A great startup lawyer does more than prepare documents and answer legal questions. They challenge your assumptions, help you distinguish what you believe from what you know, and guide you toward better business decisions. If your lawyer only executes what you ask for, you are not getting the full value of outside general counsel.

Written by Svetlana Kamyshanskaya Pantelic, Founding Partner, Primum Law Group

Recently, I spent a weekend at a meditation center doing inner work. One thing I have learned about these experiences is that they are always unpredictable. I never know what will come up, what I will discover about myself, or what reflections I will take home.

This time, I found myself thinking about assumptions. How many decisions do we make based on assumptions without even realizing it? How often do we confuse what we believe to be true with what is actually true? And how many mistakes could we avoid if someone challenged those assumptions before we acted on them?

Naturally, my thoughts turned to business, startups, and the founders I work with. When you think about it, building a startup is largely an exercise in making assumptions and then trying to validate them. Founders assume:

• There is a market for their product.
• Customers will pay for it.
• Their business model will work.
• They have the right team.
• Investors will recognize the opportunity they see.

There is nothing inherently wrong with that. Without assumptions, there would be very little innovation. Entrepreneurs have to believe in something that does not yet exist. But there is a fundamental difference between having a vision and treating every assumption supporting that vision as an established fact.

The danger isn’t making assumptions. It’s forgetting that they are assumptions. And this is where having the right advisor can make an enormous difference.

Over the years, I have come to believe that one of the most valuable things I can do for my clients is not necessarily to answer their legal questions. Sometimes, it is to:

• Ask questions they haven’t considered.
• Challenge something they believe to be true.
• Point out a risk they don’t see, or don’t want to see.

This is not always comfortable. Founders are naturally optimistic. They have to be. Building a company requires conviction, resilience, and an extraordinary amount of confidence in their vision. But that same confidence can sometimes make it difficult to distinguish between assumptions and reality.

A good advisor should not simply validate the founder’s thinking. A good advisor should help the founder test it. Let me give you an example.

Two founders decide to start a company together. They have complementary skills, share a vision, and genuinely believe they are the perfect match. They are going to develop an amazing product, build a successful company, and perhaps create the next unicorn.

But is their compatibility a fact? From where I stand, it is an assumption. They may be absolutely right. But they have not yet experienced the pressures that come with running a business together. What happens when:

• They disagree about strategy?
• One founder wants to raise capital while the other prefers to bootstrap?
• Their expectations about commitment, compensation, or leadership turn out to be different?
• One of them decides to leave?

These are not questions founders necessarily want to discuss when they are excited about launching their company. But they are questions worth asking.

As outside general counsel, my role is not to tell founders that their partnership will fail. It is to help them recognize that its success is not guaranteed, and prepare accordingly. For example, we may recommend a four-year equity vesting schedule with a one-year cliff, supported by appropriate company repurchase rights. If everything works out, wonderful. The founders continue building the company together. If not, the company has a mechanism to protect itself.

But here is the important distinction: the real value wasn’t drafting the vesting agreement. It was recognizing the assumption, challenging it, and helping the founders understand why they needed the agreement in the first place. The document is simply the tool we use to implement the advice.

Many founders initially think of lawyers in terms of transactions and documents. They need to incorporate a company, issue stock, establish an equity incentive plan, sign a commercial agreement, or close a financing round. And, of course, all these things need to be done correctly.

But what if the client is asking for the wrong thing? What if the proposed transaction is based on a flawed assumption? What if the biggest risk is not in the contract, but in the business decision that led to the contract?

A lawyer who simply prepares what a client requests may deliver technically excellent legal work. But an advisor who understands the business can offer something more.

This is where the role of outside general counsel becomes particularly valuable. Unlike an attorney engaged for a single transaction, outside general counsel has the opportunity to understand the business over time: its history, founders, investors, relationships, challenges, and long-term objectives. That context matters. It allows us to recognize patterns, connect decisions that may appear unrelated, and anticipate consequences that may not be obvious when looking at a single transaction.

Sometimes the most valuable advice I give a client is to:

• Proceed.
• Negotiate differently.
• Reconsider the decision altogether.

The value of outside general counsel is not measured simply by the number of documents produced. It is measured by the quality of the decisions we help our clients make, and the problems we help them avoid.

There is another dimension to this that connects directly to my reflections from that weekend. It is relatively easy to question an assumption when we are not emotionally invested in the answer. It becomes much harder when that assumption is connected to our identity, relationships, or vision of the future.

A founder may be deeply attached to the belief that their co-founder is the perfect partner, that a particular investor is exactly what the company needs, or that the business is ready to scale. And the more invested we become in these beliefs, the more difficult it can be to recognize evidence that contradicts them.

This is why an outside perspective matters. Not because an advisor necessarily knows the business better than the founder. The founder will almost always have a deeper understanding of the product, the market, and the vision. But a good advisor brings something different: experience, perspective, independence, and the willingness to ask uncomfortable questions.

The objective is not to replace the founder’s judgment. It is to make that judgment better informed.

I don’t believe founders should stop making assumptions. Entrepreneurship requires making decisions in the face of uncertainty. There is no way around that. But before making an important move, I encourage founders to ask themselves three questions:

• What am I assuming to be true?
• What evidence do I have to support that assumption?
• What happens to my business if I am wrong?

And perhaps one more: Do I have someone around me who is willing to challenge my assumptions, even when I don’t want to hear it?

At Primum Law Group, this is how I think about our role as outside general counsel. We certainly draft agreements, structure transactions, and help companies navigate legal requirements. But the most meaningful part of our work often happens before a single document is drafted. It happens in conversations where we help founders distinguish assumptions from facts, recognize risks, evaluate alternatives, and make more informed business decisions.

My weekend at the meditation center reminded me that we all have blind spots. And sometimes the most valuable thing another person can offer is a perspective that helps us see what we couldn’t see on our own.

So the next time you evaluate the value your lawyer brings to your business, don’t just ask what documents they prepared. Ask yourself: When was the last time my lawyer challenged my thinking, helped me see something I had overlooked, or changed the way I approached an important decision?

Because the best advisors don’t just help you execute your decisions. They help you make better ones.

Have you ever had an advisor challenge an assumption that changed an important business decision? I’d love to hear your experience.

Primum Law Group serves as outside general counsel for startups and growing companies. Learn more about our outsourced general counsel services.

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