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!)

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.

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.

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.

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.

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.

Did you like this post? Sign up for our newsletter and we’ll send you the latest impact investing and Impact Engine news each month.

We 💖 Flyover Country

By Jessica Droste Yagan

In past blog posts, we’ve written about the next generation of social entrepreneurs in Chicago, why impact entrepreneurship is thriving in Chicago, and the newest players on the Chicago impact scene. Inc.com published a piece recently that said when it comes to social entrepreneurship and building companies with the intention of a greater good, there’s no better place to be than Chicago. Still, we get a lot of questions from investors on the coasts about why we’re based in “flyover country” — as if it’s a disadvantage.

Actually, it’s a point of pride and advantage. Being in Chicago doesn’t prevent us from investing in coastal entrepreneurs (who make up 39% of our current portfolio and, in several cases, held rounds open for us because they valued our participation as a member of their investment syndicate). But we also see a lot of startup companies in between the coasts led by great entrepreneurs with innovative and impactful business models, that get overlooked by investors on the coasts. We think being here means we get the best of both worlds.

We’re always happy to remind people why we love being based where we are.

Booming Tech

Over the last decade, the middle of the country has cultivated a community of thriving tech entrepreneurs and startups. We’ve seen the startup scene transform Chicago, bringing excitement and optimism, renewing our creative culture, and inspiring innovation. As Yazin Akkawi recently wrote, “the entrepreneurial spirit in Chicago has never been more alive…Chicago attracts get-shit-done, no-nonsense leaders.” Steve Case agrees with us: check out Rise of the Rest, his nationwide effort to highlight the work of and invest in entrepreneurs outside of Silicon Valley and NYC. It also doesn’t hurt that operating costs are lower and talent more loyal outside of those markets.

Booming Venture Capital

As the tech startup scene continues to grow, so does the venture capital ecosystem. Hyde Park Angels recently released its 2017 Midwest Startup and Venture Capital Market Analysis, an in-depth and insightful overview of current investment and venture capital trends in the Midwest. Research shows that the Midwest is the biggest venture capital presence outside of California, with Chicago leading the nation with the largest number of exits producing returns over 10x.

Values

Our Impact Engine values include humility, authenticity, and scrappiness — and they could easily be mistaken for “Midwestern” values. When Crowd Companies’ Jeremiah Owyang asked his Midwestern colleagues to share how they define Midwestern values, the three themes that emerged were a strong work ethic, modest integrity and helping others. Researchers from the University of Cambridge analyzed personality traits of 1.6 million Americans and found that the Midwest is the most “friendly” region of the country. We’re always eager to ask “how can I help?” without expecting reciprocation, and we’re deeply passionate about our community. We identify strongly with that approach, and it’s reflected in how we work with our entrepreneurs and investors.

Civic Leadership

It doesn’t surprise us that impact investing is thriving here because Midwesterners have always brought a civic-minded outlook to all aspects of life, and have long been paving the way in activism and civic engagement. From fighting for eight-hour days and fairness, justice and equality at work, to ending corporate greed and poverty, Chicago is considered the birthplace of the American labor movement. Today we’re still moving the needle on human rights and community service. States like Iowa, Minnesota and Illinois allowed same-sex marriage years ahead of New York and California. In a 2009 study on Americans’ volunteering habits, the Corporation for National and Community Service found Midwesterners to be most charitable with their time, with 30.2 percent of people in the region having volunteered in the past year.

In summary, we’re in the best place we could be. The Midwest has all the best ingredients for a thriving social entrepreneurship and impact investing community: a growing tech and venture capital ecosystem, strong values, and a rich history of civic leadership. We’re also a direct flight from a central location to pretty much anywhere else in the country we want to invest or partner. We look forward to working with you to build the impact investing ecosystem, wherever you are!