Alicia Skruba Of 900 North Michigan Shop: 5 Ways Empathy Will Affect Your Leadership

An Interview With Cynthia Corsetti

LONGEVITY: Having empathy creates a safe environment. People who feel safe are likely to stay. People who stay become invested. People who become invested are the greatest asset any leader can have.

Empathy, the ability to understand and share the feelings of another, is increasingly recognized as a pivotal leadership trait. In an ever-evolving business landscape, leaders who exhibit genuine empathy are better equipped to connect, inspire, and drive their teams towards success. But how exactly does empathy shape leadership dynamics? How can it be harnessed to foster stronger relationships, improved decision-making, and a more inclusive work environment? As part of this series, we had the pleasure of interviewing Alicia Skruba.

Michigan native and marketing and business development maven Alicia Skruba knew from a young age that her talents belonged in Chicago. Armed with a Bachelor’s in Business Administration with a focus in Marketing from Western Michigan University, she took a leap of faith right after graduation into the vibrant world of Chicago’s fashion and marketing scene.

Alicia’s career began as a rollercoaster of stock market-like ups and downs. She zig-zagged between some of Chicago’s top restaurant groups, advertising agencies, and corporate relocation gigs for a solid decade, searching for her true calling. Just when she thought she’d never find her place, serendipity struck. She landed the job at 900 North Michigan Shops in 2014, and the rest, as they say, is history. Starting her journey at 900 in marketing, Alicia’s role quickly expanded to include events, sponsorship, advertising sales, and boutique leasing. Known for her meticulous curation of events & clients, she ensures that each one perfectly complements the building’s aesthetic and ethos.

Alicia’s superpower lies in her ability to empathize with the diverse range of small business owners nestled alongside larger corporate powerhouses. Believing people are more important than spreadsheet numbers, she enjoys all the highs with the building retailers, while also unflinchingly having their backs when the blues inevitably come a-knocking.

A blend of wit, approachability, and luxury is at the core of Alicia’s marketing philosophy for 900 Shops. She believes 900 isn’t just a retail destination; it’s an escape from the frenetic energy of the city. From the lighting to the sound and even to the air quality, she works tirelessly with her team to create an ambiance that keeps visitors coming back for more, all while fostering a sense of community and belonging within the brand. In addition, she walks through the doors daily with the mindset that there is always room to evolve. As a result, she’s never off her game.

Outside the bustling world of 900 Shops, Alicia loves traveling abroad, exploring Chicago’s eclectic neighborhoods, indulging in culinary adventures, and basking in the beauty of northern Michigan’s summer and winter scene.

Thank you so much for joining us in this interview series. Before we dive into our discussion about empathy, our readers would love to “get to know you” a bit better. Can you share with us the backstory of what brought you to your specific career path?

This might sound juvenile, but the movie What Women Want led me to this career path. I watched Helen Hunt as an advertising executive, laser-focused on her vision for brands, and I was hooked. Whenever I question my path, I watch the movie again and feel reinvigorated.

Can you share the most interesting story that has happened to you since you started your career?

My most interesting stories occurred between my careers. I’ve worn many hats over the past 20 years. When people say the road to success is about the journey, not the destination — they aren’t kidding! Between different companies, I was unemployed for almost a year. The recurring theme during those gap years was the story of growing through failure. Many define success as a monetary achievement or a public accolade. However, my achievements were the battles I won when I put my head down every night during unemployment. Trying to mentally cheer myself on to keep fighting was the challenge of my life. I had to keep telling myself that things wouldn’t always be this way and that I needed to wake up and try again. I would fall asleep listening to motivational YouTube videos and TED Talks night after night. Ten years into my professional life and after four or five different failed career paths, I finally found a career home where my talents were utilized and I could make a difference within the brand. Oddly, I miss those nights. It was during those nights of struggle that I discovered who I was. Those were the nights I was writing my stories of success. It’s ironic that “failing forward” is the most interesting story when looking back.

What do you think makes your company stand out? Can you share a story?

I like to think I have a unique ability to see the potential in a brand very easily. When I started at 900 North Michigan in 2014, it was a well-respected property in Chicago on Michigan Avenue’s Magnificent Mile. However, it was dated and needed to be re-imagined. For years, I would approach the 67-story, mixed-use building — home to luxury shops, the Four Seasons Hotel, offices, residences, and parking — and see the beauty in the project. But I also saw the massive amount of missed opportunities and potential. I wanted to transform the dark and quiet luxury mall into an escape from the frenetic energy of Michigan Avenue. I could see malls becoming cool again, with sophistication being reinstated in a way it hadn’t been since the late ’80s and early ‘90s.

