How Do You Know What A Manager Or Supervisor Needs Help With To Be Successful? Part 1

Help your struggling managers and supervisors
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This is the first of a series of articles about methods you can use to answer the question “how do you figure out what a manager or supervisor needs help with to be successful?” (Future articles will be linked here.)

It might be helpful to read the previous article or listen to the podcast “What’s the One Thing that Will Improve Employee Performance” to get more context of the conversation.

Figuring out how to help a struggling manager is different. If you’re watching an electrician, a pipefitter, a carpenter, then you know you can observe their actions and pinpoint the issue. If a carpenter isn’t using a hammer correctly, if a welder is trying to save acetylene but taking more time to make a cut and making a ragged cut at that, you can see what is happening and help them to fix it.

Helping a manager or supervisor can be more challenging than helping a tradesperson.

We all struggle with something in our personal and professional lives. Some struggles are not that big a deal – we can continue to fight it or just let it go. Like me trying to play basketball. No point in wasting time or energy on that, so I let that go in my teens. It wasn’t that the game wasn’t important to me; it was that I had grown too fast and hadn’t developed the coordination – at the age of fourteen I was wearing shoes so big you could use them as a snowboard.

But there are areas in our lives where we feel a passion for the activity, that thing we love doing but maybe we start out sucking at it. Like driving a car. We want the results. We want the road trip and the camping and the fishing. We start off with lurches, dents, and dings. We want the results of the road trip – a feeling of time well spent and accomplishment.

We want to catch not just fish. We want a strike or a spare, not just to roll the bowling ball down the lane. We want to golf below par – as if par is average. Par is anything but average for the average golfer, but it’s the idea that keeps us coming back.

We want the win, not just race.

And then there is being a manager or supervisor.

Everyone wants to be a manager until they are one.

We get the promotion then it’s like, “WTF? They never told me THIS is what it would be like!”

Often, in our pursuit of happiness, in our race to win, we struggle. And we don’t know what is causing the struggle is or how to fix it. We need help figuring out why we might be failing at a task.  This may include a hobby or a honey-do at home, or a have-to-do at work.

In the article I referred to at the beginning, I talk about struggling with sliding sideways off my horse. It took almost two years to fix it. With my limited knowledge and my limited perspective, I couldn’t figure it out on my own. It took an outside observer to help me solve the problem.

I also struggled for many years as a manager. I was failing in place as so many managers do. I had the title, the position, and even the office but not the skill set to survive and flourish as a leader.

I struggled until my boss gave me insights into why I struggled and tools to help me work on them.

When we’re struggling with something we may not be totally aware of it. We may simply say to ourselves, “Life is hard – get over yourself.” Sometimes the unawareness is simply a product of our culture – we do it that way because that’s how it’s always been done. We do it that way because everyone we know did it that way. And it’s wrong, but they didn’t figure it out either. A great example of this is the “my way or the highway” method of leadership.

But if we don’t know that we don’t have to struggle, if we don’t know there’s another way, we don’t stop and think about the possibility of fixing it.

So maybe we don’t even know that we need to fix something. It’s like having chronic pain for so long that we just deal with it. We accept it as part of our lives. Then one day we go to the chiropractor and with one simple tweak, BAM!  We’re all fixed!

At that point, we realize we didn’t know how much pain we were in until we got better.

It’s the same way with being a manager or supervisor and struggling with something. Which is why we need help. That help often comes from an outside observer like a riding instructor, a chiropractor, a boss, book, coach, or mentor.

If you are a leader, you are that outside observer.

When you see a team member or an employee struggling how do you know exactly what they need help with? How do you figure out what the one thing is that will help them be successful?

The first method may seem obvious but for some reason, it’s often overlooked. And it’s not quite as simple as it sounds.

If you want to know what your manager or supervisor is struggling with just ask them!

But as usual, there is more to it than just asking the question, “What do you need help with?”

To increase the odds that your observations and help will be taken the right way, there are three things you need to consider. Even though you know they need help they to have to admit it to themselves first. And then they have to feel safe enough and be willing to admit to others they need help.

Especially when they have to admit it to their boss or a co-worker.

Since we’re talking about managers and supervisors here that may be a little more difficult to get them to admit. Why? Simply because you put them in the position therefore in their mind they’re already supposed to know what to do.

  1. Content and context – What will you ask? You have to ask questions that will give you information and give the employee insight into what they are struggling with. Simply asking questions that can be answered yes or no rarely gets you closer to the information that you need.

Here’s an example:

With one of my clients, we were having a conversation about their struggles at work. I had started the conversation by talking about the fact that I ask a lot of questions to help them think, not to put them on the spot.

Two of the questions were, “What are your co-workers saying?” and “What are your bosses saying?” He eventually told me that one of the things that they’re consistently asking him was about getting back to people. “Why don’t you return my phone calls, texts, emails, whatever…”

I asked him why he didn’t return phone calls, texts, or emails? And he said, “I really don’t like talking to people. They just need to trust me that when they give me something to do I will do it. I’ll let them know when it is done.”

It’s better if you ask questions that cause the person to stop and think and then have them describe to you what they’re struggling with.

  1. Technique – How will you ask? This includes not only the method you’ll use such as texting, a phone call, in person, or by email. It also includes your body language and tone of voice.

Asking in person is the best method. Having a conversation with them allows you and them to create an understanding of the situation and help them admit they need help. The person you’re trying to help may feel like you’re putting them on the spot. But you can reduce that feeling by adjusting the way you ask and the words that you use.

For instance, when I start a consulting or advising job I interview each person on the team individually. This means I ask a lot of questions. But I preface that work by saying to them, “I know that people often feel like they’re being put on the spot when they’re being asked questions. That is not the case here. If at any point you feel like you’re being pressured or may not have an answer to a question right now, that’s fine. Just tell me and we can work with that.”

  1. Timing is everything – When do you ask? The worst time to ask is when you’re doing an annual review. Most managers have heard this is when you should ask the question, are they have had it asked of them. They will ask something like, “What can the company do to help you?” or“ What can I do to help you?”

But, to the employee, it feels like a throwaway question – one that isn’t going to be taken seriously. And by that point in the review, the employees I have talked to feel that asking for help would make them look weaker than the review has already made them feel.

This happens because by the end of the review the employee is feeling emotionally overwhelmed. During and after reviews it is human nature to focus on the negative feedback even if the review is a good one overall. It’s human nature. So asking the question at the end of the employee review is not a good time at all.

So when is a good time to ask a manager or employee what they are struggling with? The best time is as close to the time frame that you observe their struggle as possible. It’s not always best to do it in the moment because when they’re struggling they’re stressed. If possible give them time to relax and then have a conversation with them.

If you have to step in at the moment you see the struggle, maybe because it’s a safety issue, or their part is critical to the success of a project, then do so, but be aware of how you do that.

As always remember that safety begins with leadership – that is significant here because before you have the conversation you have to develop the relationship so that they feel safe enough to open up to you.

Here’s a ProTip:

Before anyone opens up to you they need three things:

  1. They need to be able to admit to themselves that they are struggling and need outside help.
  2. They need to believe that they are safe in admitting that they are struggling and won’t lose their job.
  3. They need to know you have their back and won’t shame or embarrass them.


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