When Should You Hire a Lawyer? A Practical Guide for Founders and Operators
As margins get tighter and legal budgets come under the microscope, one question keeps coming up from founders, operators, and fellow executives:
“When do I really need to hire a lawyer?”
It’s a fair question. As a Chief Legal Officer who regularly works with outside counsel and specialized experts, I understand the balancing act—you want to stay protected, but you can’t run every piece of paper through a $750+ an hour law firm.
Here’s my practical take: If budget were no issue, I’d always recommend having a lawyer review all of your agreements. But I also live in the real world and I know legal dollars are finite.
So here’s how to prioritize where to spend, minimize risk, and stay lean without leaving yourself exposed.
1. Keep Your Form Agreements Current (Review Every 1–2 Years)
Your “standard” documents, i.e. services agreements, NDAs, offer letters, contractor agreements should not stay static. Laws change. Your business evolves. The market shifts.
If it’s been more than 12–24 months since you’ve refreshed your templates, now’s the time.
✔️ Have you pivoted to a new customer base or industry?
✔️ Are you working across new geographies or jurisdictions?
✔️ Are there new regulatory requirements (data privacy, employment law, etc.) that should be addressed?
Regular updates to core templates help avoid fire drills down the line and reduce the need for expensive, last-minute legal work.
2. Evaluate the Materiality of the Agreement
Not all contracts are created equal. Before looping in counsel, do a quick materiality check. Ask yourself:
a. What’s the size or strategic impact of the deal?
High dollar value?
Mission-critical services or tech?
Impact on IP or ownership rights?
b. How long are you locked in and can you get out?
A one-year marketing agreement is different than a five-year vendor contract with no termination for convenience.
c. Is there exclusivity or restrictive language?
Anything that limits your ability to work with others (clients, partners, industries) deserves a second look.
d. Does it involve employees, IP, or equity?
Any contract tied to hiring, ownership, or compensation should be reviewed—full stop.
e. Is this in a heavily regulated industry?
Fintech, healthcare, insurance, education, AI—if you’re in one of these spaces, the stakes are higher and legal complexity grows quickly.
If you answered “yes” to any of the above, it’s probably time to call counsel.
3. If You’re On the Fence, Err on the Side of Early Review
When in doubt, think of a lawyer’s review as a combination of:
Insurance against downstream disputes, and
An opportunity to improve the business terms of the deal.
Many lawyers (myself included) can offer quick-turn, fixed-fee reviews that keep you moving without blowing your legal budget. Often, a short consultation can highlight terms you didn’t even know were negotiable.
4. Please Don’t Draft Contracts Yourself (Even with ChatGPT)
Look, I love ChatGPT and legal tech has come a long way. But auto-generated forms that are not somewhat tailored to your needs can be vague, unbalanced, or riddled with hidden landmines. They’re frameworks, not final products.
You’re not a lawyer. (And even if you are, you’re likely not an expert in every area.) Don’t try to draft mission critical documents from scratch using generic templates. That $0 “DIY” document could cost you thousands later.
Bottom Line: Be Strategic, Not Reactive
The goal isn’t to over lawyer your business, it’s to be smart about when and how you use legal support.
✅ Refresh your templates
✅ Triage high-risk contracts
✅ Call counsel when the stakes are high
✅ Don’t DIY the tough stuff
If you’re trying to scale smartly, control costs, and still keep your business protected, I’m always happy to be your “lawyer friend” for a gut check or review.
Legal doesn’t have to be a bottleneck, it just needs to be thoughtful.
Want more practical legal strategy from an operator’s lens? Subscribe and share with someone who’d benefit.
https://bradfordtobin.substack.com/
This post is for informational purposes only and does not constitute legal advice.