10 Questions College Coaches Should Ask Before Trusting Financial Advice

In the last post, we established that titles don't tell you enough, and that disclosure doesn't guarantee understanding.

Across this series, we've also taken a lengthy tour through the history of rules, regulations, standards, exceptions, forms, disclosures, lawsuits, acronyms, and regulatory patch jobs that make up the financial services industry, which is useful knowledge right up until you're sitting across from an actual human being talking about your actual life.

This is where preparation meets execution.

It's one thing to understand that, in theory, "financial advisor" can mean a lot of different things. It's a whole 'nother ball game to be in a meeting with someone who sounds professional, dresses the part, has a clean-looking recommendation in a nice little binder, and is talking confidently about your retirement account, your insurance, your investments, your benefits, or what you should do after changing jobs.

This is usually where a lot of coaches either shut down or default to instinct.

Sometimes that instinct says, "This person seems sharp, I trust them."

Sometimes it says, "I don't understand this well enough, so I'm just going to avoid the whole thing and hope that when I'm ready to retire, my retirement accounts don't start with a negative sign."

Frankly, neither reaction is crazy.

As a college coach, you're used to evaluating people. You evaluate recruits, staff members, parents, administrators, vendors, trainers, consultants, and pretty much anyone who crosses your path claiming they can help your program if you just give them enough money, time, attention, or access. You know the difference between someone who understands the work and someone who just knows how to talk around it.

The goal here is to apply that same filter to financial advice.

My goal is not to turn you into some sort of securities attorney. You don't need to memorize regulatory standards or learn the inner workings of every financial product on earth. I don't even do that, because it sounds miserable.

The goal is to give you questions you can actually ask.

Questions that make the relationship, incentives, tradeoffs, responsibilities, and coaching fit harder to hide behind paperwork.

The goal is to give you questions that make the relationship, incentives, tradeoffs, responsibilities, and coaching fit harder to hide behind paperwork.

A good financial professional should not be offended by these questions. In fact, they should welcome them. If someone gets weird, defensive, vague, or starts drowning you in jargon, that tells you something too.

So before you trust the recommendation, start here.

10 Questions Coaches Can Actually Ask

The standard is not "you received the disclosure." The standard is "you understood what the heck it meant."

The questions themselves, however, are not the standard. The answers to those questions are where the standard starts to show up.

What good professionals do above the minimum

Here's something important to distinguish.

The questions to ask your financial professional are not a trap.

I'm not asking you to interrogate every financial professional you come across like you're conducting a deposition. You're using these questions as a litmus test to understand how your professional views disclosure, whether as the finish line or as the starting point.

A good professional will not be offended by direct questions. Frankly, they'll probably appreciate the fact that you're coming prepared and caring enough to ask. A good professional will be able to take your questions and answer them in a way that gives you more clarity.

Of course, that doesn't mean every answer will be simple. Compensation arrangements, conflicts of interest, product details, account rules, tax issues, and legal responsibilities can all be complicated.

But complicated is not an excuse for vague.

A good professional should still be able to help you understand what you're paying, how they're getting paid, where potential conflicts of interest may arise, and what that means for the recommendation in front of you.

A good professional should not treat plain-English explanation like a personal attack. I think this one is a little bit about ego and dependency. A good professional isn't interested in confusing you to the point that you feel helpless and dependent, because really, what good does that do?

Would you ever coach your athletes like that?

Would you ever throw terms and jargon and semantics at a player so that they can't learn to do anything on their own?

Clarity is part of the job.

You can't make sound financial decisions without being clear, and you can't be clear without simple, effective communication. Finances are complicated, but also, they're really not. Nobody's asking you to learn the ins and outs of stocks and bonds and REITs and every other made-up sounding acronym out there.

A good professional gives you options. Those options aren't always better, from a technical standpoint. But it's not about giving you three equivalent options and saying "choose." It's about demonstrating how certain actions and decisions have differing ramifications. Giving multiple options can actually strengthen the initial recommendation if done thoughtfully.

