Part 2: Asking About Deals

“Where do you go with THIS story?” It’s a question we are often asked in our interview coaching. This post is the next in a series that will discuss common “story archetypes” that candidates share, and what kinds of information you are seeking with your follow-up questions in each.

If you’re interviewing a senior exec, or someone involved in sales or M&A, you are likely to spend a lot of time talking about DEALS. Closing a key account. Landing a critical partnership. Buying or selling a big asset. These stories are fun, but it’s hard to know where to dig (and where NOT to dig).

The first thing to verify is that the story is, in fact a “deal story”—i.e., it’s about LANDING the deal, not what happened thereafter (or some ancillary thing they did beforehand that enabled OTHERS to land it). If a candidate says they are proud of a big sale, contract or deal, and you’re not sure if they played a part in actually landing it, just ask what their biggest contribution was. If they talk about actually landing it, it’s a DEAL story.

As with all positive events, we want to know WHAT they did, HOW they did it, and we want to CALIBRATE the magnitude or impact of the event. Let’s look at each category, and the kinds of questions you can use to uncover the right information.

The "What"

Get clear on the nature of deal itself, and its impact on the company. This is usually brief.

• “Tell me more about that deal” “Who was the [client/target/partner/etc.]?” “What were the terms of that deal?”
• “What was the impact of that deal on the company?” “What happened as a result of that deal?”

The "How"

Get clear on what they specifically did to get the deal across the line. There are several sub-categories of questions that often (but not always) apply:

• Basic “how” content: “What about that deal are you most proud of?” “How did you get them across the line?” “What was most remarkable about landing that deal?”
• We vs. I (establishing the candidate’s personal role vs. a group accomplishment): “What was your unique role in landing that deal?” “What did you bring to the table in making that deal happen?” [If still not clear] “What wouldn’t have happened if you were not involved?”
• Competitor comparison: “Who else was in the running for that deal?”...[after response]...“What did you do that they didn’t?”
• Peak Moments (deeply understanding what makes their work noteworthy): “Tell me about the moment when the deal really happened.” “Tell me about the biggest challenge you faced in making that happen.”

The "Calibration"

Establish the magnitude of the accomplishment with respect to targets, stakeholder expectations or relevant peers.

• Targets: “What metric did your boss/Board/CEO use to measure deals like this?”...[after response]...“And how big was this deal on that measure…[after response]...“What was the expectation/average deal size/total target?”
• Stakeholder expectations: “What did [boss/CEO/key stakeholder] have to say about that deal?” “What feedback did you get about that deal?”
• Peers: “How common was it to land a deal like that?” “How did that deal compare to what your peers were doing?”

The above suggestions are not a linear script; you will probably only use 4-6 of them in unpacking a given deal story. You should get a sense—from understanding the nature of the person’s role—which questions are most likely to be relevant and fruitful.

When do you know it’s time to move on? When you feel like you could tell the rest of the hiring team about: (1) the nature of the deal itself, (2) the story of how the candidate made it happen, and (3) some quantification or reference point for the magnitude of the deal and/or its impact.