How to Develop the Skill of Asking for Help

Learn strategies to help develop the skill of asking for help, how to determine who to ask, and how to make the ask when you need it.

How to Develop the Skill of Asking for Help
Photo by Fernando Venzano on Unsplash

I have a strong memory of sitting at the foot of my stairs at 10 pm at night with the vacuum at my feet with my head in my hands crying. It was the night before my husband, Dana, was coming home after several days in the hospital getting chemo.

Our house was a mess and I wanted it to be nice for when he came home, but I was just so tired. Between running our business, visiting the hospital, and the stress of what we were going through, I was spent. Cleaning our house felt like a monumental task. I needed help. I had needed help for a while. But I hadn’t asked. I had tried to do it myself and, on that particular night, had finally hit a breaking point.

I can’t remember if I finished cleaning that night but I do know the next day I asked a few of my friends if they could recommend a house cleaning service.

It wasn’t a big ask, but it was an admission that I couldn’t do it all myself, which was hard. At that time I had prided myself on being able to take care of everything. Dana was the one with cancer, I could manage the rest. What I didn’t think about was that part of ‘managing the rest’ was taking care of me too.

I ended up hiring a cleaner who came every two weeks and took something off my plate at a time when I desperately needed that space. It was a small change, only a few hours every few weeks, but it had a big impact on my mental health.

All I had to do was ask.

Photo by Annie Spratt on Unsplash

Ask any leader or someone you deem ‘successful’ in your life how they got to where they are today, and I guarantee they will tell you it involved a lot of help along the way. No one gets ahead or becomes an expert in their field without the help of any number of people from different areas of life sharing wisdom, giving advice, providing feedback, or even just being supportive.

Unfortunately, the common (even romanticized) messaging many people have internalized is to be independent, pull yourself up by your bootstraps, and grind forward. Asking for help is internally framed as a weakness and something to avoid.  

But if you think about it, that's pretty silly.

Why wouldn’t you bring in someone who knows more than you, is better at something than you, or has more resources than you? Especially if that person wants to help?

What stops you from asking for help?

Being caught up in your head stops you from asking for help. Making assumptions about what other people will think stops you from asking for help. Being afraid of being shamed stops you from asking for help. Being stubborn and prideful stops you from asking for help. There is often some variation of:

  • “I don’t want to be a burden...”
  • “I don’t want to look stupid...”
  • “I will just figure it out on my own...”
  • “I should know how to do this...”

And so you spend an inordinate amount of time, energy, and money struggling alone… guh!

What does it mean to ask for help?

Asking for help means admitting:

  • You don’t know how to do something;
  • You don’t have the ability or skill to do something;
  • You could do something better or faster with assistance than alone;
  • You are not perfect or a completely self-sufficient robot.

I joke, but those are all hard. Asking for help can feel vulnerable which is not an easy position to willingly put yourself in.

And asking for help often gets blown out of proportion in our own minds. Like we are somehow the worst for needing others. But if you think about it, asking for help is a social contract.

It's a request,  maybe a favour, and definitely not a demand or a requirement.

Asking for help is an opportunity to learn, make yourself better, make something go faster, or avoid something painful.

So how do you do it?

Photo by Annie Spratt on Unsplash

How do you develop the skill of asking for help?

Asking for help is a skill--and like any skill, it takes practice. It’s a muscle that needs to be worked to get stronger. Every time you ask for help it gets a little easier and eventually, it doesn’t feel quite so uncomfortable. Mostly.😅

Here are 6 things you can work on or think about in order to help you develop the skill of asking for help:

  1. Notice when you are struggling
  2. Evaluate when it’s time to ask for help
  3. Trust other people to set their own boundaries
  4. Flip the script
  5. Weigh the consequences
  6. Weigh the benefits

1. Notice when you are struggling

Similar to learning to say no, developing the skill of asking for help starts with noticing. You have to be aware when a behaviour is happening before you can change it! A daily reflection practice is a helpful way to gain this awareness. As you look back on each day and ask yourself how it went you are going to think about the hard parts of your day. Then take the next mental step and ask:

What am I going to do about it?

