Finding the right estate planning attorney can feel overwhelming and choosing the wrong one can cost you time, money, and peace of mind. In this Tuesday Triage episode, I walk you through six practical steps to help you identify the right fit for your needs, avoid common pitfalls, and trust your instincts throughout the process. Whether your estate is simple or more complex, these tips will give you clarity and confidence in choosing the attorney who can best serve you and your family.
What Jill discussed
·Why referrals are a great starting point but not the finish line. Referrals from trusted friends, advisors, or professionals can point you in the right direction, but they shouldn’t be the only factor in your decision. You still need to do your own due diligence and trust your gut.
·How to match the attorney’s experience to your unique needs. Many people think their estate is “simple,” but often it’s more complex than it appears. Jill breaks down what circumstances generally qualify as a “simple estate,” what makes an estate more complicated (tax planning, business ownership, beneficiaries with special needs, blended families, family vacation properties), and why the distinction matters when choosing an attorney.
·The role of clear communication. Estate planning comes with lots of legal jargon. A good attorney explains things in plain language, helps you understand how legal changes impact your plan, and leaves you feeling more confident, not more confused. Jill share tips on how to test this before you hire someone.
·Why experience makes a difference. Beyond knowing the law, seasoned attorneys have seen how family dynamics and real-life complications play out. That experience allows them to anticipate problems, avoid mistakes, and guide you through both the expected and the unexpected.
·Looking for a clear process and transparent pricing. A solid estate planning attorney doesn’t just draft documents — they help make sure your plan actually works by funding trusts and aligning beneficiary designations. Jill talks about flat fees vs. hourly billing, what you should expect in a quote, and how to make sure there are no surprises.
·Why comfort and trust are non-negotiable. You’ll be sharing some of your most personal details with your attorney. You need someone you feel heard and respected by, and someone who moves at a pace that feels right for you. Credentials matter, but so do instincts, and ignoring them can be costly.
Resources and Links
The Death Readiness Podcast
Episode: 32
Title: 6 Steps to Finding the Right Estate Planning Attorney for Your Situation
Host: Jill Mastroianni (Solo)
Published: September 16, 2025
Jill Mastroianni (00:00):
How do you find the right estate planning attorney — and avoid the wrong one? That’s the question we’re unpacking today. And it comes from Jeremy in Michigan… who also happens to be my husband.
Welcome to the Death Readiness Podcast. This is not your dad’s estate planning podcast. I’m Jill Mastroianni, former estate attorney, current realist, and your guide to wills, trusts, probate and the conversations no one wants to have. If your Google search history includes, “Do I need a trust?” “What exactly is probate?” and “Am I supposed to do something with mom’s Will?” you’re in the right place.
(00:45) Choosing an attorney can feel overwhelming. I’ve been there. I once needed help on a personal matter in a completely different area of law than I practiced, so I did what most of us would do — I asked a trusted colleague for a referral. He asked someone he trusted, and before long, I had my recommendation.
From the very first meeting, I had a knot in my stomach. This recommended attorney kept me waiting past my appointment time while I could hear him in the hallway, casually chatting — maybe even flirting — with a younger colleague. I can’t believe I moved forward with him after that.
Later, when I emailed him a question about my case, he simply forwarded my question to another attorney — someone from another law firm, representing another client, potentially adverse to me — and asked that attorney for the answer. I even found myself double-checking his research and correcting both the facts and the law in his court pleadings.
We spent thousands of dollars and got no closer to a resolution. I was an experienced attorney, working alongside other high-powered attorneys — and still, I felt confused, taken advantage of, and ashamed for ignoring my gut. The financial toll was steep, but the lost time was even worse.
(02:01) Referrals can only take you so far. Even now, I feel sick thinking about how stuck I felt — like if I didn’t stay with him, I’d have no one. But eventually, I did find someone better.
It wasn’t on my first try, but this time I trusted my instincts. The attorney I hired wasn’t flashy, but she was smart, experienced, honest, and transparent about her fees. Most importantly, she understood me, my values and my priorities.
