Part 7: Asking About DECISIONS

Candidates–especially senior-level ones—frequently tell stories about tough decisions they had to make. This usually comes up when talking about a big accomplishment or achievement in their past, but it can come up in other contexts as well.

Imagine that you are interviewing a candidate who is currently CTO at a SaaS company. She tells you about her recent decision to sunset a legacy code base used by many long-time customers. She is quite proud of this decision, and you want to dig further.

As always, we will use our WHAT, HOW and CALIBRATION framework for follow-up questions. But unlike some of the other story archetypes, I recommend going in order!

WHAT: start by understanding the decision itself

Interestingly, this is often the most important, and most challenging, part of stories about decisions—specifically, understanding what made the decision such a big one. Think about the toughest decisions you’ve made in your own career. You will probably find that one or more of the following factors was at play:

• High stakes (the consequences for a bad decision were very high).
• High uncertainty (there was very limited data upon which to make a decision).
• High conflict (key stakeholders had very different opinions on the right course of action).

A good first follow-up question for our CTO is simply “What made the decision so challenging?” You will usually hear the candidate point you in the direction(s) above directions fairly clearly:

• Stakes: “The wrong move could tank us. But then again, so could inaction.”
• Uncertainty: “We had no idea what the real risks were, nor the upside.”
• Conflict: “There were some very senior people, with very strong opinions, on both sides.”

Depending on which of the factors above you hear, you may want to ask an additional question about the decision itself, until you feel you could explain the situation briefly to a third party.

Next, learn HOW the person made the decision

Most of the time, your next question will simply be “How did you end up making the decision?” From here, you will notice that candidates focus on a few factors, depending (again) on what made the decision challenging:

• If the story is primarily about high STAKES (but not uncertainty or conflict), the conversation is typically shorter. Basically, they had to make a hair-raising call, and they did. You may want to ask about what that experience was like for them, but you can pretty quickly get on to the CALIBRATION part.
• If the story is primarily about high UNCERTAINTY, you will want to explore how they HANDLED (or dealt with) the uncertainty. Avoid asking how they RESOLVED it. They may not have! Just see what steps they took, and if they were able to find a way to put more data behind the decision.
• If the story is primarily about CONFLICT, be prepared for a lengthier discussion of stakeholder management—who they had to convince, what steps they took to get there, etc. These can be very revealing conversations, especially when stakeholder management is critical for the new role in question.

CALIBRATION: finally, get the end results of the decision vs. some benchmark

This final part of the discussion is also fairly straightforward. We typically just ask some version of: “What ended up happening?” The candidate will likely give you the outcome from the decision—what resulted for the business. At this point, you can treat it like any other result—you simply need to compare that to some benchmark, such as their targets/goals or the expectations of a key stakeholder (often the boss).

In summary, the flow is pretty simple:

• When you encounter a DECISION story archetype, start by asking “What made that decision so challenging?”
• This should reveal whether it was STAKES, UNCERTAINTY or CONFLICT (or a combination) that made the decision difficult. Explore a tad more if helpful.
• Next, ask “How did you end up making the decision?” and dig into the information that is most relevant, based on the 3 factors above. Be prepared to go deeper on CONFLICT stories.
• Finally, ask for the result (“What ended up happening?”) and calibrate that vs. targets or a key stakeholder’s expectations.

A final note–these stories are often quite brief, especially if the decision does not involve a lot of interpersonal conflict (or creative, gritty data gathering). Please avoid trying to “squeeze too hard” on these stories if that’s the case. Candidates will often talk about a big decision purely because it was an emotionally significant moment. That simple emotional/motivational content may be even more revealing about the candidate than the details of the situation or the decision itself!