How to Know When It’s Time to Hire a Business Coach

Noe Khalfa
Worth The Journey Blog
11 min readJul 1, 2020

Running a business is never as straightforward as it sounds in your inspired 2am fantasy. Figure out if it’s time to get support and hire a business coach.

[Image description: An individual with pink nail polish holds up their phone, trying to decide whether it’s time to make the call. A strange futuristic object lies on their computer, but no one seems to know what it is. Unsplash.com]

We are ideas people, let me tell you. In fact everyone on our team, and most of our collaborators have at least two business projects going on. And then we each have a backlog of countless ideas for businesses, projects, events, and products. And I know you do too. It’s part of living and breathing as an entrepreneur — you’re an idea machine.

But you may have come to realize, as we have, that running a business is never as straightforward as it first sounds in your inspired 2am fantasy.

Does this sound familiar? (Please read with a genuinely enthusiastic tone, not a sarcastic one.)

  • “OMG, I’ll just teach yoga and people will pay to take my classes!”
  • “OMG I’ll just make dadaist t-shirts and sell them online. I’ll make millions!”
  • “OMG I was born to be a relationship therapist. How hard could it be? My friends come to me with all their issues anyway!”
  • “OMG why don’t I just turn my hobby of handcrafted natural cosmetics into an online shop?!”

The theme is the same, besides beginning with “OMG” and ending with an exclamation mark, each of these ideas gets at the most basic root of business, “I offer a service or product, and people pay me.” Simple enough right?

Honestly if you have an idea like this you’re already off on the right foot — you’ve got enthusiasm and a willingness to say your ideas out loud, and both of those are necessary for any entrepreneur.

And yet, when that idea suddenly grows and you find yourself dealing with things like branding, business cards, a website, accounting, lead generation, marketing campaigns, backend tech systems, and all the other business necessities, everything gets complex very fast and it can feel like that 2am fantasy was just, well, a fantasy.

So here’s the bottom line:

Hiring a business coach can help you make complex decisions, simplify what’s overwhelming, and keep you inspired to keep growing your original vision.

Being guided by an expert is like having a ship’s navigator on the high seas during your journey back from the Trojan war. Without someone who’s traversed the waters before, you’re likely to get sidetracked by distraction sirens, drawn into Charybdis‘s whirlpool of endless tasks, or have your head chomped off by the Scylla monster of debt and failure.

I may sound a touch dramatic, but my dad read me Greek myths for bedtime stories so what do you expect?

Now some of those mistakes are good lessons that each entrepreneur needs to learn. You know, character building stuff, like learning how to handle the steering or learning to fix a leak.

But things like … spending a bunch of money on designs you never end up using, or hiring someone who only adds more complications to your business, or building and rebuilding your website only to realize you have created a sea-monster of complexity are completely avoidable if you’ve got someone beside you who’s sailed this sea before and knows where the secret monsters are hidden.

If you’re reading this article, you are probably at the point of considering whether it’s time for a co-captain (or two).

Hopefully this blog article answers most of your questions, but if there’s anything you else you’re curious about, leave them in the comments below and we’ll take care of you.

This article is organized by stages of business, so you can best asses whether it’s time to hire a business coach for your specific business growth stage.

Let’s dive in.

Stage 1: Starting a business

[Image description: A mug of probably cold-by-now coffee sits alone on a long wooden table with the text “begin” on it’s side, enticing you, it’s owner to take a sip and begin. Unsplash.com]

Stage 1 is when everything is new and you’re moving from idea to implementation. When you’re here at the beginning, it might be worth hiring a business coach to solve the following issues.

Getting a realistic look at your idea’s viability and potential business models

Let’s revisit one of the exciting business ideas I brought up in the intro to this article: becoming a yoga teacher. With a realistic look, each of those ideas could become a thriving business. You can absolutely start a yoga business and make it big, but one thing you should know is that teaching only weekly classes won’t make you enough money per amount of energy it will take from you.

I like to teach with clear examples, so let’s do some quick math. The average yoga teacher with 2–6 years experience makes ~$50/class if they’re lucky. And if you want to gross a small salary of $48k/year, at that rate you’d need to teach 20 classes/week or 4 classes/weekday. As someone who used to teach a lot of yoga classes, that is an unreasonable amount of classes for one human to teach. Unless you’re a golden retriever, you’ll burn out real quick.

