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If you want better results, have better conversations

Recently, I was wrapping up a Zoom call with a business owner when he asked me for some advice about a next-day sales team meeting.

He said he was looking for a way to jazz things up a little at the top of the meeting, to get his team’s brains warmed up and moving. I told him to grab a pen and I started firing off some of my favourite exercises and questions (which, as a reminder, you can find in Chapter 5 of this book!)

As I watched him frantically scribble on the other end of the call, however, I paused.

“What time is your meeting tomorrow?” I asked, to which he replied, “9:30.”

I said, “Okay, I have a client at 10, but do you want me to join the Zoom for the first 15 minutes and run through these questions I just gave you?”

He sighed a big sigh of relief, and said: “That would be awesome.”

So, that’s what I did. The next day at 9:30, I showed up to their virtual sales meeting. To kick things off – and by way of an introduction – I said the following: “I don’t know anything about your industry, but I’ve worked with sales teams for 20 years, and those who play at the highest level leave clues.”

I continued: “One of the things they do best is they are deeply focused on their weekly work. To help them achieve that focus, they answer very similar questions every single week.”

At this, I got everyone to take out a pen and paper. I explained that I would ask them a series of questions, and give them one minute to answer each one.

“Some will be questions you’ve never thought about before”, I added, “but try not to overthink it.”

“What does winning look like in the next three days?” I asked.

“How do you need to act differently to achieve those results?” I asked.

“What do you need to stop doing? What do you need to start doing?” I asked.

And so on and so forth.

When the 15 minutes were up and the pens stopped moving, I prepared to take my leave.

“Great, you’ve got all your answers,” I said. “I’m done for today, but you aren’t. Your next mission is to have a conversation with everybody in this room, including your head honcho (my client), and you’re going to take up each question.”

Then I logged off.

About three hours later, I got a call from my client. He told me it was their best meeting ever. When I asked why, he said the focus, sharing, and conversation were off the charts. He asked if I would be willing to come in and do these kinds of “meeting boosters” more often.

Before that day, I didn’t have a name for this service. It wasn’t even on my menu of services. It was born out of a need, which came out of a conversation, and an openness to respond to the need that was expressed during that conversation.

It’s been several months since I started offering these “meeting boosters”, and the changes in my client’s team – their outlook, their energy, and yes, their sales – have been phenomenal.

None of this would have been possible without the conversation that started it all, and the many extraordinary conversations that followed.

So, what conversation do you need to be having?

The one thing that will set you apart from the crowd

Between social media, emails, texts, and Zoom meetings, we have never been more connected than we are today.

By that same token, we have never been more distracted.

In the battle for focus, many of us are losing – and it’s no wonder. The smartest minds in Silicon Valley are, in fact, being paid big bucks to grab our attention however they can – and to keep it.

The growing body of research on focus reflects this losing battle. Studies show that most people find it challenging to focus for more than five minutes. And yet most of us would agree that we do our best and deepest work when we’re in a highly focused state.

So, let me ask you this: when was the last time you were in a highly focused state, free of distraction?

In the aftermath of ‘Slap-Gate’ at the 2022 Oscars ceremony – the details of which I’m sure I don’t need to rehash here – I read on the news that Chris Rock banned cellphones at his comedy shows. Those in attendance had to either leave their phones at home or submit them to a ‘coat check’ for devices before settling in for the 90-minute show.

Upon reading this, I couldn’t help but wonder: for how many people was this the first time they had ever been away from their phone for so long? How many of them were nervously laughing as they handed their phones over to coat-check, only to spend the next 90 minutes fidgeting and reaching for their phantom devices?

For many of us, the idea of being away from our phones for any period of time is enough to make us squirm. And yet, as Cal Newport talks about in his book, ‘Deep Work’, the key to profound productivity is in fact carving out that time for distraction-free work – and committing to it again and again.

Let me be clear: I’m not talking about hours of phone-free time every day here. Start with 30 minutes, and see where that gets you.

If you want to play at a whole different level, you need to be really intentional about your daily focused time. For me and my all-star clients, building this habit has been absolutely essential.

