Posted: January 25, 2017 by Eli Randel, Director of Business Development


I invented a drinking game. I came up with it in grad-school while…. drinking.

Here are the rules:

Ask your group a provoking choice question. If all choose the same answer, then it was a bad question and you take a drink and try again. If you can split the panel, then it was a good question and you choose someone to ask the next question. Encourage debate. It keeps the brain moving even while you’re potentially ingesting liquids that slow it down.

Some examples (it’s usually not a PC or PG game – a sense of humor is required):

(1) Would you rather be 8’6” or 4’3”?

(2) Would you rather have one or three ____­_____? (pick a body part there are two of; risqué parts usually generate great debates)?

I get to interview lots of people and consider myself good at improvising conversation on the fly. But I would like to come up with a list of questions to help me recognize patterns and establish a more consistent process. However, like my game, if everyone answers a question the same way, I think it’s a bad question. Below are questions I’ve recently been trying and why some are flawed and require me to “DRINK”.


FIRST TASK: Don’t read off your resume and give me a 60 second introduction so I know who’s on the other end. 

Better than “tell me about yourself,” followed by them and I reading their resume together. This is a task. A pitch. If this takes more than two minutes, they aren’t following instructions and aren’t concise. Both forgivable, but I believe everyone should know how to tell their story in a proverbial elevator.

1. What are your work habits: work harder or smarter?

DRINK. 95% choose “smarter.” No one wants to be perceived as working less-than-smart. In my experience those few who choose “harder” are sincere and probably have a chip on their shoulder which I like. Bad question.

2.  If forced to choose would you be all-guts or all-brains?  

DRINK. Most choose “guts.” They think it’s what I want to hear. Or maybe just the act of submitting a resume shows guts. A former boss and now partner told me years ago: “Two equally talented people are separated by audacity.” Clearly a “guts” guy.

3.  If this position gets filled by someone else but we want you to join the team, which job would you take assuming you were qualified: CFO, CMO, COO, Chief-Deal Maker, or Jack-of-all-Trades?

DRINK. 90% of the time they will choose J.O.A.T. to be safe (yawn). I immediately eliminate that option and ask for a new answer. Being forced to decide quickly, the candidate sometimes gravitates towards sincerity but usually chooses COO (another neutral pick). Two things I want to uncover (a) if a phone interview and they need me to repeat the options, they aren’t ready to take notes; (b) if applying for a sales role and they want to be CFO (or vice-versa), they might be going against their natural wiring.

4.  Politics aside, if you were hosting President Trump for dinner, what would you cook for him?

(a) can the candidate put politics aside? Opinions are great, knowing when to express them is crucial; and (b) less important, but can the candidate cook? To me it shows self-sustainability, independence, and the ability to follow a recipe. My favorite answer: “Trump probably eats $300 steaks once a week so I wouldn’t try to impress him. I would make something comforting and master the best macaroni-and-cheese recipe.” She recognized she couldn’t compete with the chefs whose cuisine he eats, and chose to differentiate and find an area where she could compete. Smart young lady.

5.  If money and ability was not an issue, what non-business career would you have pursued?

I’m genuinely curious. I want to know the candidate’s interests and roots. I’m surprised how many can’t/won’t answer the question. Did they dream of being a businessperson at age 5? If anyone wanted to be a fireman, I can assure them the business world will provide plenty of fires to put out. Me: the next Jimmy Page.

6.  What are you like outside of the office?

DRINK. An open-ended question shouldn’t generate the same answer, but I seem to always get some version of: “I like to exercise and spend time with friends. I like the outdoors and mostly relaxing on the weekend.” Considering the amount of colleagues I’ve run into at bars and restaurants in my life, I don’t buy this.

7.  What did I miss? Famous sibling? Unique talent? This is a chance to brag without being obnoxious.

Sincerely, what did I miss? Not that it will guarantee you a job, but is the candidate the son of your biggest potential customer? Were they a serious athlete (athletes are usually disciplined, coachable, and competitive)? Some people are humble and don’t like bragging. I’m asking them to brag about or share something.

It’s a work-in-process, and I hope to get recommendations to share. My goals:

(A) Catch the candidate off-script to strip away their façade so they reveal their actual selves,

(B) See if they are able to connect with their audience (me), think fast, and sell themselves,

(C) Ensure the candidate has a sense of humor, and

(D) Differentiate myself. They may be speaking with several firms and can get fatigued and go on auto-pilot during the usual fluff (where will you be in five years?). Following the job and resume related questions, I think a more loose and conversational approach sets the tone for a potential working relationship. They will also likely remember me.

LAST QUESTION FOR ANYONE WILLING TO ANSWER (I’ll have a drink and buy all respondents one if the answers are all the same):

Would you take $7MM (tax-free) today, if you could never earn money again (you can work without pay, but no salary, no interest, no home appreciation, no investing)?

Eli Randel

career choicesEli Randel is Director of Business Development based in CREXi’s Miami office. Eli spearheads CREXi’s growth and sales throughout the east coast as well as overseeing the national sales team. Prior to joining CREXi, Eli was director of dispositions for Blackstone’s Invitation Homes. Eli has also held management positions and production roles with Cohen Financial,, LNR and CBRE where he began his career spending three years in Investment Sales before leaving to obtain his Master in Business Administration from the University of Florida.