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Kerwin Rae: “The challenge of maintaining calm and assertive leadership that demonstrates trust”

The challenge of maintaining calm and assertive leadership that demonstrates trust — This is one of the biggest challenges I see for business owners when it comes to a remote working environment. Right now, your success in business relies on how well your team can trust you and that comes down to leadership. Because here’s the thing, […]

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The challenge of maintaining calm and assertive leadership that demonstrates trust — This is one of the biggest challenges I see for business owners when it comes to a remote working environment. Right now, your success in business relies on how well your team can trust you and that comes down to leadership. Because here’s the thing, anyone can be a leader when times are good and things are going well. But when shit hits the fan like it has done now with Covid 19, and things are changing enormously from one moment to the next, what does your leadership look like?


As a part of our series about the five things you need to successfully manage a remote team, I had the pleasure of interviewing Kerwin Rae a businessman, entrepreneur, investor and international speaker. As one of the Australia’s leading business strategists helping business owners succeed for over a decade, he has consulted in 11 countries and over 154 different industries and taught over 100,000 people the world over through his seminars and workshops. To date, Kerwin has helped his clients make well in excess of hundreds of millions of dollars.

Kerwin has addressed and worked with all levels of business, specializing in small to medium businesses, and national and international franchise groups. He has also coached thousands of consultants and coaches in numerous countries on business development, marketing, sales, human behavior, and entrepreneurial psychology.


Thank you so much for doing this with us! Before we dig in, our readers would love to get to know you a bit better. What is your “backstory”?

I was diagnosed with dyslexia and ADHD as a kid and as a result of that I had people telling me I was stupid for a long time.

When you grow up hearing those stories on repeat, you tend to believe them.

I failed nearly every class in school and didn’t read a full book cover to cover until I was 23.

It wasn’t until I figured out my purpose and passion of helping people, and helping business owners succeed, through a series of building and growing my own successful businesses, that I realized, hang on, I’m not stupid at all.

In fact, I quickly learnt that once I set my mind on something, I stop at nothing to achieve it and actually have insane levels of discipline and motivation.

I’ve dedicated my life to business growth and high performance. I love helping others tap into their superhuman potential and stretch past their limits.

Can you share the most interesting story that happened to you since you started your career?

How much time do you have? It’s hard to pin-point a single event, but one story in particular that really changed the trajectory of my life and business was the time the one-and-only Gary Vaynerchuck absolutely tore my social media strategy to shreds.

It was 2015 and we had Gary come and speak at an event we were running in Las Vegas. At the time, we were using social media ok but we were getting a decline in our rate of return and our cost per conversions were going way up.

Gary after the show, took one look at my strategy and basically told me it sucked and I was like, “Yes, thank you, I need this, don’t hold back”.

After that, I turned things around, hired a full time filmmaker, started producing content like crazy and now we have reached in excess of 450 million people through social media and our business has transformed in more ways than I could have imagined.

It is insane to think of the ripple effect one person can make in your pond and how far that ripple can extend out into the universe — it has impacted the lives of so many people and I’m eternally grateful for that.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I am a huge fan of mistakes because I believe they are the key to success. I have this saying that failure, by design, is there to give you the lessons that you need to get to the next level.

Earlier on in my career I learnt a big lesson about money. My first year in business, I made 780,000 dollars and I spent 1.2 million dollars on my Amex — yikes! I was so frivolous with custom suits, sports cars and a beachfront house.

That was not the first time I had lost it all but it was a time that really taught me the value of money and the power it has to make a difference in the world — when it isn’t wasted. I don’t think there is anything wrong with making money as there is no amount of poverty you can acquire that can change the world, but now I invest it where it matters and live a modest life where I practically dress like a bum.

What advice would you give to other CEOs or founders to help their employees to thrive and avoid burnout?

I always say that if you want to consistently perform at the highest level you have to invest in becoming your highest self and that means seriously looking after your body with good nutrition, sleep, meditation, breathing, water and health.

I also live by intermittent fasting and have untapped levels of energy because of it.

Not only that, but look at the stories you are telling yourself. Do you have, “I’m so tired, I can’t do this” playing on loop in your mind or are you saying things like, “This is easy, I have so much energy, I can do it”?

Some other quick tips are to avoid multitasking and focus on one thing at a time and a little something called the 90/10 rule.

This is where you work in intervals of 90 minutes with no breaks or distractions and you do what needs to be done, then you take a 10 minute break to refresh and rest. That is a game changer for avoiding burnout and I’d advise any CEOs to teach their employees to work in this way.

Ok, let’s jump to the core of our interview. Some companies have many years of experience with managing a remote team. Others have just started this, due to the COVID-19 pandemic. Can you tell us how many years of experience you have managing remote teams?

