Diagnose, then commit.
Is the company you're evaluating on the wave, or off it?
Most candidates evaluate a company by reading its history. It’s the worst possible way to tell whether you’re joining the wave or missing it.
The thing nobody tells you
Company history is a polished narrative. Funding rounds. Logos. The press releases that survived. It tells you what the company has been. It says nothing about where it is right now.
The real diagnosis is simpler: on the wave, or off it. The wave is the last twelve months of momentum: the market signal, the velocity of decisions, the pace of hiring, the trajectory of the one metric that matters. The season is where the company sits relative to that wave: building toward it, riding it, or past it.
The landscape is moving fast. Some companies are going public on bets they placed two years ago. Others look impressive on paper and have quietly lost the moment they were riding. You won’t see the difference in the history. You’ll see it in the next twenty minutes of conversation.
Five questions to read the wave before you commit
These are the questions I tell candidates to ask in the second-to-last interview. They surface in twenty minutes what you’d otherwise learn at month four. The hard way.
1. What’s the one bet this company is making in the next twelve months? Companies in a strong season name it in one sentence. Companies past their peak give you three vague themes. Companies, before their season, admit they’re still figuring it out. All three are real seasons. The only question is which one you want to join.
2. What’s changed about your business in the last ninety days that wasn’t in the deck? Tests whether the founder is tracking their own momentum. Recent, concrete answers mean the moment is live. Stale answers, or answers that match the deck word for word, mean the moment already passed.
3. Who are the last three people you hired, and what did each of them turn down to say yes? Quality of talent and competitiveness of the offer, in one question. If they’re pulling people away from top companies, it’s a real season. If they’re winning because they were the only offer on the table, it isn’t yet. Both are answerable. Be honest with yourself about which one you’re joining.
4. What did you decide differently this quarter than last? Velocity of strategic change. Companies in their season iterate fast and can name the iteration. Companies pass it, freeze it, and call it focus.
5. If I joined and built one thing in my first six months, what would make it obvious I picked the right wave? The future-self test. It forces the founder to make the bet from your side of the table, not theirs. If they can’t, the trajectory they’re selling is one they want to be on, not one they’re on.
Why this matters more than it did a year ago
The cost of joining the wrong wave went up this year. AI moved the value of the work upward: what used to be junior is now senior, and what used to be senior is now executive. Companies on the wave compound that shift. Companies off it argue about titles while the work that actually matters goes undone.
The candidates who read the moment before they say yes don’t get fewer offers. They get the right ones. And the offers they pass on save them a year.
What I’d bet on
Don’t read the deck. Read the wave. History tells you who they were. The wave tells you who they’re becoming.
I made you a worksheet for the five questions. Print it. Bring it to your next interview. Fill in one column per company you’re talking to. Patterns surface fast.
In two weeks, Issue #3: what “AI-forward” actually looks like in a candidate, and why most people who claim it don’t have it.
One ask. Reply with one line: a company whose wave you read wrong, and what you’d ask differently next time. I read every reply.
Jeremy