Ideal Outcomes

Asking the Tough Questions to Find the Right People



By Jason Richmond, CEO and Chief Culture Officer at Ideal Outcomes, Inc.

I’m the first one to admit that Millennials typically get an unfair shake in today’s society. It’s my professional belief that Millennials actually offer companies unprecedented advantages: highly educated, tech savvy and of course, always looking to build upon the culture of a company for the greater good. With that being said, there has been somewhat of a “trophy trend” where people feel that the younger generations need to be coddled and cared for- especially in the workplace. The result is Human Resource departments that fear legal ramifications from being too tough on employees.

If you ask the CEO of one marketing company, she believes it’s well past time for all of that to stop, “they make you think there are questions you can’t ask- or things you can’t say. I’m sick of it because frankly, it doesn’t work. Sometimes the tough questions need to be asked- especially when hiring.” Backing up her claims is a recently published book by Kim Scott called Radical Candor. The premise is simple: “care personally and challenge directly.” Since then, this particular CEO has long since gone back to asking the questions that get to the root of who the candidate truly is: background, intentions, skill sets. It’s less of an abstract conversation and more direct, ultimately saving everyone time and money.

Here are her top 3 questions when sizing up potential:


“People think this isn’t a good question, but if you can’t answer why I- the person in charge of seeing this company succeed- should hire you- the person being employed to help me achieve said success- then are you really the person for the job?”


Secondly, she seeks to find out about their family background, always starting with the candidate’s birth order. Key personality markers such as: older, middle or youngest child, can help executives or managers understand certain behaviors and mindsets. “I always ask them to tell me about a childhood memory. If it’s a positive memory than chances are they are optimistic people; if it’s negative, I would have to suspect that they are a pessimistic individual”- which typically works against a thriving company culture.


She says her clients are looking for “a subtle combination of grit and finesse”- and chalks this up to having the ability to push through difficult situations and to see projects through. “I want to hire people that are willing to work to overcome obstacles no matter what they may be. In the end, I’m always looking to hire future owners.” Ultimately, she knows a thing or two about grit. Starting her business from the ground up, she now has a wildly successful consulting group who are currently producing at higher rates than ever before. Perhaps it’s just simple luck to have the level of talent currently making up her base of 14 employees- or it was getting back to the basics of direct, honest interviewing to ensure that the person signing on the dotted line is exactly the right fit for her company going forward. I’ll leave that up to you.