Over my 20 plus years in business I’ve had periods on and off working with different people remotely but mainly for the last five or so years our team have all worked together in one office. There have been exceptions during this time and we have some incredible talent work remote for us outside of the COVID 19 pandemic, but our focus has been on scaling the team in house.

In my experience, what makes a good remote team is what makes a good in-house team. It comes down to having the right talent.

Your team could make or lose you millions of dollars, so when it comes to hiring, it’s important to get it right. But in order to get it right you have to know the difference between staff and talent.

Staff tick the box. They do what they have to do in order to get paid and that’s as far as it goes.

Talent are people who are passionate about their role and their ability to help drive the business forward.

Everyone has the potential to become talent, but not everyone wants to become talent.

Managing a team remotely can be very different than managing a team that is in front of you. Can you articulate for our readers what the five main challenges are regarding managing a remote team? Can you give a story or example for each?

(Five main challenges & how we can address them, answered all in one below)

The challenge of maintaining calm and assertive leadership that demonstrates trust

This is one of the biggest challenges I see for business owners when it comes to a remote working environment.

Right now, your success in business relies on how well your team can trust you and that comes down to leadership.

Because here’s the thing, anyone can be a leader when times are good and things are going well. But when shit hits the fan like it has done now with Covid 19, and things are changing enormously from one moment to the next, what does your leadership look like?

The reality is, your team need you more than ever right now. They need strong and assertive leadership that demonstrates trust at the highest level.

In uncertain times, you need to demonstrate certainty.

So how do we do that in a remote environment?

A couple of things.

To me, leadership isn’t about telling people what to do. To me, the most important part of leadership, especially at a time like this is offering people a vision, a direction or a purpose that they can believe in. One that gives them hope.

It means getting clear on your company purpose — which is why you exist.

Next you have to be clear on your mission — which is despite all the distractions and noise, what is your company trying to achieve in the next 10 years.

Now, when you combine these two things together, what do you have? You have a vision of the world that is different from how it is currently right now.

To me, a great leader is someone who is very clear on their vision and they’re able to communicate it in a way that is inspiring and empowering to those within their team that creates an upbeat level of performance.

Especially during tough and uncertain times.

That’s f**king leadership. And that’s what creates a level of trust that will see your team stick with you and feel safe and supported while transitioning into this new remote landscape.

The challenge of maintaining the culture

So much of the success we have in our business rides off our strong team culture. And for us that team culture has been built on proximity.

A culture that has been built with a friction of bodies in the same place, and by friction I’m not talking about negativity, I’m talking about the energy that’s created when people come together.

This generates the vibes, the essence and the feeling of the company. It creates a space where people feel part of something special and bigger than themselves. A real purpose and a real mission.

This friction has literally been created from a lot of contact hours together. Keeping the bulk of our team together has worked well for us in the past, so like many other businesses we have been faced with the question of how do we maintain our culture?

So for us, we’ve had to adapt by simulating our social settings in a way where people can connect online.

We have really replicated everything we would usually do in our Sydney office — be it family lunches, team planning, personal training sessions, birthday acknowledgements…and we have made a real point of still doing all of that stuff that the team love online — over Zoom to keep up that connection and maintain the culture that we have worked so hard to build.

And it’s been great to see team members stepping up and organising things like trivia nights and digital dance parties so to be honest by nature of putting such a strong emphasis on our culture, as a result we’ve probably strengthened it in this remote environment.

I recommend all businesses find ways to adapt like we have to keep that proximity and that connection strong.

The challenge of measuring performance

Look, working remote is not for everyone. We have had team members who are very autonomous and in most cases, work harder and produce more results than they would in the office because they have no distractions and are just head down ass up the whole time.

On the other hand I have had people and different teams work remote where it really hasn’t worked for a number of reasons. What I will say though is that it comes down to performance each and every time.

So you as a business owner have to have a framework in place to measure that performance to see whether or not remote working is right for that individual. And this is where it is your job as a leader to set the level and the standard of what is expected from each individual in this environment.

Because as all of my team now know, and as all of your team should know, if they don’t perform then no one is going to have a business. We are not operating is calm seas right now. We’re in a f**king storm. And it’s not going to be over anytime soon.

So everyone of my team know, their job, my job, and the community is dependent on every single one of us performing to the highest level.

And as a result of this, I would expect a level of inspiration and motivation, based on the desire to actually have a job when a lot of people aren’t going to have a job.

The fact that everyone is not going to come out the other side of this pandemic with a job is probably going to inspire and motivate people to perform at a whole new level — because if they don’t there won’t be a business to work for.

Now what performance in this landscape looks like will vary from business to business — your job is to get clear on what that looks like for you and then communicate it to your team so everyone is across what the standard is from a remote perspective.

If you’re concerned about monitoring your teams progress and results, then it might be a good idea to do what I do — start every day with a video call where your team outline what they’re going to do that day, then wrap it up with a video call at the end of the day and report how you did.

