As you approach your retirement years and also soon after you retire, you face a serious of critical decisions that are often more complex, with higher stakes, than the saving and investing decisions you had to make throughout your working years. But by asking questions—of yourself and others with hard-won life experience—you have a better chance of making the right choices.

The upcoming holidays are often times when families get together for shared meals and extended visits. This year might be particularly poignant if family members haven’t seen each other for a long time due to the pandemic, and there will be lots to catch up on.

Still, it’s also an excellent time to ask some thought-provoking questions about retirement. By doing so, you can learn much from your older relatives’ life experience, and everybody at the gathering might gain insights by reflecting on the questions and kicking around the answers.

5 thought-provoking questions to get started

With these ideas in mind, here are five straightforward but thought-provoking questions about retirement that might help inspire your holiday discussions:

Question 1: What would you consider to be a successful retirement?

Question 2: What would a good “average day” in retirement look like (not doing things on your bucket list)?

Question 3: What’s on your “bucket list” to do after you retire?

Question 4: How did you (or will you) decide when to retire?

Question 5: For relatives who are already retired: What advice do you have for those of us who are still working, based on your experience? For example, are there things you wish you’d done differently? What steps are you glad that you took?

There’s research backing up the importance of asking these questions: You’re more likely to make better decisions if you’re emotionally engaged to tackle potentially tough retirement choices. Examples of potentially difficult decisions include when to retire, when to claim Social Security, how to deploy your retirement savings, and whether you should move to a location or home that better supports your life in retirement.

The first three questions are designed to encourage you to envision your life in retirement. This can help inspire you to invest the time is takes to determine how you can support the life you really want in retirement.

Look for the best time to ask these questions. It might—or might not—be best to bring up these questions during the big holiday dinner. Instead, you might bring them up when you’re relaxing before or after dinner, or maybe while taking a walk outside to burn off that holiday meal.

3 extra credit questions that can help older relatives

There’s been a growing awareness that some retirees might experience diminished decision-making capacity as they age into their 80s and 90s. This could make them more vulnerable to incurring significant losses due to making mistakes, exploitation, or financial fraud.

Often these risks get ignored until it’s too late, when losses have already occurred. With this in mind, here are three more questions you could ask of relatives whom you suspect could be vulnerable:

Question 1: Do you get stressed or easily flustered when dealing with your bank, insurance company, or investment firm?

Question 2: If you learned something important about finances (either yours/ours, or just in general), would you feel comfortable bringing it to my attention?

Question 3: Have you received any odd emails lately, Grandma?

This last two questions are courtesy of TIAA, a large retirement provider and insurance company. If you’d like to see more questions on this topic, TIAA has prepared a guide to help adult children and parents discuss finances, including conversation starters and two lists of helpful questions that adult children and parents can ask each other.

As a result of these discussions regarding financial vulnerability, if an older family member wants to prepare a plan to protect their money as they age, the Thinking Ahead Roadmap is a helpful website that guides them through the necessary steps.

The gift of your time and these discussions could be the best gift that you give each other this year. You’ll gain valuable information and also help your older relatives feel helpful and wanted.