How to help when a team member is struggling

Tip of the hat to Julia Borgini on LinkedIn who originally shared this article by Claire Lew. Its conceit is that asking employees is “how can I help?” is actually the worst way to help. I tend to agree! If we dig a little deeper it’s really about paying attention and empathy—two incredibly important traits that leaders need.

The topic struck a nerve with me so I wanted to share a few thoughts.

Asking “How can I help?” is indicative of lazy leaders

As Claire says:

When you ask, “How can I help you?” you’re not offering any specific ideas or suggestions for how you can be more helpful. Rather, you’re relying on the employee to do the hard (and delicate) work of figuring out how you need to improve as a leader.

100% true. In fact I think it’s an even greater indicator of laziness: that you haven’t been paying attention to what’s going on on your team. Because if you’re an attentive and proactive manager, you should already have an idea of whatever your team is struggling with. Granted it may be an external issue that’s coming from outside the workplace, and you need to navigate that with extra sensitivity, of course. But, a good manager needs to be aware of what’s going on the team day to day, so when you do find it’s time to offer help, you can be more specific.

It also assumes everyone is willing to admit they need help

Not everyone wants to accept help when offered so bluntly. Some people are too proud to admit they need it; some are too shy, or prefer to internalize challenges. Some (too many) corporate cultures have made it uncomfortable for employees to admit they need a hand—with anything, but or small. It’s like saying “my door is always open” and patting yourself on the back for being so welcoming; you’re assuming everyone is comfortable coming to you directly. Sure, some people are OK speaking up or answering the question. But many aren’t. Put yourself in the shoes of your team first, and try to think: If I were in their position, how would I want my manager to approach me when offering help?

Try adjusting your management style to your teams’ personalities

When you’re managing a team, it’s important to understand that every team member is different; they respond and react to situations differently, the learn differently, they engage differently. It’s one of the biggest challenges I found when I first had people reporting to me, and it took time to even identify it as an issue; but now it’s a challenge I look forward to: getting to know the people I work with, figuring out how to work with them, learning how they respond to the work and the culture and the challenges in front of them. How do you figure these things out? Communications 101: Talk to your team, and listen when they talk to you.

Figuring out the right questions to ask isn’t easy

Claire says a good place to start is to point out your own shortcomings when asking employees what’s up, as a way to break the ice. For example:

– “Do you think I’ve been a little micromanaging with how I’ve been following up on projects?”

– “Could I be doing a better job outlining the vision and direction for where we’re headed?”

– “Have I not been as cognizant of reasonable timelines, like I should have?”

I like the idea but as I note above, I don’t think one approach works for all. So here’s an alternative one: open a general conversation about what you think they need help with. “Tell me about the northeast regional sales campaign,” or “How’s it going working with IT on the automation integration?” This sets the stage and allows them to open up, if they’re ready; if not, it allows you to ease in to more specific, or pointed questions. “I noticed that we’re a bit behind on the first round of emails, what do you think is holding us back?” “I’ve worked with George in IT before, he can be a tough nut to crack. How’re you finding him?” In this way, you’ve shown that A) you’re paying attention to them, and B) you’re giving them the opportunity to self-identify and own the problem.

Once the problem is identified, shift the focus to the solution

So now that you’ve done the good boss thing and helped figure out the problem (without assigning any blame), it’s time to really provide your value as a leader: Actually helping solve the problem. Depending on the employee and the specific problem, there are a number of approaches you can take:

  • The “Here’s what we’re gonna do” approach: This works when the employee is stuck or is one that really just likes to take direction. But this might be too “bossy” for some, who want the responsibility of figuring out the solution.
  • The “What do you think our next steps should be” approach: This allows the employee to own the solution, but be careful: If they really are struggling, they may feel like you’re hanging them out to dry. (A combination of these two can work: “Here’s what I think, what do you think?”)
  • The “Let me tell you about the time…” approach: Give the employee a specific example of a similar situation, and tell them how you solved it. Ask them if they think a similar approach will work here. This way you’re showing your experience, giving them confidence you know how to solve the problem, and still giving them the freedom to take the solution for themselves.


The above probably sounds like a lot of effort on the part of the leader, and I know we’re all busy doing a million things; even if we had all day to focus on people management it still wouldn’t be enough. But listening to your team and helping them solve problems really is a top priority for managers and leaders—so make the time to talk, listen and find the right problem solving approach that works for each employee.