The Highlights
Deals die all the time because of poor legal counsel.
Collaborative > combative (every single time).
M&A experience isn’t “nice to have”, it’s required.
You’re engaging a practical closer, not a philosopher.
Don’t hire a Harvey Specter
A list of questions to ask to assess fit.
Your Lawyer: A Hidden Risk or Critical Asset
I’ve seen many deals die from lawyer drama or their lack of M&A experience.
Many sellers obsess over price, terms, and transition. The one thing that often gets overlooked is the lawyer(s) they’ll hire to help get their deal across the finish line.
A fact in dealmaking is this:
Your lawyer’s mindset matters as much as their skillset.
Are they a collaborative closer? A gladiator looking for a battle? An anchor keeping the ship stuck in the wake? I’ll give you 3 guesses to figure out which one will get your deal done..
The bottom line is they are your practical protector. If their prerogative is to “win every point” by attempting to beat the other side into submission and turn straight-forward terms into week-long sparring matches, get ready for a shake up in the final stages of closing (and a hefty legal bill to boot).
A lawyer is akin to a car mechanic in the sense that their clients know very little or less about the subject matter at hand. They’re being implicitly trusted as advisors to provide transparent and honest guidance. If you hear that your car will catch fire because of the engine light warning displayed on your dash, that’s pretty tough to ignore (whether it’s true or not).
It’s sometimes difficult to differentiate a perceived legal risk from a real one, but an effective lawyer distills the essence of legal jargon, walks you through the pros and cons, and helps you focus on what will move the needle toward close vs. what shouldn’t be compromised because it presents material exposure.
What Makes a Great M&A Lawyer?
They’re not just sharp. They’re practical and intuitive. They know when to stick and when to slide. Most importantly, they maintain the spirit of the deal while protecting you.
A few key components to focus on:
Communicate clearly and promptly (shouldn’t take 1 week for responses)
They understand M&A deal mechanics
They understand the goal is to close, not to “win”
Work with buyer’s counsel, not battle against them
They protect you (and the spirit of the deal) without launching nukes
They don’t pretend they're Harvey Specter
Common Mistakes Owners Make..
Using an attorney with zero M&A experience
Hire their cousin’s lawyer because he’s cheap
Choosing the most aggressive attorney they can find
Not asking who's actually doing the work (associate vs partner)
Engaging legal counsel without vetting a few options (2 to 4 is what I recommend)
Forgetting that they are the final decision-makers and their advisors (including M&A advisors) work for them
Preliminary Questions You Can Ask Lawyers to Vet “Fit”
What is their current workload?
Estimated cost range for a deal of this size?
Do they have any vacation or time away forthcoming?
How much involvement do they have on the deal vs. their associates?
Assuming no delays or major roadblocks, what is a reasonable timeframe to complete the work at hand? (can we meet the anticipated closing date?)
What is their overall approach to closing deals? (Collaborative? Adversarial?)
The best deals are done when both sides work together. Lawyers are risk managers. Let them manage your legal risks, rather than commandeer the entire deal.
Tangible Takeaways:
Interview 2-4 options before committing.
M&A experience = mandatory. Not optional.
Avoid lawyers who posture like trial attorneys.
Focus on their deal approach, turnaround time, and experience.
Don’t focus strictly on the lowest cost option to drive your selection.
Remember your role: you make final decisions, they protect you.
Always do a pre-deal call to level set and establish context on material terms.
Trust your gut when selecting a lawyer to collaborate with you.
When you’re selling your business, you don’t need a sword. You need a shield and a handshake.
Follow @exit_expert on X for more practical advice on selling your business.