The Ultimate Recruiting Road Map: Get the Right People in the Right Seats

Jon Wengrow Dwoskin
4 min readAug 19, 2020

I like to tell my clients ABR: Always be recruiting.

Why? Not having the right people in all the right seats will anchor your growth. You can’t get to where you want to be with only the people you have now. You may need more support staff, more salespeople, more whomever — so always be on the lookout for them. Recruiting should be a proactive act, not reactive.

Getting Started

  • Do a five-minute Phone Screen with candidates who look promising.
  • Use an Interview Metric of 10 face-to-face interviews to 1 hire.
  • Interview each person four times to make sure the same person keeps showing up and gets better each interview. Make each interview different — 1:1, company meeting, include other team members, meet at a coffee shop, etc.
  • Candidates should be 15 minutes early to interviews, show up in business attire, have a notebook/pen ready, and questions to ask.
  • Look for candidates who are coachable and strong listeners — and who smile and are excited about the job.
  • Some good opening questions will keep you from wasting your time:
    * On a scale from 1–10, how badly do you want to …
    * Have you been to our website?

If the answer is not a 10+, you have the wrong person. If they answer no to visiting your website, you have the wrong person. End the interview within five minutes. Thank them for coming in, stand up and let them know when they can answer above a 10 to please call and set up another interview.

Separate the Wheat from the Chaff

When talking with prospective employees, keep an eye and ear out for candidates with these qualities:

  • Coachable
  • Competent
  • Likeable
  • Proactive
  • Street smarts
  • Problem solver
  • Inner strength
  • Team player
  • Leadership qualities
  • Courage
  • Integrity

Ask yourself, how will they perform under pressure?

Ask these Questions

Tell me about a situation where you …

Tell me how you make a decision.

How do you make a decision when your “boss” is not around?

Tell me how you lead.

Tell me how you look at something with different eyes and make it better and more effective.

Tell me about a time you lost your cool and how you recovered.

Why do you want to leave your job?

What would your best friend say about you?

What would someone who hates you say about you?

How do you resolve conflict?

Tell me a story about your discipline.

Tell me a story about when you were proactive.

Tell me how you learn.

Tell me how you continue your learning.

Tell me a story about how anyone has coached you to be better and grow.

Tell me something exciting.

Why are you are sitting in front of me?

Tell me about a time you and a co-worker didn’t get along and how you resolved it.

Tell me about a time when your boss pissed you off and how you handled it.

How do you incorporate balance into your life?

What do you consider a productive work day?

How do you define work/life balance?

Tell me about a time in your life you realized something in hindsight.

What you do when you are wrong?

What type of winner and loser you are?

Tell me about your ego.

Tell me about your good and bad habits.

High-Level Interview Questions

How do you problem solve?

On a scale from 1–10, how badly do you want to____________________?

Tell me a time you took a complete abstract idea and turned into a business/product.

Tell me what you say to people who come into your office having a meltdown.

Tell me how you influence someone who doesn’t like or respect you.

Tell me how you manage people who don’t take notes.

Tell me how you get someone who is all science to see the art.

Tell me how you hold people accountable without micromanaging them.

Tell me what culture means to you. How do you create, maintain it, evolve it and/or change it?

Explain to me the steps in growing a company.

Tell me how you look at the big picture and break it down into daily goals.

Tell me how you forecast change. How do you create that change today in preparation for tomorrow?

Tell me how you make a decision.

Tell me how you admit you’re wrong?

Tell me how you learn and how you continue learning.

Tell me how you implement systems, processes/methodologies into the workplace.

Tell me the last three books you have read and the one lesson you got from each.

How did you implement those idea(s) into the company?

Tell me what book you are reading now and why.

Tell me what you do to prevent yourself from burning out.

I am sure you noticed that there are some really tough questions in there. Asking yourself these same questions is a good exercise as you grow your company — and yourself.

Think Big!




Jon Wengrow Dwoskin

I help successful business people get unstuck and grow their business as a business coach, speaker, podcaster and author of my book, The Think Big Movement.