Chelsea Baldwin of Business Bitch: “Train on the delivery & teamwork process”

It’s important to know the boundaries of the task. You need to know what’s included and what’s not included in what you expect the person to do. This can be hard sometimes, especially if you’re delegating something you’ve never delegated before. When I started outsourcing things like accounting and payroll, for example, I didn’t know […]

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It’s important to know the boundaries of the task. You need to know what’s included and what’s not included in what you expect the person to do. This can be hard sometimes, especially if you’re delegating something you’ve never delegated before. When I started outsourcing things like accounting and payroll, for example, I didn’t know what was included in what, or what was typically done by accountants and payroll people.

As part of my series about the “How To Delegate Effectively and Be Completely Satisfied With the Results”, I had the pleasure of interviewing Chelsea Baldwin, Founder & CEO of, where she’s helped hundreds of new and growing entrepreneurs start and grow their own businesses. She’s a multi-business entrepreneur herself, and has had lots of experiences delegating all kinds of different tasks to grow her companies, which she shares in the interview.

Thank you so much for joining us in this interview series, before we dive in, our readers would love to get to know you a bit better, can you tell us a bit about your backstory and how you got started?

Thank you for having me!

My name is Chelsea Baldwin, and I’m the founder of Business Bitch, LLC, and and a multi-business entrepreneur.

I’ve been self-employed for over a decade, and I actually started my journey of self-employment due to a recession… kind of like the one we have going on now.

In 2010, I graduated with a degree in journalism, and it was my biggest dream to work for Rolling Sone, interview rock stars, and write up cool stories on them.

I knew I probably wouldn’t rocket to the top of the journalism industry at 22, so I tried getting jobs at smaller newspapers or smaller magazines to get started. Along with the recession, though, ten years ago was right around them time when newspapers started going online and e-readers were coming out, and print media felt like it was a collapsing industry. A lot of publications were starting to collapse, and the others weren’t exactly in the mood to hire, so it was near impossible to get a job, even at the smallest newspapers.

In the meantime of trying to get a job, I went online and started to look at the option of freelance writing, and found some opportunities to freelance online. That evolved into my career, and I learned a lot about writing on the Web, optimizing what you write for search engines, and how to make sure each piece of content contributes to a company’s bottom line of more revenue.

I used that knowledge to eventually land a job as Content Director at a small app development company, was promoted to being their CMO, and then quit after a while because I didn’t like the office culture or the 9–5, Monday-Saturday thing.

I decided to go back to freelancing and soon after that I started my first company, which is now a copywriting agency.

Because I was able to get such good results for my clients with that company, I started to get asked to do consulting and coaching. For a long time I tried to provide that under the same umbrella as my the copywriting agency, but eventually it became really obvious that they wouldn’t work well together.

I separated the two efforts, and now is where all the business coaching happens.

Can you tell us a story about the hard times you faced when you first started your journey? Did you ever consider giving up? And where did you get the drive to continue even though things were so hard?

I had a lot of times when I felt like my business ideas weren’t working, or I felt like giving up. For a long time, actually, I sort of had a go-to coping mechanism to just start filling out job applications to make myself feel better.

I never actually took any of the jobs, but it was really funny how I always seemed to do that right when I was on the verge of a major breakthrough.

At one point, for example, right before I launched my first digital course under the copywriting agency, I really felt like I was up against a wall and some guy messaged me on slack about interviewing for this really cool job position.

I went through the whole process, and I don’t really remember who dropped off first in the conversation, but right after that I launched the course, there was a demand for it, and the launch went really well.

But in addition to that there were definitely a number of times before I found my really firm, solid ground as a self-employed person where I got freaked out for a moment about my finances and thought that a steady paycheck from a 9–5 would be a lot better, even if it meant trading in my freedom.

Ultimately, though, I knew I valued my freedom more than anything else, and I wanted to hold onto the self-employed vision I had for my life. I’d heard too many people at later stages in their lives say they regretted not going for their dreams, and I decided I didn’t want to be one of those people who just gave into something that was easier.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or take-always you learned from that?

Lol, a few things come to mind here, but one is really sticking out:

When I was first dipping my feet in the pool of higher-paying freelance writing clients, I didn’t yet understand how to set expectations and boundaries that kept everyone happy, and a few situations blew up because of that.

