#129 - 6 Better Questions Women Can Ask a Certified Financial Planner About Retirement

Eric Blake: Welcome to another episode of the Simply Retirement Podcast. I am your host, Eric Blake. Joining me once again is Wendy McConnell. Wendy, how are you?

Wendy McConnell: I'm good. How are you?

Eric Blake: I'm doing well. I'm doing well. We're expecting some... I'll call it... we'll call it cooler weather, going from, like, 105 to 95 pretty soon, so I'm excited.

Wendy McConnell: Cooler weather is 95?

Eric Blake: About our weather, yeah. Holy moly, it has been, yes. So it actually might even get to the low 90s. We'll see if we're lucky or not.

Wendy McConnell: Wow. I mean, I woke up this morning, it was 58.

Eric Blake: Wow. So I have to say, at the end of this week, yeah, at the end of this week we're actually... yeah, I'm going to be in your general area, we'll call it. My wife Dawn, her birthday is this coming Sunday, which will be September 20th. We're recording, I don't know when this episode will actually go out, but we're taking a trip up to New York City for her birthday. So we leave here in a couple of days.

Wendy McConnell: Nice.

Eric Blake: So we'll get some good weather for at least a few days there.

Wendy McConnell: Have you been to New York?

Eric Blake: We have. Yeah, we've been up there a couple times. Well, first time was, like, 2018, kind of a graduation for my son, and my daughter was about to graduate from college at about the same time, so we went up then, and then we went up a couple years ago, '23 maybe? My wife and I went up there for her, probably for her birthday again.

Wendy McConnell: You've got to go at Christmas one year. It's so beautiful.

Eric Blake: I'm sure it is. I'm just... the cold, I... no, I don't know. Oh, yeah. I don't know if I could handle that.

Wendy McConnell: Yeah, go right after Thanksgiving.

Eric Blake: When we went the first time, we took the kids. It was March, and it was cold.

Wendy McConnell: Yeah.

Eric Blake: And gee, ugh, I know I sound like I'm complaining about 105.

Wendy McConnell: You sound like a big baby.

Eric Blake: I'm more the hot weather than the cold weather, no matter what, so.

Wendy McConnell: Why can't it be 95 degrees in November? Okay, I got it.

Eric Blake: All right, so let's get to the good stuff. So as you know, one of the goals of this podcast, when I started this podcast, it was not only just to provide education, but I also wanted to help women ask better questions. And because it's hard to become an expert, I'm not expecting our audience to be experts in all these different things that we talk about, because you're not doing this on a day-to-day basis. But if you're looking for answers, it always starts with asking better questions, right? And I came across this article, it was on the AAA website, and the title was Questions to Ask a Certified Financial Planner About Retirement.

Wendy McConnell: Okay.

Eric Blake: Okay. And the article suggests six questions that you would bring to a meeting with a financial planner, and they're all good questions, and I think every woman who's getting close to retirement deserves answers to these questions. But I would actually consider these questions very... I wouldn't call them basic, wouldn't go to that extent to call them basic, but I would call them kind of... what I would call table stakes questions, meaning that they're basic questions that a retirement planning process should help you answer. Okay? But you should not expect, or I would argue that you shouldn't even want, complete answers to all six questions during that first conversation with an advisor. And I'll explain why as we go through these six questions. But then what I want to do is I'm going to give you six better questions to ask as you decide whether this advisor and their specific process are actually right for you to help you answer the original six questions.

Wendy McConnell: Kind of like, "I see your questions, but I raise you..."

Eric Blake: Raise you six more better questions. That's right. Okay. So here are the questions. Let's start with number one. So the first question is, how much do I need to retire?

Wendy McConnell: Hmm.

Eric Blake: Pretty straightforward, but the answer to me depends on when you want to retire and what you want your life and spending to look like, right? Question two is, am I saving enough for retirement? Now, the issue I have with that is enough depends on what you're trying to accomplish. When you want to retire, how much income are you going to need, and of course, how much are you saving or how much could you save if you're not on track? So am I saving enough is very relative, relative to when I want to retire, relative to how much you already have saved. That's a big one. Most importantly, how much do you need to do the things you want to do in retirement?

