Your one thing is your most valuable opportunity.

Every leader has one. The decision that defines the next chapter. The conversation that changes a partnership. The plan that’s bigger than anything you’ve run before. Not a crisis — a moment. The kind you want to walk into prepared.

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

Typical executive coaching abides by the principle: coach the person, not the problem. We take a different route. We coach your one thing, and you transform in the process.

Ask yourself to name your one thing and you’ll come up with one of three answers.

Something to deliver.
The initiative with your name on it: an AI rollout you’re still learning yourself, a new executive team that has yet to gel, a plan bigger than anything you’ve run before.
Something to uphold.
A value you won’t trade away to get it done, like spending entrusted capital as carefully as your own, or leading in your own voice in a role someone else defined.
Something to leave behind.
The impact that outlasts this initiative: the careers built on your team, the pocket of strong work that holds inside a system you can’t control.

Most leaders are carrying all three.

You measure yourself by two questions:

Did I do what I said I would do?
Did the people around me also do well?

Consultants

Know your business.

Hand you answers.

[ Upside ]

Works in the middle.

Because the middle is where the work gets done.

Coaches

Work the human side.

Hand you questions.

We work alongside you while you tackle your one thing.

We get into your work with you, sometimes looking at the details, other times stepping back to connect the dots and make sure that your direction upholds what is most important to you.

We led before we coached, so we help you navigate both your business mandate and the human dynamics that come along with it.

We don’t promise that everything will get easier. The hard parts tend to stay hard, but your one thing gets moving, you get clearer about what matters, and you’re steadier through the uncomfortable stretches.

Your one thing gets moving. You get clearer and steadier.
That’s the upside we’re named for.

Two ways to work with us.

Two coaches, one project.

Approximately three months.

One of us leads the conversation while the other listens for what goes unsaid. It includes sessions with you, confidential conversations with stakeholders we choose together, a facilitated group dialogue, and a written brief with recommendations.

One coach, one quarter.

Six 60-minute sessions.

A private place to think through a hard stretch of work and test decisions before you make them.

Both begin with the same thirty-minute conversation.

Begin a conversation

Your coaches led before they coached, and continue to be supervised in their own work.

Founder & Practitioner

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.

Certifications: PCC (ICF)

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.

Certifications: PCC (ICF), CPCC (CTI)

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.