How to Approach an Employee You Think Is Struggling with Debt

Employers Can Provide a Helping Hand to Employees in Need

No employer or boss likes to see his or her employees struggling with debt. Most of us have “been there done that” when it comes to debt, learning from our own financial mistakes rather than those of others. Later, when we see others we care about struggling with similar challenges to those we overcame, we too often take the “wait and see” approach to offering help. We don’t want to appear nosey or make the person feel incapable of what my teenaged kids called, “adulting.”

So, we say nothing. We offer nothing. We do nothing, other than hope they figure it out without dragging others down with them.


I am a pretty decent swimmer. I grew up skiing on a northern California lake every Friday in the summertime, but let me make this clear. If you EVER see me drowning in ice-cold water because, for whatever reason, my limbs are cramping up, PLEASE throw me a rope or, even better, a lifesaver. You don’t have to jump in to save me. In fact, I would prefer you don’t get mixed up in whatever trouble I am in. But, I will never be offended that you tossed me a lifesaver in case I need one.

Why is our reaction different when it comes to drowning in debt and financial problems? We know when someone is in trouble. The signs are pretty clear, even at work. Let’s start with a good employee who works hard, is well trained, and gets along well with your other employees. How do you know when your employee starts to struggle with finances? Here are a few signs that, individually, may not be indicative of financial troubles but taken together are pretty clear:

  • He/she may begin by mentioning their financial frustrations to a coworker

  • You may hear that your employee is donating plasma (which might give them an extra $50 to $90 a week in spending money)

  • He/she may complain here and there about a creditor (credit card, medical office, car loan lender, etc.)

  • He/she will have a worried look on their face or a wobbly sound in their voice when on “personal” calls during work hours

  • The employee may start arriving later than usual

  • He/she may begin taking extra-long lunches

  • The employee may begin leaving work before their shift is over

  • He/she may make early morning phone calls and leave voicemails informing you that he/she has to stay home today “for personal reasons”

  • Your HR manager soon tells you that a wage garnishment has been ordered for the employee

  • The employee may even begin asking you for a paycheck advance, “just this once,” that turns into a regular affair

  • To no one’s surprise, this employee eventually stops showing up at all or notifies you that he or she has found a better paying job, even though you find out that the new employer may only pay a few dollars more per paycheck

At what point do you grab the lifesaver and toss it to your employee? He or she does not want you to jump into the cold water next to them, but they would appreciate a tool or two to get out of the bind they are in.

Far too many employers either wash their hands of the whole affair, justifying a lack of action by saying that the company will be better off after the employee finally quits. On the other hand, perhaps the boss has more debt than they care to disclose and does not want to feel like a hypocrite by giving advice they are not following themselves. Then again, maybe the boss just does not know what tools will help or even where to find them.

Let’s admit the answer to this first issue: allowing a good worker to slip away rather than help them is just poor leadership. A leader leads. A leader does not let go because he or she is uncomfortable.

As for feelings of hypocrisy, would you watch me drown as you stood on the riverbank, just because you don’t know how to swim? Of course not. You would find something to toss to me.

Finally, let’s talk about where to turn and what, how and when to throw it. Here are some do’s and don’ts:

  • Don’t throw the lifesaver to the individual when other employees are around. Pull the employee into your office or visit them in their office and express to them your sincere concern that they may be struggling with personal or financial issues that worry you.

  • Do empathize. If you have ever been in financial difficulties, consider sharing how you felt and how you addressed them. If you are still in financially troubled waters, you may at least consider saying, without getting into details, something like, “We all struggle financially and pretty regularly.”

  • Don’t tell the employee you know what the problem is or how to fix it. Part of adulting is taking responsibility for the problem and determining the solution.

  • Don’t offer to advance a loan to pay bills. Paycheck advances are usually Band-Aids on problems that will continue to fester and spread unless addressed at the root.

  • Do offer some tools “to consider if you think they might help.” Employee Assistance Programs usually have some limited budget counseling available at no cost to the employee. Programs like our Money Fit Financial Wellness portal can offer much more in-depth budget, credit, and debt counseling.

Being the boss is more than just paying salaries and earning a profit. Entrepreneurs and business owners, I know frequently talk about the responsibility they feel to watch out for their employees. Business managers and owners know that their employees depend upon them for a job to pay for their rent or mortgage, their children’s schooling, and other wants and needs. Such a responsibility weighs heavily on many bosses. So when it comes to noticing an employee struggle financially, take comfort in knowing that there IS something you can do, and it WON’T make the employee resent the intrusion.

Be sincere, be empathetic, and be clear about the tools they have access to. If you can get to them soon enough, you might also just be their next hero.