Wendy McConnell: Okay.

Eric Blake: Then we get to question three, which is, when can I afford to retire? Another maybe key question. It is very much dependent on all these other factors, how much you already have, how much you're saving, all these other things we've talked about. But I also talk about your vision for retirement and things you want to do, but also whether your plan has enough flexibility for the unknowns. So just simply asking, "Can I afford to?" What else could happen throughout your retirement years? Life changes, healthcare changes, economic and tax law changes. So asking this question is important, but I think more important is the process the advisor actually utilizes to help you answer that question.

And as we've gone through these first three, I wanted to share a little bit of perspective that I take with those first three, because the way I think about these first three questions, and part of the reason I don't think you should expect answers to these questions during your first conversation with an advisor, is because I consider these first three questions more of what I would call retirement plan levers. So not immediately answerable questions, because we first have to understand what your goals are. When would you like to retire? What's your target retirement date? What do you want retirement to look like? And of course, what are the things you want to be able to do? And then once we understand that, we can determine whether you appear to be on track or not.

Wendy McConnell: Okay.

Eric Blake: Right? So we have to have that initial conversation about what's our destination, right? And if you're not on track, which lever would you prefer to adjust first, right? So what I mean by that is you might choose, if I'm not on track, if we come back, we do an analysis, and we say, "Okay, you're not quite on track to where you want to be," which levers would you pull in order to get you on track? So if you're not on track, you might say, "Well, I might choose to save more so that I can retire at a specific age," right? Or you might choose to live on less so that you can retire at that ideal age. Right. Or other people would rather delay retirement, retire a little bit later, so they can have a specific amount available to support the life that they're looking for when they actually get to retirement as well. And ultimately, it's probably some combination of all three. But again, that's why I talk about the levers and not being able to... I shouldn't really be able to give you a true answer to those first three questions in a first meeting. Because I need to understand where you're going, where you want to get to first. And if you are on track, then we say, "Well, is it possible that with some slight adjustments," or again, adjusting those levers, "could you actually retire earlier?" Right? Or could you live on more than what you planned for? And these are all decisions you, as the prospective client or as the client, should have input on. It shouldn't just be me as the advisor telling you what the answers to these questions are. This is a partnership.

Wendy McConnell: Yes, you're going to retire at this age, and you're going to have... that's right. Like, could you imagine?

Eric Blake: That's why we talk about these... these are good questions. They're not, I wouldn't call them bad questions, but there are better questions to help put these specific questions into better context, I would say.

Wendy McConnell: Okay.

Eric Blake: And again, it comes back to what I talk about, is this process. There should be a process, and you as the client should be involved in that process, because it's your life, it's your goals, it's your dreams. So I tell prospective clients all the time, "It's not my job to simply answer these questions. My job is to help you turn your goals and your dreams into a plan that you can act on, and act on that plan with clarity and confidence." Right? So now let's get to the next three questions in this series. Next one, and you're going to know that I love this question, of course: When should I claim Social Security benefits?

Wendy McConnell: Yes.

Eric Blake: So again, it is a good question, but how can I answer that question without the context of all the other questions that we've already shared, right? Well, I can't tell you when to claim Social Security if I don't know when you want to retire, how much you want to live on, and what else you have, right? Yeah. So we've done multiple episodes. I love talking Social Security. You know that.

Wendy McConnell: Uh-huh.

Eric Blake: But again, Social Security decisions, especially for women, whether you're married, you've gone through divorce, you've been widowed, should be coordinated with everything else, the rest of your retirement plan, including your other income sources, your taxes, your investments, and of course, your family circumstances.

Wendy McConnell: Mm-hmm.

