Everything I Learned About Leadership, I Learned in Retail

In my professional journey, I've held numerous leadership roles, from being a young manager to a team of 20, to project manager, and serving a chief of staff Additionally, I've led nonprofit boards and founded organizations. But the foundation of my leadership knowledge? The numerous retail jobs I held in my teens and 20s.

Here’s a look at the leadership lessons retail has imparted on me, transforming me into the leader I am today.

1. The Power of Providing Options

One of the core tenets of retail is always having options for the customer. When I worked at a CD and DVD store in the early 2000s, we had to find solutions even when we didn't have exactly what a customer wanted. We could special order items and have them shipped to the store for them to pick up, often saving them shipping costs and our special ordering process provided them access to exclusive products they weren't able to get online.

In leadership, this principle translates to offering choices to team members and customers alike. For instance, if someone is interested in attending a costly conference that the organization can't afford, we brainstorm local opportunities (less expensive) or alternative experiences that offer similar value. It's about finding ways to meet needs creatively, fostering growth, and maintaining morale.

2. Handling Difficult Situations with Empathy

Retail is rife with challenging customer interactions. Dealing with angry customers who feel let down by a product or service taught me to listen and work through barriers to meet their needs. As a leader, I apply this by staying open to feedback, acknowledging grievances, and focusing on resolving issues constructively. This approach not only diffuses tension but also builds trust and rapport within the team.

3. The Art of Motivation and Influence

Upselling in retail wasn't just about boosting sales—it was about understanding the customer’s needs and demonstrating how additional products could benefit them. For example, offering a warranty for electronics showed a commitment to customer satisfaction.

In leadership, motivating a team and selling ideas are critical. Whether it’s securing resources or gaining buy-in for new initiatives, I learned to communicate the value clearly and inspire others to see the potential benefits, driving collective effort towards shared goals.

4. Teamwork and Building a Thriving Culture

Retail taught me the importance of teamwork and the ripple effects of individual actions. In food service, for instance, if a team member shirked their duties, it placed an unfair burden on others - significant extra cleaning, time and temperature documentation -  disrupting their entire shift. It taught be the importance of interdependence. On the best shifts I ever had in retail, there was camaraderie, a sense of shared goals and a supportive environment that made even the toughest shifts manageable.

Leadership requires recognizing that every team member's actions affect the whole. Fostering a culture of accountability and mutual respect ensures that everyone contributes positively and understands the impact of their work on colleagues and the organization.

In any leadership role, fostering a culture of support, collaboration, and respect is key to achieving success. When team members feel valued and connected, they are more motivated, engaged, and committed to the organization’s vision. 

5. Speaking Up and Being Clear

Early in my career, I worked in the food service area, but I was eager to develop my skills in other areas. I expressed my interest in being cross-trained and learned to make drinks at the Starbucks connected to our store. This allowed me to fill in for colleagues during breaks or when we were short-staffed, and it taught me a crucial lesson: no one can read your mind.

People often don’t know you’re hungry for promotion or eager to take on more responsibilities unless you tell them. It’s easy to wish that others could just understand our ambitions and act on them without us having to say anything.

However, the reality is that people are usually focused on their own success and lives. They don’t have the time or ability to guess our intentions. I once worked for a boss who expected her team to read her mind, and it was a challenging environment. This experience reinforced the importance of clear communication. A good leader must articulate their emotions, expectations, and goals effectively. Expecting others to guess what you want is not only unrealistic but also unfair. 

6. Valuing Metrics and Analytics

As a cashier, my speed and efficiency were monitored and measured against set benchmarks. This experience highlighted the importance of metrics in assessing performance and identifying areas for improvement.

In leadership, leveraging data and analytics is essential for making informed decisions and driving progress. Metrics provide objective insights that help refine strategies, optimize operations, and enhance overall performance.

Retail may seem like a stepping stone in one’s career, but for me, it was a masterclass in leadership. The skills and insights I gained from serving customers, collaborating with colleagues, and striving to meet sales targets have been invaluable. They have shaped my approach to leadership, making me a more empathetic, effective, and dynamic leader. Whether you're starting in retail or leading a large organization, the lessons from retail can provide a solid foundation for leadership excellence.