There are two keys to making this work:

Key No. 1 is putting it in your calendar at the same time every day. Scrambling to find the time each day, within an already packed schedule, simply doesn’t work.

Key No. 2 is letting everyone else in your life know that you’re embarking on this new daily mission – or at least, those you regularly interact with on a day-to-day basis. That’s because you’re not only changing your own behaviour; you’re changing the behaviour of everyone around you. During that precious half-hour, you should be virtually unreachable.

At first, mind you, this new habit will feel extremely weird. There’s no getting around that. In this day and age, we’re not used to being without our extra limb. But stick with it, and I promise the results will be life-changing.

We are the company we keep

In my previous life as a traveling keynote speaker and corporate trainer, I got to meet a lot of interesting people. Often, I would find myself going out to dinner with the people who hired me, along with their top sales teams. It always provided a nice opportunity to speak a little more candidly with the people I’d been working with.

Usually, about halfway through dinner, I’d ask something along the lines of: “So, how are things really going?” That’s when the real stories would come out – the stuff they felt they couldn’t really talk to anybody else about.

Time and time again, I would hear some variation of the same thing: at this stage in their careers, and in their lives, they felt they should have more. They had the house, they had the car, they had the vacations. And yet, that little voice in their heads was always telling them it wasn’t enough; that they weren’t enough.

They were constantly beating themselves up, and they didn’t feel they had anyone to talk to about it. Worse still, some of them felt bad for even wanting to talk about it. They had the attitude that “this is just how it is when you’re at the top of the mountain” and that was that.

I couldn’t help thinking there had to be a better way. I’d tell them that I worked with a lot of business leaders in a lot of different industries, and what they were describing was very common. And without fail, after these dinners, I would go back to my hotel room and think, “How can we better serve these business leaders, so they know they’re not alone?”

It took me a long time to come up with an answer. However, I strongly believe that when you keep asking questions, it leads you to the answers. And I was right.

The idea came to me in a business meeting in Toronto, as I was listening to a fellow coach talk about a mastermind group they were running. Now, a mastermind group isn’t a new idea. It was coined by Napoleon Hill in his book, The Law of Success, in 1925. The basic idea is a peer-to-peer mentoring group in which members help each other with their problems.

So, it wasn’t like I was hearing about this idea for the first time. It just so happened to be the exact right time I needed to hear it. My ears heard “mastermind group” and my brain whispered: “what if I put them all in the same room?”

As soon as I got home that day, I sat at my desk and wrote down all the names of the people I’d want to invite to this very special meeting of the minds. I came up with 14 names.

Next, of course, I had to think of a venue. At the time, I was doing a lot of work for LinkedIn in Toronto and New York. I texted a friend of mine at the Toronto headquarters – one of those super-sexy offices of the future with people going around on scooters and hitting up the staff room pool table on their lunch hours – and asked if they’d be willing to host us. He said sure.

And so, within a matter of minutes, I had the idea, the people, and the venue. Now all I had to do was get the word out – and explain what exactly I had in mind, which turned out to be a slightly taller order than anticipated.

My prospective guests were all from vastly different industries. The only things they had in common were:

  1. I thought they were ridiculously smart – and ridiculously cool
  2. Every single one of them had expressed a need, either directly or indirectly, for some kind of community

As I went around and made my pitch – a three-hour group coaching experience at the LinkedIn office in Toronto – I got asked the same question by pretty much everyone I approached: “Who else is going to be there?”

They weren’t asking this question for social climbing purposes. They were asking it because that little voice in their heads was telling them they didn’t belong. I know this because I asked, and time and time again, they responded with some variation of the same answer: “what if I’m not at everyone else’s level?”

I did my best to assuage their concerns. In the end, 13 out of 14 agreed to come.

The night before the big event, I hardly slept. I was trying something for the very first time. I knew all these people individually, of course, but now I was putting them into the same room – and they were all feeling varying degrees of imposter syndrome. What if it didn’t work?

The next day, as I looked out at the nervous sea of faces in front of me, I remembered that honesty is always the best policy – and went with it.

