What You Need To Understand Before Hiring A Freelance Business Coach

Discover what to watch out for when hiring a business coach to grow your freelance business and get 14 tips on how to find the best coach for you.

Hiring a coach

I’ve owned a creative agency since 2005. In that time, I’ve had the opportunity to work with some incredible coaches and mentors who have helped move my business forward in big ways and helped me grow as a person. But the first two times I invested in professional coaching were complete and utter disasters and cost me tens of thousands of dollars.

I was new to freelancing and the concept of coaching and was sucked in by magical promises spewed from coaches who were like politicians on the campaign trail.

The first time, I was in my twenties, I had two babies and a huge mortgage on a new home, and I had recently quit my full-time job. I needed to build my business quickly and the first coach I met said she could help. She promised that she could help me achieve everything to the moon and back and was really pushy and relentless.

I did eventually hire her and after just one call instantly regretted it. For an entire hour, she did nothing but list 100 things I should be doing and wasn’t and about 25 things I needed to buy or invest in right away. I think I hit my overwhelm limit in about 10 minutes and it only got worse.

The second time was a couple years later and this coach also made huge promises. The difference this time was that she claimed to have built a successful agency already, which naturally made her a great choice as a coach. She promised to show me her system, give me all the tools she had already developed, and guide me on my way to grow my business. It really did seem like the perfect fit — after all, I was hiring someone who had achieved what I wanted to achieve.

But that was all a lie.

After I signed the contract and paid huge amounts of money, there was no system, there were no tools, and there was no guidance. Every interaction with her after the sales was unprofessional and left me feeling uncomfortable. What’s worse is that I felt tricked and duped.

Both experiences were incredibly difficult learning experiences.

They could have turned me away from coaching forever, but I’m an optimist and as I met more people are shared my story, I found out that:

  • I was not alone. There are a lot of shady people out there claiming to be coaches. There are also a lot of good-hearted people who want to help others by offering coaching but just aren’t qualified.
  • What these two women promised wasn’t actually business coaching.
  • There are amazing coaches who can help you achieve your goals and support you along the way — but you have to do the work to find them.

A coach guides a client in the process of achieving a specific personal or professional goal by helping them bridge the gap between where they are now and where they want to be. A coach walks alongside you as you do the work and follow your journey, helping you avoid obstacles, stay on track, and keep moving forward.

What I learned from my poor experiences with coaching is that:

  • A coach isn’t going to make your problems disappear.
  • A coach isn’t going to magically make you a success.
  • A coach isn’t going to be your savior.
  • A coach isn’t going to do the work for you.

It’s not easy to admit, but when approaching those first two coaching relationships, I was looking for someone to help me find a shortcut and to avoid some of the hard work. I was enamored with the idea that they had already done the work and were willing to share that work — and I believed the promises of wild success because I wanted to believe it.

But that’s not how business coaching works.

You have to take responsibility for where you are at and where you want to go. You have to own your stuff and muck through it. You have to do the work, all the work.

When working with a coach, they are going to guide you, to operate as a sounding board, to ask the hard questions and offer a fresh perspective, to help you gain clarity, to motivate you to take action and keep going, and to hold you accountable. A coach isn’t going to clear the path of all obstacles and make it easy — in fact, parts of your journey may be harder with a coach because they aren’t going to let you get away with laziness, excuses, and self-sabotaging behavior.

The Problem With Business Coaching

The problem with the coaching industry is the same problem the graphic design, web design, and web development industries have. Just as anyone can call themselves a designer or developer, anyone can call themselves a coach, even without experience or receiving any professional training and certifications. This then leads to unqualified people offering coaching and creating less than stellar experiences.

There are four major issues you need to watch out for when hiring a business coach:

01. One Time Achievements

There are people that achieve something one time and immediately begin offering coaching to others who want to achieve the same thing.

Be careful of these single achievement coaches. Achieving something once doesn’t mean they can do it again, doesn’t mean it wasn’t a result of circumstance, timing, or luck, and doesn’t mean their system is proven or that what they did once will ever work again.

