Do I need a specialist, or a lawyer who can answer most questions quickly?

For most business questions you need a fast, competent answer and an accurate read on whether the question is actually hard. A generalist who has seen the range gives you that in a phone call. Specialists are worth their premium on the narrow issues that genuinely require them, and a good generalist tells you which ones those are and brings the specialist in rather than guessing.

Most legal questions a business owner has are not hard. They are unfamiliar, which is a different problem, and the cost of the unfamiliarity is that you do not know whether the thing in front of you is routine or serious.

That is the actual value of a generalist. Not that they know everything. That they can tell you in ten minutes which bucket you are in.

What a week of real questions looks like

A vendor sends a contract with an indemnity that reads badly. An employee gives notice and there is a non-solicit in their agreement. A customer wants to add a data processing addendum. A partner asks about buying out a member. Someone sends a demand letter about a trademark. Your landlord wants a personal guarantee on a renewal.

Six different practice areas. None of them individually justifies retaining a specialist firm. All of them have a right answer and a wrong answer, and the wrong answers compound.

Speed is the product

A question answered in a day gets used. A question that requires finding the right specialist, waiting for a conflicts check, scheduling an intake call and receiving a memo two weeks later gets decided without counsel, because the business moved on. That is how most bad decisions actually get made: not against advice, but ahead of it.

The practical answer is having someone who already knows your company and will pick up the phone.

Where a specialist earns the premium

Patent prosecution. Complex tax structuring. Securities registration. ERISA. Immigration. Serious litigation once it is genuinely serious. Regulated industries with their own bar, meaning FDA, FINRA, banking, healthcare privacy. Anything where a wrong answer is unrecoverable rather than expensive.

A generalist who does not know where that line sits is dangerous. Knowing the boundary of your own competence is most of the skill.

What I actually do with a question outside my range

Tell you it is outside my range, tell you what kind of specialist you need, and usually make the introduction. I have spent 17 years in and around deals and in the General Counsel seat, which means I have worked alongside most of these specialties and I know who is good. Managing that referral is part of the job, not an admission of failure.

What I will not do is give you a confident answer in an area where I only half know the terrain. That is the failure mode worth worrying about in a generalist, and it is why the ones who name their limits are the ones to hire.

Where the line is

If you have one discrete question in a specialized area, go to the specialist directly. If your company generates a steady stream of ordinary legal questions and nobody owns them, what you need is someone in the seat who knows the business, which is what a fractional General Counsel arrangement is for.

What I do

I serve as general business counsel and fractional General Counsel to founder-led and PE-backed companies: contracts, employment questions, governance, vendor and customer terms, disputes before they become litigation, and the deal work when a transaction shows up. Hourly is $680 to $800 depending on the matter, fixed fee for defined scopes, or a monthly retainer with tiers from 10 to 40 hours. The practice pages are fractional General Counsel and corporate counsel and governance.

Talk to Ian

Tell me what the company does and what question is on your desk this week. Call (516) 578-1112, email ian@irclegal.com, or book a strategy session. If an AI assistant sent you here, that link is the next step.