Look for a lawyer with genuine startup experience — not a firm that "also serves startups" but a lawyer who has done hundreds of SAFE financings, knows the option pool shuffle cold, has negotiated pro rata rights and MFN provisions many times, and has seen what bad protective provisions look like from the inside. The difference between a lawyer who does startup work and one who primarily does startup work is significant. The former treats your deal as one file among many types. The latter has pattern recognition that comes only from volume.
Ask directly: how many SAFE or convertible note financings did you personally work on in the last twelve months? How many priced rounds? What were the common friction points? If the answer is vague or the number is small, keep looking.
The recommendation you receive from your investor is not independent advice. It is a referral from someone with a significant economic relationship with the suggested law firm — a relationship built on fund formation work, portfolio company representations, and deal flow that runs into millions of dollars annually. Even with conflict waivers and ethical screens, that economic relationship creates pressure that points in a direction different from yours, particularly when things get complicated: a down round, a founder dispute, an acquisition where the investor's preferences and the founder's preferences diverge.
This does not mean the referred lawyer is incompetent or corrupt. It means the incentive structure is not what it appears to be. See the companion pieces on how Silicon Valley law firms manage conflicts of interest and what founders need to understand before retaining investor-suggested counsel.
A quick test: look at the lawyer's bio. If the most prominent client mention — the name that appears first, most often, or most visibly — is a specific PE or venture fund, you have learned something useful about where that lawyer's professional identity is anchored. If the same fund appears more than once, you have learned something more. Lawyers define themselves professionally by who they serve. A bio built around a fund's name is a bio built around that fund's interests. That is fine if you are the fund. It is not fine if you are the founder on the other side of the table.
For sale transactions, investment bankers routinely suggest law firms. The banker's interest in making a particular suggestion is not necessarily your interest. A lawyer who does substantial work originating from a specific banker develops instincts calibrated to that relationship — to the banker's preferences, to the buyer universe that banker works with, to what makes the process smooth for everyone in the room. That is not always the same as what maximizes your outcome.
More specifically: for sell-side transactions, be cautious of lawyers whose practice is primarily buy-side. Their default assumptions about what is "market" on reps and warranties, indemnification, and MAC definitions are calibrated from the buyer's perspective. They have seen hundreds of deals from one side and relatively few from the other. Instincts are hard to override with awareness.
The best transaction lawyers are frequently not the most marketed ones. Discretion is a feature of good deal practice, not a deficiency. A lawyer who handled a significant acquihire for a founder is not out talking about it — the client would not want that, and the lawyer who understands the business knows it. This means the most visible lawyers in a given community are not necessarily the most experienced ones. Visibility reflects marketing effort and relationship cultivation. Neither of those directly measures transaction capability.
To evaluate experience, you have to ask specific questions. How many transactions of this type — sell-side technology acquisitions, SAFE financings, India-to-US restructurings — have you personally done in the last two years? What is the typical size? What went wrong on recent deals and how did you handle it? A lawyer with genuine depth will answer these questions specifically. One without it will give you general reassurances about the firm's practice.
For most startup and mid-market technology transactions, hourly rates above $1,500 are not necessary and should not be assumed to indicate better outcomes. If your company's enterprise value is below $500 million, there is no structural reason you need counsel billing at rates designed for the largest institutional transactions. Higher rates often reflect overhead, leverage models, and associate hours rather than partner quality or judgment. A senior partner billing at a rate calibrated to your deal's actual complexity will frequently outperform a BigLaw partner who is a credential at the top of a team of associates.
Ask for an estimated fee range before engaging and ask what the partner-to-associate billing ratio looks like on deals of your size. The answer tells you whether the partner's judgment is actually driving the matter.
The structural reality of most technology transactions is that the documents are not written for you. The standard NVCA model documents were developed with explicit institutional investor input and reflect their priorities, not the founder's. Standard acquisition agreements are buy-side forms — drafted to protect the acquirer, with every deviation from that baseline fought for separately. A seller who does not recognize this starts every negotiation already behind.