That’s why in today’s episode, I want to take you behind the scenes and give you 6 steps to finding the right estate planning attorney. Beyond the steps, I want you to advocate for yourself — and above all, trust your gut. Whether it’s choosing an attorney, or making any big life decision, your instincts matter.
(02:44) If you’d like more support with the estate planning process, my Estate Planning Support Services make the process simple and manageable. I’ll help you get organized, find the right attorney in your state, prepare you for meetings with your attorney, attend your attorney meetings, if you’d like, and make sure your plan is clear and ready to implement.
Learn more at deathreadiness.com/services. The link is in the show notes.
Before I get into the six steps to finding the right estate planning attorney, I want to take a moment to define what that really means. When I say “estate planning attorney,” I don’t mean a lawyer who dabbles in wills between real estate closings and divorce cases.
You need someone whose practice is centered on estate planning, trusts, and probate. Why? Because this area of law isn’t just paperwork — it’s loaded with technical rules and hidden pitfalls, and the right drafting makes a huge difference.
(03:40) Now, let’s go through these 6 steps to finding the right estate planning for you.
#1: Ask for a Referral
Referrals from financial advisors, accountants, or trusted friends can be a great starting point — just don’t let them be the only thing you rely on.
Yes, I still go the referral route, even after my own terrible experience. In fact, the attorney who eventually fixed the mess from that first lawyer? I found her through referrals, too. The difference was that this time, I trusted my gut.
So yes — ask for referrals. But don’t follow them blindly. And remember, your friend’s estate planning attorney may have been perfect for their situation, but not for yours. You still need to do your own due diligence to make sure the attorney is the right fit for you.
#2: Match the Attorney’s Experience to Your Needs
Do you have a simple estate — or a complicated estate?
Most people will tell me they have a simple estate. And most of the time, they’re wrong. So let’s break this down.
Now, there are exceptions to every rule, but here are some general guideposts:
(04:50) A simple estate usually looks like this for a married couple: you’re happily married, you own everything jointly, if you have kids, they get along, no beneficiaries have special needs, you both have traditional jobs (you’re not business owners), and your estate doesn’t exceed the state or federal estate tax exemption. In short, you don’t need tax planning.
I’m going to include a link in the show notes to an episode, Why you shouldn’t worry about the estate tax, if you want to learn more about tax planning.
On the other hand, a complicated estate can mean different things:
(06:20) And let me give you a real-life example. A recent client swore her estate was simple. She’s in her early 50s, never married, no children. Sounds simple, right?
But here’s who she wanted to include in her estate plan: her adoptive parents, her four adoptive siblings, the biological child her adoptive brother with special needs had placed for adoption, her biological mother, one half-sibling through her biological mother, and the minor children of another biological half-sibling.
That is not a simple estate.
So here’s the takeaway: one person’s idea of ‘simple’ isn’t necessarily simple at all. When you’re referred to an attorney, look at their website and think carefully about whether their skill set actually matches your circumstances.
(07:13) Don’t be afraid to ask the attorney directly whether they’ve worked with situations like yours. You may not always get a perfectly honest answer — but if you don’t ask, you definitely won’t get one at all.
Even just putting the question on the table gives you valuable information: how they respond, how confident they sound, and whether they can point to relevant experience. That alone can tell you a lot about whether they’re the right fit.
A good estate planning attorney should help you anticipate conflict (with siblings, ex-spouses, blended families) and structure your plan to minimize it.
#3: Prioritize clear communication.
(07:53) Estate planning is full of jargon. You’ll hear terms like lapsed legacy, codicil and per stirpes. A good attorney cuts through all of that and explains things in plain English. You should leave a meeting feeling more confident, not more confused.
One way to test this? Look at the content they’ve put out. If they’ve written articles or blogs, read them. Do they make sense to you? If they’ve been a guest on a podcast, listen to an episode or two. Do you actually understand how they explain things?
