High Probability Poker: The Art of Side Door Interviewing

In interviews, the questions we ask should serve two goals. First, they must have a high probability of gathering relevant, predictive information about the candidate. Second, they should avoid telegraphing exactly what we’re looking for or what the “right” answer might be.

When the intent of the question is obvious, candidates are far more likely to exaggerate or slant their answers to please the interviewer rather than answer truthfully. This is the typical job interview and it's lose-lose: the company is unable to gather quality data on the candidate, and the candidate feels pressured to "perform" rather than share their story.

That’s where the concept of High-Probability Poker comes in—a strategy where you aim to spend your time on high-value areas to gather crucial information but so do without revealing your hand.

The Challenge: Two Goals in Tension

There is a subtle tension in effective interviewing. On one hand, you need to ask questions that are likely to surface useful insights—that’s the “high probability” aspect. On the other hand, you want to avoid giving away too much about what you’re looking for because this can lead candidates to shape, exaggerate, or even outright lie in response to your questions. When you telegraph what you're looking for, you increase the odds that you'll receive corrupted data. Even otherwise honest candidates may want to please you—and all of them want to receive a job offer. 

To get this balance right, you can employ what we call Side Door Questions. Instead of directly asking, “What's your best example of installing metrics into a struggling team and holding those team members accountable?”—a question that telegraphs what you’re assessing—you might instead ask, “Let’s talk about the team you inherited at [XYZ Co.]. What was the team like when you came in?”...“What actions did you take?”... “What was your biggest missed opportunity with that team?”.” And you could ask about key team members that they've interacted with and the feedback they would receive as a manager.

This approach gets candidates talking about their past behavior and decisions in a real scenario, without the pressure of figuring out the “right” answer to please you. And if you do that across multiple teams/companies you're either going to hear about accountability or you're not and either way you'll get be betting information that is much more "pure" than if you had asked for it directly and revealed what you were looking for. 

The Balance: Non-Leading Questions First, Direct Questions Later

The power of High-Probability Poker lies in building a structured interview guide that balances Side Door questions early in the process with Front Door questions later. That way you maximize honesty during most of the interview while also ensuring that you get a few questions directly at the key competencies you care about.

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