My role at 900 was to focus on marketing and leasing the first seven levels, which were retail spaces. Ownership had toyed with renovating the retail section for years but never wanted to pull the trigger. A few years into my time at the property, our CEO and VP approached me and my coworker. They wanted to know what was “cool.” We knew exactly what they needed to see. We lined up seven of Chicago’s best restaurants, bars, and coworking spaces so they could see the elements we envisioned for 900. It felt like a light went off. They saw the need for light, bright, and airy spaces. They saw the desire for simplicity but with extremely intentional design. They saw how lighting, music, and all the elements of ambiance impacted the consumer journey and increased dwell time, which could increase revenue for our retailers. More than anything, they finally saw the vision that many of us had seen so clearly for so long.

It all came down to timing and staying ready for when the ideas were ready to be received. My company has always known I am ambitious for change, though I know that all good things take time and that vision needs to be met with strategy.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Listening and Relaying the Lessons: To lead, you must hear the issues. I’ve been organizing events for as long as I can remember. When hosting a personal or professional event, there are always a lot of pros in each respective field (florists, lighting, photography). Early in my career, I learned that having your squad of vendors was key. However, I didn’t know what qualified as a great vendor. It took years of listening to each of them and understanding their craft. Ultimately, this allowed me to lead events and my team more effectively. I could anticipate problems and educate my team on what to expect. Listening to those vendors helped me gain their respect and retain their partnership.

Authentically Connecting: People want to help people they like. Whether it’s a client or someone I work with, I want to know them and understand what makes them tick. I want to feel connected to them so our interactions aren’t just surface-level business dealings. I have a younger team member who I learned struggled with depression. I didn’t learn this during a business meeting, but over a happy hour I scheduled specifically to get to know him better. By hearing this, I was able to navigate my interactions with him more effectively. Life is happening all around us while we grind away at work. I think it’s important to understand who we’re working with and to make it the best experience possible.

Vision and the Boldness to Share It: To lead, you must give people something greater than themselves to strive for. No one wants to follow subpar ideas. As I led a group of retailers into renewing their leases, I had to give them a vision of what our property could be. I couldn’t downplay it, but I couldn’t hype it up too much either. Ownership hadn’t yet signed on the dotted line to confirm that the project would move forward. It was game time, and they needed to know the dream was possible and that the vision was theirs. Fast forward seven years, and all of those retailers are still on the property, and the vision has become a reality.

Leadership often entails making difficult decisions or choosing between two good paths. Can you share a story with us about a hard decision you had to make as a leader? I’m curious to understand how these challenges have shaped your leadership.

My previous coworker, who technically held a higher title than me, decided to leave our company. I was offered her job and was extremely torn. However, part of leading is knowing when to say no. Taking on that role would have held back our brand. Part of knowing your brand and leading it is allowing it to evolve, even if it means stepping outside of your comfort zone. Releasing control to someone else was extremely challenging for me. It tested my leadership skills. But sometimes, to lead, you have to step aside for the greater good and lead from a different, less obvious position.

Thank you for that. Let’s now jump to the primary focus of our interview. Let’s begin with a basic definition so that we’re all on the same page. How do you define empathy in a leadership context, and why do you believe it’s a vital trait for leaders to possess in today’s work environment?

Empathy is putting yourself in another’s shoes. Often, it’s not just about putting yourself in their shoes but walking in them. It can be easy to lead a team, but are you doing it with longevity in mind? If not, you could be burning out your team, causing them to move on, and leaving you to burn out as well because you have to keep rebuilding the team. This effort takes away from the business goals at the forefront. By understanding your people, you can better understand what they need. If your team truly feels like you’re in it with them, they’ll be taken out of a state of fear. By doing this, they’ll begin to communicate more effectively, and their productivity will increase. The positive impact snowballs from there.

Can you share a personal experience where showing empathy as a leader significantly impacted a situation or relationship in your organization?

I had a retailer who was unable to make rent. He had three strokes and was extremely stressed because of his new business. He felt like he was going to be kicked out of his space because he wasn’t paying rent. All the profits he was making were going toward his mental health. However, his overhead was insanely high because he was paying people to work in his store so he could make all his doctor’s appointments. As a result, he had subpar employees running his retail space who were not nearly as skilled or knowledgeable as he was.