Be sure to look at the wins and the bottlenecks around where team members might need additional support.

The challenge of efficient communication

For me personally, I like being in the same room as people around me and a big reason for that is because it increases the speed of communication. There’s no disconnect. There’s no, “Oh I’ll pick up and ring — oh they didn’t answer the phone, now I gotta call them back”.

If you don’t have efficient communication pathways mapped out it has the potential to really slow things down.

Because if you don’t, the challenge with a remote working environment is that there will be an interruption to the flow and speed of communication.

It’s critical that a business develops ways and means of managing the technology and the hardware around this and that there are rituals and disciplines required to do that.

For example, you’re obviously going to need to make sure everyone has a good internet connection, a computer to work from, and webcams/phones to conference call on.

Communication up and down the line is key to avoiding bottlenecks and keeping the workflow running smoothly, so daily video calls and some sort of messenger tools like Flock or Slack can help ensure everyone is on the same page.

The challenge around setting up for remote

Look, I touched on this around the communication piece but it’s worth diving into further.

You have got to get the foundation right when it comes to remote working and that starts by not assuming that everyone is going to be automatically setup to work remote. Some team members might need support here.

You have to ask the question, ‘Does my team have the right equipment to be able to work from home?’

Things like internet access, a desk, an environment that’s safe and where they can focus. Ensuring they have a laptop or computer and a phone etc…

What are the main systems they will need to use? Will they be able to access all of the information they need in order to be able to perform at the highest level? Do you need to provide them with software?

It’s really important not to assume that everyone is in the same position when it comes to being able to work in a remote environment and for some team members that means providing additional support in order to get the job done.

In my experience, one of the trickiest parts of managing a remote team is giving honest feedback, in a way that doesn’t come across as too harsh. If someone is in front of you much of the nuance can be picked up in facial expressions and body language. But not when someone is remote. Can you give a few suggestions about how to best give constructive criticism to a remote employee?

Being in business for any period of time is going to require you to have difficult conversations, and look that’s even more important in a remote situation given the high levels of communication that are required in order to make this environment work.

For me, whether it’s a tough conversation or if I’m giving constructive feedback either remote or in person, it’s really simple… you have to check your ego at the door. Intent counts more than technique.

So when it comes to having a challenging conversation, leave all of the emotion out of it and come in with the intent to heal the situation or add value, or come from a place of support to the team member.

Your intention should always be to improve the situation.

Can you share any suggestions for teams who are used to working together in one location, and now forced to work remotely?

Usually the biggest issue around working remote is communication, which in most cases is resolved by creating more touch points. For example, our team huddles have never been more important.

We now have a leadership huddle, with the entire leadership team, three times a week at 9:00am just to ensure that we’re creating as many touch points as we possibly can, so that nothing’s missed, there’s no misinformation or more importantly, miscommunication.

If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

That’d be a movement of consciousness. And I don’t mean that necessarily in a spiritual context, although it has spiritual parameters.

Consciousness breeds responsibility, and unconsciousness breeds blame and ignorance.

When people blame due to their own ignorance of the role that they play, they become a victim and they lose all their power.

Whereas when we start to become more conscious, and we see our role in everything, we can recognize that we are the common denominator in our problems. It’s our thoughts that are shaping our reality.

By becoming conscious we can take full responsibility of our lives and ultimately take our power back.

What is your favourite life lesson /quote, and how it’s relevant in your life, or an experience you’ve had?

Life is painful, suffering is optional. There’s always going to be pain present, in every situation. There’s always going to be some level of resistance. There’s always going to be some level of tension. But it’s how we perceive that pain that will determine if we are suffering.

For instance, there’s a difference in noticing you have a sore back and saying, “My back is sore” and getting on with it, compared to every five minutes going, “My back hurts. Oh my God, my back hurts. Do you know how bad my back hurts? My back hurts so much worse than what yours does”.

And when that becomes a talk track that we repeat on a regular basis, we enter into suffering. That talk track can be applied to your relationship. That talk track can be applied to your business. That talk track can be applied to your health. If you see your circumstances as constantly reminding yourself of how bad that situation is, you’re going to experience a very high level of suffering.

But if you can acknowledge the situation for what it is, which is, it’s perfect, but it feels imbalanced then all you need to do is resolve that balance by finding out, or resolving that pain.

Now, for me, that looks like — “I’m in pain right now, but what’s the benefit of this? How is this serving me? What skills, knowledge, and experience am I gaining from this pain that’s going to make me better?”

And that pain can be resolved, and in many cases, transmuted into forms of appreciation and gratitude.

Any form of pain is just unrealized potential. It’s something within the body that’s communicating that there is more.

If you’re in pain in your relationship, that means there’s more potential there. You just haven’t found it.

Whether it’s pain in business or in your personal life find out what the solution is to that pain, and that pain will, in itself, resolve from suffering, into transcendent potential.

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