Skip the Pride: Asking for Help as a Business Owner

by Jessica Henslee | Sep 2, 2026 | 0 comments

The desire to avoid asking questions because we regard them as a sign of failure or weakness isn’t something exclusive to business owners. But as an entrepreneur, there is often an extra level of discomfort when admitting you need help.

 

Entrepreneurs are optimistic, ambitious, and independent. You believe that you are capable of solving any challenge that comes your way, and you pride yourself on doing whatever needs to be done. With that mindset, asking for help can feel like a weakness, a deficiency in character, or a sign that you are not cut out for business ownership.

 

Every business owner eventually encounters a problem that they cannot solve on their own. In these moments, pride gets in the way. They may continue trying to solve the problem themselves, even when they know they need assistance. As a result, the problem could persist for months or years, potentially creating even larger problems for the business down the road.

 

This is not a situation that you want. So, being comfortable with asking for help — when you truly need it — is essential.

 

Asking for help doesn’t mean you are in the wrong field. It doesn’t mean your work ethic is weak or that you aren’t cut out for owning a business. It doesn’t mean anything, other than the fact that you needed some assistance. 

 

Being vulnerable and humble enough to ask for help takes a lot of courage, actually. And that is a strength that business owners need.

 

Knowing that you need help and actually asking for it are two different things. Learning to recognize the difference and becoming comfortable asking for help when you need it is an important skill for any business owner.

Why Asking for Help Benefits You

There are always unforeseen challenges, new obstacles that you never imagined would be an issue, and operations that are completely outside of your expertise. You won’t know how to do all of it.

 

This is why asking for help is essential. As a business owner, you must acknowledge your personal strengths and weaknesses. When you identify a weakness, don’t let your pride prevent you from seeking help. For instance, you have a basic understanding of accounting. As you have more employees, managing the accounting duties takes up more of your time and effort. You are weaker in this area than someone who is a full-time accountant with years of experience. Have them take over the responsibilities instead.

 

When you do this, you free up your time. Instead of pushing through a weakness of yours, letting someone else handle it lets you take care of your strengths. Perhaps your strength is in sales, so you’ll have more time for getting new customers to your business. Or it’s in design, so you have more time overseeing design work for a growing client base. When you delegate certain tasks to someone else, you gain more freedom.

 

Also, you gain insight and perspective into the areas you are less knowledgeable about. Asking someone for help expands your professional network, while creating a connection between you and someone more skilled in a particular area. That person can grant you additional insight into your own operations. You don’t need to become an expert in their field. But by knowing the basics, you are in a better position to monitor their accuracy and efficiency.

 

Finally, being open to and requesting help in certain areas improves how your employees see you. People are more aware than you may think and they pay close attention to how you respond to situations you are unfamiliar with. When you don’t know the answer and you refuse to acknowledge the problem or pretend you understand it when you don’t, you undermine their confidence in you.

 

But if employees see you addressing the issue and seeking assistance, they view you asking for help as a responsible decision. That instills confidence in them to do the same, which improves the overall effectiveness of your business.

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When Should You Ask for Help

There are many signs that you need to ask for help. When you feel overwhelmed or stressed, for example, reach out to someone else. Having them take some of the load makes your life easier.

 

Another time when asking for help is important is when you are losing track of all your projects. This varies for each person and for each project. Some business owners can effectively handle 10 projects at once; others struggle with 3 or 4. The difference isn’t that one owner has more skills than the other. The difference is the complexity of those projects. The 3 projects may have a lot of moving parts, while the 10 only have a single, straightforward task. Either way, the point is to seek help if you are struggling with your projects. 

 

And don’t let your pride get in the way. I have worked for business owners who are clearly mixing up projects and struggling to keep everything in order. Yet, they would never admit to it. Be honest with yourself: if you need help, you need help.

 

Other signs you should ask for help:

 

  • Your mental, emotional, or physical health is deteriorating

 

  • You’re losing focus on your main mission

 

  • Your workload is negatively affecting your personal relationships

 

  • Your area of expertise does not cover the area where the issue is

 

In essence, there is something about your business that just isn’t working. 

 

Perhaps you have adopted the “fake it ‘til you make it” mentality and are powering through the challenges. But those challenges persist and the faking is not getting you any results. Maybe you have already tried everything you can think of to solve your issue, but none of it works. Things are just not going the way you expect them to and it isn’t because of a lack of trying.

 

It’s because you need someone else’s help to solve those issues.

Finding the Right Help

You know that you need to ask for help by this point. You are struggling and your business is struggling. It’s time to put thoughts into action.

 

But you are stuck. You wonder if asking for help would make you look bad (spoiler alert: it won’t), and you have no idea who you would even ask. Asking for help is different from knowing that you need it. Keep reading to learn about how you ask for help as a business owner.

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Consider Your Existing Network

Before you start evaluating any professional who may help you, start your search closer to home.

 

Begin by considering your family and friends. This is often more challenging. If asking for help is already difficult, imagine admitting your need for help to a loved one. But, it makes sense in some cases. The most obvious reason is cost.

 

You are running a business, so you don’t always have extra cash lying around to get the professional help you need. Instead, turning to family and friends can bring you expert help with no or minimal financial cost to you. This is a big advantage as a business owner. However, do not rely on friends and family for everything, especially for things they are not familiar with. Free does not automatically mean qualified. 

