By Jessica Lanning, JD, CFP®

Attention all you late 40-, 50- and early 60-somethings who have attempted and “failed” to hire a financial planner: Simplify your hiring process. This article will tell you how. 


Financial Planning, Groundhog Day-style

Chances are pretty good that you’ve repeatedly experienced some version of this scenario: You spent several hours reviewing your investments, paying your bills, and reconciling your accounts. Maybe you reviewed your budget and your savings. You dreaded going to work the next day, started dreaming about retirement, and played with a few online calculators to see if you could quit next month. 

The numbers look pretty good, but then you start to worry about what-ifs. What if inflation goes crazy? What if I don’t get a 10% return on my investments every year? What if Social Security runs out of money? What if I end up like my mom, needing expensive care in the last years of my life? 

Oh, and you forgot to factor in the roof you will need in 10 years and the car that needs replacing. Now you start to wonder what else you’re not thinking about, what other potholes you can’t see. 

You decide you better get a professional to give you “another set of eyes” on your situation. Your future and possibly your family’s future hangs in the balance of your “I don’t know.”

You move into action. You do a couple of Google searches. You get some referrals. You start making calls to financial planners. 

Half of them tried to sell you something. One ran a 10-minute financial plan and told you that you can nail down the details when you come in. A couple of planners turned you down because you didn’t have $5M in investible assets or more. One said she doesn’t do a tax analysis, and that you’ll have to hire a CPA to do that.

Much like your doctors these days, the majority looked like teenagers, and you thought, “Nothing’s happened to them yet. How can someone who’s not lived a lot of life tell me how to manage mine?”

You hang up from the last call. 

You feel bad about yourself for not having more money, even though you have excellent money habits and you’ve done everything right. 

You feel like an idiot because someone brought something to your attention, that you hadn’t anticipated, and you’re a smart person.

You feel discombobulated by the jargon and the sales pitches, even though you knew that was coming. 

You simply cannot walk into one more “store” wanting six apples and a bag of flour and walk out with three bananas, a bag of sugar, and one apple. You think, “Enough already. I’m doing fine on my own. I’ll keep doing what I’ve been doing. I’ll go to work tomorrow, and I’ll worry about this another day.” 

Six months later, you do it again. Just like in the movie Groundhog Day, where the main character relives the same day over and over again, you revisit this place, waiting for the shift to happen.

You’re not alone, and you’re not wrong.


Your Frustration Is Not Your Fault

Aside from perhaps the nutrition/food/wellness industrial complex, there is no other industry that is as self-serving and as full of misinformation and half-truths as the financial services industry. 

The more confusing we can make it, the more you need help, and the more money we can make. 

I know because I’m in it. I’m a fee-based financial planner. 

I’ve heard some version of the above story a million times. Repeat after me: My frustration is real, justified, and not my fault. Take a deep breath. When you rally enough energy, optimism, and brain cells to attempt this task again, revisit your strategy.


Where the Complication Happens

Finding a financial planner is a bit like buying a new car. You do your research, you go out and do test drives, and before you know it, your search for a four-door sedan has you eyeing an all-wheel drive SUV. “Wait, wait, wait,” you think. “What was it that I want and really need?” You re-center yourself and choose the right car.

The same goes for hiring a financial planner. 

Potential clients often get frustrated hiring a financial planner because they’re not clear on what they want or when they find what they thought they wanted it’s not what they thought it would be like. Along the way, a million other variables get thrown in, they get intrigued by sales pitches, and their thinking gets jumbled. Of course, it’s much easier to quit at that point.


Uncomplicate This Task

You need to find:

  • Someone you like and trust.
  • Who is skilled enough to handle your situation.
  • Provides the services you need.
  • For a reasonable price.

Start with the personal aspects: whether you like and trust this person. It’s a harder task and paramount. The rest is checking off boxes. 