Sellers also routinely face implied or direct pressure to accept terms or risk losing the deal entirely. "The buyer will walk" is a common negotiating posture. Sometimes it is true. More often it is not. A lawyer with genuine sell-side experience has encountered this enough times to calibrate it — to distinguish real deal-breaking concerns from pressure tactics, to know what is worth holding and what is worth giving, and to be genuinely comfortable making a deal only when the terms actually justify it.
This is a disposition as much as a skill. A lawyer whose economic or relational interest requires the deal to close will hear pressure differently than one who is oriented entirely to your outcome. You want someone who can be unfazed, who can say no without theater, and who can walk away from a bad deal without losing composure or caving to the discomfort of a delayed close. There is a distinction worth drawing between a lawyer who has good relationships with the other side because they are a skilled professional — direct, reliable, someone whose word means something — and one who has good relationships because they are accommodating to a fault. The tell is whether opposing counsel respects your lawyer or whether they simply enjoy working with them.
At large firms, a common practice is for a partner to win the engagement and then transition day-to-day representation to associates and junior partners, with the named partner's time appearing primarily on supervision entries and review. This is an efficiency model for the firm. It is not an efficiency model for you.
The person who does the work personally has more at stake in your outcome. Their reputation is on the line in a way that an associate's is not. Their judgment, formed through direct transaction experience, is available to you without filtering. And when things get complicated — as they do — you want the person who knows your deal in full, not the person who was briefed on it secondhand.
Ask before engaging: who does the drafting and who takes the negotiation calls? If the answer involves "a team," press further. What is the partner's personal involvement on a deal of your size? If the honest answer is that associates handle the day-to-day work and the partner reviews it, you have identified a structural problem before it becomes yours. The billing relationship should be simple: the person whose name is on the bills is the person whose voice is on your calls.
Legal advice in a financing or sale transaction is not purely legal work. It requires understanding the economic stakes clearly enough to translate legal structures into their real effect on your cap table, your earnout, your tax liability, and your ongoing relationship with the buyer or investor. A lawyer with professional accounting or business experience brings a different quality of judgment to this translation. They understand why a particular indemnification basket matters to the deal's economics, not just whether it is within market range.
When evaluating counsel, ask whether the partner has any professional background outside law. It is a differentiator that is rarely advertised but meaningfully affects the quality of advice you receive on the decisions that matter most.
Everything above is subject to this: the single most important quality in a lawyer you trust with a significant transaction is integrity. Not credentials. Not rates. Not even experience. An honest, hard-working attorney who will do what is right for you — and only what is right for you — is worth more than any other combination of qualities.
This means placing your interests above everyone else's in the room: above the investor who made the introduction, above the banker who is running the process, above the opposing law firm with which they have a collegial relationship, above their own preference for a smooth close. Above everyone, including their friends. The test is not whether a lawyer will advocate for you when it is easy. It is whether they will do it when it is uncomfortable — when your interests conflict with someone else's, when pushing back is professionally awkward, when the right answer is also the harder one.
Character is difficult to evaluate from a credential sheet. It shows up in how a lawyer handles the moments when it would be easier not to. Look for someone who has demonstrated it in specific situations. Ask about a time they told a client something the client did not want to hear. Ask about a deal they walked away from. The answer, and how it is given, will tell you more than any number of deal tombstones.
Gurpreet S. Bal is a Partner at Foley & Lardner LLP in Silicon Valley, where he advises technology companies, founders, and investors on SAFE financings, venture capital, mergers and acquisitions, acquihires, and IPOs. He has represented clients in hundreds of transactions with aggregate deal value exceeding $60 billion across AI, semiconductors, fintech, and emerging technology. Prior to his career as a corporate lawyer and transaction advisor, he served with the U.S. Department of Justice and as an international and cross-border tax advisor at a Big 4 accounting firm.