“Welcome, and thank you so much for being here and for trusting me to host this event,” I said. “I want to start by saying that most of you reached out to me ahead of today and said you were nervous because you thought you’d be hitting out of your weight class. I’ll say again what I probably said to you then: ‘Fuck you – what about me?! I have to lead this whole group!’”

Everyone threw back their heads and laughed. In that moment, the anxious energy in the room was disarmed.

It was the perfect foundation from which to kick off some introductions. I asked everyone to tell the group a little bit about themselves – and then to state how they knew me. As we went around the room, and everyone told stories about our respective relationships, the atmosphere got more and more relaxed. Within an hour and a half, everyone was sharing things they didn’t share with anybody else.

I sat there, dazzled and delighted by how quickly this group of people – who had been total strangers before today – came together. As they each shared their stories and their struggles, they learned that they weren’t, in fact, alone. The transformation in their faces, and in their body language, was incredible. Simply put, they were in a room with people who got it.

Of course, the real test came at the end of the session. We had arranged to have snacks and cocktails at the restaurant downstairs for anyone who wanted to continue the connections. To my amazement, everyone showed up, and the party went on into the night.

For the next three months, I continued working with this same group. I’ll never forget this one moment with a friend of mine, who works for a big ad agency. Her name is Stephanie, and she just so happened to be the youngest person in the group by far. During one of our sessions, after listening to everyone else share what they were going through, Stephanie stood up and said: “It’s intimidating being the youngest person in the room. But – and I say this with love – it’s also extremely liberating knowing that you guys don’t have your shit together, either.”

The room erupted with laughter.

The truth is that so many of us have that little voice in our heads, the one that insists on telling us we aren’t enough in one way or another. The only way to address that little voice – or at least, the only way I’ve found that works – is by having real, honest conversations. In finding and fostering community, we learn how to start embracing all the parts of ourselves – including the parts we usually try so hard to hide.

Takeaway Tip:

Do you have a group of people you can have open, honest conversations with on a regular basis? If not, consider exploring some different coaching programs. There are so many out there – from my monthly membership program, which brings together leaders around the world via Zoom, to groups like Strategic Coach or Entrepreneur’s Organization.

The path you choose is up to you, but it starts with a question. Ask yourself: who is my support team? If you don’t have one, ask yourself: How can I start my own, or find my community, today?

Review the Game Film

I always said I never wanted to be the guy who said things like “back in the old days”, but bear with me here.

Back in the old days, if your favourite hockey team didn’t play a very good first period, you knew the coaching staff would spend intermission reviewing plays from the last 20 minutes – and making adjustments for the team to implement when they get back on the ice.

Nowadays, the turnaround time is a lot faster. As soon as a player hits the bench, he’s looking at a tablet with a recording of a play he ran mere seconds earlier. He’s reviewing what’s working and what’s not, and instantly making adjustments for when he goes back on the ice in two minutes.

In hockey, the practice of reviewing the game film has evolved with the times – and it’s practically second nature.

In life, not so much.

A lot of my clients are sports fans. They watch SportsCenter and enjoy watching all the best plays of the game – and the bloopers, too. I like to ask them: “what were your highlights this week? What were your bloopers?”

It turns out it’s a lot easier to review your favourite hockey team’s recent performance than to reflect on your own.

But what I want to know is this: if we sent a film crew to follow you around all day, what would we learn? Would we see you going into yet another one of those Zoom meetings that nobody likes but nobody wants to say anything about? How many hours would go by just watching you answer email after email on your phone? Where would we find ourselves groaning, saying, “Oh god, when he does this, everything goes downhill”?

It’s high time we start reviewing the game film in our own lives. And I’m not talking about the kind of annual review you might experience in a traditional workplace (a ridiculous ritual that so many companies insist on repeating… like, sure, neither of us can remember what we had for breakfast yesterday, but let’s talk about everything that happened in the last 12 months.)

To effectively review the game film of your own life, the key is to do it every week. All it takes is asking yourself three questions – which can be answered individually or as a team:

  1. What went well this week? (it’s important to capture the wins, even in our toughest weeks)
  2. What didn’t go so well this week (or what were the challenges of this week)?
  3. What’s one thing you will do differently next week?



