What Romantic Relationships Teach Us About Leadership (and Vice Versa)

February 6, 2026

Published in:

Leadership & Management

Anne-Wallis Droter

EO Global Staff Writer

A smiling man in a dapper suit leans confidently against a wall. — Justin M. Riordan. Photo courtesy Kitta Bodmer Photography

At first glance, business leadership, and romantic relationships can seem like entirely different worlds. One world is built on strategy, execution, and results; the other on trust, communication, and emotional connection. But talk to any seasoned entrepreneur long enough, and the overlap becomes impossible to ignore. The same dynamics that determine whether a relationship thrives or fractures—clarity, commitment, boundaries, accountability, and honesty—are the very forces at work inside our companies and leadership teams.

In The Monogamy Spectrum, Justin M. Riordan, EO Portland elumni, explores how relationship patterns can reveal deeper truths about how we show up, make decisions, and lead, both at home and at work. EO members who have read the book often find themselves nodding in recognition, seeing their leadership challenges reflected in the language of relationships, and their relationship patterns echoed in their businesses. When we understand one, we become more capable in the other.

As an entrepreneur, the quality of your leadership will never exceed the quality of your self-awareness.

– Justin M. Riordan, EO Portland

With Valentine’s Day around the corner, now is the perfect moment to explore this intersection within your entrepreneurial mindset. We asked EO Portland members who have connected with Justin’s ideas what insights they gleaned about their own leadership journeys from reading his book. Here’s what they shared:

What concept from The Monogamy Spectrum surprised you the most?

“I was surprised how directly relationship dynamics mirror leadership dynamics. I expected the material to be personal, but I did not expect it to be so operational. The same skills required for healthy partnership — trust, honest communication, and emotional accountability — are the exact skills required to lead a strong organization. Once I saw that connection, I could not unsee it.” – Geoff Metts, Founder, Five Star Guitars

“The distinction between interdependence and codependence really landed for me, especially as an entrepreneur who defaults to taking responsibility and fixing things. It made me realize how easily care can turn into over-functioning, both at home and at work.” – Dré Slaman, Founder, Farm to Fit

“The idea of always rewarding honesty was hard to accept at first, but is so powerful and thought-provoking. Most importantly, the practice exercise in the book helped me to build that muscle and become more self-aware.” – Cameron Madill, Founder, PixelSpoke

Did anything in the book reveal a blind spot or habit you had not noticed before?

“It helped me see how unspoken expectations quietly create friction in relationships.” – Dré Slaman

“The book revealed a blind spot for me around unspoken assumptions. As an entrepreneur, I am used to optimizing systems and solving problems, but I had underestimated how often I relied on assumed alignment instead of explicit alignment. Justin’s work helped me see that avoidance of clarity is not kindness. It is simply delayed conflict. That insight has been transformative.” – Geoff Metts

What’s your biggest takeaway for other entrepreneurs?

“Any relationship (even with employees, vendors, business partners) involves a spectrum where you must clearly define boundaries and agreements explicitly—and if you don’t, you may wind up with ‘broken rules’ or ‘infidelities’ that one or the other didn’t even know they agreed to. This can quickly ruin a professional relationship. Don’t make someone sign a ‘contract’ they didn’t know existed and then try to swing around and hold them accountable. It won’t work.” – Cindy Free, Founder, HR Annie Consulting

The idea of always rewarding honesty was hard to accept at first, but is so powerful and thought-provoking.

– Cameron Madill, EO Portland

“If you are unintentional about your company, you won't get the results you want. Why would your relationships, both personal and professional, be any different?” – Cameron Madill

“My biggest takeaway was that clarity is kinder than accommodation. It’s something I now remind myself of daily!” – Dré Slaman

What did you learn about partnership that applies directly to leadership in your company?

“Relationship dynamics don’t just apply to personal or romantic relationships. They are similar if not the same (minus the romantic side) for any relationship, and impact how I lead my business. For example, I am very transparent with my team overall, and more transparent with my leadership team. At the same time, I define the guardrails of what I will or won’t share—company finances are an example.” – Cindy Free

“In terms of partnership and leadership, the lesson that applies most directly to my company is intentional communication. Clear agreements build trust. Trust builds speed. And speed built on trust is one of the greatest competitive advantages a business can have. This book helped me understand how to create that foundation more deliberately.” – Geoff Metts

“I realize the social dynamic as well. I have friends who also work or lead on my team, and we clearly define the spectrum of where that personal friendship shows up at work, and where the professional relationship shows up in the friendship. We have a mutual understanding, and we respect the boundaries in each scenario. When they get crossed, we talk and reestablish that spectrum if needed.” – Cindy Free

Lead with Clarity, Empathy, and Integrity

As an entrepreneur, the quality of your leadership will never exceed the quality of your self-awareness. If you aim to lead with more clarity, empathy, and integrity, take a page from Justin’s book and explore the spectrum of relationships from his unique perspective.

Whether you’re building a company, a business partnership, or a romantic relationship, the fundamentals of trust, alignment, and intentionality still apply.

Justin M. Riordan, an EO Portland elumni, is a serial entrepreneur, keynote speaker, and author.