Perfection is the Enemy of the Good

Chief Legal Officer & Chief People Officer, Gilt Groupe

In the fast-paced world of e-commerce, Kathy Leo has learned that getting the work shipped out the door is often more valuable than making it perfect

When Kathy Leo came aboard Gilt Groupe Inc., an innovative online shopping destination that offers its members special access to inspiring merchandise and experiences at insider prices, the rapidly growing company was in need of internal organization. Initially brought on as general counsel and later accepting the twin responsibilities of putting its legal and people matters in order, Leo set to work instituting strategies that favor straight talk, solutions, and superior results.

1. Be an expert, but be practical

To be able to digest the law and to think about solutions for the business is a skill that must be developed, but is invaluable once mastered. For Kathy Leo, her high road when faced with a business challenge is not to say no, but to think creatively about what can be done to create win-win situations for the business. Part of that process involves identifying all the risks up front, mitigating them when possible, and ultimately developing an educated assessment of the reasonableness of a course of action given the particular business goals.

In her own experience, Leo recalls that there have been times in which a business deal presented serious potential risks, but she has instilled with her team that sometimes, on balance, getting the deal done may be more important to the business than a specific identifiable issue that can’t be resolved in the negotiation. In these instances, she and her team are able to see the forest through the trees for the betterment of the enterprise.

2. Establish formalized processes as early as possible

Processes save time. When Leo joined Gilt it was suffering from a pitfall of fast-growing companies: as problems emerged, short-term solutions were applied like buckets of water to a fire, but they never made reacting to the flames any easier or more efficient. The disorder was especially precarious because, as an international company operating in the United States, Ireland, and Japan, Gilt requires Leo and her team to be conscious of country-specific discrepancies, as well as the nuances of the company’s 4,000 brand relationships.

Whether Leo or any member of the business needed to confirm expiration dates or terms of agreement, time was invariably wasted tracking down answers. “At some point, young companies need to ask what processes will make life easier going forward,” Leo says, “and that has to be a continuous effort to improve performance.”

3. Perfection is the enemy of the good

Lawyers tend to be perfectionists. As a new attorney, Leo was no different. The change for her came when a sage colleague told her, “Clients don’t always want ‘A’ work.”

When Leo made the shift to in-house legal services, the volume of work was incredible. Her boss had a policy called the 80/20 Rule. “The thought was if you put increasing effort into a given task, you’ll get proportionally worse returns,” Leo explains. “I learned very quickly that often ‘good’ is good enough, and I should spend the most time, effort, and resources on the most critical activities that will make a difference to the business.”

Not only is the pace of her industry a factor in Leo’s delegation technique, but the fact that she is in-house requires her to be more responsive than if she were working at a law firm. “People want you to be practical,” she says. “They aren’t impressed that you can catch every issue in a contract. They want you to get it done.”

4. Never compromise on hiring

When a résumé crosses Leo’s desk, she is not looking at experience to glean a candidate’s skill set, but rather their potential. “What’s true for lawyers is true for HR generalists,” she says. “Technical skills are only a small part of someone’s success. Hire the best athlete, and you can teach them your cultural criteria.” Equally important as résumé review is the interview process, and Leo prescribes an engaged, thoughtful chief legal officer or chief people officer to carry it out.

Outsourcing these tasks can become costly for the executive looking to save time. Leo says participating in interviews and reference checks gives her the opportunity to prime references for trouble spots and candidates for their strengths and weaknesses. She also recommends allowing interviewees to interact with each level of the business to gauge their interpersonal aptitude and ability to be a team player.

5. Excel at being a business partner

The legal department didn’t always garner the same respect at Gilt that it does now. That respect had to be earned. And in the corporate world, respect translates to partnership in the business. “I don’t expect lawyers to just be lawyers,” Leo says of her staff at Gilt. “I expect them to advise people at all levels of the organization and in capacities beyond legal counsel.”

By changing the way her department responded to requests, Leo was able to change its perception by the other business units. In line with her solution-oriented approach, Leo fostered a culture of execution and a sense of urgency.

6. Value transparency and respect candor

It should be obvious that Leo has no time to waste in the high-velocity environment Gilt provides, which is why she prefers candor to skirting around issues. For the Internet retailer, or any business for that matter, operating without a hitch often requires a dedication to trust and transparency. “People waste a lot of time if concerned with the agendas of others,” Leo says. “I don’t want people to second-guess their benefit to the business because that slows us down and stifles creativity.”

Similarly, the company as a whole must be honest and clear about its direction, allow­ing everyone to contribute to its goals and successes. Though each department may have its own role in the business plan, Leo says it is important not to let the business functions fall into a network of silos that don’t communicate or work together. “I make sure someone owns each part of the process,” Leo explains. “We don’t have time to be retreading old ground.”