I wanted to retain this tenant. He was motivated and talented, and I knew he could be profitable if he could get through this. I was finally able to arrange a face-to-face meeting with him. He was beyond stressed and scared that the meeting was to terminate his lease. After reassuring him that he wasn’t losing his lease, I was able to guide him to solutions. After reviewing his overhead, we decided he needed to work just two days a week in the store. This would save him enough in overhead to get out of his rent troubles. It also allowed him to get back in the store and get a pulse on what consumers wanted.

Often, what people need is just to see light at the end of the tunnel and feel like they have someone helping them through that tunnel.

How do empathetic leaders strike a balance between understanding their team’s feelings and making tough decisions that might not be universally popular?

Feelings are fluid and can vary from person to person; no one can dictate them, and there’s no way to forecast them. On the other hand, decisions are concrete. Any strong leader should be able to base decisions clearly on the facts. Feelings have to be stripped away, and all you can do is decide based on the facts. Empathetic leaders wouldn’t be able to be empathetic if they factored in all the feelings that their decisions stirred up. This could cripple any leader and hurt the team’s greater goal. Empathetic leaders walk a fine line. The only way to avoid crossing it is to stay consistent and factual when it comes down to the wire.

How would you differentiate between empathy and sympathy in leadership? Why is it important for leaders to distinguish between the two?

Simple: Empathy is proactive, while sympathy is reactive. I never want to be sympathetic because it means I’m behind and wasn’t able to see something coming. Often, this can’t be avoided because life can’t be forecasted. However, if you’re an empathetic leader, you’ll be in tune with your people and likely know what’s happening before it becomes a situation that spirals out of control.

Seeing the difference between the two is like looking in the mirror: are you pretending to be empathetic, or are you genuinely empathetic?

What are some practical strategies or exercises that leaders can employ to cultivate and enhance their empathetic skills?

Get out of the box — literally. Whatever space you’re leading in, escape it. The biggest part of empathy is vulnerability. Allowing others to see you outside of your daily “superhuman leadership” persona will help them feel more connected to you. If you feel like you’re “working” on your empathetic skills, then you’re likely on the wrong path. You should aim to feel like you’re connecting with people. If you have that feeling, then they likely will too.

Based on your experience and research, can you please share “5 Ways Empathy Will Affect Your Leadership”?

1. FULFILLING: It will make leading more fulfilling, and you’ll have a greater impact on those around you.
2. LESS THINKING: Much of the difficulty of leading will be removed because you won’t be constantly guessing. People will give you the answers to leading them.
3. EASE: Success will come easier. People want to help those they feel connected to.
4. INFECTIOUS: Empathy becomes infectious. You lead, but your leadership style starts to influence others, and suddenly you have a tribe of great leaders operating with the same ethos as you.
5. LONGEVITY: Having empathy creates a safe environment. People who feel safe are likely to stay. People who stay become invested. People who are invested are the greatest asset any leader can have.

Are there potential pitfalls or challenges associated with being an empathetic leader? How can these be addressed?

Absorbing the feelings of others is the absolute biggest pitfall. It’s one thing to be connected and understand people; it’s another to take on their problems and think you can be the savior. Some battles aren’t yours to fight. The only way to address this tightrope walk is to know when to step away.

Off-topic, but I’m curious. As someone steering the ship, what thoughts or concerns often keep you awake at night? How do those thoughts influence your daily decision-making process?

Self-doubt keeps me awake, making me wonder if I’m foolish for being empathetic. I question whether it’s hindering me and if I’m absorbing others’ feelings too much. However, after years of this daily debate, I look at the results of my empathy and realize it has gotten me this far — so I must be doing something right!

You are a person of great influence. If you could start a movement that would bring the most good to the most people, what would it be? You never know what your idea can trigger. :-)

Being more human. Too often, we are like robots, just doing what others did before us. I think if we tapped into one another a bit more, we’d find that situations are easier to handle than we make them.

How can our readers follow you online?

Instagram @Aliciaskruba. I keep this more personal, but I drop an introspective thought here and there.

Thank you for the time you spent sharing these fantastic insights. We wish you continued success in your great work!

About the Interviewer: Cynthia Corsetti is an esteemed executive coach with over two decades in corporate leadership and 11 years in executive coaching. Author of the upcoming book, “Dark Drivers,” she guides high-performing professionals and Fortune 500 firms to recognize and manage underlying influences affecting their leadership. Beyond individual coaching, Cynthia offers a 6-month executive transition program and partners with organizations to nurture the next wave of leadership excellence.