Without regular reflection on what’s working (and what isn’t), the mind will keep doing what it’s always done. We will keep repeating our old habits unless we pause and ask ourselves why we started doing them in the first place – and more importantly, whether or not they’re continuing to serve us.

So many of my best practices today came from reviewing my own game film. For example, whenever possible, I try and turn an email into a phone-call. This is a rule I created for myself after noticing that, whenever I responded to a query via text or email, a lot would get lost in translation. In reviewing my game film, I realized that a five-minute phone call can quickly bring much needed clarity to both parties, saving me a lot of time and effort in the long run.

Another adjustment I made – and that many of my clients have made – involves keeping some pretty serious boundaries around phone use, particularly first thing in the morning. In reviewing my game film, I noticed I was repeatedly and rapidly losing control of my calendar when I reached for my phone immediately after waking up. So, I made it a rule not to look at my phone for the first few hours of my day – and the change has done wonders for my daily schedule.

All of this – and much more – wouldn’t have been possible if I hadn’t started asking myself those three simple questions. The people playing at the highest level – those who are really seeing progress in their lives – ask themselves these same questions every week. Do you?

Takeaway Tip:

Start reviewing your game film – ASAP. By yourself or with your team, answer the following questions:

  1. What went well this week?
  2. What didn’t go so well this week?
  3. What’s one thing you will do differently next week?

Find The Solution That Is Perfect For You:

What’s the score?

Imagine you missed the beginning of the game.

Your favourite team is playing, but you were out at dinner or otherwise tied up. You walk in the door, turn on the TV, and… what? What’s the very first thing you look at?

The score. Of course.

In the world of sports, this is a no-brainer. At any given moment, we want to know if we’re winning or losing.

So, why is it so much harder to apply this same thinking to our professional lives?

Chances are, if I called you up on a Wednesday afternoon and asked, “what’s the score?”, you’d say, “excuse me?”

Not only do most of us not know whether we’re winning or losing on any given day, we don’t even know what game we’re playing. We haven’t defined what winning looks like from week to week – let alone how to keep score.

We all know it would be ridiculous to remove scoring metrics from the world of sports – can you imagine watching a hockey game where no one cared who won? – and yet many of us go through life without keeping track of our own goals and misses.

The thing about keeping score is that it’s really very simple. When I ask you on a Monday morning, “what does a winning look like for you this week?”, I want you to be able to define that. If, by Friday afternoon at 4 p.m., you’ve won the Stanley Cup for this week, what does that look like? And how are you going to do make it happen?

One of my clients’ favourite tools for defining and keeping track of their weekly wins and misses is my Weekly Scorecard. When creating each of their personalized scorecards for the week, I ask the question: “What are the habits and routines that, when you do them, everything goes great in your life?” This doesn’t need to be more than two or three things.

At the end of the week, they must give themselves a score between 1 and 10 on everything that they’ve deemed important for a winning week.

My own Weekly Scorecard includes items like: “Left My Comfort Zone”, “Learned From My Community”, and “Created and Served.” Yours, however, can and should include whatever feels meaningful to you and your own definition of a winning week.

For my clients, this one simple tool has been a game changer. It keeps them focused. It helps them reflect on the things that went well, as well as the things that didn’t go so well, and make adjustments for next week.

And, when I call them up on a Wednesday afternoon and ask, “what’s the score?”, they have an answer.

Takeaway Tip:

Every Monday morning – or on Friday afternoon before you finish work – define what a championship week looks like next week. That alone will help you increase you focus.

To help you get started, consider the following questions:

  1. What are the habits and routines that make up a winning week for me?
  2. How can I keep track of those?
  3. What gets in the way of defining what a winning week looks like for me?

Playing to Your Strengths

I want to rewind the tape a little to my very first corporate gig.

About 25 years ago, I was running a workshop in Toronto on how to improve your recruiting process. At the end of one of the sessions, I was approached by a business consultant who asked if I would be open to bringing this same workshop to one of his clients – a big international company. His name was Barry, and he said the company’s engineering department – and specifically, its management team – would get a lot from a program like mine.

