Women Of The C-Suite: Lauren Siegel of Trepwise On The Five Things You Need To Succeed As A Senior Executive

An Interview With Vanessa Morcom

I don’t need to have all the answers, but I need to understand my limits. Find the “experts” and bring them in. And stay open to letting people surprise you…those experts may actually be different from who you think they are. I’ve worked on projects where I learned the most about an organization from the person who worked in the mailroom — because they interacted with everyone. They had a keen insight on the culture dynamics of the place, and that provided extreme value to our project.

As a part of our interview series called “Women of the C-Suite,” we had the pleasure of interviewing Lauren Siegel.

Lauren Siegel is Managing Director of Trepwise, a New Orleans-based strategy consulting firm, where she brings years of proven experience in strategic planning, human-centered design, organizational culture, and more to both her clients and the Trepwise team. Since joining the organization in 2016, she has built relationships with and led strategic and growth planning efforts for dozens of clients in the nonprofit, for-profit, and public sectors.

Thank you so much for joining us in this interview series! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

Being raised by a doctor and a lawyer, I always assumed the “right” career for me would be clearly defined and linear. When I was little, I wanted to be an astronaut. But then someone told me I’d need 20/20 vision for the space program — and since I wore coke-bottle-thick glasses in second grade, that dream was crushed.

For a number of years, I wandered aimlessly through my education, continually waiting for a vocational epiphany. I considered everything from diplomat to pastry chef to public health advocate to oyster-shucker. Nothing truly felt right. Until…during a transition time after grad school, I did a bit of consulting work for some friends and family — marketing plans for CPGs, running analytics for digital ads, strategic advising for a restaurant business, and setting up processes for a new tech startup for nonprofits. And I loved all of these things! That’s when it clicked. This…this is what I want to do. I want to do it all.

A client of mine introduced me to Kevin (founder and CEO of Trepwise), and immediately, it just felt right. I had found my professional home, getting to work with an amazing, innovative, and passionate team serving our community in meaningful ways. And here I am, almost eight years later, still loving it!

Can you share the most interesting story that happened to you since you began leading your company?

I earned the title of Managing Director about four years ago, and that title changed a lot for me. People started to see and treat me differently. Something happens when your title changes from one of many to the sole person in that position. First, of course, you start getting hundreds of cold tech sales emails. (Laughing…)

When you’re featured as a leader, people perceive your power, and they want to be near you. I quickly realized that while my clients and team were seeing me differently, I was still interacting with them in the same way. I found that I needed to change my behavior in order to better serve them as a leader. For me, holding power is a resource, a means to an end, and I have a great responsibility to be really intentional about sharing that power. After doing research and reflection on inclusive leadership, my philosophy became “power with” as opposed to “power over,” so I had to consciously shift how I showed up, ensuring others around me had the space to exercise their rightful power as well.

The thing about power dynamics is that they are always changing, depending on who I’m with and what room I’m in, and I am continuously aware of it. It’s a great responsibility to hold power, and it’s an eye-opening experience to consistently move in and out of rooms where I’m the most or least powerful. For example, in a single day I’ve gone from leading a culture session with a dozen executives who see my knowledge as authority and are furiously jotting down notes on how to strengthen their teams, to a Zoom presentation with the mayor’s office where my strategies are a tiny slice of a much larger city system, to facilitating a room of neighborhood residents who are sharing ideas on what would make their quality of life better. The key to power is naming it and deciding the best way to share it based on your values and desired impact on those around you.

It has been said that our mistakes can be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

On my second day with Trepwise, with no warning, I was put on the spot to lead my first client meeting. It was definitely an “oh, sh*t” moment, but I just went with what I knew. I named the problem — it’s my first day and I’m still learning — and then just made a joke out of it. I often make myself the butt of my jokes, and it makes people feel at ease.

I’ve found that self-deprecating humor is a useful tool in many situations. I know myself best, so when I don’t know what to say, I just say something funny about myself. When people laugh at something together, it creates commonality. So, if we can all laugh at the fact that I’m totally whatever at that moment, then we can connect, build trust, and move forward.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

First, let me say that I wouldn’t have gotten anywhere without any person on my Trepwise team, my client network, and my family and friends. I’m a big believer that every interaction shapes who we become…and there are so many people who have stood with me over the years!

