Why Sherri Manning ditched law for a career in HR

When Sherri Manning was attending law school in the early 1990s, she did not expect her path would lead her to the world of HR.

Sure, she had always been interested in what makes the workplace tick, having started her law career specializing in the Employee Retirement Income Security Act (ERISA) and benefits law. She also spent three years drafting legislation around health insurance and pension benefits. But as much as she enjoyed the legal profession, she realized that she was meant to be in HR.

"The thing that inspired me to make a career transition…is the desire to see things from beginning to end,” said Manning, now the chief people officer (CPO) at Olo, a company that helps businesses scale their online ordering and delivery services. “As an attorney, people will drop problems on your desk, and your job is to solve problems and to consult with a company. In HR, I get to do everything from designing the idea to rolling it out and seeing the impact that it has on the business and in people’s lives.”

Manning’s experience in benefits law gave her a leg up when she entered HR.

"I had the same problems on my desk as an HR professional that 30 days before, I had had on my desk as a lawyer,” Manning said. “It was about whether this particular company could or had to offer COBRA benefits if they were closing down a division, and it was just so much more meaningful and human.”

It also taught her the importance of making human connections and how HR leaders can be an advocate for both employees and the business.

"I find that either people have had an experience with HR where they’re like, ‘Oh, I can’t trust them. All they do is represent the company,’ or…they think that HR’s job is only to do the employee advocacy thing,” Manning said. “The balance is key to strike and it’s the hardest part of my job, but the most important.”

Over the course of her 26-year HR career, Manning developed a mantra that has helped her balance the needs of her organization with what’s best for its employees: Lead with heart, but lead with smarts.

“I have to make sure that what I’m doing is both heart-sensitive and smart-sensitive,” she said. “If I only lead with the heart, I can be doing things that are really caring but are almost heavy with ruinous empathy, that aren’t connected to the reality of the business situation.”

Finding that balance has required greater transparency and a culture where employees have a clear understanding of why some not so popular business decisions need to be made.

Take health insurance benefits, for example. They’re always in flux, as a result of higher drug prices and other costs, and “very close to an employee’s heart,” Manning said. So, it’s important to find the most economical solution for both the employer’s bottom line and the employees’ wallets.

“Anytime we make changes to the benefits that we offer, I want to let them know what we considered before we made a change,” she said.

In the case of health insurance benefits, those considerations include how much the company is spending, what employees want, and what is happening in the marketplace.

“I try to be very transparent about how we’re balancing those three things,” Manning said. “I find that if I am transparent and honest with people that they may tell me, ‘Quite honestly, I don’t like it, but I understand it and I can see that that’s a reasonable business decision.’”