With some apprehension, I agreed to have lunch with him the following week to discuss the details. In the meantime, however, my mind was racing. I had never done a corporate event like the one he was describing. I seriously doubted whether I could pull such a thing off – or if I was even qualified.

As Barry and I sat down across from one another on the day of our lunch meeting, I still wasn’t sure what I was going to say. I didn’t want to disappoint him, but I couldn’t really imagine saying yes, either. Then, he told me what they were willing to pay. It was equivalent to three weeks’ salary of the job I was doing at that time – for a 90-minute presentation that I’d already developed.

Contrary to what you might think, I did not do a little happy dance at the sound of this news. In fact, my reaction was the total opposite. That doubting little voice in the back of my head kept whispering: am I really worth all that money?

Still, it was an opportunity I couldn’t pass up. I attempted to gulp back my anxiety, and said yes.

About three weeks later, the big day finally arrived. Let me tell you: I didn’t sleep one wink the night before. As I got out of bed and put on my suit and tie, I kept glancing at my home phone (this was, of course, long before the era of texting.) I found myself half praying for the call that would say: “let’s reschedule.” It didn’t come.

I arrived at the company’s headquarters and I was practically sweating out of my suit. When Barry saw me, he could tell I was nervous.

“What’s the matter? You’re really good at this,” he said.

“Sure,” I replied. “But the people in that room are all seasoned, veteran managers and engineers.” Who was I to try and tell them anything?

Then Barry said exactly what I needed to hear in that moment. He said: “Yeah, they’re all excellent managers and excellent engineers. And if you were going in there to teach them about managing and engineering, I would say you should be nervous. But you’re not.

“You’re going to talk to them about improving their recruiting practices, and when it comes to that topic, you’re going to be the expert in the room.”

I nodded, shook off my nerves, and walked into the room.

And it was awesome.

It went so well, in fact, that at the end of the session, the boss came up to me and asked if we could book more sessions. He wanted me to not only continue working with the same team, but to bring this workshop to the company’s other managing teams.

I ended up doing that workshop six times, and each time, Barry’s words rang truer. Each time, my confidence grew as I realized I was indeed the expert in the room on what I had come in to talk about. If I had just played it safe and refused to bet on myself, I never would have come to that invaluable realization.

At the same time that I was learning to play to my own strengths, I was learning about the importance of letting others play to theirs.

It was a few sessions into my work with that original group – the managers of the engineering department. I had gotten to know them quite well over the previous few weeks, and one day I noticed they seemed a bit down. After a bit of back and forth, I found myself asking: “what is that you guys really want?”

There was a moment where no one said anything. Then, one brave gentleman spoke up.

To my surprise, he said: “Shawn, we want our old jobs back.”

He explained that they were a group of engineers who loved engineering. They went to school to solve problems. They were good at solving problems. They were so good, in fact, that they got promoted to management. As it turned out, managing people was probably their least favourite thing to do, and now their unique engineering skills made up a very small percentage of their day-to-day lives.

He concluded his speech by asking, on behalf of the group, if I would be willing to speak to their bosses about this issue. They had tried advocating to have more of the things they loved incorporated into their workdays, but their pleas had seemingly fallen on deaf ears.

I wasn’t sure how, but I said I would try.

I went home that night and got to brainstorming. And brainstorming. And brainstorming. How on Earth could I get their bosses to see what was going on?

About a week later, I had a meeting with their bosses. As we all sat down, I asked: “is anybody in here a hockey fan?” Luckily for me (and lucky it was a Canadian company), everyone put up their hands.

“Just for fun,” I said. “Who do you think is the greatest hockey player of all time?”

Perhaps unsurprisingly, the consensus was: Wayne Gretzky.

“Okay,” I said. “Second question: what’s the most important position in the playoffs?”

Once again, everyone was in agreement: the most important position in the playoffs was that of the goalie. Strong goaltending was essential, especially at crunch time.

“Okay, cool,” I replied. “Would you ever have Gretzky play goalie in the playoffs?”

Everyone laughed. Of course not, they said. Gretzky played centre. Putting him into net would be ridiculous.

