How To Keep Business Owners Happy With Your Service

Reflections Of A Small Business Owner Turned Freelancer

Hi, I’m Annie Aaroe, a b2b email marketing specialist for SaaS companies…

But I’m also Annie Wadsworth, owner and operator of my family’s local bagel shop in Upstate, New York, aka “The Bae-Gal”

I keep two names, one of them my maiden name, because it helps me separate my two professional identities. But the more I work as Annie Aaroe, a service provider for other business owners, the more I’ve realized just how much these two sides of my persona are incredibly linked. And it’s that link that helps me understand, viscerally, what a business owner wants from their service provider… and give it to them. 

As a business owner I’ve hired countless agencies, freelancers and sole-proprietors over the last two decades. And I’ve had a few good experiences. But honestly, most of these relationships over the years left me feeling a bit cheated, unsatisfied, and sometimes down right pissed off. But these experiences have helped me become a better service provider. I know exactly what business owners want and that has made me irreplaceable in the eyes of my clients. In this article I’m going to share some of that knowledge with you. 

I’d like to help you see through the eyes of your business owner clients and begin to understand what matters most to them. If you can think like a business owner, I guarantee it will help you build a strong, in demand, service based business where your clients rave about you.

A Brief History Of How I Got Here

I’ve owned my family’s bagel shop for almost 20 years now. My father-in-law started the business almost 35 years ago, so now I’ve officially owned it longer than he did. That fact is actually kind of crazy to me. I do love my bagel shop. But it’s not exactly what I thought I’d be doing with my life when I graduated with my Ivy League English degree and a concentration in creative writing. I’m a prime example of life not working out the way you thought it would. 

But over the years, as the business has changed and seen boom years and bust years, minor and major transitions, and a global pandemic, my identity and my heart have become more and more woven together with my business. And though sometimes I want to pull my hair out and walk away, it’s actually out of the struggles that my love for my small business has grown the most.

But I always knew I didn’t want to run this business forever. Especially when I started looking forward towards the years when my 3 teenagers will start graduating and building their own lives, I began working on building my next career as a writer, currently as a digital marketing copywriter. After about three years working for clients in my copywriting “side-hustle” I, not at all surprisingly, settled into the b2b space, writing emails and helping strategize with business owners about their copy and email marketing. As a business owner myself, the b2b space is perfect for me, because not only do I love working for other business owners, but as a b2b copywriter, I’m often writing copy for an audience of business owners as well.

Today I work part time running my bagel shop, with the help of my husband and our incredible staff, and part time for clients as a marketing strategist and copywriter. Over and over again I see the crossover between what my client’s are experiencing running their businesses and the struggles I experience running my business. It keeps me humble, present and always understanding. I trust you will learn something valuable from my experience.

The Most Important Thing

I am going to risk sounding pretty trite when I say this, but the single most important thing, from a business owner’s point of view, when hiring a service provider, is that they feel like you care about their business. This might sound obvious, and you may even be saying, “I do care about their business” and think I’m not telling you anything new.

The point here isn’t simply that you care about your client’s business. The point is that your client FEELS like you care about their business, and that your level of caring for their business matches the investment your client is making in you. Let’s say you are charging $10,000 for your services, and your client runs a one million dollar business. Basically they need to feel like you care about their business at least one hundredth as much as they do. And for most business owners, their business is like another one of their children. Seriously, their level of care is nearly immeasurable. Their business is their life. So getting them to feel like you care, even just one-hundredth as much as they do, it’s not exactly an easy thing. Especially when you are working for multiple clients at one time. 

Here are some tips you can incorporate into your business to effectively communicate to your client that you care. If you follow even just a few of these ideas, it will set you apart from others in your industry and help you to stand out to your client as someone they can trust. It will mean this client will keep coming back to you for help, and also pass on your name to others.

Tip #1: Ask About and Listen To Their Story

It doesn’t matter what type of service you offer, in fact, the more out of place this approach seems, the more it is going to endear you to your client. Of course some clients are going to be more into sharing personal stories than others, but pretty much everyone likes to talk about themselves. Take advantage of that fact and use it to create a basis of understanding between you and your client. Hearing the story of how they got started, or why they started this company, or what drew them to this industry, is going to provide you with important background information when you’re helping to solve a problem in their business, and it might help you take an approach that is going to resonate more deeply with your client.

I advise you to schedule an initial conversation, after you’ve signed a contract with the client, or at least after they’ve agreed they want to work with you, and use the time to dig into the story of how they got started in their business. Write down a list of questions to help you get started, and then let yourself be curious and ask plenty of follow up questions. Try to get a solid understanding of the “why’s” behind their business, and how they are personally connected to whatever they offer in their business.

This might seem awkward, to both you and the client, at first, but I encourage you to push through that awkwardness and always start your conversation here. Don’t skip over this step and spend the beginning of the conversation talking about what you are going to do for them. Instead, spend the majority of the time focused on them, and getting to know the origin story of their business. This approach will likely find the transition into talking about your ideas will go more smoothly. When you begin by showing a real interest in your client’s story, they will likely be more receptive to your ideas because now you have their trust.

Tip #2: Establish A Schedule for Communication – And Stick To It

As a service provider we sometimes make the mistake of leaving the burden of communication on our client. I guess people think, well if they want something from me, they’ll ask for it. 

