When is the right time to hire a coach for my business?

Stephanie Wasylyk
7 min readMay 10, 2022

It is completely possible to have a successful business and never hire a coach.

Surprised to hear me say that?

Think about it for even a minute, and you know of course it must be true. Technically, you could consider coaching a luxury.

And yet, I’m a coach.

I was speaking to a client who said, “I’ve been in business a long time, I’ve seen my colleagues hire coaches and I regret not hiring one sooner because I see how far ahead they are now.”

Because that’s the truth of coaching. It helps people go from good to great. It’s for people who know there’s something more, or know they’re missing something, and they need help to figure out what that is. It’s likely a coach can help you get there faster and smoother than you would on your own, but it doesn’t mean you would never get there yourself.

I want to write this post as an alternative perspective to what most coaches will tell you. I want you to know you don’t have to be pressured or guilted into hiring someone when you can’t afford it or you don’t need it at this point in your business. I want to help you be discerning and confident in your decision to invest in yourself and your business.

But first, when is it NOT a good time to hire a coach for your business?

Don’t hire a coach if you:

· Absolutely can’t afford it. If you’re going to panic because you don’t know how you’ll feed yourself or pay your rent, you should not be investing in a coach. I would suggest you get a job or make some money first, maybe not in your business of choice, and wait to invest until you know you will be able to pay for it. You should not bank on making your money back immediately, since that rarely happens, especially when you’re desperate. I also personally don’t believe in going into debt for coaching, but only you can decide what your debt tolerance is and what you need coaching for. That said, I do believe it’s okay to take a little bit of risk when you’re investing (in a coach or otherwise) as long as it won’t financially ruin you.

· Are way too busy with something else in your life to dedicate time to work on your business. The exception would be if it’s your business that’s causing you to be so busy, then a coach can help you free up some time (more on that later). In this case, I’m talking about if there’s a certain life event happening that takes your attention away from your business. For example, I absolutely did not have a coach for my business when my daughter was born. I was hardly keeping my business afloat and not making any big changes because I already had so much change happening in my life. I did hire a coach before that to prepare, and many months after she was born to get back on track.

· Are looking for a magic solution. Coaching is about you looking deep and reflecting, then doing the work to make things happen. If you’re looking for something to magically make everything go away without you putting in any effort, you’re looking in the wrong place. But I suspect you wouldn’t be reading this if that was you :)

· Already have another coach for the same purpose. This is a grey area because lots of people get advice and support from multiple places at the same time. What you don’t want is too many cooks in the kitchen. It can also happen that, if you have too many people supporting you, and they’re all giving you action items to work on, you get overwhelmed and can’t get it all done. It’s totally okay to stagger your help so you can make the most of each one, or to hire a coach to support you through a certain process you’re learning from somewhere else. Notice, though, if you’re over-investing like this because of self-doubt, because then it might be important to get to the root of that first.

· Are good with where you are. It’s also okay to just be happy with where you are in your business and enjoy things as they are. Being content is different than being complacent or avoidant. If you’re content and you’re working the way you want to be working, then great! You don’t have to invent a problem where there isn’t one. If you know what you need to be working on and you’re actively doing that without a problem, then keep doing what you’re doing until you no longer know what’s next.

Those are the main mistakes I see people make when they decide to hire a coach.

So when should you hire a business coach, then?

Hire a coach if you:

· Have run out of ideas to solve your problem. It can be helpful to speak to someone with different experiences than you, and someone who can help you look at new perspectives. There are likely lots of things you haven’t thought of or have dismissed too early.

· Are sitting down to work and you’re confused about what to work on next. Without a plan you’ll be working in circles, procrastinating, or doing things that aren’t impactful. A coach can help you come up with a plan so you can stay focused moving forward.

· Need to make a transition. It’s common for entrepreneurs to build a business, then realize that actually it’s something else they’d like to work on that would be more fulfilling. It can be scary to navigate that transition from one thing that feels safe to another that feels risky or unknown. Coaches make great thought partners for this, and fantastic cheerleaders.

· Find yourself working way too much for way too little money. When this happens there are lots of variables that could be off. It’s possible the solution is purely a business thing, but it’s also likely there’s some self-doubt running the show. A coach can help you explore your profitability and efficiency, investigate ways to balance working on your business vs. in your business, and most importantly, what your beliefs are about the way you’re doing business. I’ve also found some simple time management strategies can be game-changing for most business owners.

· Are trying to make a decision you can’t seem to figure out on your own. You might not be trusting yourself, or you’re lacking the confidence to be decisive. You might feel too close to the situation to think clearly, or the decision feels too important to make it on your own. A Thought Partner could be the perfect solution.

· Need someone to process your thoughts with or someone to bounce ideas off of. Similar to the point above, many of my clients are verbal processors and need the time and space to work things out with someone else. A good coach won’t get tangled up in your thoughts and agree with everything you say — they’ll call you out when they notice something is off, and challenge you to go deeper.

· Want to get a new initiative or offering off the ground. It can be scary to do something new or to put yourself out there on a larger scale. Plus, there are so many options to explore when you’re putting together packages or new services! A coach can help you with the logistics, and also with the inevitable self-doubt that will come up along the way.

· Are overworking, overgiving, overthinking, or overwhelmed. It might be time to simplify things or set some boundaries. A coach can help you notice the patterns you have in these situations, and lovingly support you to get back to a healthier way of doing business.

· Feel dissatisfied with how you’re working or how your life is going. You may have lost sight of your values, or you’re off track from what you really want from your business. You might be following someone else’s plan or working in a way that isn’t right for you. Maybe you aren’t making the impact you want to be making in the world. It could be helpful to get to the bottom of what’s really going on so you can move forward on a better path.

· Know you can be doing things better and want to go from good to great. It’s not always about hiring a coach to fix the bad stuff. Sometimes you just want things to be even more awesome! A coach can help you see opportunities you might have missed and areas for growth.

Of course you may hire a coach for a combination of these things, or something else entirely. As much as it’s common practice in marketing to advertise solving very specific problems, the truth is there are infinite possibilities when it comes to business coaching. The important thing is to find a person you resonate and align with and see if it’s a fit from there.

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