, Presence, and Imagination. Who I work with: Product, Engineering, Design leaders navigating career inflection points, AI transformation, scale-up friction, or other critical moments where you need a sounding board and thought partner. I'm also passionate about working with Women-in-Tech and Underestimated Leaders across all disciplines. If you want a coach who is kind enough to tell you the truth and tough enough to walk through it with you, let’s talk.

Coaches professionally

Experience level: Executive

60+ people coached for Leadership Coaching

$4,000

 
Sign in
Free events
Programs
    Grounded Product Leadership for When the Stakes Get Higher by Diana L. | Leland