6 Things You Should Know Before Hiring A Coach

Because when you hire the right one, your life will change forever

8 min readNov 15, 2020

In 2000 I was preparing to leave the Army after an eye condition I didn’t know I had ruled me ‘unserviceable’ for the military aviation career I’d dreamt of since I first heard an Iroquois helicopter aged 7. A strategy I employed to cope with the transition and to buy time to work out my Plan B was to attempt selection for the Australia age group triathlon team. I didn’t have an athletic pedigree. I had an entry-level bike, a history of swimming and an unimpressive track record, at 6'5″, of running.

I needed a coach. I joined a triathlon squad, and the obsession with training began. A year later, I move to a high-performance coach who ultimately helped me achieve my place on the national team. I found this coach through word of mouth. He had prepared and worked with multiple national athletes taking them to the highest echelons of the sport.

His athletes’ results spoke for themselves. If you tracked their progress over time, you could see how their swim, bike and run splits had improved. And at the end of the day, it was those results that mattered.

Fast forward to today. I’m a father, husband, educator, and I’m building my fifth company. I actively invest in learning. I leverage every leadership and fellowship lesson I learned in the Army. I also have experience as a serial entrepreneur, and mentors and mentees, which reinforce my rate of learning.

That might sound like a relatively complete approach to leadership and development, but midway through 2019, I had a realisation.

Almost 20 years ago, I paid a coach to help me achieve Australian team selection, a goal which upon setting seemed utterly unrealistic. My determination and work ethic alone wasn’t going to be enough. It was my coaches guidance and encouragement, and the fact I incentivised him to help me succeed, made the difference.

Today, I have a different goal. Starting with my family, I’m on a mission to positively impact the lives of 100M people through entrepreneurship, and personalised healthcare via my company Drop Bio.

That’s the ambition. And it wasn’t until 2019 that I asked myself why I didn’t have a coach.

The point of sharing this self-indulgent reflection as the context is that if you are serious about changing the status quo for yourself to make a dent in the universe, you need a coach. Alongside a strong work and learning ethic, they become your force multiplier.

If this is a revelation or you didn’t know there were coaches for non-athletic pursuits, here are the six lessons I’ve learned thanks to being very close to two of the coaching world’s best-kept secrets.

I’ll introduce you to Melissa and Andy shortly, and if by the end of the blog post you think it worthwhile to learn more about coaches, I do hope you reach out to both of them.

1. Great coaches do three things well

First, they help clarify your purpose and what drives you. That can sound trite because of the noise that often surrounds the role of purpose, how to define it and how it’s measured. The truth is that there’s a lot rolled up into one’s purpose and it can only be understood over time and by being asked the right questions.

The second thing that great coaches do well is they hold a mirror up to the people they work with to show them their reality and potential, to congratulate them, keep them accountable and to call bullshit when needed. And the quality of the reflection is directly proportionate to the quality of questions they ask. The better the question, the clearer the reflection and that matters because the most significant payoff of clearly seeing yourself in this mirror is improved self-awareness, an essential ingredient to success.

Finally, great coaches are relentless in their pursuit of knowledge to support your success. Instead of relying on one framework to regurgitate to new clients, they are on a journey of continuous improvement, the byproduct of which is fresh insights that broaden your perspective and continually reinforce your interest in self-improvement.

2. Coaching isn’t mentoring

Before going any further, it’s important to know what coaching isn’t, and it isn’t mentoring.

While coaching and mentoring share a common basis of trust and interest in each other’s journey, mentoring, at least in my view, is a more episodic and tactical approach to problem-solving. Coaching, on the other hand, dives significantly deeper to understand purpose before walking, somewhat intimately, side by side through periods of discovery, acceleration and consolidation.

3. 50% of coaches are below average (and then some)

Unlike in sport, where results of coaches and athletes speak for themselves, the credentials of executive, performance and (my favourite) business coaches are far more challenging to determine.

After all, anyone can slap the title of ‘coach’ next to their name and market themselves as someone who can elevate you to new levels.

In my experience, executive, performance and business coaches occupy an industry which is, for the most part, broad but (generally) shallow. Broad given the volume and diverse backgrounds of people attracted to coaching.

And shallow in terms of capability.

With a low barrier to entry, it’s relatively straight forward to only sell experience or sell a particular framework in the hope that it will apply to large groups of customers.