Before I could lose my nerve, I said: “So, why did you put all your engineers into net? You guys took a bunch of Gretzkys and made them goalies.”

There was a pause – one that was just long enough to make me wonder, “uh oh – did I overstep?”

Then – and I swear you could practically see it – the lightbulbs came on above their heads.

In the next couple months, the company made some pretty massive changes. I came back half a year later and those engineers were like different people, because now, they were playing to their strengths. They were allowed to do what they did best, and everyone benefited from it.

The simple fact of the matter is that everyone should be playing to their strengths – as often as possible.

Time and time again, I’ve worked with entrepreneurs who have reached a certain (albeit highly impressive) plateau with their business. Their problem is that they don’t know how to take things to the next level. They’ve spent the last decade hustling day and night, taking care of everything that needs taking care of. And of course, this is important. Especially in the early days, there can be a lot of long hours and a lot of busy weekends.

But there comes a point – which typically comes when things have been going really well for a good long while – when every entrepreneur needs to take a long hard look at how they’re spending all their time. They need to start thinking and acting a little differently. This is where it becomes so critical to identify your strengths, and to start investing more time in those strengths.

This can be a long process – figuring out what your unique strengths. But it’s absolutely essential if you want to get to the next level. And if you’re reading this book, it might be time to start figuring out yours.

To get my clients to start reflecting on this subject, I often ask some variation of the question: “what is the one thing that, when you do it, everybody wins?”

The answers I most commonly hear in response are things like: “investing time to think on the vision of the business” or “investing in key relationships” or “investing in my team and their growth.”

Deep down, they know what they’re really good at. And you probably do, too.

The real kicker comes when I ask: “what percentage of your time last week was invested in doing that thing you’re really good at?” The answer is usually alarmingly low – somewhere between 10 and 20 percent.

One of the quickest ways to improve not only your profits, but your health and your relationships – not to mention the profits, health, and relationships of your entire team – is to have everyone playing to their strengths every day.

That means saying no to things that fall outside of your strengths. And that can be a tough pill to swallow at first. But when everybody plays to their strengths, we all win. The sooner you and your team embrace this, the better.

Takeaway Tip:

Ask yourself: what are my top three strengths? If you need a little help, just fill in the blank: When I ______________________________________, everybody wins.

Then ask yourself: what percentage of my week last week was invested in playing to my strengths? What’s one thing can I do differently next week to increase that percentage?

The Power of Being Radically Honest

Early on in the pandemic, one of my clients came to me with an opportunity to bring some of my material to a larger national group that he was involved in.

He told me the group was made up of top industrial painting companies across the United States, and they met twice a month via Zoom to expand their knowledge on a variety of pertinent topics. He wanted me to come in, provide a bird’s eye view of what I do, and pitch my services. Ten minutes tops, he said.

At the meeting, I talked about the new program I had recently developed, which took my essential teachings and broke them down into an engaging four-week curriculum of classes. Out of the 14 companies in attendance, 13 signed up for the course, which would kick off in the following weeks.

It was through this experience that I met Charlie… Or, rather, Charlie met me.

Charlie was at my first class, though I didn’t know it; he was off screen, while his boss was the one in front of the camera. Charlie emailed me to say he had some questions about the course content; as I’m wont to do, I asked him to give me a call.

In the one-on-one that followed, I learned that Charlie was the right-hand man at his workplace, a $30-million company based in Texas. He told me that, some months ago, his boss had suggested he look into getting some coaching to develop his business muscles. He had since attended a couple of different courses and groups, but nothing had felt quite right. His boss knew the value of coaching, however, and told him that it was a very personal decision. You will know when you’ve found the right coach for you, his boss had said.

At the end of that first class with me, Charlie knew. He had turned to his boss and said: “Shawn is my guy. I want him to be my coach.”

Now, I’ll note here that this was never the intention of this program. My goal was not to recruit new clients, but simply to try and cater my material to a larger audience, which was a unique challenge in itself. I knew I had no chance of inspiring change if my audience was bored out of their minds, and so I had tried my best to keep my sessions engaging, lively, and based on two-way communication.