But the opposite is actually true. When you’re working with a small business owner they are going to be some of the busiest, most overwhelmed people you’ll ever work with. Their minds are constantly full of new ideas that pop up in their minds at the most random and inconvenient times, urgent problems that they are the only person on the planet who can solve, and lists of tasks they feel they need to do and never have enough time for. All of those things are constantly crowding your client’s mind. And all of that on top of the daily tasks required to actually run their business. You, as a service provider are never going to be on the top of their mind, at least not until they have a problem with you. You definitely don’t want to wait until your client is reaching out to you because there is a problem with you. 

Instead, establish at the beginning of your relationship with the client, a system for checking in with them on a regular basis. In my copywriting business this is often once a week, if I am working on a specific project for a client. For other clients I check in just once a month. Even if they don’t have work for me at that time, I still check in on a regular basis. I send an email at the end of each week (or month) letting them know my progress, a checklist of what I plan to work on next and a list of any things I need the client to do to help the project move forward.

Pick a schedule that makes sense, but most importantly stick to it. When your client learns they can depend on your consistent communication, they know they never have to worry about whether you have time for them. They also know that you care enough to reach out. They also will be relieved that they don’t need to remember to contact you when they need something, because you’re going to take care of remembering. This approach takes one simple task off their already overflowing list, and they are going to love you for it.

Tip #3: Choose Clients You Genuinely Like

This next tip is the most helpful if you’re able to choose the types of clients who you work with. If you’re still taking any and all business that comes your way, this tip might be harder to follow. But as you build your business, pay attention to the personality of the clients you work with. Work harder to keep the clients who you genuinely like, and let the people who aren’t as likable pass on to someone else. When you attract clients who you actually like as people, it makes it easier to establish a rapport, and you’re both going to like working together for the long term.

I suggest you give a personal touch to your interactions with your client. This might be as simple as asking about their weekend getaway when you shoot off an email on a Monday morning, or it might be as involved as sending a small gift on their birthday, or when you finish working on a project for them. Either way, with this tip you want to lead by example. Don’t be afraid to share a little bit about your personal side with your client, and see how they respond. Obviously you don’t want to let go of professional boundaries, especially when you are first getting to know the client. But if it feels natural to talk a little about not work related things with your client, I suggest you go with it.

In my twenty years of experience as a business owner, the service providers that I end up sticking with, are always the people that I get along with personally. This doesn’t mean I become actual friends, but it does mean that I look forward to interacting with them. Since I’m a talkative person, I tend to get along with other people who like to talk. But a connection can be built by two more reserved people, and they probably get along with each other in part because they are both reserved. 

Tip #4: Pay Attention To The Data

When you work with business owners they may be super aware of the numbers and constantly running their own reports and making projections and decisions based on data. But more often than not, they are not spending as much time as they probably would like looking at the data because they are so busy putting out small fires and running the day to day of their business.

But you should definitely be focused on the data, and when you show your client that you are paying attention to their data, it will likely give them a huge piece of mind. I’m not suggesting that you start generating reports on a weekly basis and asking to attend the business’s shareholder meetings. But I do suggest that you reference the results of your work as a basis for future suggestions and solutions that you offer to your client. And if you have access to data from before you started working with your client, you can reference that as well.

Whenever you show your client that you are paying attention to the data behind their business, it shows that you care about their business on a core level, maybe even more thoroughly than your client in some respects. Don’t get lost in the first three tips, which are all about the person to person connection and forget that you always should make data driven decisions if you want to stand on solid ground, and keep your client’s trust.

Tip #5: Work “Cleanly”

Imagine you are a construction worker for a second, and you are building a new closet for your client. You could build the most sturdy, beautiful new closet for your client, but if you leave your work space a mess, and by extension your client’s house, at the end of each day, there’s no way you are going to get asked back. 

The same principle applies when you’re working for a client in their business. You want to clean up after yourself, and you want to present yourself in an organized way. These are basic principles of any relationship in business; show up on time, come prepared so you’re not wasting anyone’s time, and take notes so no one has to repeat themselves.

The reason I include this tip here is because the reason behind it is specific for business owners. In a corporate environment certain behaviors are expected because it’s built into the culture. But just because you’re stepping out of that corporate culture, and into a small business, doesn’t mean you can do things your own way completely. By adapting a certain level of orderliness in your service business, you let the small business owner know you take them seriously, and that you take yourself seriously.

I’ve seen too many freelancers who seem to think that just because they work for themselves, that they can do things completely on their own schedule and in a totally laid back manner. In my opinion, that laid back style has to be earned, and you earn it by showing up as a professional first and working hard to earn the complete trust of your client. 


Small business owners are some of the most proud, and some of the most stressed out people you will ever meet. But they are also some of the most inspiring visionaries you can work for, and that is why it is so rewarding to earn their trust and help them to grow their business. When you use your heart as well as your mind to build a connection with your client and with their passion for their business, it can be incredibly rewarding for all of the people involved.

If you have any specific questions for me about running a business, or working with business owners, I’d love to chat. You can reach out to me via email. 

For copywriting or freelancing questions, reach out to me at

For small business or bagel questions shoot an email to

I can’t wait to hear your thoughts!

Hi! I’m Annie Aaroe, a b2b marketing strategist. To find out more about story-driven, conversion copy and strategy that’s tailored for tech and SaaS brands, visit my website,, or shoot me an email at

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