Preface: How to Deal With Difficult Lawyers: Silence, Neglect, and the Cost
Four months after my daughter Alyssa was born in 2014, I saw something that, at the time, felt like a dilemma.
Looking back, I’m embarrassed I didn’t handle it immediately.
I won’t get into every detail, but our nanny did something that frustrated me. She did something I’d explicitly asked her not to do—she was spending too much time on her phone and not actually watching Alyssa enough. Nothing “happened”. Still, I remember standing there, knowing it was wrong, and doing nothing.
And instead of saying something right then, I cowered.
I did what I’ve seen so many people do later when they’re in trouble. I started rationalizing.
Who’s perfect?
It’s not devastating.
She’s responsible for my daughter.
If I upset her, what could happen when I’m not watching?
Finding and training someone new could be difficult.
So I swallowed it. I overlooked it. I moved on.
That little moment—me staying quiet because I didn’t want to deal with discomfort—has shown up in my work more times than I can count.
I’m not going to turn this into a parenting story. The specifics in this book are the cases—what happens when people stay quiet with the person representing them. That’s the heart of How to Deal With Difficult Lawyers.
Why people stay quiet with difficult lawyers
It’s the same reason so many defendants stay quiet in front of their lawyers.
They don’t want to upset them. This person is representing them in front of the government, in front of a judge. It feels risky to challenge the person who has the wheel. So people nod. They convince themselves: my lawyer has it handled.
And that’s how difficult lawyers—sometimes through ego, sometimes through laziness, sometimes through sheer disorganization—end up controlling the pace, the facts, and the narrative.
Your silence trains it.
What neglect looks like in real life
Too many defendants get steamrolled.
Calls stop getting returned. Answers get vague. Months pass. Decisions get made without you. You’re told what happened after it already happened.
Sometimes it’s subtle. Sometimes it’s not.
A lawyer in Detroit wrote this to a client:
“If I wanted your advice on the sentencing memorandum, I would have shared it with you. Stop sending me videos of federal judges. I’ve been doing this 35 years. Nothing I don’t know.”
Read that again.
That’s not “confidence.” That’s contempt. And if you’re the person paying—if you’re the person whose future is on the line—contempt is a warning sign.
Here’s another example I’ve seen more than once, and it’s the kind of thing that makes my stomach drop.
A sentencing memorandum gets filed with the wrong details about the defendant—facts that clearly belong to someone else. Boilerplate paragraphs, wrong background, wrong personal history, errors so obvious a stranger could spot them. The lawyer blames a paralegal.
But the truth is simpler: he never read it. He never shared it with the defendant. He never asked the defendant to confirm details. And when he got caught, he didn’t accept responsibility—he deflected.
And the defendant? He didn’t know what to ask. He didn’t know how to get involved. He didn’t know he was allowed to say, “Show me the draft before it gets filed,” or “Walk me through what you’re submitting in my name.”
That’s why How to Deal With Difficult Lawyers exists.
You shouldn’t have to do this—but you do
For nearly 17 years, I’ve watched the same pattern unfold: longer sentences, more regret, millions wasted. And the regret is often worse than the lost money or the extra time—because it comes with a specific kind of shame: I knew something was off, and I didn’t say anything.
I don’t hate lawyers. Many are good. Some are excellent. If you found one who believes in you, communicates, pushes you, and is willing to go above and beyond, good for you.
But it’s uncommon.
And I’m not talking about “busy.” I’m talking about difficult lawyers—the ones who treat basic questions as disrespect, who default to vague answers, who disappear until they need something signed, who act like your involvement is a nuisance.
You shouldn’t have to do this. But you do—because you’re the one who pays for the outcome.
Who this book is for
This book is for the person who regrets the lawyer they hired.
Or the person who likes their lawyer but keeps feeling something is off and can’t put their finger on it.
Or the person who knows they’re being ignored but is afraid to confront it.
And here’s the point: firing the nanny isn’t the lesson.
I eventually fired the nanny.
But what changes if you still don’t know how to hold people accountable?
You can fire the nanny. You can fire the lawyer. You can hire a new one. But if you still can’t have the uncomfortable conversation, you’ll repeat the same pattern. It’s like switching chairs on the Titanic. It’s still going down.
Holding a nanny accountable requires discomfort. Holding a lawyer accountable requires even more discomfort. It requires you to stop apologizing for asking basic questions about your own life.
That’s the promise in How to Deal With Difficult Lawyers: not more information—more accountability.
What you’ll get in How to Deal With Difficult Lawyers
So here’s where we go from here.
I’m going to show you the horror stories—the neglect, the silence, the arrogance, the avoidable mistakes that cost people years of their lives. Real cases. Real consequences.
I’m also going to show you the opposite: people who overcame their fear, learned how to have the uncomfortable conversation, held their lawyer accountable, and earned the best outcome they could earn.
And I’m going to make this practical.
How to hire a lawyer without getting trapped
You’ll learn how to evaluate a lawyer before you sign—especially when the lawyer is charming, confident, and “busy,” which is often how difficult lawyers sell themselves.
Questions to ask that force clarity
You’ll get questions that stop vague answers. The kind of questions that make a lawyer show their work, explain their plan, and commit to timelines in writing.
Sample emails and letters that work
You’ll see sample emails and letters we’ve written for people in our community—messages that get returned, questions that get answered, and next steps put in writing with dates.
Final warning before you read on
If you’re willing to have difficult conversations and learn how to hold your lawyer accountable, keep reading.
If you’re not willing to do that, stop reading now.
FAQs
What does “How to Deal With Difficult Lawyers” mean?
How to Deal With Difficult Lawyers means you stop relying on hope (“he’ll call me back”) and start relying on clarity: written next steps, drafts shared before filing, dates, and direct answers.
Is How to Deal With Difficult Lawyers anti-lawyer?
No. How to Deal With Difficult Lawyers is pro-accountability. Great lawyers exist. This book is about what to do when yours isn’t acting like one.
What are signs of difficult lawyers?
Vague answers, contempt for questions, drafts not shared, decisions made without you, missed deadlines, blame-shifting when mistakes are caught, and no plan in writing.
What if I’m afraid to confront my lawyer?
That fear is the point. How to Deal With Difficult Lawyers shows you how to confront issues without threats—just calm, specific, written communication.
Author
Justin Paperny (hey, I’m writing about myself in the third person!) is an ethics and compliance speaker and founder of White Collar Advice, a national crisis management firm that prepares individuals and companies for government investigations, sentencing, and prison. He is the author of Lessons From Prison, Ethics in Motion, and the upcoming After the Fall. His work has been featured on Dr. Phil, Netflix, CNN, CNBC, Fox News, The Washington Post, and The New York Times.