Eric Blake: Question five is, what healthcare costs should I expect? And again, I really like this question, but it is so individualized. If I said somebody could give you an answer right off the bat, I don't think it... to me, it might be a red flag, because you can talk about the basics, but not everybody is basic. So you think about, you know, an advisor should be, again, looking at the context of everything else. So we need to know family history, your own health history, what your other income sources are. Because we think about, like, even just Medicare itself and what the cost of Medicare is, everybody thinks, "Well, Medicare's going to cost this." Well, what if I have a higher income amount? What if I'm above some of these thresholds, and now I've got to worry about Aunt Irma, Irma surcharges, that they're going to cost me more, right?

Wendy McConnell: She is annoying, isn't she?

Eric Blake: She is, very annoying, yes, especially when she comes by surprise. And that's the problem. She comes knocking when you're not ready.

Wendy McConnell: Right, always.

Eric Blake: But you think about, and then what if I'm retiring before 65, right? What's that going to cost me? What am I going to do about healthcare before age 65? Am I going to have to look at COBRA from my previous employer? Am I going to have to look at Affordable Care Act coverage? So again, a good question. It should be considered as part of the overall equation here, but it is a question that needs more context.

And then the last question that they shared was, "How long will my retirement savings last?" Right? And as you can probably tell from the first three questions and my thoughts on those questions, those retirement plan levers have to come into play, because this question cannot be answered without first knowing how much you need, whether you're saving enough, and when you want to retire.

Wendy McConnell: So it depends.

Eric Blake: It depends. Because all those decisions, they all affect how long your savings are going to last.

Wendy McConnell: Mm-hmm.

Eric Blake: And the decision on Social Security, the decisions on healthcare, all those come into play. So your spending, your investment returns, your taxes, your inflation, healthcare costs, how long you will live, all affect the answer to, "How long will my money last?" Right? And I think a financial planner, they can prepare projections, test different scenarios and different situations, but no one can ever guarantee any written result. I can't guarantee you anything. But that's why I think these six questions shouldn't really get a final answer during that first conversation. They should all be in context of what are you trying to accomplish, what are your goals, where are you at today? And that's why we talk about, we have our Simply Retirement Roadmap, and the whole idea behind that is we need to first identify where are you going, what's your end goal, where do you want to be in retirement, but also where are you starting today, what's your starting point? Because we can't get you from point A to point B if we don't know all these different details. So again, you deserve answers to these questions we've talked about, these first six, but the advisor first needs to understand your goals, gather all the right information, and I believe follow a very clear process for helping you reach the answers to those questions.

Again, they're all good questions. You deserve answers. But when you're first deciding whether to hire an advisor, I believe there are six better questions.

Wendy McConnell: Here we go.

Eric Blake: Ready to get to the good stuff?

Wendy McConnell: Yes.

Eric Blake: So here's my first question: What is your process for helping me answer these other six questions? Right? What information are you going to need? What meetings are going to take place? What analysis are you going to do to help me answer these questions? And when should I expect recommendations?

Wendy McConnell: Right.

Eric Blake: Right? And I think the advisor should be able to clearly identify what that process looks like, and help you understand what happens next. Right? What happens today, what's our conversation look like, what's our next step, when are we going to meet again? Again, when will I actually have recommendations or suggestions as to what I can do to help answer those questions? Right? I think it also is a very important question: What experience do you have helping people like me with these issues and answering these questions specifically for people in my situation, right, that have gone through a divorce or have been widowed? What is your experience with helping me answer these types of questions or facing these challenges that I face on a day-to-day basis or on a long-term basis?

Wendy McConnell: I'm not getting it.

Eric Blake: So you think about experience. So I talk about this a lot, where, you know, think about a financial advisor and who they're working with.

Wendy McConnell: Mm-hmm.

Eric Blake: Well, if I'm the financial advisor that works with higher earning, dual income, younger children, saving for college, well, if I were you, let's say, use you as an example. So you come to me at your age. You're thinking, "All right, I'm looking at retirement." And if I don't have experience in helping you make decisions on Social Security or identifying when you want to retire, what are some of these other... healthcare costs in retirement versus healthcare costs when you're 35? That's what I mean by understanding the experience of helping me answer those questions that apply to you directly.

Wendy McConnell: Okay. Would that be more than just having a new client going through your process, or is that, you know, what everybody should be asking for?