I remember one lady in particular who was an editor for a very popular marketing blog at the time wanted me to write something about Twitter. I don’t remember exactly what the topic was, but I remember doing a great job of writing to fill the specifications she sent over to me.

She got back to me with her feedback, realized she didn’t actually want me to write about the topic she first mentioned, and basically ask me to re-write the entire article from scratch, which would have been a lot of work.

I didn’t want to do all that work without being properly compensated, so I fought her on it a little bit. I told her, “I write what you told me to write, and even put in all kinds of great examples you didn’t specify needing. I’m happy to write an additional article, but this is a great article on its own.”

She, of course, fought back and we both got really frustrated and she fired me from the blog without paying me for that last article.

It’s funny to think about it now, especially because now I’d know exactly what steps to take to prevent this and they seem so obvious to me. I could have just taken a step back to say, “Okay, we clearly didn’t communicate well on this, so let’s take a moment to work together to improve our communication and expectations with one another.” She would’ve been happier, and I wouldn’t have lost a client.

What do you think makes your company stand out and can you share a story?

I think the name of my website is enough to help it stand out on it’s own, lol. You usually don’t see a URL like and forget about.

But also, once people get to the website, they either really resonate the message of “cast the bullshit aside, get shit done, and impatience is a virtue,” or they don’t resonate with me at all.

I’ve got a bit of a polarizing message that has really triggered some people, but just as much as it triggers some, it resonates highly with my target audience and keeps them coming back for more.

For example, I’ve been a lot more active on LinkedIn lately. When I updated my profile on LinkedIn, I wrote “” as the first thing that shows up under my name… where most people put their job title. But, by making that change and having my URL show up anywhere and everywhere my name shows up, I’ve gotten SO MANY positive responses and messages from strangers saying things like, “Oh my God, I saw your website under your name, I had to check it out, I loved it!” or “Clearly you are the kind of person I want in my orbit. Love your business name.”

Of course, some other people can’t believe I have the audacity to call myself that in a professional setting, but it really does stand out and attract the right people in, which is the whole point.

Which tips would you recommend to your colleagues in your industry to help them thrive and not burn out?

This is a really good question, because so often we can get caught up in making long to-do lists, especially when we’re ambitious and have big goals.

When your to-do list gets too long, though, you’ve got more things than you could possibly handle in a day, a week, or a month, and that’s not healthy: mentally, emotionally, or for your sleep cycle.

One of the tricks to get over this that works really well for me and my clients is to imagine being a hot-shot CEO (or if you are a CEO, imagine being a CEO of an even bigger company) who is giving you advice on your business.

What would that hot-shot CEO call you out on for not prioritizing in your business?

Those are the 1–3 things you need to prioritize above everything else.

If it’s not one of those 1–3 things, then you need to either drop it off your to-do list completely, because it’s not having the growth impact you need, or you should outsource it.

For example, if you already have a really solid business in place but you want to scale it, but you’re not really marketing as much as you should to do so.

Obviously, that hot-shot CEO is going to cal you out on that. They’ll ask you why you aren’t pushing your content out there, why you’re not running ads, or why you’re not doing a better email campaign.

Those are the things to prioritize, not the little things like “Oh, I need to make another Instagram post & make sure it looks pretty;” especially if Instagram isn’t where you get most of your customers.

SO MANY solopreneurs or small business entrepreneurs get caught up in that though, because that’s what they think the see other successful business owners focusing on, when in reality the successful people they look up to either don’t manage their Instagram at all, or they just do it when they have leftover time after doing the tasks that drive actual growth and revenue.

Shifting to this style of focus takes a lot of things off your to-do list, which helps prevent you from burnout.

(It also helps you grow your business faster, which is a great side effect and helps with the feeling of mental burnout, because you’ll be seeing rewards for your actions.)

None of us are able to achieve success without some help along the way. Is there a particular person you’re grateful towards who helped you get to where you are, and can you share a story?

Yes, definitely.

Truth be told, I don’t even know how many peoples’ programs I’ve bought, so I definitely can’t name every person, but they’ve all helped me learn the skills I need or adapt the growth mindset needed to take my businesses to the next level.

The first business coach I made a big 1:1 investment in was Harriette Hale. I actually started working with her well before Business Bitch came into existence, but she really did a lot of hard work of beating my head into a brick wall about getting my mindset on point. (I was stubborn and grew up with a lot of conditioning, so I’m sure it wasn’t easy for her.)

