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How to Interview Potential Employees or Contractors – A Systems Thinking Approach

Hiring people is one of the most important things you’ll do as a business owner or team leader. Do it well and you’ll reap the benefits for years to come. Do it poorly and you’ll be paying the price of extra stress, long weekends, and lots of frustration.

Interviewing is a key part to hiring, but not something that is taught in schools or even at many companies. In my corporate career, I was interviewing and hiring people for seven years before I was offered any training on how to do it well (and that was my third management job).

In this article, I’ll cover a system that you can use to help make sure you have the best interviews possible so that you can make great hiring decisions.

Before the Interview

Like most things, completing a good interview starts before the interview even begins. There are three sides to the prep work.

Think Through The Role

First, you need to consider what role you’re trying to fill. What are the important skills needed? What kind of experience does the person need to do a good job? How much time do you need this person to work each week (i.e. is it a full-time role or part-time)?

If you haven’t taken the time to answer these questions, do this first. You can use tools like a time study to help you better understand what you need. You can learn more about time studies here or review last week’s article on general hiring.

Ultimately, you should end up with a list of “must-haves” and a list of “nice to haves” for both skills and experiences when you’re done with this planning.

There are a few things I want you to consider when you’re going through what you need vs. what you want when it comes to skills and experience.

First, be realistic about your expectations. This might be harder if this is your first hire, in which case you might need to approach it with a little trial and error. Ultimately you want to be sure you ask for a reasonable set of skills and experience and that you don’t create a job profile of a unicorn (i.e. somebody that doesn’t really exist).

Second, when you think about what skills and experience are must-haves vs. nice to haves, consider what you want to teach vs. what you don’t want to teach.

Oftentimes, hiring managers overemphasize skills for a job that are easy to teach and pass on candidates that have really good skills that aren’t easy to teach because they aren’t seen as “core to the job.”

Here’s an example of what I mean by that.

One of my last corporate hires was for a software administrator position. It was an entry-level role and I was looking for someone with 0-2 years of experience with the software. I had several candidates that fit the profile well that had 1-2 years of software experience coming out of college.

I ended up hiring someone that only had a couple of months working with the software in test environments but had worked as a flight attendant for 10 years. Why did I do that when the role was to administer software?

Imagine the skills you learn being a flight attendant for 10 years. Dealing with difficult people. Being in situations where you have no control over what’s happening but have to make people happy. Communication skills. Positive attitude.

This candidate also showed they could learn on their own and were motivated to do so.

Think about how hard it would be to teach these skills to someone. How long would it take you to teach the patience of dealing with angry people that is learned from 10 years as a flight attendant?

Now consider how long it would take to teach someone the basics of administering software that has really good training and loads of resources available.

Teaching software is easy, but the other skills brought from 10 years as a flight attendant would be a nightmare to try and teach.

Think About the Team

The second side to the prep work is to think through the team members that you already have. If it’s just you, that’s easier, but still think through it.

You also want to consider the team you want to have. This might be your first hire with the expectation of hiring more in the near future.

Thinking through the team, you want to ensure you have a balanced skill set for the team that relates to the work the team needs to accomplish. Think through what skills you already have (this could be your own skills if the team is currently “just you”). Think about what balance of skills you need to be successful in the coming months and years.

This is also an opportunity to evaluate the diversity of your team. Diversity comes on many different levels, so think through the “Customers” this team serves or might serve in the future and ensure you are building a team representative of your Customers both current and future.

One mistake I see here often is that leaders try and build teams of all type-A personalities. I would highly encourage you to avoid this in most situations. You do not want a team where everyone is super aggressive and always looking for the next huge challenge to overcome and always trying to save the day. You must balance your team out with people that are driven to get to the next level and people that are solid performers looking to come in and just do a good job.

Think About the Environment

The third side of the prep work is to think about the environment this person will be working in. The environment includes things like the pace of work, physical constraints, and general work environment.

Hiring someone to sit behind a computer and answer emails alone is a much different environment than hiring someone to work on a construction crew of 20 to build a house.

Having an understanding of the level of ambiguity of an environment is an area where I see many people get hung up. What level of instruction or help will be provided for this person? Are they going to need to figure a bunch of things out or are they going to be following a strict script that they can’t vary from?

The type of person you’d want to hire to follow a script is much different than the person you’d hire to drop into an ambiguous environment and expect them to figure out the highest value activities they should be working on. You’ll want to be able to consider that in your interviews and have questions prepared to assess the candidate’s fit to your environment.

The Interviewers

Depending on your situation, you’ll likely have more than one person involved in interviewing the candidate (exceptions for solo entrepreneurs making their first hire).

It’s always best to get more than one opinion on potential candidates. Pick current employees that will provide you a diverse perspective to participate.

Coordinate ahead of time with the people that will participate to ensure you cover different topics. You don’t want to have three different people interviewing that all ask the same questions. There’s no one right answer on how to do this, but align interviewers to their individual strengths.

Organizing Questions

With the initial planning done, you’re now able to start organizing your questions for the interview itself.

When you think about what questions you want to ask, one of the most important things I recommend is to not ask any “pop quiz” type questions. Consider the following options for questions.

Can you tell me what the knowledge areas of project management are?


