About Coaching Breaking Asphalt The Steeper Path Contact Get your Alignment Score

Some people arrive at coaching knowing exactly what needs to change. Others arrive with a feeling they can't name yet. Both are the right starting point.

What they share is this: they're good at what they do, they've done the things they were supposed to do, and something important still isn't working. The life they're living is the life they could live. Not the one they should.

That gap is what we work on.

We start with the gap. Then we build a path across it.

Where are you now. Where do you want to be. What's standing between the two. Everything else follows from those three things, including how long we work together, how often we meet, and what we focus on.

Some people get to where they want to go in as little as three months. Others have worked with me for three years. My minimum coaching commitment is three months and twelve sessions because real change takes time to take root. After that we work together at whatever pace makes sense for you and the work you're doing.

Most people start at four sessions a month for the first three months, then move to two once they have momentum. We set a goal, work toward it together, and keep adjusting based on what's actually happening.

The goal isn't a better version of the career you already have. It's the one that actually fits who you are.

I work with a small number of people at a time.

Not everyone is a good match for what I do and I'll tell you honestly if I don't think I'm the right person for where you are or where you want to go.

Most of my clients fall into one of two camps. The first are senior leaders and high performers who are successful by conventional measures and privately aware that something important isn't working in their career, their leadership, or their relationship to the work itself. The second are leaders in product and engineering who are performing well and want to go further, building better teams, making better decisions, and doing it in a way that's actually sustainable.

Both start in the same place. A clear-eyed look at who you actually are and what alignment with that looks like in practice.

If either description sounds like you, we should talk.

The work varies. The approach doesn't.

Some clients come in with a specific challenge: a transition, a promotion, a decision they can't make. Others come in with a feeling they can't name yet. Both are valid starting points.

What doesn't vary is the approach. We work from who you actually are, not who the role requires you to be. The SEPARATE Framework gives us a shared language for what alignment looks like, what's getting in the way of it, and a path toward building a career and life that actually fits.

Coaching with me isn't about quick hacks.
It's about lasting alignment.

Lenn provides me a safe space to continuously evaluate my journey and ensure it aligns with my most authentic self. He gently reroutes me when I get lost, always graciously and patiently, helping me pivot away from behaviors leading to dead ends. Lenn is not what I expected to find, yet exactly what I needed.

Chelsea R.
USMC Veteran · Cisco

He doesn't just explain a framework or way to think, but creates the forum for his clients to reflect and come up with what's best for them. This is what is so special about him.

Ranjani C.
Senior Leader
Lenn Pryor
A few spots open

If this sounds like the kind of coaching you've been looking for, let's find out if we're a good match.

The first conversation is a no-obligation call to see if working together makes sense. I'll be direct about whether I think I can help.