9 Effective Ways the Pros Use to Identify Struggling Employees



9 Ways to Identify, and Help, A Struggling Employee

Periodically, employees come across a particularly difficult task or situation. While sometimes it is a good challenge to work through, other times it can become a real struggle, one that leads to stressful days, sleepless nights and missed deadlines. To find out how to determine whether an employee is feeling challenged or overwhelmed, we asked members of the Young Entrepreneur Council the following question:

“Being able to gauge when employees are struggling can be difficult. What question do you think is the most effective in determining whether your employees are struggling with something they’re working on? “



Identifying, and Helping, A Struggling Employee

Here’s what YEC community members had to say:

1. Set Up One-on-One Conversations

“Rather than focus on a specific question, I find it most helpful to have a standing one-on-one with direct reports at least once per week. It’s not only regular time for difficulties and grievances to come to the surface, it’s the establishment of a relationship that allows for struggles to be shared.” ~ Tim ChavesZipBooks Accounting Software

2. Get Them Out of The Office

“I find that one of the simplest ways to get an employee to open up is to simply take them out to lunch. By leaving the work environment, their walls come down and they are usually much more forward with issues they are facing.” ~ Phil LaboonWUDN

3. Don’t Question, Observe

“Determining whether an employee is struggling is important. Doing so early can be crucial to helping the employee and your business succeed. The best way to know if a team member needs help is by reading the small signs that happen long before a conversation about the struggle will. When I see an employee spending less time at her desk than elsewhere (like the water cooler, for example), I know there is an issue. Most people’s first tactic when they feel challenged by something is to try to avoid it. I’ll generally pop by, and ask the employee to tell me about where she is at in the task she is working on. This opens a non-judgmental dialogue, and lets me then ask some questions to help her start thinking about ways to approach her project. Letting her have the breakthrough herself is both a confidence booster, and an energy driver, and it leaves her feeling empowered, rather than watched.” ~ Vanessa NornbergMetal Mafia





4. Ask How You Can Help

“By acknowledging the potential issue first, the employee doesn’t feel the extra pressure of having to tell me along with struggling over it. I let them know I am there to help, which helps create an atmosphere of teamwork from the beginning. The question also focuses on finding a solution which improves the employee’s confidence that we will. If there isn’t an issue, no harm was done.” ~ Amanda ElmsMetis Genetics, LLC

5. Remove the Obstacles

“For better productivity, ask employees on a regular basis what can make their jobs more difficult and what makes it easier. Ask them what hurdles prevent them from reaching or exceeding their goals, and then come up with a way to remove those obstacles. Sometimes, you make a greater impact from taking away those things that hinder process instead of working in a vacuum and creating new systems or processes that really won’t get the results you want.” ~ Blair ThomaseMerchantBroker

6. Make Honesty Easy

“Asking for help is hard. Your team wants to appear confident and competent. A question like, “What can we do to help?” cuts through the instinct to dismiss or hide problems and allows the employee to jump right to potential solutions. If there is no problem, the answer can be “Nothing. I don’t need help.” If there is one, describing support they need is often easier than admitting they need it.” ~ Ryan WilsonFiveFifty

7. Make ‘Asking’ a Consistent Part of Your Management

“We ask every team member, warehouse staff, customer service and management to rate their work experience on a defined scale of 1 to 10. It is informal and takes one minute in one-on-ones. We don’t probe into responses during the check-in, but it makes communication a structured and expected part of our management. If we see scores dip, then we can proactively step in with in-depth support. ” ~ Saloni DoshiEco Enclose, LLC

8. Look for Discussion

“I’ve found this to be an issue with some of the writers on my freelance team. While I’ve managed to successfully find a group of versatile and high-quality writers, sometimes I’ll assign projects out of their league. The way I know is by noticing changes in the way they talk about their current assignment: If they’re not so forthcoming with information about their progress, there can be an issue.” ~ Bryce WelkerCrush The LSAT





9. Talk with Other Employees

“Ask their co-workers how they think they’re doing. These co-workers are closer to the day-to-day experience of working with this employee, so they will likely have a better idea on what they’re struggling with. Communication makes all the difference.” ~ Andy KaruzaFenSens

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The Young Entrepreneur Council


The Young Entrepreneur Council The Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world's most promising young entrepreneurs. In partnership with Citi, YEC recently launched StartupCollective, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses.

One Reaction

  1. Aira Bongco

    Yes. You’ll never really know unless you ask them. Plus, asking your employees allow you to approach them first so they’ll be more likely to tell you how they feel.

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