 

For instance, you have an uncle who has been working in business taxes for 30 years. See if he can help with your taxes. You also have a niece who is just entering into the tax industry and has mainly completed her education on YouTube. Don’t have her handling such complicated matters. You need someone suited for the job.

 

If no friends or family have the know-how in the area you need help with, look at professionals who already have an established connection with you. These can be people you grew up with, someone you met and connected with at a conference two years ago, or someone you’ve been having a rolling conversation with via email for the past two months. It doesn’t matter. The point is that you already have a connection to them and they have the expertise you need for getting the right help.

Be Specific

Not every complaint about work comes through as a request for help. So, make sure you ask for help directly. Don’t beat around the bush and hope that the other person gets what you are implying. It doesn’t often work. Not because they don’t want to help, but because they legitimately did not realize that you were asking for help.

 

Along that same line of thinking, don’t be vague when you ask.

 

Identify the specific issue you need help with. Let’s say that you need to update the content on your website or need someone to manage your blog. You’re going to look for a writer/website manager skilled in your industry, not for someone with vague writing experience.

 

If you are clear about what you want to accomplish, you’ll be much more successful finding a professional to help.

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Personalize Your Request

Generic contact messages are often ignored. I mean, think about it: you are a business owner. Do you have time to respond to every generic outreach you get?

 

Most likely not.

 

It’s the same with other professionals. Having a clear idea of the issue you are trying to solve helps with finding the right professionals to ask. But after that, you still need to consider the time and effort requirements necessary for your request. If you need a business plan drawn up, don’t ask a busy CEO. They may have the skills you need, but they won’t have the time. You need the right balance between skill and available time in a professional.

 

With that, send a personalized message that addresses their skill, your need for help, and the amount of time necessary for the task. This is more effective than a generic cry for help and shows that you did your research beforehand.

Do Your Homework

Before reaching out to a professional, make sure they can provide what you need at a price you agree with. 

 

If you are requesting help from your existing network, this information is not readily available. In this case, send them a message demonstrating why they would be able to help and requesting additional information about their availability and possible prices for their service. The same is true if you are asking a stranger for help, but they don’t offer regular services. They just work in the area where you need expertise.

 

If you are seeking work from freelancers or others who offer varying services, make sure you agree with what they are offering. If there is a professional charging $500 for something you believe should be $200, don’t try convincing them that their price is too high. You can still reach out and request their help; some are open to accepting reduced prices for certain things, but do not assume that will be the case.

 

Find a professional offering services at a price you agree with.

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Offer Assistance in Return

As I mentioned earlier, not everyone offers assistance for a fee. So how do you make your request for assistance more enticing?

 

By offering them something in return.

 

If paying for a service isn’t an option, consider bartering. You are both professionals; they just happen to be strong in areas that are unfamiliar to you. If you are strong in sales, offer them some sales tips for their team. Or if your strengths lie in writing, provide some writing services.

 

Whatever you offer, have it make sense for your request. If all you need is two hours of their time to look over your books for that year, don’t offer them 30 blog posts. Offer them a couple posts instead. Something that makes sense for what you are getting out of it. 

 

It’s the same as when you deal with payments. Some prices are not worth the service. Make sure that whatever you offer for trade makes sense for what you get and what they give.

Be Grateful

This is an elementary concept: when someone helps you, thank them. But it doesn’t only apply to children. Even as adults, stick to this lesson.

 

You are requesting help from someone. When they agree, be appreciative. They helped your business move forward and you freed up some of the obligations on your plate. Demonstrating that you appreciate their help is how you foster long-term connections. In the future, you may need their help again. If they remember you positively because you were thankful for their service the first time, they are more inclined toward helping you again.

 

Showing appreciation may also foster network connections. Perhaps you don’t need help from them, specifically, but they are connected with someone who can help you. Getting a first-hand recommendation, and a positive one at that, increases your chances of getting the assistance you need.

 

Remember, it is still a trade, so offer them something in exchange for their services. But having a network of professionals who are strong in areas you aren’t improves your ability to handle your business as it grows.

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Seeking Help is Not a Weakness

Many of us have hang-ups about reaching out to others and owning our vulnerabilities.

 

But that doesn’t change the fact that it’s an important skill. It requires courage, strength, and honesty, all of which are beneficial for business leaders. Recognizing that you need help and actually asking for it makes both you and your company stronger. It instills confidence in your own abilities because you can’t have strengths without weaknesses. And it proves to you that you understand your abilities enough to know where your strengths undoubtedly lie.

 

It also boosts your team’s confidence in you. Seeing their leader be humble enough to seek help speaks loudly to employees. You demonstrate that your commitment to your business is stronger than your commitment to maintaining your own pride.

 

That being said, be conscious of who you ask for help from. Seek help from professionals who have the skills and experience you need. Check their qualifications, references, familiarity with your industry, and any potential conflicts of interest. Not everyone can provide you with the help you need, so make sure you ask the right people. Otherwise, you’ll end up getting help from someone unqualified, then having to get additional help from someone more qualified.

 

Capable business owners aren’t people who know everything. 

 

Capable business owners know when they don’t know something and have the judgment to find a person who does.

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