When evaluating a business coach, it is critical that you do your homework. For example, if you’re a freelance designer or freelance developer and you are considering hiring a coach, find out:

  • How many years did they freelance?
  • Are they still doing client work? Do they still have skin in the game?
  • Approximately how many clients have the worked with?
  • Have they had to fire a client?
  • What are they doing to continue to learn and stay on top of the industry?
  • What was their average net income while freelancing and how many hours a week did they work?

The last thing you want to do is unknowingly hire a coach who just achieved the thing they’re touting for the first time — six-figure income, booked out business, automated systems, agency expansion — and haven’t proven their approach over time.

02. Money Making Promises

Google the term “business coach” and you’ll find about 896,000,000 results. There is no shortage of coaches offering to help you build a successful agency, reach six figures and even seven figures, or grow a team. While some of these coaches are legitimate and more than qualified to share their expertise and guide others, many are not.

For example, claiming to have made six figures doesn’t make it true and doesn’t tell the whole story. A person can invoice $100K but only personally make $50K after expenses. Is that who you want to be learning from and guided by? Or would you rather learn from the person who invoices $250K, netted $100K, and only worked 30 hours a week?

When a coach is making claims about their income as part of their marketing and sales strategy, you need to ask questions to get the real story.

Ask questions like:

  • Have they themselves reached six figures? How many years in a row?
  • Did they hit six figures in gross (total sales) or net (after expenses) earnings?
  • If gross, what was their actual net income and profit?
  • If net, how many years have they netted six figures?
  • How many hours a week do they out in and how much vacation do they take?

03. Alignment Of Experience

If you’re looking to grow a successful agency, you need to look for a coach who has already grown a successful agency and has already walked the path you’re about to walk — someone who can come alongside you and point you in the right direction and help you navigate obstacles.

A coach may claim to have grown a successful agency, but did they just create their agency last year? Is it even the type of agency you’re thinking of. Have they built the same type of agency you want to build? In this case, you need to ask questions to gain clarity about their agency experience and business model to make sure they can provide the proper guidance.

Ask questions like:

  • How many full-time employees does your agency have?
  • How many regular subcontractors does your agency work with?
  • When did you hire your employees?
  • Have you had to fire employees?
  • Can you tell me about a recent challenge you faced with a subcontractor and how you handled it?
  • Did you have an office or was your team distributed?
  • What type of clients did your agency work with? What was your niche?
  • How many different clients and projects do you work with at one time?
  • What percentage of your business was recurring revenue?

04. Misguided Motivation

I talk to a lot of designers and developers who are burned out and over client work. They are looking for an escape — a way to no longer have to do client work — so they turn to coaching because they think it will be easier and they’re tired of sitting behind their computer doing the work.

The problem is that business coaching is so much more than that.

In a successful coaching relationship, the coach:

  • Preps in advance of calls and meetings
  • Follows up with you to provide accountability
  • Digs into your business and is invested in your success
  • Asks the hard questions
  • Provides avenues for fresh perspectives, critical thinking, and strategic evaluation
  • Offers guidance and recommendations

When considering a coach who currently does or used to do what you do now, you need to ask questions about:

  • Their process and how they work
  • How accountability works
  • How they learn about you and your business
  • How they prep for calls
  • What happens when a client is struggling or not meeting goals
  • What activities their clients do between calls/meetings to meet their goals?

Also, ask about why they are offering coaching and how long they have been coaching others and find out if they have a coach and/or mastermind group. You want to find someone who walks their talk and believes in coaching so much that they themselves invest in coaching.

And you want to find someone who isn’t just looking for an easy way out of client work… because coaching is client work. Critical client work.

Now let me be clear:

The goal of the questions, due diligence, and homework I’ve outlined is purely to achieve transparency up front so you know the full story and can feel confident in and great about investing with the right coach.

Just because someone is new to coaching or doesn’t have many years of experience as a coach, it doesn’t mean they aren’t going to be a smart choice. Likewise, just because someone offers coaching “on the side,” it doesn’t mean they aren’t qualified or serious. It may just be a sign that they are looking for another way to help others, have a desire to make a greater impact, or want to pay forward the good fortune they have personally experienced.

