November 12, 2026Spot the Business Rules That Are Worth Breaking with Leah Solivan

Every company runs on its own set of business rules. Some are written into handbooks and policies, but most are not. They live in habits, in how a meeting is run, and in what a team quietly assumes is allowed. After years of conversations with leaders, I’ve noticed that the business rules people follow most closely are often the ones nobody remembers choosing.

That idea stayed with me after my conversation with business rules keynote speaker Leah Solivan. Leah has been the founder in the room, the CEO making the call, the seller across the table from an acquirer, and now the investor deciding which founders get to try. From that view, she can see which business rules hold a company up and which ones only hold it back.

Leah Solivan

Her way of sorting them is simple. She calls them beams and barriers. A beam is structure. It’s there for a reason. A barrier is an old assumption dressed up as a requirement. The trouble is that both kinds of business rules look the same from the inside. You only see the difference when you stop and ask why a rule exists.

I’ve been thinking about that question ever since. It’s easy to say that leaders should challenge the status quo. It’s much harder to know which parts of the status quo deserve a challenge. This article is my attempt to work through what Leah taught me about telling the difference, and about the habits that make it easier.

🎧 Watch and listen to the podcast episode: YouTube • Spotify • Apple Podcasts • Amazon Music

Learn Business Rules Before You Break Them

The first lesson from Leah is also the least glamorous. Before you break business rules, you have to understand them. It’s tempting to skip that part. Startup culture loves the story of the outsider who ignores everything and wins. But when I look at Leah’s path, I see something different. She studied mathematics and computer science at Sweet Briar College and began her career as a software engineer at IBM. Those fields are built on precise rules. You can’t write working code by ignoring how a system behaves. You learn the logic first, and only then do you earn the right to bend it.

That’s the part many people miss about business rules. A rule you don’t understand is a rule you can’t safely change. If you break it by accident, you pay for it later. If you break it on purpose, knowing why it was there, you’re making a clean choice, and you can own the result. The difference is not boldness. The difference is understanding. I think that is why Leah’s background in STEM matters to this conversation. It trained her to ask how a system works before deciding how to improve it.

What I find useful is that mastery gives you more than permission. It gives you a map. Once you know how the business rules in your industry came to be, you can see which ones were built for a real problem and which were built for a problem that has since disappeared. A pricing habit, a hiring pattern, a way of organizing a sales team: each one started as an answer to a question. Some of those questions are still open. Many are not.

This is also why leaders who want to drive innovation need patience before they need courage. Innovation without a foundation is noise. Innovation built on real knowledge is a deliberate move, and other people can trust it because you can explain it. That is a quieter kind of bravery, and I think it lasts longer. When someone asks me how to start questioning business rules, I now give the same answer: study them until you could teach them, and then see what is left standing.

Tell a Beam From a Barrier in Your Business Rules

Here is the distinction I can’t stop using. A beam holds weight. Take it out and something falls down. A barrier only blocks the way. Take it out, and you can finally walk through. Leah’s point is that most business rules arrive without a label. Nobody hands you a list that says which is which, so you have to test each one yourself.

The test is a question, and it’s a good one: Is this rule a beam or a barrier? Asking it feels almost too simple. But think about how rarely we ask it. Most teams treat their business rules as weather, something that happens to them. Leah treats them as design choices that someone made at a specific time, for a specific reason, under specific conditions. Once you see a rule as a choice, you can ask whether the conditions have changed.

I’ve seen this play out in business leadership more than once. A company keeps a process because it has always had it. A manager insists on a reporting rhythm because the last company did it that way. An industry prices a certain way because the first big player did. None of these are laws. They are inherited habits, and they pass from one generation of leaders to the next without anyone checking whether they still work. That is how a barrier becomes invisible. It stops looking like a decision and starts looking like the way things are.

The other half of this lesson is about restraint. Innovation doesn’t mean breaking everything. Beams are real. Honest accounting, safety standards, and fair treatment of customers and employees all protect the whole structure. A leader who removes them in the name of disruption isn’t brave, just careless. What I took from Leah is that the goal is not to have fewer business rules. The goal is to have the right ones, and to know the reason behind each.

That is also a corporate culture question. Culture is largely the sum of the unspoken business rules a team lives by: who speaks first in meetings, how mistakes are handled, what counts as a good idea. If you want to change a culture, start by naming the rules nobody has named. You can’t sort beams from barriers until they are out in the open.

