Part of The Holistic Musician Academy
Dec. 22, 2022

The Dark Side of Digital Coaching: 5 Red Flags

The Dark Side of Digital Coaching: 5 Red Flags

From European Llamas that preach Buddha was a blue-eyed white man to hipstery millionaires who’ve asked me to burn money as part of an ‘abundance’ exercise, I’ve been through some interesting experiences in the name of ‘teaching’, to say the least.

And with the advent of online commerce and education morphing into a mainstream format, the spilling over of questionable mentorship practices is only a natural bi-product.

Before we go blame the format though, it helps to understand how easily the medium can be used as a scapegoat for poor teaching practices. When in reality, the source of the issue lies where it always has.

Poor teaching.

That being said, some of the methods we’ve grown used to relying upon to choosing teachers, coaches, and mentors can feel absent when we’re trusting a floating head on a screen with vulnerable information and your hard-earned money.

Here are a few pointers to spot red-flags and find the right mentor for your needs:

1. Discovery

How did you find your coach? (Or vice versa)?

Ideally, through personal correspondence, word-of-mouth, or during an online search like ''How to play kazoo backwards on a unicyle''.

And hopefully, they’ll have enough online presence to give you a fair idea of what you're signing up for.

But if you found them through an ad that popped up on your feed, then chances are that’s a cookie being fed into an algorithm, and qualifying you as a ‘lead’ (potential consumer) for the ‘product’ (in this case, an online course or coaching services).

To be clear, this is not a red flag in itself. As a solo artist-preneur, I can confirm that it can be standard practice many of us use to scale the reach of our audiences. Nothing wrong with that.

It get’s tricky though, when the product being offered is being marketed so expertly, that it ends up promising more than it delivers.

That really sucks! I speak from experience here.

To make matters more complicated, some of the best artists and teachers don’t really have great marketing skills and do a crap job of making their value apparent. So unless they’re an exception or have outsourced this part of the process, chances are your first point of contact is not the coach themselves, but a marketing professional.

(Again not a bad thing, but the takeaway here is don’t let the packaging make the decision for you).

So what do you do?

A little research. On your coach.

Don't worry, you don't have to hire a private eye for this. Some easy steps are:

1. Digging into Podcasts/Tutorials where you can hear them engage, speak and perform as they would with you in a class or a session.

2. In the case of musicians/artists, taking a listen to their music and collabs. You don’t have to love the genre or everything they do. But do they seem honest? Authentic?

2. Their ‘Why’

Believe it or not, online education has been around for way longer than most of us realize.

My teachers Kai Eckhardt and Phil Maturano have been doing it for over a decade.

And one of my business mentors, Sean Ogle, even longer. Among more recent folks, check out my friend Noah Kellman (who'll be on our podcast next season as well). And ueberguru Kenny Werner  has been doing online classes (many of them for free) since the pandemic.

Point being: there are LEGIT folks out there. 

The difference since the Pandemic though, is that a lot of people who were too lazy to change their ways earlier were forced to look at alternative methodologies to go about their 'business'. 

Not a bad thing per se. Personally, I think it’s even kinda cool.

Here’s the thing though. Now, everybody and their dog is an ‘online entrepreneur’.

Again, not a bad thing, people should do what they want.

But what it has resulted in for the education sector, is the unleashing of overwhelming quantities of redundant information following near-identical marketing strategies that want to shove a can of FOMO down your throat so you’ll go buy their course.

The collateral damage? Legit educators out to make a difference. And your growth.

But there’s a litmus test. Something that distinguishes the legit educators from the Charlatans very easily.

Their ‘why’!

* Why is that person on your screen talking to you?

* Asking you to buy their course or get on a 1:1 session?

* Or enrol in their membership?

Spoiler alert - there are broadly only two options here:

A: They realized they can make money off you.

B: They are passionate about teaching. And WANT to help you. Cos your success is in alignment with their idea of their own fulfilment.

Now if you're anything like me you're wondering, ‘wow, how many of these peeps would genuinely consider my success their own’😳?

Chances are your answer would be ‘ hmm…probably not that many🤔 .

And the sad truth is that you might be onto something there 😔.

4. Payment Policies:

The best online coaches I’ve worked with (Graham Cochrane is a fantastic example), will usually:

1. Offer some refund policy (with exceptions - you can’t refund 1:1 sessions endlessly).

2. Make an effort to understand your goals.

3. Make sure the two of you are the right fit before asking for money.

4. Discourage you to join if they feel the two of you are not.

5. Suggest someone who might be able to help you.

The offers to scrutinize carefully are those that use clickbait like ‘anybody can do this’ as their headliner.

Nobody is an ‘anybody’. And you should definitely be neither!

Others to avoid are those who’ll flood your inbox with meaningless sales pitches sans any meaningful content or attempts to build a relationship.

Takeaway: While not always a rule-of-thumb, every clients needs are unique. And cookie-cutter solutions are rarely a good investment.

5. They make it about themselves:

While accolades and achievements are not worthless, coaches who open with their own instead of asking about your goals first are a no-no.

Especially if it’s a pattern.

Mind you, not all coaches (including the good ones) are perfect. And striking a balance between establishing credibility and serving is not always easy.

But the fundamental idea here is that YOU are the hero of this story. YOU are the one whose growth is the center of attention.

So if your mentor keeps banging on about themselves for the hours you’re paying them for, best get the F out of there.

5. Won’t walk the talk

You’d think this was a no-brainer but you’d be surprised at how often students or clients fail to notice the inherent contradiction between what their teachers preach and practice.

To be fair, depending on what area of specialization we’re talking about, this can be an infinitely complex theme, and context is of utmost importance.

But if your coach is blatantly in breach of his own policies like not showing up on time frequently, being judgemental while telling you not to, being permanently out of shape while teaching fitness, or being culturally insensitive while teaching equity, you wanna be careful continuing an alliance with them.


The Online-Education ‘industry’ is set to be a billion-dollar one over the next few years.

Ironically, qualified, passionate educators who’ve been making a difference in people’s lives for years the way online gurus keep promising to on Instagram, are some of the last people to know about this development. Let alone fathom its implications.

Which means most of the people on your feed? They're mostly just folks who have their marketing game together. A lot of them don't even bring ANY real-life experience to the table. 

And that’s really all there is to it.

That doesn't necessarily mean they're all crap teachers either. But what it does mean is that you have to get to know them first before you invest.

The good news? There are many out there (yours truly included) who have been doing this for a while now.

For whom teaching online was never a quick fix-scheme, but an outlet to GIVE to society.

On our own terms without academic jargon or outdated methodologies getting in the way (FYI I just finished getting myself a Masters Degree in from The London College of Music, so I'm intimately familiar with the challenges that come with that as well).

It’s one of the most exciting times to get educated. And to educate. And as is often the case during era’s of great beginnings, there’s also a lot of S*** stuck to the ceiling. Try and choose a mentor who owns their share of the same, and helps you identify yours.