I went to her because I had a big vision for myself and my life as an entrepreneur, and I felt like she could help me see the things I couldn’t yet see in business and mindset-wise.

Lately, I’ve also been really grateful for Katrina Ruth, who says she “works with people who kick their own ass, and then she kicks it a little harder.” She’s someone who’s made over 15 million dollars in online business, and she pushes her clients with no-nonsense advice and quick action to do the same thing for themselves.

I haven’t invested more than a couple hundred dollars in her programs yet, but those programs and her free content have really helped me breathe fire into Business Bitch and come out with some really cool offers that my audience has been loving, and therefore buying.

For example, one of the things I really care about with Business Bitch is having affordable offers that anyone can access to take their business idea to the next level, so I didn’t think it’d be a business model where I could make a ton of money in one go.

However, thanks to one of her programs, I realized that I would actually *love* to offer a high-ticket service of one person per month where I essentially take the business idea that’s in their heads and set it all up for them in one month or less, so they can finally get going on living their dreams. It’s not cheap, but for the work done, it is affordable, and couldn’t be more aligned to the message of “impatience is a virtue” that I live and breathe with Business Bitch every day.

Thank you for all that. Now let’s shift to the main focus of this interview. Delegating effectively is a challenge for many leaders, let’s put first things first. Can you help articulate to our readers a few reasons why delegating is such an important skill for a leader or a business owner to develop?

When you are a leader you have a job to do, which is leading your people. Likewise for business owner, you have to lead your business. The job of leadership takes a lot of time and mental energy, so delegating tasks that don’t directly correlate with your leadership responsibilities frees up your time and mental space to be a better leader.

For example, right now, I’m speaking this interview and I’m going to delegate the transcription of it into written text.

Doing this interview is a part of my leadership, but taking the time to type out the words is not. Someone else can do that just as effectively as I can, and once I’m done answering these questions, I get to go back to my other tasks. Any time I would spend typing would be time I spend not creating other leadership content or working with people as a leader. Ditto for when I’m taking the time to do admin tasks that aren’t super important.

Delegating is a super important skill to learn, but it can be hard because you feel like you’re the one who knows and “gets” your work better than anyone else. When you delegate, you also have to hand over some responsibility, which is scary for some people.

We’ve all heard the phrase “if you want it done right you have to do it yourself,” but when you’re a leader, you need to trust (and therefore inspire) others by trusting them. Especially if you’re a business owner who has people working for you: you can inspire them to go bigger and to go bigger with you by trusting them with something really important than needs to be done in order to grow your company… and as a result, their inspired work actually helps your company grow more from their efforts as well, and not just your own. They’re invested in your success too, in other words.

Even if the person you’re delegating to isn’t a permanent member of your team, there are still other benefits: like them being able to complete something a lot quicker than you can. (Again, like me outsourcing the typing of this interview.) When you do things like this, you’re basically multiplying your efforts by letting other people do them. I could sit here for a few hours to transcribe this interview, or I could let someone else spend those few hours “being me” and I get to multiply those few hours so I can lead my business and my online community in a bigger and better way.

Can you help articulate a few of the reasons why delegating is such a challenge for so many people?

I think it comes back to the stories we grew up with:

  • You have to take responsibility for yourself
  • If you want something done right, do it yourself

These saying get reinforced all the time, and while there is some merit to them, a lot of people let themselves be limited by them.

Also, doing a good job of delegating takes time, so sometimes it can feel like you’d be better off just doing something yourself instead of going through a long hiring and employee onboarding process where you have to spend more time teaching someone how to do something than it would take you to just do it yourself.

Of course, the ultimate goal is to invest some time upfront doing the training so you have a lot more free time later on, but when we feel crunched for time or money in our businesses, a lot of us just opt to shoulder the full responsibility ourselves because it seems easier in the short-term.

In your opinion what pivots need to be made either in perspective or in work habits to help alleviate some of the challenges you mentioned?

I think a change in perspective is the first thing that needs to happen.

A lot of times, people get into entrepreneurship holding the vision of them diligently working behind their laptop, doing the fun and the hard tasks of business, and growing their company as a result of their intelligence, savvy, and dedication to their vision.

There’s nothing wrong with starting out with that vision, but chances are you started a company because you actually want to move past that phase to become more successful and to be more of a business owner, rather than someone who’s constantly squirreling away their time at mundane admin tasks.

