Your one thing is your most valuable opportunity.

What’s your one thing?

Every leader has one. It’s the decision, the conversation, the relationship that has to move and just won’t. Your team softens what they tell you. Your board wants answers, not your doubts. So it sits with you alone, at 2am, with no one to test it against.

We get your one thing moving — and keep it moving.

Tell us your one thing See if it fits

A leader walking alone through morning light

THE CHALLENGE

You’re probably not here because something failed.

You’re here because the skills that made you the best in the room — closing the deal, fixing the problem yourself — are now the ones keeping you from leading the people who should be doing it.

Understanding your one thing was never the blocker. Moving it is.

THE DISCIPLINE

We’re expert at one thing: getting what you’re stuck on moving — and keeping it moving.

The Upside approach draws on executive coaching, systemic supervision, and behavior modification — built on decades of combined experience leading before we coached. We’ll show you what you’re too close to see, find the one lever that actually moves your one thing, and make sure every session ends with something moved, not just understood. None of it is a framework we drop on top of you. It’s built on the strengths and values you already lead with.

Typical executive coaching

UPSIDE

Focus

Treats you as an individual to develop, lifted out of the system that is actually producing the problem.

Puts you back inside the system you operate in, which is where the problem and the way through both sit.

Method

The coach keeps a careful distance and waits for you to arrive at your own answers.

We act as a capable peer in the practice ring with you, there to make you tougher to beat.

Experience

Whatever experience the coach carries, the method keeps it out of the room.

We bring our professional experience straight into the work and put it to use on your problem.

Start

The engagement eases in with discovery and a distant goal before anything real gets touched.

We start on the material problem in front of you now and save the deeper groundwork for later.

Outcome

Skills limited to the goal you declared in discovery.

You leave with development that transforms how you make decisions and trust yourself, to keep and carry into whatever comes next.

HOW WE ENGAGE

It moves on day one. Then we make that repeatable.

01 · Fit

An initial call.

You tell us your one thing — the thing you haven't said to anyone. We tell you straight whether we can move it, and if we can't, who can.

Most people are wondering if it's okay to talk about their one thing with someone they don't already pay. It is.

02 · Scope

Three months, six sessions.

The first session gets your one thing moving. Not planned, not framed — moving. The next five keep it going and turn that momentum onto the next thing you've been carrying, and the one behind that.

It feels like the first time in a long time, if ever, to be the one being thought about, instead of doing the thinking for everyone else.

03 · Cadence

One hour, every two weeks.

With you or your leadership group. Partner-team alignments and senior leadership cohorts are designed in close coordination with existing advisors or internal stakeholders.

By the second month, most clients say it's the hour where the week stops spinning and they work out what actually matters.

04 · Extension

Move up and move on.

By session six you've moved three or four things you'd been stuck on, and you've come to learn how it's done. Some leaders take it from there. Some want us in the room for the next set.

Either way, you leave with momentum you didn't have. The honest assessment matters more than the renewal.

✻ Step 01No commitment required. The first conversation is exactly that — a conversation.Begin a fit call

WHO WE ARE

We’re called Upside Partners because the upside is almost always trapped in the thing you can’t move. Your one thing isn’t your problem, it’s your most valuable opportunity, sitting still because no one’s helped you get at it.

Founder & Coach

Dave O'Connor

Dave spent two decades leading inside professional services, startups and media companies before he began coaching. He has coached clients in the NFL, national politics, creative agencies, healthcare systems and film studios. He learned firsthand what it costs to lead without anyone to think with, and built Upside to be the room he wished he'd had. He still keeps a thinking partner of his own, because no one should have to make the big calls alone. He lives in Lake Forest, Illinois with his wife Meg and their two Border Terriers, Fred and Mary.

"When I first launched my own coaching business, Dave entrusted me with navigating some deeply consequential topics with him. The qualities that made him a pleasure to work with as a client are why I love working with him as a partner — relentless curiosity, emotional honesty, and the kind of creativity that inspires action." — Mike Tamayo

Lead Practitioner

Mike Tamayo

Mike spent 28 years inside the tech industry, first as an engineer, then as the kind of leader who realized along the way that the technical answers had stopped being the hard part. Initially applying a coaching mindset within the companies where he worked, he eventually started his own business to help leaders examine the deeper patterns, motivations, and values shaping how they think, decide, and influence others. His clients include senior executives, founders, and emerging leaders across a wide range of industries — people who want a place to think honestly about the challenges they face and the leadership they want to offer. Mike lives in Denver, Colorado with his wife and two cats.

"I met Mike through a mutual friend and he became an essential part of a couple major transitions I went through as my coach. I love working with Mike because he evokes in me truths I can spend weeks if not months trying to find alone, and then I actually get moving on them." — Dave O'Connor

Name your one thing.

No deck, no prep. Tell us the decision or the conversation you can’t stop thinking about, and we’ll tell you honestly whether we can move it.

Begin a conversation