Eric Blake: Let's come back to our Social Security example. I think that's always where I come back to as kind of the key example, the best example of working with clients in different life stages. So for somebody who's typically working with a 35-year-old... right? They may not necessarily have the same experience in answering these big, important Social Security questions. What am I eligible for? If I was divorced, now I'm going in, and we talk about this concept called gray or silver divorce, which is basically divorce and you're, say, in your 50s or 60s. Well, for the last 30, 40 years, you had an idea of what Social Security was going to look like or what retirement was going to look like. Well, now that's all changed. So now what is this going to look like going forward? So understanding the 10-year rule when it comes to divorce, or understanding the ability to say, well, if I've got a lady who's coming to sit down with us and she's in her 60s, she's lost her husband, what are the decisions she needs to make about Social Security? Around what... am I eligible for my own benefit? Will I be able to switch to a survivor benefit? So understanding those complexities when it comes to something like Social Security, that takes experience, and that's what I would ask: "What is your experience in dealing with these challenges? What is your experience dealing with Social Security? What is your experience dealing with retirement income and the tax implications of retirement income?" When I start drawing, where am I going to draw? Where should I be drawing money from first?

Wendy McConnell: Gotcha.

Eric Blake: Those are different conversations than, again, somebody who's just trying to save for retirement, who's, again, in their 30s or 40s. Saving, where am I saving my dollars? Am I balancing between retirement and education for my kids, right? So that's why I talk about, what is your experience in helping people like me deal with these issues.

Wendy McConnell: Okay.

Eric Blake: Does that make more sense?

Wendy McConnell: It does make more sense. Thank you.

Eric Blake: Hey, everyone, it's Eric. Hope you're enjoying today's episode. I want to take just a quick moment to share a resource I think you'll find valuable. Have you ever found yourself asking, "How much can I put into an IRA this year?" Or, "How much can I earn before my Social Security gets reduced?" Those are the kinds of questions that come up all the time, and the answers change, often more than you'd think. That's why we created a free two-page tax and retirement planning cheat sheet, updated for 2026, with the key tax, Social Security, and retirement numbers all in one place. You can download it right now at thesimplyretirementpodcast.com/retirementcheatsheet. It's a simple reference you can keep handy whenever questions come up. Now, back to the episode.

Next question I would ask is, how will you help me understand my choices and the trade-offs involved? Okay. So you should understand why a recommendation has been made, what are the choices that were considered, and what you may gain or give up with each of those choices.

Wendy McConnell: Mm-hmm.

Eric Blake: Right. So you think about what the trade-offs are. So if I've got to make one decision, if I'm saying yes to one thing, I'm probably having to say no to something else, right? Back to our questions about timing from the standpoint of saying, well, if I come back to you and say, "Well, you're not quite on track to live this lifestyle," what adjustments should we think about making? Should you potentially consider delaying your retirement? Should you consider reducing your lifestyle, living on less, in order to still have the retirement that you'd like? And as I discussed going through the six questions provided by the article, these are not questions that should be answered by the advisor without your input and your guidance, right? So you shouldn't expect to have the expertise that the advisor does, but you should be confident that it's your plan, and it's based on your decisions. I think that's really important.

Question four is, how do taxes fit into your retirement planning? And if I would ask this to the advisor, how do you stay current on tax law changes, right? So the first six questions provided by the article, taxes weren't even addressed. Right. So if you're talking about retirement planning, how do you avoid talking about taxes, right? And almost every single financial decision you make will have tax implications, right? And I can only guess that the question was left out simply because not all CFPs or certified financial planners actually provide tax planning advice, or more importantly, even have the practical experience with tax planning.

Now, all CFPs must go through an education and testing requirement in order to get that designation, and it does include tax planning. But I think it's also important to understand that not all firms even allow tax planning advice, right? And not all CFPs, not all certified financial planners, have experience in those issues, especially in those retirement years, which is why I think this question should be included, right? Because taxes affect your income, your investments, your Social Security, Medicare, Roth conversions.

Wendy McConnell: Everything.