I had also invited the participants to reach out to me in between classes if they needed help with their homework, which is how I ended up having this conversation with Charlie.

About hallway through our call, however, I noticed that Charlie seemed a bit nervous, and so I asked him what was on his mind. I wanted to know: what exactly was he looking for?

Charlie paused for a moment, and finally asked: “would you ever consider working with a person like me?”

At the time, I wasn’t entirely sure what he meant by that – “a person like me.” Nevertheless, I walked him through my intake process – detailed in Chapter 5 – and we scheduled a follow-up call so I could get a better sense of Charlie’s goals, and determine if we could work well together.

By the end of that second call, it was pretty clear to both of us that we were a great fit. We connected on so many levels. And so, I told him what coaching for Charlie might look like.

It was then that he finally revealed the source of his nerves. After a moment’s hesitation, he said: “Shawn, I have to be honest with you. I’m not an educated man.”

For a moment, I was puzzled. “What do you mean?” I asked.

“Well,” replied Charlie. “I know you’re probably used to working with people who have all kinds of degrees. I only have a high school education.”

In that moment, I went from “pretty sure” to “absolutely certain” that Charlie and I would be a good fit.

In my previous life working in corporate North America, I rarely saw that level of radical honesty. I did, however, see a lot of letters after people’s names. These were people with lots of formal education in their back pockets, but who never showed the kind of courage that Charlie had just displayed to me.

Don’t get me wrong; I have nothing against a college education. But education comes in many forms, and the best lessons in life are often the ones we learn outside a “formal” classroom. I felt compelled to remind Charlie of this.

“You’re the No. 2 man in a 30-million-dollar company,” I said. “Don’t ever use the word ‘uneducated’ again.”

I also told Charlie that about 80 percent of my clients “only have a high school education”, and out of that 80 percent, 100 percent have created businesses from scratch that are successful. One hundred percent of them have created great jobs and opportunities for their teams and their families.

Before they could get to that place, however, they had to be radically honest with themselves – honest about their strengths, and the things (or thoughts) that may be holding them back – just like Charlie had done with me. My all-star client Jim Kaloutas put this beautifully during a recent interview:

“I’ve seen a lot of entrepreneurs who think they’ve arrived. They’ve achieved a certain level of success and they don’t want to push beyond it, because then they’re going to be confronted by the fact that there’s a limit to their current capabilities.”

For me, this quote from Jim puts into perspective just how much our lives can change depending on the conversations we have – especially the conversations we have with ourselves. When we shine a light on all the doubts and fears in our heads, that’s where all the magic is.

The journey that Charlie and I have been on since that first meeting has been nothing short of amazing. And it all started with being honest.


Takeaway Tip:

Ask yourself: What is the voice in my head telling me? Who do I need to have an honest conversation with? And when am I going to have it?

Owning Your Calendar

A lot of people like the idea of focus time, but they can’t wrap their heads around where to find it in their already-crammed calendars. And I understand where their trepidation comes from, because the truth is that their current calendars probably are crammed.

This is where a ‘Stop Doing At All Costs’ list comes in handy.

For me, making this list was the very first thing I needed to do in order to start working on my future vision. Before I could even think about setting aside focus time with my phone off, I needed to stop saying yes to things that weren’t serving my future vision.

Some of the things on my ‘Stop Doing At All Costs’ list included:

  1. Jumping into emails first thing in the morning.
  2. Working without a plan.
  3. Letting everybody and everything else grab my attention at all times – that includes texts, emails, social media, etc.
  4. Saying yes to the people and projects that don’t feed my future vision.
  5. Indulging in the old habits that don’t serve me.


I want to focus on Item #1 for a second, because it’s a really important one.

Back before the pandemic, I was doing a live session at a corporate retreat with about 180 people. I started my session by asking the following question: “When you wake up, how many of you reach for your phone first thing?” There was a ripple of laughter, but about 90 percent of the audience put their hands up.

The truth is that way too many people reach for their phones before they get out of bed, before they even get a chance to stretch or look over at their spouse. And when you do this, you’re effectively saying ‘I don’t want to drive the bus today.’ You start looking at all those emails and texts and meeting requests that came in overnight, and you’re letting everyone else dictate your day.

