What are some good financial questions to ask?

If I get one question more than any other, it's this one. Whether someone is interviewing a financial advisor or simply trying to figure out what's important to know in their own financial journey, many people simply don't know what's most important to keep an eye on. As I work with those age 50 and over, I would like to help frame your mind on what Certified Financial Planners™ concentrate on with their clients, each and every year. 

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While there are no set questions or specific needs that are applicable to everyone, there are issues, concerns and curiosities that do apply to virtually everyone's financial well-being. We will cover the main categories that you should be asking questions on, to ensure you put yourself in the best position to achieve a lifetime of financial well-being.

1. Goals- While goals are your own, the most important questions you should be asking around goals is are they achievable.  Goals will come in many forms, but the primary conversation will be around having enough money to live a lifestyle you desire. Your question if you are not retired is "how much do I need to save to live the way I want?" Conversely the question as you near retirement is "how much can I spend each year to ensure I never run out of money?" As this answer is based on many factors, other questions could  be, "what would be an appropriate investment portfolio based on my comfort level and goals?" "What are the best vehicles to save money in?" "What is the most tax efficient way to withdraw money each year?" As goals can involve many more things than just lifestyle and spending, this is certainly not an exhaustive list but absolutely forms the base for your plan as addressing one area will automatically lead you to ask "Now, what do we do on this topic?" It's a puzzle you are creating, and this subject is the frame.
2. Social Security- The most common question you will ask is, "when should I start?" While obvious on the surface, I would suggest you rephrase social security questions for better answers. The question that will garner you potentially the most money over your lifetime should be, "based on our family health history and earnings record, what is the best combination of start dates to optimize our lifetime benefits?" As a side note, a question should never be posed to a friend or family member on when they started. It has no bearing on you and their reasoning may be faulty or done without math.
3. Taxes- Obviously, you know the first basic question. "How do I pay less in taxes?" Good start but remember taxes affect everything from your job to your investments to your social security and possibly even your estate. While there is no nice and neat question that covers all of it, a more comprehensive question can and should be, "based on current tax laws (or anticipated), is there any way to minimize taxes or strategies I can employ to reduce taxes not only now, but also offer a tax smart plan for retirement?" I know, I know, that is a mouthful! Unfortunately, the tax landscape is always changing and there is no one size fits all strategy. Each year you will need to see what opportunities are at your disposal and may have to adjust on the fly depending on which way the Washington wind is blowing.
4. Healthcare- At age 50 and beyond the issue will be anticipating Medicare option and Long Term Care. If you are closer to age 50, the first question needs to be, "can I self-insure for Long Term Care and if not, may I see a traditional as well as hybrid option to protect my wife and I?" The question is never, should you get it, but rather what the best approach is based on what you can afford. The longer you wait past age 50, the more expensive it will get and the potential increases that you may develop conditions that will increase the cost even more or, make you or your spouse uninsurable If you are closer to age 65 and you are now trying to get up to speed on Medicare, the question should be "what are the pros and cons for Medicare Advantage and traditional supplement options?" As someone who headed up a Medicare Advantage plan, I think way too many people spend extra money on traditional supplements when an Advantage plan will not only save more money but offer many more benefits. That said, there are still cons so will need to choose based on facts and what is best for you. 
5. Estate- The question I get asked the most is, "Do I need a Trust?" The question should be instead, "this is what I hope to accomplish with my assets and for my family. How best can I make that happen?" Although trust creation cost has come down a good bit through many online services, it's more important to tailor a plan to your wishes first, and in some cases, because of potential taxes. A trust in many cases will give you more control postmortem and also help your children in some cases cut down on the lengthy time often devoted to probate. A second great question should be "how do I ensure that my beneficiary designations flow according to my wishes on all probate/trust assets as well as direct transfer assets?"(e.g., IRA's, Life Insurance)
6. Investments- Lastly, most ask me "What are your returns on average?" or "How much money can you make me?" Awful, awful questions. Your goal in life is not to run out of money, so the question could be, "what return do I need in order to maintain our lifestyle for the rest of my life?" This question not only answers how much risk you have to take, but also creates more of a personal benchmark approach instead of trying to keep up with random benchmarks that have no bearing on your goals. ​  

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There are obviously lots of great questions in many areas that could be phrased more personally, but a good rule of thumb if you haven't noticed already, is that they should all be based on you and not what anyone else did or plans to do. Make it about you!