That being said, I count Leslie Alley, the former executive director of French Market Corporation, as one of the most influential people in my career. She was the first person beyond my own family, friends, and team who truly advocated for me. She got me into important rooms with big decision-makers to ensure that people knew my name and my value. She created a seat at many tables for me, supporting my work and lifting up my voice. It was Leslie who brought me into the conversation on the Audubon Riverfront Development and gave me space to lend my voice to the future of our city. Because of her, I’ve had the privilege of playing a part in recreating the footprint of the French Quarter, my city’s most recognized neighborhood.

Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader?

With shared leadership and a new structure at Trepwise, there’s a lot of give and take. There are many decisions we make that are relatable but sometimes difficult. For example, I have to make choices about performance feedback, hiring and terminations, whether to push work back, and whether or not to pursue a particular client. I have become jokingly famous among my team for leaning into tough conversations.

Other choices — more difficult choices — arise occasionally in conversations with clients with regard to equity. At times I’ve had to speak very directly to a client about their personal and professional values, their style, and their legacy. I’ve had to help a client see how their words and actions affect their own teams and their broader community and ask them if that’s truly how they want to be seen, if that’s how they want their organization to be perceived.

In these types of situations, it’s important to weigh the relationship risks, but there’s also great value in living my values, being vulnerable, and opening the floor to talking about difficult topics.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

Good executives have to hold all of the many different truths in an organization. This means our heads are full of tensions, contradictions, excitement, and exhaustion. It’s our job to take in all of these truths and then organize and process them so we can understand where we are, the possibilities of where we can go as a company, and strategically where we should head next. Then we have to turn around and remember all of those truths as we communicate and motivate the next level of leaders to carry it to their managers, down to their teams, etc.

It requires a lot of constant observation — noticing things, staying ever-curious about them, and filing them away in our minds for when we have to make big decisions.

Because, at the end of the day, we are leading companies, but companies are groups of people, all with their own value and motivations to bring to the table.

What are the “myths” that you would like to dispel about being a CEO or executive? Can you explain what you mean?

It’s a myth that you get to do less work. It’s not less work; it’s bigger work, brainier and more present. Most days it’s hard to clock in and out, so you have to put measures in place to care for your brain. Learning is soothing to me, so I listen to a lot of podcasts, webinars, and audio books on happiness, balance, and social-emotional learning. These topics help me recenter my needs, but they also teach me how to be a better leader. I particularly love Feel Better, Live More with Dr. Rangan Chatterjee.

It’s also a myth that everyone will listen to you. No, actually, it’s you who has to listen more, because people can become afraid to share things with you. You have to be ultra-trustworthy and empathetic.

And it’s a myth that strangers will respect you more because of your big fancy title. There are rooms where people want to talk to me only because I’m the managing director. There are also rooms where no one wants to talk to me because I’m not a “traditional” executive type. And there are rooms where people want to talk to me because I’m just Lauren. In all those environments, what’s most important is for me to be authentic. Yes, I’m in a position of leadership, but who is Lauren? When I let people in on that intel, it’s the best experience.

In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?

There are still the traditional challenges that have been talked about for many years: A woman saying something in a meeting and being ignored or skipped over, and then a more junior male colleague makes the same point at the same table in the same conversation and is lauded for it. Also, women are often expected to ask all the questions, get to know everyone, and make people feel comfortable and engaged, and it’s exhausting when we’re expected to be the social glue in corporate settings.

Another challenge that’s just as significant but isn’t talked about quite as often is that women have fluctuating types of energy. For example, from one week to the next, my ability to go on stage and speak to 300 executives could plummet, while my desire to work from the couch and dive into a 40-page stakeholder report might skyrocket. I’m willing to admit that this is due to my biology as a woman — and there are many studies out there that confirm it. It’s perfectly normal, and there’s no shame in it. It’s a fact that women need different things as we move through our biological cycles. In a client services environment, however, we are on all the time, and that expectation has been set across the male-dominated industry. As women executives, we need to talk more about our own needs and strategize solutions that can benefit everyone.

What is the most striking difference between your actual job and how you thought the job would be?

I am someone who makes decisions based on my intuition. I like data, facts, figures, history, and perspectives to guide me as backup, but my intuition has never been wrong. When I moved into leadership, I assumed that my intuition would become quieter and my analytical brain would rise to the occasion to decipher the best path of action. I assumed I’d be buried in financial reports, capacity measures, and Tableau analyses. However, that has not been the case at all. From hiring to interpersonal issues to client selection, my intuition has continued to be the best guiding power I hold. Actually, there have been times when I’ve made wrong choices because I didn’t listen to my gut, so I’ve learned my lesson!

Is everyone cut out to be an executive? In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive? Can you explain what you mean?