What TaskRabbit Taught Me About the Business Rules of Work

Leah’s own story is the best case study I know. She founded TaskRabbit in 2008, before the gig economy had a name, before two-sided marketplaces were a known category, and before most investors had a way to say yes to what she was building. The business rules of the day said that work happens in an office, from nine to five, for one employer. Leah looked at that and asked whether it was a beam or a barrier.

What strikes me is how she went about answering it. She didn’t just write a plan. She became the first Tasker, tooling around Boston on a Honda scooter and running errands for strangers. That detail tells me a lot about how to question business rules responsibly. You can’t judge a rule from a distance. If you want to know whether a barrier is real, you go and stand where it stands. She tested whether people would trust a stranger with their errand, and whether a stranger could build a real income doing it. The model worked because she proved it with her own hands first.

The scale that followed is worth noting. She served as CEO for eight years, raised more than $50 million, grew operations across 44 cities, and completed the company’s acquisition by IKEA in 2017. But the result I think about more is the one nobody can put on a slide. Many people began to see work differently because of what she built. One chapter of our conversation focuses on how TaskRabbit helped reshape the 9-to-5 work relationship. That is a change in an assumption, not just a product.

This is where the future of work conversation gets real. Most talk about it stays abstract. Leah’s version is concrete. Somebody had to question the business rules of employment well enough to build something people would actually use. It takes an entrepreneur willing to be the first customer of her own idea. I think that willingness to do the unglamorous work of proof is what separates a rule-breaker from a rule-ignorer.

Cross-Train Your Brain Before the Business Rules Trap You

One of the more surprising threads in our conversation was Leah’s move from ballet to building technology products. On paper, those look like two different lives. Leah doesn’t treat them that way. Training in dance and training in code both teach practice, repetition, and attention to detail. But they also give her two different ways of seeing a problem, and that is the real gift.

Here is what I think is going on. Every industry has a set of business rules that feel obvious to the people inside it. They feel obvious because everyone inside has learned the same things, read the same books, and gone to the same conferences. When all your mental models come from one place, you can’t see the edges of that place. Someone trained in a different field walks in carrying different instincts. They notice what the insiders stopped noticing.

I think of this as cross-training. Athletes do it to avoid injury and to get stronger in unexpected ways. A runner who lifts weights isn’t wasting time. A leader who studies art, music, or a different trade isn’t wandering off topic either. They are building a second set of eyes. When a problem refuses to budge, those eyes may notice that a so-called law of the industry is really just a habit from one corner of the world.

This is something education often gets wrong. We reward early specialization and treat curiosity outside the main track as a distraction. Leah’s path argues the other way. Her ballet training, her math degree, her years as an engineer, and her time in the founder’s seat were never wasted, because each one fed the others. Her story is the kind of inspirational and motivational example that works because it is practical. You can start today. Pick a skill far from your job and spend a few months on it. Then watch what happens the next time someone defends the business rules with “that’s how it’s always been done.”

Why Range Gives You an Edge When Business Rules Change

The common advice is to pick a lane and go deep. Leah pushes back on that, gently. You don’t have to be a single-field expert, and extreme specialization may actually limit your creativity. When I thought about it, I realized how often I’ve watched narrow expertise turn into narrow thinking.

Depth still matters. Nobody wants a surgeon who dabbles. But depth in one place and blindness everywhere else is a risky mix, especially when the ground is moving. Business rules change, sometimes slowly and then all at once. The specialist who has memorized the current business rules can be caught flat when they shift. The person with range has more ways to adapt, because they’ve already seen how other fields solved similar problems.

Leah’s current work makes this vivid. At Precedent.vc, she manages three funds and a portfolio of more than 150 companies, including Nanit, Ourplace, and Pacaso. Those companies span AI, fintech, consumer, retail, digital health, and marketplace businesses. No one can be a deep expert in all of those. What an investor in that position needs is range: the ability to spot patterns across industries and to ask sharp questions of founders who know the business rules of their own space far better than she does.

I find this reassuring for anyone who feels behind because they didn’t follow a straight line. A winding career is often an asset in disguise. In the business world, we tend to tell the tidy version of success: one goal, one path, one win. The truth is usually messier, and the mess is where the range comes from. In technology especially, where a skill that is hot today can be old in five years, range works like insurance. It lets you move when the ground does.

Where AI Can Make Room for Human Thinking

AI came up in our conversation, as it does in almost every conversation now. What I liked about Leah’s view is that she doesn’t frame it as a threat or a miracle. She frames it as a way to create more room for human thinking. That small shift in wording changes what leaders should do with the technology.