Most importantly, a good professional connects any recommendation to your coaching reality. It's not just about "this is what is typically best." It's about what makes sense for your life, your job, your timeline, your contract, your benefits, your family, your cash needs, and the fact that your career absolutely will not sit stilllong enough for generic advice to stay applicable.

Think about what it means to be a great coach.

If you simply showed up, followed the rules, oversaw practice, turned your paperwork in on time, and didn't get fired, does that automatically make you a good coach?

No. If anything, if that's all you did, you'd probably be a pretty sucky one.

Good coaches prepare, teach, correct, adapt, communicate, develop and care.

Good financial professionals do the same thing.

So how do you actually evaluate all of that without making things more complicated than they have to be?

A simple evaluation framework

The ten questions above are useful on their own, but you don't need to memorize every word. They're just to get you into the right ballpark so you can evaluate the answers.

The answers should help you evaluate five things: role, money, responsibility, tradeoffs, and coaching fit.

Role

Start with the basic title, then work your way deeper. Is this person an investment adviser? A broker? An insurance agent? A tax professional? An estate attorney? Something else?

Remember that this person can wear more than one hat. The same recommendation can look different depending on whether it comes as part of ongoing advice, a transaction-based recommendation, a product sale, education, or coordination with another professional. Identify what roles your professional is capable of filling, and if you don't know, be sure to ask!

A good answer will provide clarity, be specific, and should tie back to the current recommendation.

Money

What you're trying to figure out is simple. How does this person make money? As we've mentioned before, there are a lot of different ways to get paid, and they all create their own incentives.

None of that means anything negative on its own, of course. There's a weird cottage industry in the world of financial advice where advisors will use their compensation structure to virtue signal, and frankly I think it's all baloney. Good professionals deserve to be compensated for good work, in whatever form that takes.

You just also deserve to know how it works too.

The way your advisor makes money should give you some clarity on how they think and work.

For example:

If someone gets paid only when you buy a policy, move an account, roll over a plan, or place a trade, you should understand that. At the risk of repeating myself, that does not make the recommendation bad. It just means the compensation is connected to the action being recommended.

That's the point of asking.

You're not trying to shame someone for getting paid. All you're trying to do is understand what work is being compensated, what incentives are attached, and whether the recommendation still makes sense after those incentives are clearly explained.

We've been taught in society that it's not "polite" to ask someone else about their pay. But a good financial professional should have no problem talking about it.

The only bad answer when it comes to how a financial professional gets paid is one that dodges the question.

Responsibility

You'll start to get a feel for the answer here as you figure out role and compensation, but it's better to know than assume.

The level of responsibility your financial professional takes on can vary depending on whether you are getting a one-time recommendation, buying a product, receiving education, getting ongoing financial advice, receiving ongoing investment management, or something else entirely. Just like role and compensation, there is not one correct level of responsibility here, but you have to be clear about what relationship you are actually in.

Sometimes, all you need is a one-time recommendation. Maybe your life has been a mess, and you just need someone to sit down, clean things up, and tell you what to do next. If you can handle it from there, fine. There's nothing wrong with that.

But you should know that going in.

Otherwise, you may expect the relationship to be over while your professional thinks their responsibility to you is ongoing, and they may have made the recommendation with that in mind.

The reverse is just as true. If you're looking for ongoing advice and your professional is trying to give you a one-off recommendation, that can cause issues too.

It's all about matching the level of responsibility to the relationship you actually want.

Tradeoffs

A financial professional who acts like a recommendation has no downsides better be ready to back up that assertion with some cold, hard facts, because most things in life have tradeoffs.

As a coach, you understand that. Time spent practicing hard is time that could have been spent recovering or mentally preparing. Time spent recovering and getting fresh is time that could have been spent getting more reps, more conditioning, or more technical work. Time spent in the film room or studying game plans is time that could have been spent on the practice field. You're constantly making decisions where every gain asks for something in return.