I think being a good executive is about self-awareness, connection, advocacy for what’s best from a human perspective, and numbers (and humanizing the numbers). But it’s not natural. It has never come naturally for me. Perhaps some aspects of leadership align with certain personality traits in a particular individual, but most of it is learned.

I’ve always been perplexed by the idea that someone is or is not “cut out for” leadership, because that sounds so passive — like a predetermined destiny. Executive leadership is anything but passive. In fact, it’s a decision that starts with self-leadership. So I don’t believe that you’re born a leader or you’re not. I believe that you spend your years honing skills until you discover what it is you could potentially lead in — and then you have to learn how to lead it. But part of the leadership journey is also becoming very aware of what you aren’t good at and making choices to learn or fill in the gaps with the skills and support of others.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

1. Generally, people all want the same thing — a safe place to rest their heads, full bellies, time with their families, a chance to live into their values, etc. When someone is acting off, it’s probably because they feel like something is missing or being threatened. When you’re leading people, it’s your job to try to understand what that is and leverage your power to change it within your influence. For example, in one of my projects, I needed to understand why residents were resistant to change and development. I expected to hear truly different things from different neighborhoods based on income, culture, and demographics, but surprisingly, I heard the same thing again and again — residents wanted to feel like they belong in their neighborhoods, and that sense of belonging felt threatened in the face of change.

2. Tension, disagreement, awkwardness…they’re all intensely human feelings. They are beautiful, and they cannot be rushed or ignored. Making space for these feelings creates an environment of vulnerability and authenticity. I used to think I had to show up perfectly all the time…Phew, that was a lot of pressure! It left me paralyzed when situations didn’t go exactly as planned (which, BTW, they never do). It took a few years into my career to understand that agility is more influential, and much more enjoyable, than perfection.

3. I cannot be everything for everyone — and that’s okay. Sometimes my needs and limits create disappointment for others (and for myself), and I can’t avoid it. I can only be true to my values and communicative of my needs and expectations. It’s funny to me that I plan for a living, while so much of my own leadership journey has been about living in the present, moment to moment, and focusing on what must be done immediately to achieve the best outcomes.

4. I don’t need to have all the answers, but I need to understand my limits. Find the “experts” and bring them in. And stay open to letting people surprise you…those experts may actually be different from who you think they are. I’ve worked on projects where I learned the most about an organization from the person who worked in the mailroom — because they interacted with everyone. They had a keen insight on the culture dynamics of the place, and that provided extreme value to our project.

5. Less is more. Sometimes giving less is actually the best path forward. It doesn’t mean that you are less, but it’s not healthy to overcommit, overwork, over-volunteer, etc. Over time, our company had gotten into a deep habit of underpromising and over-delivering at the expense of our budgets and timelines. Then, a few years ago, we took a step back in our own planning retreat and made a conscious decision to simplify what we do and how we deliver it. Instead of approaching each project so intensely in every aspect, we decided to focus the customization on relationships while codifying the process and deliverables. Now, we are fully leaning into a human-centered approach where I have totally different types of friendships with each of my clients and teammates, but the work we put out is much more streamlined and consistently top quality.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

What would society look like if no parent had to worry about the care and upbringing of their children? How much freer might we be? What could we achieve with that extra mental capacity? Part of the reason I am not yet a parent is because I see the stress and overwhelming sacrifice that come with it…and I am a person of privilege and resource, at that! I truly empathize with all parents, but especially those who have fewer resources or are raising children in challenging situations (such as single parenthood or raising children with special needs).

With that in mind, I’d like to inspire a movement toward recentering parenting in our society — not only teaching people how to parent from young adulthood but also establishing policies that provide additional support for parents, such as paid family leave. Some European countries even provide an attendant, free of charge, to new mothers to help them adjust to the role of motherhood. What could it look like if we in the US adopted that kind of attitude and provided that type of assistance? And what would it look like to extend that level of support to different stages in the parent/child journey?

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

I wish I could have had the opportunity to meet Josephine Baker. She’s no longer living, but I would so love to have heard her stories. She was a performer and a fighter. She leaned into the contradiction of civil rights and playing Black character tropes. She was a person of great influence who strategically navigated her career to make a statement to the world. She seemed fearless…and she was fascinating!

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

About The Interviewer: Vanessa Morcom is a millennial mom of three and founder of Morcom Media, a performance PR shop for thought leaders. She earned her degree in journalism and worked for Canada’s largest social enterprise. She can be reached at vanessa@morcom.media