Think about what you do now.  When you are struggling, what is your instinct?

  • Do you automatically just power through, regardless of how hard it is?
  • Do you avoid the struggle until someone holds you to account for it?
  • Do you even consider asking for help? If you do, what are the thoughts and feelings that come with it?  

The key is to learn not to wait too long before asking for help. You don’t need to wait until your head is in your hands because something got so hard you are at the end of your rope. Notice, and then decide to take action.

2. Evaluate when it’s time to ask for help

I am not saying that every time something is hard you should not try or default to asking for help, but that you need to be able to step back and evaluate WHEN help is appropriate. Some questions you can ask yourself are:

  1. How much time have I spent on this problem already?
  2. Do I have the time (and patience) to keep working on this problem alone?
  3. Is the problem something I know I am not good at?
  4. Is the problem something I should learn how to overcome?
  5. Is working on this problem costing me time and energy that is better spent elsewhere?

Sometimes you are tired and after taking a break on a problem you come back to it and figure it out. Not every problem requires help! But some do, and it is important for you to be able to take the time to evaluate which problems are worth digging into on your own, and which ones are better approached with some backup.

Photo by Tim Mossholder on Unsplash

3. Trust other people to set their own boundaries

As I mentioned above, “I don’t want to be a burden” is the excuse I most often hear when someone explains why they avoid asking for help. Everyone has a lot on their plate and asking for help will only add to it. Right?

Wrong. While it is important to be respectful of the person or people you are asking, you have to trust them to set their own boundaries.

Most people like helping others and like to be asked to share their expertise. You have to give other people the opportunity to make their own decisions. Either they will be happy to help you or they will tell you they can’t. Either is a reasonable outcome because giving help after being asked isn’t a requirement. Remember, help is a request, not a demand!

4. Flip the script

Think about a time when someone asked you for help. Moving day? Grocery run? Emergency babysitting? Volunteering at an event? You’ve probably been asked for help hundreds of times.

So when one of your friends (or a family member, or neighbour, or co-worker, etc.) asks for your help, do you think they are stupid or useless? Do you feel like they are burdening you? Nope!

If you’re like the people in my life, you probably rolled up your sleeves and dug in without a second thought. Or maybe quietly grumbled, but then helped anyway, and it was worth it in the end and really not a big deal. 😁

Relationships are reciprocal and we forget that it feels good when someone asks for your input or skills. It’s nice to be needed. Many people show they care by doing things for others, or acts of service. It’s even one of the 5 Love Languages!

Flip the script and ask yourself, “What would I do if a friend or colleague asked me for the same kind of help?”

5. Weigh the consequences

Take the mental step beyond how asking for help makes you feel and truly think through the potential ‘bad’ outcomes you are imagining. Push beyond the discomfort, and sometimes even shame, of asking for help, and instead ask yourself “What’s the worst that could happen?”

  1. The answer is no. So what? Ask someone else, or keep doing it yourself, which is what you were doing in the first place. You’re no worse off--and you know you tried every available avenue.
  2. They think you are stupid. “Haha, you don’t know how to change a car battery?” is the kind of nightmare that comes from the same place as dreaming you are late for a final exam. If the person you are asking thinks you are stupid for asking, are they really someone who you want in your life? Isn’t it actually stupid to struggle with a problem you could resolve if you asked for help, and the person who could help... doesn’t?

6. Weigh the benefits

What if you ask someone for help and they say... yes?!

  • What if you suddenly had another brain to work through your problem, brainstorm, or walk you through potential solutions?
  • What if you had someone share what they did in a similar situation and give you some ideas you hadn’t thought of?
  • What if you had an extra set of hands to make something happen twice as fast?
  • What if all you needed was a pep talk, and you get one?
  • What if you didn’t have to struggle quite so hard on your own?

Sounds pretty nice, doesn’t it? :)  

Photo by CoWomen on Unsplash

What does “help” mean?

