The Arena:

The Chess Move

High-Risk situations that need IMMEDIATE resolution. No sugarcoating. The real risks and the right moves to navigate a high impact situation.

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Working in Tech has become The Hunger Games

Your manager wants a status every 2 hours.

There's a reorg happening. Your scope is about to be cut. Your skip won't tell you by how much

Your last review said 'exceeds expectations.' This week your manager said 'we need you moving faster or this isn't going to work.

You're so burned out you are Googling "medical leave." You are not sure whether to stay or take leave.

A peer went over your head and complained to your skip. Now your skip is polite but distant, and you can't directly ask whether you're still okay.

You are about to rage quit. You need someone to brainstorm with.

You're reading this at 6am or 11pm in a browser tab next to a Slack thread of the latest 911 problem.

That's exactly the moment this is for.

The Chess Move is where you stop white-knuckling it alone - and work the situation with someone who's been there for 20 years and coached hundreds of Directors, Senior Directors, and VPs through worse."

Your Chess Moves

You walk in with a crisis. You walk out with a plan, and the skills to handle the next one.

1

Get the political read. Stop guessing who has power. Know exactly who to manage up, who to work around, and who to stay away from.

2

Make your workload visible. Stop absorbing impossible asks in silence. Build the business case that forces your manager to prioritize - or staff up.

3

Stay calm under fire. Stop freezing in meetings when someone attacks. Learn the exact words to say when a boss, peer, or VP is triggered.

4

Navigate a new manager. Build credibility in your first 30 days - before they form opinions you can't reverse.

5

Survive the reorg. Stop waiting to find out what happens to you. Read the signals early, position yourself before decisions get made.

6

Get clarity on your next move. Stop staying out of fear. Have a real option in 60 days - so you can decide from strength, not panic.

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Who This is For

The Arena: The Chess Move is for tech leaders in active crisis mode. Not generic professional development. Not life coaching. Not therapy. Real-time chess moves to secure your role, NOW, when everything is on fire.

You're navigating a crisis work situation. A soft PIP. A reorg. A new manager who's micromanaging. A skip you need to win back. A project that just got cut. A review that made no sense.

You're tired of Googling "how to survive a PIP" at midnight. You've read the Substacks, watched the podcasts, journaled the feelings. You need a framework, a plan, and someone in the room who's seen this move a thousand times.

You want tactical, not therapeutic moves. You're not here to process your childhood. You're here to handle the VP meeting on Tuesday and stay employed through Q3.

Who this is NOT for

You're not actually in a crisis right now. The Chess Move is designed for acute moments. If you're in a stable, growing situation and want general career coaching, this isn't the right fit.

You are looking to grow your career and get promoted. Not this program. This would be through the Private Advisory Program.

You are out of work and looking for a job. Not this program. This would be through the Private Advisory Program.

The Last Few Weeks In The Arena

Situation: "I received a 'meets expectations' review when I've been carrying three people's work. My comp band didn't move and I can't tell if I've been quietly demoted."

Actions: Mapped the political landscape: new VP, recent reorg, budget flowing downhill. Rebuilt her narrative around concrete business impact. Walked into a skip-level meeting with a proposal for more staff, not a complaint, and 2 more PMs were hired in the next month.

Situation: "My new manager was promoted three months ago. She's insecure, over-reviewing everything, and flagging my work in public Slack channels. I'm losing credibility I spent five years building."

Actions: Read what was actually driving her manager - status anxiety, worried about making a mistake in her new role. Scripted the 1:1 that reframed the relationship from oversight to partnership. The public flagging stopped within two weeks.

Situation: "My skip stopped responding to my DMs three weeks ago. I don't know what I did. I watch him answer other people on the team within hours."

Actions: It wasn't personal. He was moving her to a new role and couldn't say anything until it was finalized. We rewrote her next message so it didn't sound anxious - instead of "did I do something wrong?" she asked for 15 minutes to discuss what was next for her. He answered the same day and walked her through her new role (which was actually a step up).

Situation: "My new manager wants a status update from me every morning. She's rewriting everything, questioning my judgement, and wants to be on every email. I've been doing this job for six years and suddenly I'm being managed like a junior."

Actions: Her manager didn't know the work yet and was controlling the only thing she could - him. We flipped the dynamic. He started sending her a weekly brief on Fridays with what he'd done, what was next, and what he needed from her. Inside three weeks, the daily asks stopped and she was thanking him for the visibility.