Eric Blake: Anything that has a dollar sign, there's probably a tax impact there, right?

Wendy McConnell: Mm-hmm.

Eric Blake: And then also ask how taxes are included in the planning process, and how your plan will be updated when tax laws change. I mean, that's critical as well.

Wendy McConnell: Always changing.

Eric Blake: Which is funny, so even historically, think about some of the names of the tax laws when they've gone into effect. There... I can't remember what it was. I think it was during the Obama years maybe, but it was something related to permanent something or other. That it was like, it was a tax law and part of the name was like, like it was never going to change. But we know, right, within the next four years something's going to change. So that's one thing you can always count on. One thing that is always consistent with taxes is something's going to change. That's the only thing permanent about taxes.

Wendy McConnell: We have 1.0 and then we have 2.0 and...

Eric Blake: Oh, yeah. Yeah. Question five that I have would be, what happens once we have a plan in place, okay? Ask how often are we going to meet? What will be reviewed? Who will help me actually implement the recommendations? And what happens when life or the rules change, right? And when I talk about that recommendation piece, not all... you may be, depending on your circumstances, you might work with an advisor or the CFP and just do a plan.

Wendy McConnell: Oh.

Eric Blake: Right?

Wendy McConnell: Kind of like a budget?

Eric Blake: Not necessarily a budget, but just where you might pay a fee simply to do an analysis to say, "Am I on track or not?"

Wendy McConnell: Oh, okay. Gotcha.

Eric Blake: But they may not necessarily say, "Okay, well, now here's what we can do to help you progress with this or move forward with your plan," right? So understand, how do I go about implementing this plan that you've built for me right now? Would I be able to do it on my own? Would I be able to work with another advisor? What exactly are those next steps once I have this plan in place?

Wendy McConnell: Right.

Eric Blake: Or if you're working with somebody, so like a firm like ours, where we actually, once we've done the analysis work, we've made the recommendations, we'll walk you through exactly what it looks like if you want to implement that plan through us, and make sure you understand the fees and everything associated with moving forward with our firm in that ongoing retirement planning relationship. Right. And that's the next step that I was going to ask to, add to that, is you should also understand whether the ongoing relationship includes retirement planning or is mainly focused on just managing your investments, right? So again, depending on the firm, they may focus on everything, more of a comprehensive approach, while other firms may only focus on investments.

Wendy McConnell: Mm-hmm.

Eric Blake: Question six that I have then is, will you act as a fiduciary when advising me, and how are you and your firm paid? Okay. So a CFP professional must act as a fiduciary when providing financial advice. And just to be clear, so the term fiduciary, it simply means that the advisor must put your best interest ahead of their own when giving you financial advice.

Wendy McConnell: Well, my only issue, how do we know they're doing that? Are we just trusting?

Eric Blake: Well, and I think part of the reason why I present this question as part of my six better questions is exactly that. So number one, just understand that not every CFP is fee only. Okay? So you want to ask whether the firm or the advisor receives fees. Do they receive commissions? Do they receive both? And understanding where some of the conflicts of interest may be. So to answer your question, if there are conflicts of interest, they need to be disclosed to you. And again, you have to, to some extent, you are taking on a leap of faith, so to speak, to say, "Yes, I'm expecting this person's going to be honest and tell me the truth." But I also think back to if you just focus on those initial six questions, that may also be where you might get indications of a red flag, if those are the only six questions you're asking. Because if you start to get the feel... and my feeling would be, in your mind, if you start feeling, "Okay, these responses seem to be leading me down a specific path, maybe towards a specific product or a service, but I don't really see what the process is for the advisor understanding what I'm about and what my goals are." So I think if you're just talking about these six questions, and it's only about ultimately leading me to, well, I think giving you a solution to your problem without really knowing what your problem is.

Wendy McConnell: Okay. Yep.

Eric Blake: So it might be investment only. Or it might be... we've done an episode series on annuities not long ago. That's one of those areas that you can kind of start getting a feel. This seems to be, that's the direction this is going, is they're trying to lean towards a specific solution before they really fully understand what my problem is or what my challenges are.

