Building Great Cultures: Embracing the Light and Understanding the Shade

6 min read
Jan 23, 2019

Leaders in the workplace can transform people's lives. Margaret Wheeler is living proof of how much can be achieved when we show commitment to our employees. As Chief People & Culture Officer at Stitch Fix, Wheeler has seized every opportunity to drive positive change for her workers.

But why should leaders care? For Margaret, it’s because work is developmental, transformational, and as she thinks about her own work in her life, Wheeler says she’s had the opportunity to change as a human being because of her experiences in the companies she’s been a part of.



Earlier in her career, Wheeler worked at Starbucks as a regional training manager. When she first started her job, she spent a month in a store where she served on the frontline as a regular barista. She realized she was often the first, and possibly only person that somebody would talk to that day. This experience helped her develop a sense of empathy, not just with her customers, but also with employees.

No company can ever be bigger than their employees.

After working at Starbucks for 15 years, Wheeler then decided to join Lululemon, leading human resources (HR) and becoming the Head of People. During her time at Lululemon, the company had a practice of teaching every employee how to have a vision for their life and to set goals. Those goals were not exclusively about work. Your retention strategy might be that you want to keep people forever, but there may be an amazing opportunity for someone to move on or start a business.


Developing a successful culture

Every time Wheeler has transitioned to a new company she’s had to ask herself, “What’s correct for the company that I’m in right now?” She shared two key pieces of advice for developing a successful culture:

  • Personalize it. Think about the DNA of your own company. Create, take the seeds and inspiration, and apply what’s correct for you.

  • Be explicit and deliberate about your culture. Your actions, decisions, principles, practices, and your words must line up.


Stitch Fix was the first private company Wheeler has ever worked for after a tumultuous year at Lululemon. She knew she was going to leave, and that was one of the most productive periods of her time at Lululemon, because any trace of fear was gone since she was planning to leave.

Employee Retention Report

Growing a business by creating culture

At Stitch Fix, Wheeler started off with three other people and herself. She was the recruiting coordinator, compensation analyst, and everything in between.

Today, Stitch Fix employs more than 5,000 people in the now public company. 3,900 are stylists who are full-time employees, and there are four warehouses and 800 people in their offices. Revenues had started small. Today they have been successfully growing and continue to do so. What started off as a women’s business has now expanded to also include men’s and kid’s products. 

Margo tinycon

Stitch Fix was very deliberate in codifying what their culture was. Having worked in several industries, Margaret understands why a focus on culture is so important for organizations, saying, “There are a lot of companies, particularly in Silicon Valley, where we’ve seen the cost of not being deliberate about culture.” When managers are not proactive about shaping positive behaviors, this inaction could lead to devastating consequences for the company. According to Wheeler, “We’re all just a couple incidents away from being on a newspaper headline.”

They were also very deliberate in who they hire. What are the values? How does leadership create a future? Wheeler is proud they haven’t succumbed to a bureaucratic place as they have healthy boundaries and rules, but she’s happy that people can fully express themselves. How can you have innovation if you’re not fully expressed?

There’s a lot of talk about the roles of the HR team and CEO. One of the things Wheeler has come to learn over the course of her career is that we all generate the culture. It’s made by all the micro interactions that we have that build up to create a culture.

Some things Wheeler has seen that help drive strong cultures include an aligned leadership team. Should someone have to fight for the agenda and push uphill? At Stitch Fix, all the leaders teach the classes – not HR. They recreate that experience of hiring each other and themselves.


Shifting a philosophy to embody your values

Wheeler doesn’t like it when companies allow their headquarters and warehouses/stores to have different philosophies. Why would you have different sets of values? They have a philosophy at Stitch Fix about market-based pay. This is done in their warehouses and headquarters, but the frequency and how they benchmark is different based on location.

There are known secrets in companies and these can be damaging, especially in the top leadership roles. Sometimes people’s skill set isn’t the right fit, or they aren’t culturally aligned. Wheeler recommends avoiding saying “culture fit” because this can be weaponized and inhibit diversity and inclusion.

Wheeler asks us, “When is it time to shift a philosophy? How does leadership evolve this?” Open the vault every six months to look at your principles and ask if these things are still working. Don’t be afraid to ask questions, get feedback, and listen.

Your brand should be an embodiment of your values and persona, a philosophy passed on to your customers. Be known for great culture.

There’s a lot of default futures in companies. For example, “Now that we’re big it has to be slow.” Wheeler asks, “Why does it have to be that way? How can you be a harsh realist but not allow some future to take hold that isn't your future?”

Wheeler believes that Stitch Fix can have twice as many employees and still have an incredible culture.


Positivity versus negativity

People have shadow sides and great sides. Companies are like people – they start out with a founder, but they become their own entity. Wheeler loves all the companies she has worked with, but they all have a shadow side. For example, Starbucks had an incredible mission and value statement, one of them being “We treat people with respect and dignity.” However, when she gave performance feedback to employees, they would respond with “That’s not very respectful, and I don’t feel like you’re treating me with dignity.” It had created a culture that made it harder to performance manage and harder to direct.

Lululemon’s culture is intense positivity with a mission statement of “Elevating the world from mediocrity to greatness.” Yet, there was a suppression of talking about things that weren’t good. “It could be that positivity that plays against you,” Wheeler suggests.

One of the values of Stitch Fix is partnership. Cross functional work is intense and important. They have data scientists and engineers paired up with stylists. Everyone works together. The dark side of this collaboration is it can inhibit people from taking a leadership role and being responsible for making decisions.

What’s the shadow side of your culture?

  • Be willing to see the shadow side and talk openly about it. You must be willing to create an environment where people can talk. Be open with communication to not only be aware of any frustrations, but also to show employees you value their feedback

  • Create active strategies to strengthen what’s working and to shift the shadow tendency. For example, Stitch Fix created a Ways of Working survey, so they could check in on partnership and really measure it. They also give tool kits on how to have decision-making be better and preserve partnership.

  • Build confidence in your teams to share what they see as they work to become leaders.

Being an employee advocate and making business decisions are one and the same. Anchor your decisions around culture, values, and strategy. Don’t pit employees versus business versus customers. Find a way to be holistic.


Margaret Wheeler spoke at this year's TINYcon 2018. To reserve your tickets to next year's TINYcon, and make sure that you're keeping up to date with the latest in employee engagement and company culture, get your early bird tickets now! If you're looking for more tips or info on improving company culture, you can also read our culture report.


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