Hiring? The 1 Question to Ask Yourself (Not Them) So You’re Not Disappointed in 3 Months


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The biggest fear in hiring is that you misjudge. The good one gets away and the one you get is suddenly no longer the same person 3 months down the road. They said all the right things in the interview, yet now that the honeymoon period is over, you see what you truly bought into.

Sometimes that’s a pleasant surprise, most often it’s a confusing letdown.

Ground Game: Mentally Steel Yourself

Embrace that you will not rush this process. That it will be slow and creative rather than quick and dirty. You will have much better hires and your time is well worth it. In fact, give yourself a “As long as we hire by…” window so you do not succumb to any temptations to get it over with.

The More Touches, the More Insights You Will Glean

The more the merrier most certainly applies here: involve your people! Get the front desk person’s opinion: How did they represent themselves when they arrived for the interview? Are they gregarious or reserved? Confident or avoiding eye contact? Good handshake or dead fish? How were they on the phone with the person who set up the interview? Have someone sit in on the meeting with you and get their viewpoint.
Your team is already a family, they expect to be represented in this family decision. You will eliminate, or at least lessen, any apprehension of someone new coming aboard when they feel included in the process. And don’t skip the basics, anytime I didn’t check references I always wished I had. It eventually became a hard rule, it’s another revealing touchpoint.

Don’t have a team yet to garner feedback? Do the restaurant trick where you see how they interact with others. Or, perhaps this is a virtual role? Creativity to the rescue! Meet with them on Zoom, get writing samples for tone and clarity, put them in role play situations with a trusted friend.

Take the Pressure Off: The 80.20 Rule Helps Again

Since we know that every single brain is different, conflict is absolutely unavoidable. The 80/20 rule can serve you here, too. In every relationship, if we like 80% of the person and have some annoyances with the other 20%, that’s a pretty good ratio. Seriously. There is just no way you are going to like 100% of someone 100% of the time, not even our spouses, kids, or bff’s can live up to that (and we don’t live up to it in their eyes either…remember, we have our own 20%). Your job is to establish whether they have the right 80%. That’s hiring slow.

Finally…the 1 Question You Need to Ask Yourself, Not Them

Determine the tactical skills needed, what assessments you want them to take, questions you will ask…but, the first crucial step is to determine your MIT. What is the MIT (Most Important Thing) you need from this person? If it’s a customer facing role it might be empathy. For an entry level hire, it may be integrity and work ethic. If a team is struggling, it could be leadership skills. Often, this MIT is more important than any tactical or hard skill you can teach. When you satisfy your MIT, you will have peace of mind.
Establishing your MIT is an often overlooked and undervalued part of the hiring process, yet neglecting this is why we are upset a few months into the relationship.

For instance, one of my past clients was a wealth planner, she had experienced some bad hires but couldn’t figure out what she was derailing her process. She knew what tactical skills were necessary, but she hadn’t thought about her MIT. In her business of retirement planning it is vital that her employees are able to build trust and rapport with her clients. I mean, they are responsible for handling that person’s life savings. Once we determined her MIT, it was a matter of asking some better questions and getting a bit creative with scenarios.

Another friend of mine recently had the support of an assistant on a project basis. Once the project ended, he was saddened by the loss of support. He remembered feeling comforted knowing someone was there who wouldn’t let anything slip through the cracks. Who made him feel like he, his business, and his clients were in good hands. It was important he waited for that feeling again, it was what allowed him to do better. You must stay the course and find who fits your MIT.

What Else?

I would always ask what their interests were. What do they like to do on their own time? Do they like to spend time with others, were they involved in team sports, or do they prefer isolated activities? All these are clues to how they truly operate, how they prefer to interact with the world.
I remember an interviewee who had played lacrosse at one time. I asked if he considered himself a star player. He smiled, blushed as he lowered his head, and admitted he thought so. Now, I was intrigued. I wanted to dig in and see if he was a winner at heart who wanted the ball like Michael Jordan, or if he was Scottie Pippen and just wanted the glory and the stats.
The point is, these are the kinds of insights that can bring you closer to knowing how they perceive themselves and others. That information is gold.

Lastly…When Hiring Your Right Hand

Keep in mind if you really hit it off with someone, when they think like you, laugh at what you laugh at, when your philosophies of business are aligned…that’s a real gem. Your best bet is when you find a person whose values, personality, and work ethic are complimentary to yours.
My only cautionary word here is to be wary if they are too much like you. If they don’t enjoy the same tasks you don’t do enjoy, that’s a problem. If they don’t excel at what you don’t excel at…this is not going to move you forward. It’s why companies or partnerships have a Visionary Person (CEO) and an Operational Person (COO). Complimentary skills are necessary for innovation, traction and progress.

There are ways you can find out what’s under that polished surface every interviewee shows up with. When you base this decision only on the formal representation of this person, you will be disappointed. But, if you understand what will serve you best, you will find that right fit. Then, you will be excited about your ultimate choice. You should be wowed and pleasantly surprised with your new addition.

Karyn Chylewski
I spent 20 years working in a diverse range of leadership roles before starting my leadership coaching practice. From working as a backcountry hut master to restaurant management, to leading a team in the intense pet care industry, I learned that the key to leadership success is all in relationships. I now help leaders build better connections with their team, navigate their relationships, and understand the human side of leadership so they can become better leaders, improve team morale, and achieve higher performance. I love spending time outdoors, with my family, great wine & conversations.


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