That might work for general self-help.

Coaching isn’t self-help.

I’m sure some will find that controversial, but as I mentioned above, great coaches do three things well. Selling a general approach to self-improvement isn’t one of them.

But the good news is there are exceptional coaches out there, and you’re about to meet two of them.

4. A coach is an investment

That investment, starting from $500 to $1000 per month, can seem out of reach or an unreasonable investment when cash is tight.

But here’s how to reframe that thinking. For the sake of this argument, let’s assume a monthly coaching fee of $1,000, although it could be higher or lower. Could you reasonably expect to make better decisions that yield you savings of $12,000, avoid costly mistakes costing over $12,000 or earn an additional $12,000 in a year?

Invariably, the answer is yes.

I happily pay slightly more than that each month out of my pocket (it’s also a tax deduction given my particular circumstance) but my company could also make this investment. Many companies do because they benefit from the higher quality decision making of their leaders.

If you’re a leader in a large organisation, ask about coaching budgets. If you’re a founder in a funded venture, talk to your board about this opportunity.

The caution here, as is often the case, is you get what you pay for and the trick is to zoom out. A great coach will help improve the way you think by living your purpose. You’ll be on track to great happiness, clearer perspective and if my experience is anything to go by, well ahead financially.

5. Finding the right coach is essential

Like any high-quality product, great coaches are in high demand. Most carefully guard their time by not only having initial conversations to determine ‘fit’, but they also have a cancel anytime policy.

This valuing of time and fit is a positive lead indicator of their approach to creating value for their clients and themselves.

If a fit can be determined over say the first three months of the relationship, good things are likely to happen. If for whatever reason, there isn’t a fit, then the client can walk away, and the coach can open that spot to another potential client. This approach is exactly what I suggest in my paid audition playbook called Higher Help ( free download here).

When I was looking for a coach, I kept an eye out for fixed-term arrangements. Some coaching programs were sold suggesting ‘the process takes time’, and I’m sure it does. But rightly or wrongly, the suggestion of a fixed-term arrangement made me feel as though the coach was putting their business model ahead of my needs. I avoided those options as a result.

For the sake of clarity, it’s important to note that coaches do have different operating models. Some support individuals, while others support large organisations or both. Fixed-term arrangements do have a role when large organisations engage coaches to support an enterprise-wide leadership development program.

6. You need to come to terms with confronting yourself

A coach can hold a mirror up to you, but it’s of little use if you can’t or don’t want to hear what the reflection has to say.

When I was searching for my coach, I thought this could be an issue for me. To mitigate that risk, I thought carefully about what non-negotiable characteristics my future coach would need to possess to lower that chance of me discounting their perspectives.

I encourage you to do the same and to start the ball rolling here are the characteristics he or she needed to possess:

Had to be new to me to avoid any pre-existing bias
Had to have built companies to relate to the turbulence and opportunity of entrepreneurship
Had to operate at the top of a profession
Had to have a great sense of humour
Had to be on a learning journey

With those six lessons in mind, let me introduce you to two top tier coaches.

Introducing Melissa and Andy

It’s a pleasure to introduce you to Melissa Rosenthal, and Andy Williams, two of the coaching world’s best kept secrets.

Melissa and I have known each other for nearly 20 years, and in my opinion, she is the best question-asker in the business. She supports senior executive leaders across several industries and perhaps most impressive is her speciality in helping high growth ventures manage the growing pains of scaling talent, culture and capability.

Take a look at Melissa’s work here.

Andy Williams is my coach. One of the youngest to ever pass selection and operate at the Australian Special Air Service Regiment, he also cycled at a professional level in Europe before he became a coach.

His deep interest in unlocking performance using a combination of science and philosophy, not to mention a good sense of humour, has been a powerful asset to me.

Take a look at Andy’s work here.

One last thing…

There is no such thing as the perfect leader or CEO. It is a lonely role that comes with a daily expectation of acting unaffected by the continuous barrage of firefighting, decision making and opportunity assessment.

A great coach can help you understand you, introduce perspective and unlock enormous stores of potential. You may need to kick the tires of some coaches to find the right one, but if there is one piece of advice I would give my 30-year-old self, it’s this: Get a great coach.

Originally published at https://philhsc.com on November 15, 2020.