Before You Need to Know: How to Start The Tough Conversations

There are some conversations we all know we should have, but that we keep putting off. Talking to your parents about their health, finances, or future plans often falls into that category. It can feel uncomfortable, even a little intrusive. But asking these questions before you need to know can save you an incredible amount of stress when the time comes to make decisions, access information on their behalf, even find important or valuable items.

As a professional organizer, I often see families struggling to find crucial documents, locate passwords, or understand their loved ones’ wishes during stressful moments. These are not only logistical challenges, they’re emotional ones, too. Having these conversations now means you can honor your parents’ preferences, manage their affairs responsibly, and minimize confusion or conflict later on, when you may have the added burden of grief.

That’s why I created a new resource:

Before You Need to Know: The Questions You’ll Be Glad You Asked Your Parents.

It's a practical, editable guide designed to help you navigate these important discussions about health, home, finances, accounts, and more. Think of it as a conversation starter, a way to gather what you need while your parents can still share it with you clearly.

The guide includes prompts like:

• Where can I find a list of your medications, and contact information for your healthcare providers?

• What are your phone, computer and email passwords?

• Where are important documents like wills, deeds, or insurance policies kept?

• Are your beneficiary designations up to date?

  
  

Each section is designed to spark a conversation and gather essential information, and these questions may lead to others you didn’t know you needed to ask. My advice? Pick a time, give them a heads-up, and consider involving siblings if appropriate. The goal isn’t to pry, it’s to prepare, with love and respect. Stay strong! You can do this!

If you’ve ever decluttered with me, you know I believe that getting organized is really about being proactive. The same is true here. Having these conversations now means fewer questions and confusion later.

You can download Before You Need to Know and start using it as your roadmap for these essential conversations. You’ll be giving your future self (and your family) a great gift...that of clarity, knowledge and peace of mind.

If you want to take things a step further for your parents or yourself, resources like The Digital Wrangler can help you think through organizing your digital life for your next of kin. And I love (and use) the Nokbox (Next of Kin Box), with its 72 guided checklists, a tangible way to organize every aspect of your life in one place. Finally, if you've lost someone, visit Transference for a downloadable checklist so you know where to start.