Financial recommendations are no different. Some of the potential tradeoffs you could expect have to do with cost, liquidity, flexibility, complexity, taxes, surrender charges, ongoing fees, investment options, control, and future limitations.

You have the right to be informed of the downside of any decision you make. A good financial professional will not only help you understand the tradeoffs but should also address these tradeoffs as a part of the planning process. A bad professional will start to handwave or make things sound better than they are. Remember that if it sounds too good to be true, it probably is.

This is also where questions like "What are my other realistic options?" and "What am I giving up if I do this?" work together. One question shows you the alternatives. The other shows you the cost of choosing one path over another. Understanding both can help you make a stronger decision.

One question shows you the alternatives. The other shows you the cost of choosing one path over another.

Coaching fit

Your financial life does not move like a normal professional's financial life. Your job can change fast. Your contract can change fast. Your benefits, housing, taxes, spouse's career, and cash needs can all change with it. The planning process for you should account for that. Depending on the recommendation, a good planning process should account for things like:

A good recommendation should have already accounted for the relevant parts of your coaching life. Not every factor on that list will matter to every decision, but the important ones shouldn't be a surprise by the time the recommendation is made. If changing jobs, moving states, losing benefits, bonus income, or spouse employment could affect the recommendation, your professional should have thought about that before you had to bring it up.

But it doesn't hurt to ask.

Think of it like a stress test. Ask, "If I move to another state, how does that change things?" "If my bonus income this year is higher or lower than expected, does that impact the plan?" "What if my spouse can't find a job and our income is lower for a period of time?"

Your professional should be happy to go through all of these scenarios with you, especially if they've considered them from the beginning. It doesn't mean they'll have every answer. All you're looking for is that things won't break down entirely.

It's one thing to say, "I'm not sure how things would look if your household took a 25% pay cut, but we will have options."

It's another thing to say, "Oh yeah, that would be bad, wouldn't it?"

So, before trusting a recommendation, here are the five things you're trying to figure out:

Important to note: going through this framework doesn't guarantee perfection. It doesn't eliminate conflicts of interest. It doesn't guarantee that you'll never get bad advice.

That isn't the point.

The point is to give you a better way to evaluate what's being presented, without relying only on titles, referrals, paperwork, professional polish, or your instincts alone.

Conclusion

As a college coach, you frankly have every right to be skeptical.

You live in an unstable profession where people constantly want things from you, expect things from you, and pull your attention in several different directions while you're trying to focus on the things that actually matter. And as far as the financial services industry is concerned, we've earned some of that skepticism. We certainly haven't made it easy for people to trust us or figure out what's actually happening in the first place.

The flip side, though, is avoiding all advice because the industry is confusing isn't much of a plan.

Trusting someone blindly just because they call themselves the right thing, have the right letters after their name, came from the right referral, or come across as "professional" isn't much better.

You need a way to evaluate financial advice that makes sense for your actual life.

That doesn't mean you need to become a financial expert. You have enough on your plate already. You don't need to memorize regulatory standards, decode every disclosure document, or learn the inner workings of every product, account type, compensation structure, and legal obligation floating around the industry. That sounds miserable, and most people pretending otherwise are lying or need a hobby.

You just need to know what to listen for: the role they're acting in, how they're paid, what responsibility they're taking on, what tradeoffs come with the recommendation, and whether it fits your actual life as a coach.

You're already used to evaluating people. You know the difference between someone who talks a good game and someone who actually understands the work. Use that same filter here.

Do not just ask whether someone seems trustworthy. Ask whether they can explain the relationship, the incentives, the tradeoffs, and how the recommendation fits your actual life.

Don't just ask whether someone seems trustworthy.

Ask whether they can explain the relationship, the incentives, the tradeoffs, and how the recommendation fits your actual life.

The minimum is what the rulebook requires.

The standard is whether the advice actually helps you protect your family, your future, and your options in a profession that doesn't hand out much certainty.