Tell me about a time where your understanding of project management knowledge areas helped you in your job.

The first is more of a “pop quiz” question. These questions can be answered if the person did a bit of study on the subject matter. It’s also possible to answer the question without really having an understanding of what the answer really means. It also doesn’t guarantee any experience with the topic.

With the second question, a person couldn’t possibly answer that question truthfully without having some understanding of the knowledge areas AND experience applying their knowledge to a work situation. You’ll be able to gauge their understanding as well as their experience together.

The questions that you develop should align with the most important needs identified in your previous planning work. If you’ve identified working with difficult Customers as one of your most important needs, you should have one or more questions geared towards getting the candidate to share their experiences working with difficult Customers.

Can you tell me about a time where you were working with an irate Customer? What were they upset about and what did you do to handle it?

Can you tell me about a Customer complaint that you had to deal with and how you handled it?

Can you tell me about a time you worked with a Customer that was upset but they were happy after you helped them?

You should be prepared to free flow additional questions based on the experiences that the candidate shares which I’ll cover in the next section in more detail.

The Interview

Now all the prep work is done and you’ve found one or more people you want to interview, you’re ready to get to it!

When you start the interview, start off with introductions. Introduce yourself, your business, and a little bit about the role you are looking to fill. Be sure to share pertinent details to the business and role.

Let the candidate introduce themselves as well. Ask them to highlight a few of their most relevant experiences as they cover their background. This will help you see if they understand the role or not and you should be able to see some relevant experience and interest in the role you have.

It’s important that you listen carefully to their answers and listen for anything that you’d be able to ask follow-up questions on. Remember to keep the conversation focused on figuring out how well this person is going to meet your critical needs.

After introductions, you can continue with your list of questions that you prepared. With each answer, continue listening for opportunities to ask follow-up questions (aka the free flow questions) that will help you clarify your understanding of how the candidate will fit with your open role.

One tactic here is to focus on topics that are more of an oddity or not normal/mainstream. This will help you gain additional perspective on the candidate’s abilities and give you an opportunity to better understand how much “fluff” a candidate has in their resume. Make sure with any of these oddities you have the expertise to know what you’re asking about.

Here’s an example of where this helped me in an interview.

I interviewed a candidate that had on their resume that they had been through extensive Six Sigma training and, although not certified, were as skilled as a Six Sigma Greenbelt. Six Sigma is a process improvement methodology that includes a number of useful tools and mental models.

As I am certified in Six Sigma, I had some expertise here that I could leverage in finding out more about his experiences. I had to relate it to my open role which had important elements around project management.

I asked the candidate to share one of the projects he ran using his Six Sigma knowledge. He stumbled a bit before admitting he hadn’t run any full projects using a Six Sigma approach.

I then drilled in a bit deeper with an unplanned question. “Can you tell me then about a time you used a Six Sigma tool in any of your work?” He stumbled again before admitting that he hadn’t used any tools in his work.

I followed up with another free flow question and asked him to name any Six Sigma tool. He was unable to do so.

I also asked him about other projects he had run without using Six Sigma. He wasn’t able to articulate any projects that he had run as a project manager.

This gave me significant insights into this candidate. He didn’t have any actual experience running projects even though his resume was well written with many project management buzzwords and good looking experience. He didn’t know anything about Six Sigma and wouldn’t be able to benefit from Six Sigma tools or mental models.

It also showed me he was either unable to assess his own abilities or had no problems embellishing his resume for the job. When challenged on his abilities, he first tried to cover up his lack of knowledge before eventually admitting he didn’t have the skills.

None of these qualities fit the type of person I was looking for with this role, nor did he have any of the appropriate skills or experience to do the job well.

Finishing it Out

It’s always good to leave time for the candidate to ask questions at the end of the interview. This gives you an opportunity to see their real interest in the role that you have open. If they ask relevant questions, it also shows they’ve been paying attention. Use their questions as a gauge to understand both of these elements.

After the interviews have concluded, meet back with the others that participated in the interviews and have a debrief. Work together to get to a conclusion.

Don’t be afraid to go back to the drawing board if you go through a round of interviews and don’t find a good candidate. It’s better to take longer to find a good candidate than accept someone that will end up being a problem down the road.

Also, don’t be afraid to make adjustments to what it is you’re looking for after going through a round. You might find people are missing skills or experiences in the combination you’ve asked for and you need to rethink your job description and approach.

To Summarize the Interview System

Inputs: Job Description, Team Needs, Work Environment, Interview Questions

Outputs: Rejected candidate, hired candidate/new employee

Process Steps:

  1. Think through the role you need to fill and the needed skills and experiences a candidate should have
  2. Think through your existing team
  3. Think through your business environment
  4. Identify the people that will interview the candidates
  5. Organize the key questions to ask
  6. Hold the interview(s)
  7. Debrief with those involved in the interview(s)

Possible Metrics: Number of interviews, number of offers made, number of rejected candidates

System Product: New Hired employee or contractor

If you’re looking for extra guidance on how to apply this or other tools in your business, you can book a 15 minute call with me for $95 here.

If you have a bigger need, please email me and we can discuss how I can best help you Optimize for Outcomes.

Thanks, and I’ll see you online. Brian

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