When you shift your perspective to going beyond the solopreneur doing everything by him/herself, you start to see what needs to happen and what you need to outsource for growth to happen. From that shift in perspective then, you can start making shifts in your work habits to accommodate for that bigger vision so you can delegate the right things at the right time.

When you make the decision to have a strong shift in perspective in your business, you can take on mindsets like “Okay, even if I delegate this thing and it goes wrong, I still know that I can fix it.” So you delegate that thing until it’s successfully delegated or outsourced to someone else, and then you pick up the next thing to delegate, with that same mindset.

You know that proper, successful delegation might take some time to master, but the point is to do it right and to get it done so you can achieve the business dreams you have in mind. You know it’s a risk to take, but by taking that risk, you’re letting yourself grow your business faster… and you can always clean things up if needed, learn from your mistakes, and do better at your next attempt.

As you develop the delegating skill, you’ll get better at it and delegating any task will become much easier and more predictable.

Can you, please, share your five things you need to know to delegate effectively and be completely satisfied with the results? Please share a story or example for each one.

Yes! I’ve done a lot of delegating and have certainly made some mistakes to learn from, so I’m happy to share.

Number 1: It’s important to know the boundaries of the task. You need to know what’s included and what’s not included in what you expect the person to do.

This can be hard sometimes, especially if you’re delegating something you’ve never delegated before.

When I started outsourcing things like accounting and payroll, for example, I didn’t know what was included in what, or what was typically done by accountants and payroll people.

The first person I hired for this was my accountant to do my business taxes, but when we needed to add on payroll, I went with the person he suggested for the role. The way they worked together was pretty seamless, to their credit, but I didn’t know what was and wasn’t included in a person’s payroll responsibilities or even what *I* expected the person to do.

It turned out that folding this responsibility in actually added additional tasks to my to-do list to communicate with both of them about my numbers, instead of them just taking care of it all for me. As it turned out, I expected I’d have some bookkeeping services as well, whereas neither of them do bookkeeping.

Number 2: If you’re outsourcing a specific task, know the exact steps the person needs to take and tell the person what those steps are. (Especially if they’re outsourced help, like a hire-by-the-hour virtual assistant.)

For example, a few years ago, I switched email marketing softwares so I needed to get my email automations and campaigns transferred from one platform to another.

To “save time,” I hired someone who was an expert on the new platform I was upgrading to. I told her to copy over all the emails, campaigns, tags, triggers and automations from the first account to the second one, gave her a couple of examples, and I thought that would be enough, especially since she “got it” and was a total expert on the new platform.

While she did know what she was doing when it came for the software help I hired her for, she apparently didn’t understand the importance of visuals in marketing or keeping brand visuals consistent.

When I went into the campaigns she’d set up, the fonts were not right, the colors were off, the images weren’t added into the email body, and the formatting was off.

I realized then that she would have greatly benefited from me recording my screen & copying one of my emails over, so she’d automatically know to change the colors, choose the same fonts, and make sure the images were added in properly. She’d have known the exact step-by-step process to take, instead of guessing on what I wanted done.

If I’d made that video, we wouldn’t have then had the back-and-forth that ensued after, the task would have been done quicker, and I’d have saved money on her having to go back and fix her mistakes.

Number 3: Don’t just train talent for creativity, train them for deliverables as well.

To delegate effectively and grow an in-house team, you need to know how to train talent and communicate expectations on the end result. This can be hard, especially when you’re delegating creative tasks instead of something like data entry or running numbers.

In my copywriting agency, one of the big steps I took in growing my business was to outsource to writers so we could take on more clients than just one person could handle.

I knew from the start of the hiring process that I would only accept people who were already talented writers, but I also developed specific writer trainings. These trainings taught writers my specific methodologies for writing that worked like crazy and got 2x to 3x more conversions and sales for my clients every time. Any writer I hired couldn’t take on work until they finished these trainings.

I thought I’d done a great job with the trainings (and I had), but I was really underwhelmed with the quality of the first project that came back from another writer. She was highly talented and she’d done my trainings, but she wasn’t delivering the high quality I expected, so I had to go through and make some edits to improve it before we handed it off to the client.

My talent-training part was fine, but I quickly realized I’d only trained them on the process of writing different things, and not on the client delivery aspect.

Part of their training needs to include what’s acceptable as a creative deliverable, and what’s not. This isn’t always easy with creative work, but try to have a checklist people can go through to make sure their creative work is up to scratch before they try to deliver something to you that clearly needs some more polishing done.

