Sider Road · 1:1 Strategy Hour
Office Hours with
Jocelyn Greenky
A business strategy office hours session is one focused hour, one-on-one, for founders and executives staring down a decision they can't get wrong. Unfiltered, strategic, and grounded in 40+ years of doing the work — so you leave with a clear next move, not more to think about.
"You already know what's wrong. You just need someone with nothing to lose telling you the truth — and what to do about it."
— Jocelyn Greenky, MBA
Why this exists
The people around you are too close to tell you.
Your team has a stake in your answer. Your board has an agenda. Your family has history. When the decision is big — a division to cut, a partner to confront, a number that isn't adding up — you need a voice that owes nothing to the outcome.
Office Hours is that voice. One hour, just the two of you, where the only goal is getting you to the truth and the next step faster than you'd get there alone.
Is this for you?
Who books an hour — and what they bring to it.
Who it's for
- Founders and CEOs facing a call they can't un-make
- Executives who've run out of people they can be fully honest with
- Family business leaders where the personal and the operational collide
- Anyone who wants a fast, expert, outside read — not a six-month engagement
What people bring
- A restructuring or cut they keep postponing
- A personnel or partner problem that's gone sideways
- A pivot, raise, or exit they need to pressure-test
- A gut feeling they need validated — or challenged — before they act
How the hour works
How your business strategy office hours work.
Let's be clear
What the hour is — and what it isn't.
What it isn't
- A pep talk or an ego-stroke — you don't have time for either
- A generic coaching framework that applies to everyone and no one
- A long-term retainer you have to commit to before you see value
- A meeting you'll leave with more questions than you walked in with
What it is
- An unfiltered, confidential read from someone who's seen your situation before
- Decades of buy-side, sell-side, and operating experience pointed at your problem
- A single hour you can book exactly when the decision lands on your desk
- Dry humor included — because the truth goes down easier human
The outcome
What you leave the hour with.
Your hour is with
Jocelyn Greenky.
Across 40+ years, Jocelyn has been a buyer, a seller, an entrepreneur, and a corporate director. There are few decisions she hasn't sat inside — and few she'll let you talk yourself out of facing.
An MBA and adjunct professor, she combines hard-won judgment with sharp, dry wit to find your pain points fast and hand you a path forward that actually works. She runs Sider Road, her advisory practice, alongside her daughter.
Before you book
Frequently asked questions.
How long is the session, and how is it delivered?
What kinds of problems is this best for?
Is it really confidential?
Do I need to prepare anything?
What if my real problem turns out to be something else?
Can a single hour really make a difference?
What happens if I need ongoing help?
Need more than an hour?
Other ways to work with Jocelyn.
The strategy hour is the fastest way in. When the situation calls for more, these go deeper.
Are you ready now?
Stop overthinking it. Book the hour.
One focused hour can move a decision you've been circling for weeks. Pick a time and bring the thing you can't say out loud anywhere else.
Book your 1:1 strategy hour →Or email info@siderroad.com