Wendy McConnell: Okay.

Eric Blake: Right? And that's where I think my six questions can help you start expanding that a little bit, get a better feel for what direction, what is that process. To me, process is huge. Mm-hmm. Any advisor that you're considering should have an identifiable process to help you address these questions, and you should have confidence that they're following that process.

Wendy McConnell: Right.

Eric Blake: Right? And I think that's really, as we start to wrap up, the six questions from the article tell you what a retirement plan should eventually help you answer.

Wendy McConnell: Mm-hmm.

Eric Blake: Okay? But if you've just taken literally just those six questions on their own, to me, I think they're too reliant on the advisor and not a partnership with you as the client.

Wendy McConnell: Mm-hmm.

Eric Blake: Okay? And the six better questions help you evaluate who will guide you through the work that's being done.

Wendy McConnell: Yep, it's an ongoing process, too.

Eric Blake: Absolutely. Yeah. And during that first conversation, I would encourage you to focus as much on the questions that the advisor's asking you.

Wendy McConnell: Right.

Eric Blake: Right? Not just the questions you're asking the advisor, but what are they asking you? How are they going about understanding what your goals and what your concerns are? Are they trying to understand why you even reached out in the first place? What concerns you? What do you want retirement to look like, right? And this is also when you should begin learning about the advisor's process, what their experience is, what services they actually offer, and of course, what their compensation is.

Wendy McConnell: Mm-hmm.

Eric Blake: And you may not receive answers to the article's questions yet, but you should begin receiving answers to the questions about your advisor, and again, how are they going to go about helping you answer those questions. And to me, the next part of the process should involve gathering the information, learning more about your finances, your goals, your family, your tax situation, your healthcare, whatever other concerns you might have, and that's when the advisor can begin analyzing how much you need, whether you're on track or not, when you might retire, and of course then, how do things like Social Security and healthcare fit into that plan, right? And then when recommendations are presented, the advisor should then also explain the assumptions, the choices, and the trade-offs that were involved. And of course, you should understand what happens after the plan is created and how the advisor will be paid if you decide to work together.

Wendy McConnell: All good questions, Eric.

Eric Blake: Right. Well, and I think that's, again, just going back to our, what we call our Simply Retirement Roadmap, that's generally the path that we follow. So we just start with a general get-to-know-you call, just 20 minutes. If we agree that we're a good fit, that you feel, "Hey, I think they could actually help me answer these questions," we can then work together to decide, okay, do we take that next step? Do we move forward with that first meeting? And then ultimately, we can prepare an analysis, what we call our personalized Simply Retirement Roadmap, and then you have time to decide how we go about moving forward. And that's just one example, and every firm may have a different process, but I think, again, the process is key.

Wendy McConnell: All right.

Eric Blake: So if someone provides a specific retirement date, a Social Security strategy, an investment recommendation, any type of product solution before completing this type of work, that's when I think you start asking more questions, and that's where my six questions... I mean, I think all 12 questions are useful.

Wendy McConnell: Yes.

Eric Blake: It's just what context and what order might you want to consider asking those questions.

Wendy McConnell: Yep.

Eric Blake: A responsible answer as the advisor is if when you start asking these questions, say, you know... you might expect something from the advisor like, "Hey, you know, I can help you answer that, but I don't know enough about you yet." Right? And then the six questions in the article, again, they deserve thoughtful answers, but those answers should come from a process that includes you and considers the retirement you want to create.

Wendy McConnell: Got it.

Eric Blake: So for more help preparing for a conversation with an advisor, we're going to include a link to a couple of different episodes we've done in the past on asking these types of questions. And I think, again, that's ultimately all this is about, is helping women ask better questions as they're making the transition into and through retirement, and who's going to walk alongside you as you're making these critical decisions. We'll also include the link to the original AAA article. That's it for today's episode. Thank you, Wendy, for joining me as always. Please be sure to follow the podcast so you're notified when new episodes are released. Until next time, please remember, retirement is not the end of the road. It's the start of a new journey.