In fact, in my years of working with yoga teachers, I know of only one exception to this rule, and he’s a real eccentric teacher who you do not want to become, I promise. So before you decide to jump off the cliff and start teaching, you need to flesh out a business model with diverse models of teaching so that you can make a sustainable living — for example, a mixture of in-person classes, workshops, YouTube classes, retreats, recorded meditations, becoming an influencer, repping a yoga brand, and private lessons.

If you feel daunted by the task of creating a viable business model, it’s time to hire a coach.

Saving as much money as possible

Starting a business can get costly right off the bat. There is much to consider from rent to branding and websites to equipment and inventory to memberships and subscriptions.

Hiring a business coach will help you make heads and tails of the big financial decisions you’re faced with, and could help save you tens of thousands of dollars — much more than the cost of the coaching.

Getting your brand and audience right the first time

I’ve personally been through 6 brand redesigns and overhauls before I finally got to Worth The Journey’s clear brand identity, brand voice, and target audience. And I spent thousands of dollars on those redesigns.

What do I wish had happened instead? I obviously wish I had hired a business coach to help me get clear on the vision early on, think it out thoroughly, and guide me through each step of the process. It would have not only saved me money, but also months of time. To be totally frank, the main reason I didn’t was because I couldn’t find anyone who’s values and coaching style I super resonated with, and I didn’t know how to look for one. If that’s you as well, read our article on how to search for and find the perfect business coach for you.

Stage 2: Increasing customers and sales

[Image description: A customer at Curio: Night Market, a 2019 Worth The Journey event holds plates while a white-sweatered local business owner explains that yes, they are in fact plates. OMG it’s our own photo, how cool! I’ll link to our events page, why not.]

Stage 2 is when you find yourself wrestling with growing your business to become profitable and creating a steady income for yourself. Is it time to hire a business coach? Take a look below and you’ll see where a coach could be most helpful.

Creating a marketing plan

If your marketing plan so far consists of you posting random inspirational quotes to Instagram or realizing suddenly at 1am that you forgot to let the world of Facebook know about your new event in a week — you might be an entrepreneur.

Everyone who goes into business for themselves deals with the same questions: What is effective marketing? Should I post on social media all the time? What will make me stand out? How can I bring in new customers or clients? And sometimes you naturally discover the solutions. It’s when you get stuck that you know it’s time to bring in an outside perspective, someone who’s organized marketing campaigns across platforms with a unified message. Getting a coach here can save you literally months or years of ineffective time.

Developing your unique sales skills

I have a story for you. It’s a little embarrassing, but the lesson radically changed me, so I’ll share it…but just with you. About 6–7 years ago I started my first life-coaching business. I had never done sales before and in fact I thought sales was a horrible thing I should avoid at all costs.

Instead of doing sales, I tried to convince people why they needed the life-coaching tools I had to offer. Obviously I was doing sales (duh, past Noé), but I was also doing what I now call Toxic Sales. You know that gross thing when people try to push something on to you. Yeah that was me. Yuck!

But one day I learned a secret about sales. So there I am at a little tea shop in Seattle with potential client Fred sitting across from me talking somewhat nervously about why he had reached out about coaching. I did my usual thing of listening and trying to be helpful and wondering if the time will come to make the sale.

But then something happened.

Mid conversation he said, “…so how does this work? I saw on your website that you can do 3 months, and I was thinking I’d like to start with 3 months and then maybe move to 6 months after that if that’s ok.” I did an internal double take. But….I hadn’t said anything to convince him to work with me? How did that happen?!

I realized that I had been trying way too hard to sell, and that there were ways to let other people sell themselves on my work while I just get to hang out and have a fun conversation. After that it took me a little time to get comfortable in my sales style because it’s all about finding the ways that comes naturally to you.

A good business coaches will help you realize what your sales style is, and help you practice it. So if you have a tough time selling, or feel a lot of struggle or embarrassment around the topic, it might be time to hire a business coach.

Trying strategies you’d never have thought of

By this stage, you’ve already started your business, which means you’ve already invested a lot of time, energy, and potentially money in getting things up and running. So it’s quite possible that by now you’ve tried everything you know how to do by yourself. That’s actually the perfect time to bring in a coach. They’ll have a different and more experienced brain from yours, and that’s exactly what you need when you run out of strategies that give you great results.