It connects directly to the beam and barrier test. A lot of daily work is routine: formatting, summarizing, scheduling, first drafts. Many of those tasks exist because of old business rules about how work gets done and who does what. If a tool can take them off your plate, the real question is what you do with the time. You can fill it with more of the same. Or you can spend it on the thinking that only people can do: judgment, taste, empathy, and the courage to question business rules that have never been questioned before.

I think this is where leaders will separate themselves. Some will use AI to do the old things faster. Others will use it to ask whether the old things should be done at all. The first group gets efficiency. The second group gets a better business. Speed applied to a barrier just gets you to the wrong place sooner.

This is a thought leadership issue as much as a technical one. The next few years will reward people who can explain, in plain language, why they kept one rule and dropped another. I’d add a caution of my own. New tools bring new unwritten business rules with them. Defaults, automated workflows, and “the system said so” can harden into barriers faster than any policy ever did. The habit of asking whether something is a beam or a barrier needs to start on day one, not year ten.

Trade FOMO for the Joy of Missing Out

Two ideas from the second half of our conversation belong together. One is balancing digital noise with real-world moments. The other is trading the fear of missing out for the joy of missing out. When I put them side by side, I saw the same lesson from two angles.

Noise has its own set of rules. Think about the unwritten business rules of a modern workday: reply within minutes, be on every platform, join every call, and never look like you’re missing something. Nobody voted for these. They just built up over time. And they are barriers in the plainest sense, because they block the long, quiet stretches of attention that good thinking needs. When I ask whether a rule is a beam or a barrier, the always-on rule often fails the test.

One idea from our conversation is that sometimes the smartest opportunity is the one you decide not to chase. That’s hard to accept when everyone around you seems to be chasing everything. Any investor says no far more often than yes, and a portfolio is really a record of choices. The same is true for founders and executives. Every yes takes time, money, and attention from something else. The joy of missing out isn’t laziness. It’s confidence. A leader who feels sure of their direction doesn’t need to prove it by being everywhere.

That is leadership that doesn’t need an audience. It also leaves room for the real-world moments that feed good judgment: a long talk with a colleague, a walk, dinner with family, an evening at the ballet. I used to think of those as breaks from the work. I now think they are part of how the work gets good. Challenging the business rules of constant busyness may be the most personal rule-breaking any of us can do.

Hold Your Core Values While You Question Business Rules

The last chapter of our conversation was about sticking to your core values at your own pace. I’ve come to think it’s the one that holds everything else together. If you spend your time questioning business rules, you need something steady to question them with. Otherwise, you drift. Values are the beams that don’t move even when everything else is on the table.

“At your own pace” matters too. Not every barrier has to come down this quarter. Some changes need trust, evidence, and time. A leader who rushes can knock out a good beam while chasing a bad barrier. Leah’s career shows a long game: eight years as CEO of TaskRabbit, a major exit, and then a second act as an investor and board director, where she chairs the Compensation and Human Capital Committee at PetMed Express. Those are not the moves of someone chasing speed.

Her work on equity shows the same pattern. In 2022 she launched Precedent Collective, an initiative aimed at building a more equitable capital landscape. Think about what that implies. The business rules of who gets funded, who gets introductions, and who gets called a “fit” were never written on a wall, but they shaped who got to build companies. Questioning those business rules is not a side project. It is the beam and barrier test applied to a whole industry.

She is also one of the few Latina technologists to raise institutional venture capital and complete a major platform exit, which gives the question real weight. Her Alexander Capello Award from YPO, recognizing her work in gender equity, points in the same direction.

That is why I think her story matters to women leaders and to anyone who has been told what a founder is supposed to look like. It speaks to empowerment in a practical way too. Permission to question a rule often comes from someone who first showed it could be done. Leah did that, and then she built a vehicle to help others do it.

The Rules Worth Breaking Start With a Better Question

Looking back on the conversation, what stays with me is how modest Leah’s method is. She doesn’t ask leaders to be fearless. She asks them to be curious. Learn the business rules. Ask whether each one is a beam or a barrier. Keep what holds the structure up. Replace what only blocks the way.

Most business rules will never get that kind of attention. They’ll sit in the background, shaping decisions quietly, because questioning them feels like a risk. But the cost of never asking is higher. It is the slow cost of building a company, a career, or a life around assumptions nobody chose.

So here is what I’d leave you with. This week, pick one of the business rules you follow without thinking. Find out where it came from. Ask what problem it was built to solve, and whether that problem still exists. If it holds weight, thank it and move on. If it only blocks the way, you now have a decision to make.

That is the real gift of Leah’s work. Noticing the business rules you live by is the first act of leadership, and everything else follows. Some rules hold a business together. The rest are just waiting for someone to ask.