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Remote Hiring For Success


by Lesley Pyle, MSc., founder of HireMyMom.com 

Without the luxury of a Human Resources department, many small business owners find themselves navigating the laborious task of hiring the right team members themselves. It seems easy enough: Place a job post, interview those with the best cover letters and resumes and make an offer to the top candidate. 

But there’s reason to re-think that approach. According to the U.S. Department of Labor, the price of a bad hire is estimated at 30 percent of the employee’s first-year earnings.”

In addition, hiring the wrong person can mean more hand holding, redoing tasks, and – worst of all – costing you money. 

Why is hiring the right person so hard?

Here are a few reasons: 

  • The hiring person has not given enough thought to what they actually need from the role and the candidate. 
  • The job description does not include the goals and outcomes for the role, and only mentions the tasks and skill requirements. 
  • The interview questions are not well thought out, and do not give you an accurate picture of the candidate or how well they fit the role. 

Hiring the right candidate with the right skills for the right job can dramatically impact your company’s productivity, outcomes and goals. Your biggest asset is your team – they can help you succeed or they can hold you back. 

So how do you hire the right person for the right job?

It starts with a carefully thought out job description. 

First, it’s important to define the overall goals of the role. 

What do you desire from this candidate? Include not only the most important tasks of the job, but also the outcomes you desire for this role. Is it an increase in sales; building a community of followers and clients; higher retention rates or improved customer service? 

Your job description should also focus on what’s in it for them. Let them know:

  • What are your company goals or mission?
  • Why is your company great to work for? 
  • What do you value? Is it leadership, teamwork, independence, hard work?  

Let them decide if they think they would be a good fit for you and your business!

The Right Questions to Ask.

After you have some promising candidates, it’s time to select the ones who look like a good match on paper. First, what traits, skills and/or experiences are most important for this candidate to have? 

Once you’ve defined this, you can more clearly ask the right questions. What are some questions that will help you spot those who do or don’t have those skills or qualities?

In the book Who” by Geoff Smart and Randy Street, the authors outline a thorough process for hiring what they call “A” players. The process may be overkill for some smaller remote roles, but the basics of the process provide a solid structure for selecting the top candidates. 

The interview questions Smart and Street recommend are conversational and simple. They recommend an initial interview asking the following questions:

  1. What are your career goals? 
  2. What are you really good at professionally? 
  3. What are you not good at or interested in doing professionally? 
  4. Who were your last five bosses, and how will they each rate your performance on a 1–10 scale when we talk to them? 

Each of those questions should be followed up with “tell me more”, “how” and/or “what” to dig deeper to gain more insight about the candidate and their performance, work ethic and skill level. 

Once you’ve selected who you want to talk to further, Smart & Street recommend the “Who Interview” which “is designed to give you more confidence in your selection because it uncovers the patterns of somebody’s career history and is a chronological walkthrough of a person’s career.” They recommend walking through their past 5 jobs and asking:

  1. What were you hired to do? How was your success measured in that role?
  2. What accomplishments are you most proud of? Be listening for correlations relating to the expectations of your job. 
  3. What were some low points during that job? Or what part of the job did you not like? In what way were peers stronger than you?
  4. Who were the people you worked with? Ask specifically for the boss’ name. Ask what that person will say were their biggest strengths and areas for improvement. That lets them know you will be calling and they are more likely to give you an accurate response. 
  5. Why did you leave that job? Dig deeper into their response with more questions to more fully understand. 

The Reference Checks.

The last step of the selection process is to check references of each of the final candidates. You may want to ask them some of the same questions from above to see how similar their responses are to the candidates answers. 

Taking the time to get a more full and complete impression of someone’s work history, strengths and weaknesses and personality will help you determine who is the best match for your role. Knowing what you want and what your goals are will help guide you in this interview process. The rest will be decided by the answers you receive!


Lesley Pyle is the founder of HireMyMom.com, a boutique service connecting Small Businesses with Virtual Professionals across the country. She began her work-at-home career in 1996 with the launch of her first website: Home-Based Working Moms. Pyle was named one of “50 Women Entrepreneurs Who Inspire Us” by Self-Made magazine and has been featured in numerous publications including Forbes, Entrepreneur, Wall Street Journal, USA Today and many others. Follow Lesley on LinkedIn, Twitter  and FB.