5 Questions You Need to Ask Before You Start Hiring

By Lindsay Verstegen

Last month at Impact Engine, we celebrated our five-year anniversary with a celebration and showcase event with our investors, mentors, and portfolio companies. The following day, we continued the celebration with a gathering of our portfolio company CEOs. We were grateful to have Lindsay Verstegen, VP of Talent at ShopRunner, speak to our CEOs about recruiting and hiring, including the five questions to ask before hiring, below.

Hiring is a highly personal process, one that should be very specific to you and your company. It’s important to approach the hiring process with enough of a game plan that you’re organized, but also with agility that allows for feedback to shape the process as it plays out. I’ve outlined five key questions that get at guidelines to the hiring process that every organization should consider when expanding their team. (Keep in mind, these are not hard-and-fast rules, but rather tips that should guide you!)

  1. Who are you?

Before you begin the hiring process, it is important to go inward and answer some crucial questions to understand who you are as a company. This is a time for self-reflection. Ask yourself who you are and what you value. Remember that Sigmund Freud once said: “Being entirely honest with oneself is a good exercise.” It’s an especially good exercise when hiring. You should also ask customers and existing employees how they see you, and synthesize that information to determine your “true north.” If you’re not headed in the direction you want to be, this is the time to reroute and align your goals and vision. Hiring can often help steer more broad organizational evolution by way of the introspection that accompanies the process.

2. What is your value proposition?

Every company should have a value proposition, both a one-sentence version and a longer version. You want a version you can tell in an elevator but also one you can go into more deeply over cocktails at a happy hour. The statement should summarize why someone would want to work at your company and why it will add more value to their lives and create a richer experience than a similar organization might. It’s important that everyone at your organization knows this value proposition and can speak to it. This may seem simple but so often the basic building blocks of information are hazy and the team isn’t as aligned as needed to identify the right hire. Opportunities are lost and candidates become uninterested with no clear alignment on what the bigger value is for them both now and in the future.

3. What is your story?

One of the best ways to stand out from the competition is to share your story. People love stories. Stories humanize the hiring process by giving candidates the chance to learn about and connect with your vision and growth. Other companies may have similar job descriptions and work culture, but no one else has the same story.

4. How does the world see you?

It’s important to understand how you are communicating who you are, your value proposition and your story through your website and other outlets. This is what represents you when you’re not in the elevator or happy hour. Great candidates are always curious about interesting things going on in the world. Provide places that a potential candidate can peek into a window of your organization. What’s known about you publicly? Look at the experience of going through the “contact us” page on your website. The best talent doesn’t have much time to navigate a process that might take them nowhere. Too many processes take too many clicks and great candidates move on before the connection is made. Tools like LinkedIn and recruitment firms can be great to learn more about potential candidates through a less direct channel (that isn’t your career page), but make sure these tools are a good fit for your company’s hiring needs. You never get a second chance to make a first impression and if someone else is making that impression for you, be sure it’s the right one.

5. Do you have a game plan?

The most important thing to have when you begin the hiring process is a game plan. You want to create a process that gets the results you want and gives you the information about each potential candidate so that you can make a sound decision. It’s important to remain organized and communicate along the way. Time can also kill hiring momentum, so decide upon a timeline that works well for potential candidates and is also comfortable with your company’s needs. Take the time to get alignment across the various people involved in evaluation. A huge complaint from candidates comes from the basic concept that the interviewing panel wasn’t aligned and the depth of conversation was stifled as a result. Take the time to get your ducks in a row.

For more reading on recruiting, check out these articles below:

Lindsay Verstegen is currently VP of Talent at ShopRunner, leading the people function for the company. She lead Recruiting + People Ops at Braintree and Venmo (now PayPal companies) and, before that, was a part of the growth of early days Groupon. She holds a BFA in Musical Theatre from University of Wisconsin-Stevens Point. She ended up in the people profession after recognizing it as the place for the telling and sharing of important stories and a place for powerful connection. She’s always fiercely advocated for women inside and outside of the workplace and looks for ways to create high performing teams with diverse perspectives. Only through true diversity in team makeup does she believe companies stand a chance to build the best products of tomorrow.

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