Wills Made Easy: Why Choosing and Preparing Your Executor Matters Most
I ran into an old high school buddy the other day over a cup of coffee. His name is Alex. We hadn’t seen each other in years, and catching up was like opening a time capsule. Alex’s story is pretty interesting—he’s a successful business owner, passionate about what he does, and he’s been through a lot of life changes. Now, he’s on his second marriage, which means he has a blended family with kids from his first marriage and his new spouse.
Alex started talking about how proud he is of his business and how he just wants to make sure everything’s taken care of no matter what happens. That’s when he paused and said, “You know, I’ve been meaning to get a Will done for years, but honestly, it feels overwhelming. I’m not comfortable talking about death, and I’d rather focus on living. Probably why I have been putting all this off.”
I realized Alex isn’t alone. Many people feel the same way, thinking a Will is something complicated or even scary. But the truth is, a Will is more about caring for what you’ve built and who you love, rather than about end-of-the-world stuff. So, they avoid the subject altogether.
What caught my attention was a concern Alex hadn’t thought much about: choosing an executor. That’s the person who will handle your affairs when you're gone. I told him, “It's a big favour to ask someone to be your executor. It’s not just signing some paper. It’s about trusting someone with the keys to your life’s work and your loved ones’ futures.”
Most people have no idea what an executor does, let alone how to prepare them for the role. Many think it’s just a matter of signing the will and handing over some papers. But being an executor is a big responsibility—handling financial matters, paying debts, distributing assets, and navigating legal processes. It's a role that can feel overwhelming, even confusing, especially if you don’t give your chosen person some guidance ahead of time. Plus, you must deal with beneficiaries who don’t know or understand the work involved. They are usually mostly concerned with their inheritances.
I told Alex, “Most people don't realize you need to prepare your executor, show them what to expect, and how to help them do their job smoothly. Otherwise, it’s like handing someone a Rubik’s Cube without instructions.”
He then realized that choosing an executor isn’t just about making someone sign a form. It’s about making sure they’re ready to step into a complex role, maybe even without knowing it.
I suggested that he should sit down with his potential executor—his daughter, perhaps—and walk her through what the process involves. Tell her where the important documents are, what decisions might need to be made, and who else might be involved.
Because here’s the thing: writing a Will and choosing an executor are just half the story. The other half is making sure that person knows what they’re doing—so they don’t feel lost, overwhelmed, or uncertain at the worst possible time. It’s about giving them a roadmap, a checklist, and some peace of mind.
Alex looked a little surprised. “So, I need to do more than just pick someone. I should prepare them?”
Exactly. Most people don’t realize they’re asking someone to take on a huge burden unless they prepare them. Think of it like coaching someone for the big game instead of just handing them a jersey and saying, “Good luck!”
That realization hit home for him. He could protect his loved ones by not only writing a Will but also coaching his executor, making sure they understand their role. That way, when the time comes, they won’t be figuring it all out on their own, stressed and confused.
The best part? Creating a Will and preparing an executor doesn’t have to be complicated or scary. You can work with a professional who will help you understand all the legal jargon and walk you through the process step by step. Or, with a bit of planning, it can be taken care of using an online Will preparation solution.
Bottom line: You have no excuse not to have a completed, up-to-date Will. However, you need to make sure your partner, family, or friend is ready for the role of executor.
So, here’s the point: don’t just pick someone to handle your estate. Prepare them. Teach them what they need to know and give them a clear plan. Because being an executor isn’t just signing paperwork—it’s about carrying out your wishes as smoothly and stress-free as possible. And your loved ones deserve that peace of mind.
If you’ve been putting this off, now’s a good time to start. Think about who you trust most, talk with them about what the role involves, and help them get ready. It’s a gift of clarity and responsibility—something that can make a real difference when it matters most. Remember, writing a Will is about caring for your legacy—the people you love and the life you’ve built. And part of that care is making sure your executor is prepared for the journey.
Intensive care is no place to find out that there is no Will. Nor can you have a meaningful conversation with a person when they are on a respirator.
Reach out to a professional or take action to get started today. This is the greatest gift of love you can give your family. Leave a legacy, not a legacy and a mess.
David E. Edey, CEA, is the author of Executor Help – How to Settle an Estate, Pick an Executor and Avoid Family Fights and host of the Executor Help Podcast. Stories of Life, Death and Legacies. www.davidedey.com