Help can mean many things and it is valuable to get clarity on what you are asking for so you can clearly articulate it to the person you are asking. Sometimes you are asking for something easy and small, and sometimes something more involved. Things like:

  • A sympathetic ear when you have a frustrating client;
  • A sounding board for a new product that you are developing;
  • Another set eyes on a big proposal you are sending out;
  • Validation about feeling disappointed after losing out on a contract;
  • Encouragement when you are in the middle of hiring new employees;
  • Advice on how to remit your corporate taxes;
  • A lesson how to build a cashflow spreadsheet;
  • An experience share on what to do when you have an employee who is struggling.

When you know exactly what you need help with it is easier to figure out the next steps.

How do you determine who you should ask for help?

So you know you need help, you even know specifically what you need help with. How do you figure out who to ask?

Narrow down the type of help you need. What category does it fall in?

  1. Technical expertise
  2. Emotional support
  3. Brawn
  4. Skilled labour
  5. Practical information
  6. Experience-based information
  7. etc.

Does anyone come to mind immediately? Depending on the kind of help you need it will be more clear who to go to first. I think it makes sense to start with the people closest to you and branch out. We all have these circles of people around us with us in the middle. Who do you know in each circle that might help?

  1. Family
  2. Friends
  3. Peers
  4. Managers/colleagues/employees
  5. Institutions
  6. Government
  7. etc.

Some of you will have more people in some circles than others. If it isn’t clear who to go to, that is another form of help you can ask for. In any one of those circles, you can ask if THEY know anyone who might be able to help.

Photo by Nadir sYzYgY on Unsplash

How does someone actually ask for help?

Now you know you need help and who you are going to ask...what now?

I think the mode of request should match the size of your ask. If it is a big ask, it is reasonable to do it over the phone or in person, but for most things, an email, text, or instant message is just fine. The benefit of a written request is that it doesn’t put the person you are asking on the spot. It gives them a chance to think about it (if they need to) and set those boundaries.

Asking for help requires:

  1. Information about the problem
  2. What you’ve tried so far
  3. A specific ask for help (by time, by outcome, etc.)

A template for asking for help

A template you could email, text, message or even use on the phone might be something like:


I am working on [xyz] and ...

  • I am running into a problem with...
  • I can’t quite figure out…
  • I am not sure about…
  • etc.

I’ve tried the following ...

Are you able to send me [x information] or spend [half an hour, an hour, some time] with me to...

  • Share your experience?
  • Explain how it works?
  • Listen to my plan and provide feedback?
  • Tell me your understanding of the process?
  • etc.

I need to have this done by [date/time] or the timeline I am working in is [x].

Let me know if and when you are available. If not, all good. Thanks either way!

That's not so bad, right?!

Some additional things to consider:

  • Provide the person you are asking with enough information to make an informed decision. For example, don’t ask for help to review a proposal, but then after they have said yes send them 6 different 20-page drafts.
  • Be respectful of the person you are asking, especially if what you are asking for is their profession. For example, if you need help with your website, don’t ask your web developer friend to build it for free, ask them to help you choose a platform.
  • Be sensitive to what you know is happening in someone’s life at the time. If a colleague told you last week that they are feeling overwhelmed with their own project, don’t ask them to help with yours.
  • Depending on the type of help you are looking for, do research first. The onus is on you to put some effort in, not the person you are asking. Don’t let someone have internal, “Let me Google that for you”, thoughts.
  • Set and communicate boundaries on what you expect. Be specific about the commitment you are asking for. For example, are you asking for advice or do you need someone to listen to you vent?

My challenge to you:

The right time to ask for help is before you need it. We often know the things that we will struggle with or don’t want to deal with before we start them. Barring that, the biggest challenge I can give to you is to not wait until you are desperate for help. You shouldn’t get to the point where you are crying on your stairs. :)

Ask yourself:

  1. What are you struggling with right now?
  2. Who do you know that is able to help?

Fill out a version of the template and hit send.

My offer to you:

Ask me for help. Seriously. ME! There are all kinds of things that I can and will help with. And if I’m not the right person, I probably know someone who is.
What are you waiting for? All you have to do is ask.😊

Need a bit more help?