How To Choose The Right Business Coach

It’s impossible to choose the right business coach if first, you don’t gain clarity about exactly what problem you want to get out of the coaching relationship.

Again, if you’re looking for someone to step in and be your savior, make your problems disappear, magically make you a success, and do the work for you, you’re not going to be able to find the “right coach” and you’ll keep bouncing from coach to coach without ever achieving your goals.

You have to take responsibility for where you are at and where you want to go and you have to do the work, which starts with knowing:

  • Where you’re at now
  • What you want to achieve
  • Why you believe a coach will help you get there
  • What you want to achieve as a result of hiring the coach
  • What you think is holding you back

Knowing the answers to these questions will help you communicate with the coaches you’re interviewing, clearly share your expectations, and openly discuss if whether you are a good match.

Once you’re ready to find a business coach, use these 14 tips to find the best coach for you:

  1. Make sure there is chemistry. You need to feel comfortable talking about the uncomfortable stuff you wouldn’t share with anyone else, sharing your fears and concerns, and openly communicating your struggles.
  2. Confirm their expertise. Ask questions, comb through their website, google their name, and stalk them on social media. Confirm they walk their talk and their experience aligns with your business and goals.
  3. Talk to past clients. Don’t be afraid to ask for references and do your due diligence. A coach should be happy to provide references because you’re also demonstrating how seriously you take the relationship.
  4. You don’t need another friend. It’s okay to like your coach and even be friends with your coach, but when it comes time for your coaching session, they need to be able to dose out some tough love, call you out when needed, and tell you what you need to hear, not what you want to hear.
  5. Look for a coach interested in you and what you’re doing. While you can pay for advice and invest thousands on business coaching, you can’t buy interest. Ideally, you want to work with a coach who cares about you and what you want to achieve.
  6. Seek accountability. You want a coach who is going to listen and pay attention to your goals, what you say you are going to do, and hold you accountable, not someone who will show up to your call or meeting and ask you what you want to talk about.
  7. Look for someone who will share their failures. Failures provide the biggest opportunities for learning and growth and you want to work with a business coach who is willing to openly share their failures and what they learned.
  8. Find a complimentary skill set. If you have a weakness in a specific area, seek out a coach whose strengths are in that area so they can guide you through the challenges with experience.
  9. Secure support. When hiring a business coach, you want to find someone who is supportive, encouraging, and motivating — someone who brings out the best in you.
  10. Gain availability. Avoid a coach who is only available by scheduled appointments, is inflexible in their availability, or tries to force you into a cookie cutter program. There are going to be times you need advice and it won’t fit neatly in their perfect schedule.
  11. Look for a coach and a consultant. A coach is a guide who will help you get unstuck, stay on track, clear blocks, and achieve your goals. A consultant provides advice, solutions, recommendations, and gets in your business with you. If possible identify someone who is both coach and consultant, so they can not only shine a light on the path ahead but help you get to the end.
  12. Hire a teacher. Look for a business coach who loves to teach, share, and help others, and who demonstrates this in the way they do business and interact with others. Coaches who love teaching others will show up more powerfully for you.
  13. Seek a lifelong learner. No one knows everything, everyone can learn something, and you can always improve your skills. Hire a coach who is a lifelong learner and is continuously upleveling their own expertise because their experiences will also benefit you.
  14. Ask for a single session. This isn’t a free session, this is you hiring them for a single coaching session. Come to the session with a specific challenge you have and test the waters. This will give you an opportunity to sample their coaching style and see if it’s a fit you.

Business Coaching Works

While I’ve been burned by bad business coaching experiences, I have also worked with some incredible coaches who called me out when I made excuses, held me accountable when I set a goal, and walked alongside me when I need the support. I truly believe in the power of business coaching and transformation it can have on both the business and the business owner when there is an open, honest, authentic match between the coach and the client.

Just verify that before investing with any coach, you are ready to do the work needed to achieve your goals and you have done your homework to find the best coach qualified to help you.