Get Clear About What You Think You Want

As with so many things, start with the end in mind. Get out a journal and write extemporaneously without judgment about this question: 

“If I was sitting here three years from now, what do I want to have happened such that I feel good about my financial/retirement planning progress? “

If you expressed a desire to have professional financial planning help, ask yourself these questions:

  • What am I expecting to get out of it?
  • How will I know the relationship/service was successful?
  • How do I want the relationship to feel?
  • How long do I want this relationship to last?
  • What support do I think will help me the most?

Please notice how most of these questions are NOT about skill or price. 

Now that you have some sense of what you want, capture that into a solid list. This does not need to be set in stone but use it as a way to filter your choices. 

Go back to your previous list of potential planners based on your own searches and referrals, take away any that do not meet your criteria, and add any new prospects. 


First Contact Is 20 Minutes Or Less

Once you’ve curated your list of potential financial planners, your next task is to narrow them down to two or three. You will do this by interviewing them all. Treat it like a job. Put appointments in your calendar. 

You want to do the first outreach from your home or office, whether that’s on the phone or web conference. You don’t have time to visit them all in person, and you shouldn’t be in anyone’s office who is not going to take you as a client. That initial outreach should take 20 minutes. 


Be ready with the following information:

  • Who you are “demographically.

Example: “We are unmarried, we are 55 and 57, we have one kid who is 12 and the other is 16, we own our home, we’re in good health, I am salaried, my partner is self-employed, we make about $200K/year together, and we have about $750K in savings.”


  • What brings you to hiring a financial planner. 

Example: “We’ve been doing this on our own for the last 20 years, and as I get older and our lives get more complex, we feel we need some help. We’re worried about paying for college, taking care of my partner’s parents, and whether we can ever retire. We would also like to buy a second home, and we expect my partner’s business to grow substantially in the next two years. We need someone to tell us if we’re on the right track, and we need someone to help keep an eye on our investments.”


  • Your list of questions. 

There are a ton of questions you should be asking a financial planner. Do not plan to cover them all. Ask the ones that are most important to you and be sure to ask, “Have you served folks like us, and do you have room to take us on as clients?”

The planner will ask you lots of questions. You should be talking in generalities and round numbers. That person should also be trying to figure out whether you’re a good match for the practice.


Here’s what you want out of that call: 

  • You want to feel a “click.” Did you like what the planner had to say and how they had to say it such that it’s worth another call? 
  • You want to feel heard and seen. If you think back to the call, who was talking more, you or the planner? 
  • You want to confirm this is a good match. Will they take you as a client? You can ask this question directly without hurting anyone’s feelings. 
  • You want to feel they were qualified to meet your needs. Are you in their wheelhouse? Do they serve other clients similar to you? 

Seriously, that’s it. Twenty minutes. No more. The ones that make the cut? Call them back and set more time, ask more questions. You want to date before you get married. 

Every planner should have a process for bringing on new clients that you can follow. The planner should make it easy for you from this point. Ideally, after a few meetings, you should feel confident in hiring someone that you believe will get to know you and your family and serve you well. 

How do I know this works?  Because I do this every day.  If you need help, please reach out.  



Jessica Lanning JD, CFP® About the Author:

Jessica Lanning JD, CFP® brings focus and perspective to your individual financial needs to identify your opportunities for investment and wealth. Regardless of what you’ve done before or what “mistakes” you think you’ve made, Jessica can help get you back on track quickly and safely. As a former practicing lawyer, she brings a comprehensive approach to legal, tax, and financial challenges so that her clients can enjoy peace of mind. A huge proponent of conscious decision-making, Jessica makes sure her clients are educated and informed so that they make sound decisions with clarity and confidence. 


Lanning Financial Inc. is a registered investment adviser. The information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any specific securities, investments, or investment strategies. Investments involve risk and unless otherwise stated, are not guaranteed. Be sure to first consult with a qualified financial adviser and/or tax professional before implementing any strategy discussed herein. Past performance is not indicative of future performance.




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