Number 4: Train on the delivery & teamwork process.

As you start delegating to more than one person, you’ll quickly realize you need to be as efficient as possible in communicating with your team.

Aside from training the people you delegate to on their individual responsibilities, train them on how to communicate with you and how to communicate to the rest of your team.

Do they need to only reach you via email? Or only communicate with you via the project management software you use? Show them how to do this, in what instances to communicate where, and how to “deliver” their work when it’s finished… or how to mark something off a to-do list or notify the team that Project A is done, so it’s time to move on to Project B.

This process is different for each business and each leader, but it’s crucial to your sanity.

For example, I once had a writer who ~only~ wanted to communicate with me about a writing project via Instagram DMs, just because that’s where our initial conversation started. Needless to say, it was a hugely inefficient conversation, and I finally told her that if she wanted to keep working with me, she needed to communicate within the project documents themselves so things would be easier and faster to understand.

Number 5: Have growth in mind for each individual you hire.

You don’t always have to keep growth in mind if you’re just outsourcing tasks like interview transcriptions, but if you know that delegating is going to become a way of business for you, keep an idea in your mind of how you’d like this person’s responsibilities to grow on your team, before you ever post a job description.

For example, one of the things I’ll be starting soon with Business Bitch is hiring a writer to help me take the content of my podcast interviews and repurpose them into multiple new blog posts per episode.

Ideally, after a little while of working with me, they’d also be able to take on some social media or image-creating responsibilities.

I won’t start with delegating everything at once, but since I have this in mind, I’ll hire someone who also has a passion for social media and an eye for design… instead of just a blogger who hates social media and only wants to spend time behind a screen writing all day. The blogger who hates social media might be a good fit for the first task I want to delegate, but not the ones that come after. By keeping this in mind, I only have to hire one person, and not multiple people. This saves a lot of time with training and team onboarding, and means we’ll be able to move faster in offloading some other responsibilities because they’ll already “get” what it’s like to work with me.

One of the obstacles to proper delegating is an often-quoted cliché ‘if you want something done right, do it yourself’. Is this saying true? Is it false? And is there a way to reconcile it with the importance of delegating?

Yes! I mentioned this earlier in the interview, but I don’t think it’s necessarily true or false. To an extent, it can be either true or false, but there’s definitely a way to reconcile it without compromising one way or another.

With the five things I mentioned in the last question; like knowing the exact steps someone needs to take to do a task, training people on deliverables, and keeping role growth in mind, you reconcile the true/false dichotomy of this statement by basically multiplying yourself.

When you choose to delegate something, it’s almost always something you yourself have done before. If you’re happy with the way you did it; document how you did it. Record a video of your screen while you do something or write out a document of standard operating procedures.

By documenting before you delegate and capturing your exact step-by-step process, you’re essentially multiplying yourself. Since the person you delegate to follows your process, in a way, it is like you are doing it, without it having to take your time.

Documenting individual steps can feel really mundane while you’re doing it, but I think it’s the perfect way to reconcile the idea of delegating to save time with the idea of needing to do things yourself to do them correctly.

Thank you for all of that, we are nearly done. You are a person of great influence, if you could start a movement that would bring the most amount of good to the most amount of people what would that be?

I feel like I am already working on that movement with Business Bitch. The whole inspiration behind starting the company was to make the world a better place by changing the flow of money into the hands of good people.

With the coaching and trainings I provide on my website, I want to put money and influence into the hands of good people and well-meaning people so they can use it to create positive ripple effects throughout the world: for social issues, the environment, politics, whatever they’re passionate about.

I really want these people to have the money, power, and influence they need to make things happen, and I feel like I can help people make that happen by becoming more successful in their own businesses. We can’t make changes happen if we don’t have the resources to do so, so I’m all about putting more resources into the hands of good people.

Self-employment definitely isn’t the path for everyone, but it is the path for a lot of people, so I’m here to help the ones how have chosen it succeed as much as they can.

How can our readers further follow you online?

I am at, where you can find all my freebies, my blog, and The Business Bitch Podcast. On social media, I’m most active on LinkedIn, where you can find me under the name Chelsea Baldwin. While I’m not super active on Instagram, I do check my inbox there at least a few times a day, so my handle there is @businessbitchchelsea.

This was very inspiring. Thank you so much for the time you spent with this!

Thank you for having me!

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