Because they’ve dipped into not just their own, but many other people’s businesses, and been able to pull out aggregate wisdom, identifying what tends to work, and what doesn’t, they’re often exactly the thing you need to break the mold you’ve been stuck in.

Making your business profitable

I’m going to say something that might make your jaw drop. Ready?

It’s absolutely possible to be profitable from day 1 and to never sink your business into debt. Ever.

The jaw dropping part is that anyone can do it, it just takes some reframing of how you’re approaching business, and what you do with money when it comes in.

Most businesses start in debt. Others accumulate it over time. You’re in the majority pool if that’s you. What I’m saying is it’s normal, but it doesn’t have to be your normal. A business coach can help you figure out how to structure your business so that you’re a profit machine, not an expense machine.

Stage 3: Setting up systems and tech

[Image description: A slightly terrifying and fancy-AF dashboard of a metrics app sits open on a laptop in an unsurprisingly empty room. Unsplash.com.]

Stage 3 seems to happen overnight. You suddenly become overwhelmed by the number of tasks and todos, and much of it has built up in areas that aren’t your strong suit. If you’re stuck in a tech nightmare, it might be time to get a business coach.

Deciding between systems

Some of the hardest decisions involve choosing which of these systems to use:

  • Mailing list
  • CRM
  • Productivity software
  • Website platform
  • Accounting system
  • Online scheduler
  • Payment processor
  • Storefront
  • …and the list goes on.

A business coach will be able to help you make these critical decisions based on their industry knowledge and experience working with a spread of clients in similar and different industries. If you’ve been bogged down in the weeds of system-overload it might be time to get a business coach to help you set up the right systems once and for all.

Holding you accountable

Getting new tech and systems set up often requires that you change the way you work. And we all know that changing our habits could be slightly irksome or downright frustrating. If you tend to get frustrated with new technology, it might be time to hire a business coach. They’ll help you ramp up into a new system and make it the new habit.

Don’t get me wrong, you’ll still need to put in the work, but you won’t be alone. You’ll be held accountable by a skilled expert who knows how to teach effectively.

Working with your strengths

A good business coach will help you find systems and technology that will not only make your business more efficient, but will also play to your strengths.

I spend a lot of my time teaching and facilitating, and most of my close friends are also teachers and facilitators. One thing I’ve noticed is that the best teachers can quickly point out different learning styles when they look around a room.

They can see the fidgeters, the rebels, and the perfectionists. They treat each person uniquely according to their style.

Stage 4: Building a team

[Image description: A team member gestures to a whiteboard covered in sticky notes. The team appears to be on track, because if you look close enough you can see that most of their tasks are in a the column titled with a single checkmark. This whiteboard also features a column titled with a single heart, begging the question, why don’t we all work at this magical company? Unsplash.com.]

Stage 4 is when your business grows beyond solopreneurship. Working with other people can be both necessary and rewarding, although without proper attention it can become difficult or straining.

Working with contractors

At some point, inevitably, you’ll outgrow doing 100% of the work by yourself. That’s a good thing! It means more time to work in your area of genius, and less time doing work you’re neither good at nor particularly like to do.

While hiring contractors may become a necessity, finding the right ones can be a time consuming and costly process — and finding the wrong ones can do even more harm. Organizations will hire a business coach or team of coaches at this stage to save months of time and effort.

Hiring employees

When you’re ready to hire your first employees, or bring on new staff, it may be worth bringing in someone who has an entire hiring process already created. It’ll save you from making it all up by yourself. Business coaches also maintain hundreds of connections in a wide variety of industries, so it’s worth drawing on them before jumping to the online masses. Finally, they’ll likely be able to tell the difference between someone who looks good on paper and interviews well, and a real teammate who will help your business grow over the longterm.

In conclusion

I’ll leave you with two things. First, if you decide to hire a business coach, read this blog post on How to Vet and Choose the Right Business Coach. It’ll help you mount a non-frantic search and find a great coach.

Second, I’ll leave you with this knowledge: the primary factor in hiring a business coach isn’t about the coach, it’s about the timing. Yes, make sure they’re a good fit. But most importantly, make sure it’s the right time for you.

Take the time to answer these questions:

  • What stage are you in?
  • What obstacles are you struggling with the most?
  • What are your business goals?

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Noe Khalfa
Worth The Journey Blog

As CEO of Worth The Journey, Noé is on a mission to teach business skills to people with zero business background and elevate heart-centered businesses.