But communication alone isn’t enough. Estate planning laws change and your attorney needs to be on top of those changes. The best ones are not only up-to-date themselves, but they also know how to explain what’s changed and why it matters for your plan.
If your attorney isn’t a good communicator, you won’t understand your own estate plan. And if you don’t understand your estate plan, you’ll never know if it really does what you want it to do.
#4: Experience Matters
(08:55) Experience really does make a difference. Unless a newer attorney is working closely with seasoned estate planners who can guide them, I generally recommend avoiding an estate planning attorney who has been practicing for less than two years.
Why? Because estate planning isn’t just about knowing the law. It’s about having the experience to anticipate what families actually go through — the expected and the unexpected. The more situations an attorney has seen, the better prepared they are to help you avoid mistakes and spot issues before they become problems.
#5: Look for a Clear Process and Transparent Pricing
A good estate planning attorney doesn’t just hand over documents and call it a day. They make sure those documents actually do something. That means ensuring your assets are properly titled in a trust, if that’s part of your plan, or that your beneficiary designations are set up the right way.
(09:51) I’ll link in the show notes to my video Do You Need a Will? if you want to dig deeper into estate planning basics.
The other piece of the puzzle is cost. Estate planning can be billed hourly or as a flat fee, and I understand why attorneys use both models. But even if your attorney bills by the hour, after your initial consultation they should be able to give you an approximate quote.
And, you need clarity upfront about what’s included in that quote. For example, if you’re creating a revocable trust, do those fees include funding the trust so that your plan actually works?
I’ll also link in the show notes to my episode Why You Need — or Don’t Need — a Trust for more information on how trusts work, if you’re interested.
The attorney should have a process that goes beyond drafting, and they should be upfront and transparent about what it will cost you.
#6: Comfort and Trust Matter
(10:50) At the end of the day, you’re going to be sharing some of the most personal details of your life — your money, your family tensions, your end-of-life wishes. That means you need an attorney you truly feel comfortable with.
Ask yourself: Do I feel listened to? Do I feel respected? Do I feel comfortable with the timing and pace of the process? If the answer to any of those is no, that’s a sign this attorney may not be the right fit. Trust your instincts here — because comfort and trust are just as important as credentials.
When I was practicing at a large firm and focused on taxable estates, I sometimes had people call me about estate planning needs didn’t require special tax expertise. And if I didn’t believe my level of expertise would add value, I told them so. I’d point them to attorneys I knew personally, whose work I respected, and who I believed could serve them better — often at a lower hourly rate.
(11:48) And that’s the same approach I take now. If you’d like guidance in finding the right estate planning attorney and making sure the process feels clear and manageable, my Estate Planning Support Services can help. I’ll work with you to get organized, connect you with a trusted attorney in your state, prepare you for meetings, and even attend them with you if that would be helpful. Together, we’ll make sure your plan isn’t just finished — it’s understood and ready to put into action.
You can learn more at deathreadiness.com/services. That’s deathreadiness.com/services.
I’ll include a link in the show notes.
Finding the right fit matters not just for you as the client, but for the attorney, too. A good attorney knows when they’re the right match — and when someone else could do a better job. And that’s exactly the kind of honesty and clarity you should be looking for.
A big thanks to Jeremy of Michigan —today’s question-asker, my husband and faithful listener of The Death Readiness Podcast. Estate planning really is a family affair.
(12:51) If you found this episode helpful, please share it with someone you think could benefit from it.
This is Death Readiness, real, messy and yours to own. I’m Jill Mastroianni and I’m here to help you sort through it, especially when you don’t know where to start.
Hi, I'm April, Jill's daughter. Thanks for listening to The Death Readiness Podcast. While my mom is an attorney, she’s not your attorney. The Death Readiness Podcast is for educational and entertainment purposes only. It does not provide legal advice. For legal guidance tailored to your unique situation, consult with a licensed attorney in your state. To learn more about the services my mom offers, visit DeathReadiness.com.