That’s why this item appears first on my ‘Stop Doing at All Costs’ list.

I was determined to figure out a better way to start my day, to establish a routine that would set me up for success. I had to experiment with a lot of different things, but now my mornings tend to involve some reading, some meditation, maybe a little exercise.

Most importantly, I don’t look at my phone for the first 90 minutes of the day.

I know that committing to that (life changing) practice sounds like a tall order – just like the rest of the items on that list – but the truth is that we make commitments all the time. We put meetings in our calendars and, because they’re there, we show up for them.

I think back to pre-pandemic times, when I used to do kickboxing classes 4-5 times a week. The class I went to was at 5:30 p.m., and the funny thing is, it was always the same 15-20 people there. Over time, as I got to know my classmates, I discovered they were a pretty high-performing bunch outside the gym. I was struck by the fact that these incredibly busy people made time for this activity, and one thing they all had in common was that they put ‘kickboxing’ in their calendars.

The simple fact of the matter is that when you make a commitment, even to somebody you only know as your kickboxing buddy, you show up.

It’s all about owning your calendar.

So, what does this ‘radical’ idea actually look like in practice? To answer that question, I like to lean on the advice of one of my favourite authors, Cal Newport. In his amazing book, ‘Deep Work’, he talks about a concept called ‘time blocking.’ Time blocking is the practice of assigning a job to each hour of your day. This can be challenging at first, but the results might just blow your mind. Here’s an example of how I use time blocking in my day:

From 6 a.m. to 9 a.m., I engage in what I call my ‘Winning Morning Routine.’ Because I tend to quickly lose control of my day when I turn my phone on first thing in the morning, this block of time is a strict ‘no phone zone.’

From 9 a.m. to 10 a.m., I ‘go to school.’ This is time for reading or taking courses that support my intellectual and/or business growth. (Depending on the day, I might move this block to the afternoon.)

From 2 p.m. to 3 p.m., I work on future projects only. This is when I might find time for my daily
practice of writing down five crazy ideas, or asking myself questions whose answers could lead to future growth. This is my focus time.

At some point during the day, I will block out some time to answer emails. This may seem like a small thing, but it’s a crucial part of the time management puzzle. Before I started doing this, I would be distracted all day long. When I started restricting myself to one hour a day for checking and responding to emails, I was amazed by how focused I was able to be for the rest of the day.

Follow-through is essential here. I can’t stress that enough. If you’re reading this and thinking, ‘I’ll see if I have the time’, chances are you won’t find it. If you’re not conscious and deliberate about the way you manage your time, I can almost guarantee that your old habits will keep calling the shots.

Now, I’m by no means an expert at time blocking. It’s something I’ve been working on for a few years, and it’s still a work in progress. That being said, even in its imperfection, it’s been a total game changer for me. I can confidently say that 80 to 90 percent of my current work and opportunities were created from time blocked periods. If I had waited until I felt ‘ready’ to start this practice, I would probably still be struggling with the same things I was struggling with before.

Time spent vs time invested

How do you spend your average day?

When I make the decision to take on a new client, finding out the answer to this question is one of my first priorities. I need to know if you’re spending all your time tackling the day-to-day, or if you’re actually setting aside time to focus on ‘Future You.’

Here’s what I’ve noticed, time and time again, over the course of my career: so many people have these big future plans, but their calendars don’t reflect that. They want their lives to be different, but they don’t invest the necessary time and energy into moving themselves forward.  

Part of the blame for this lies in the myth that, in order to achieve your goals, you need to make a million dramatic changes all at once. But investing time in ‘Future You’ doesn’t need to take up all your time – or break the bank. It can be as simple as making a phone call, or signing up for a conference, or reading a chapter of this book. Manifesting ‘Future You’ happens one small action at a time. 

Think about it like this: there are 168 hours in a week. It doesn’t matter what you do for a living, or how much money you make. We all have 168 hours. It’s how you invest those hours that can make all the difference in the world.  

So, how do I find out how my new clients are actually spending their 168 hours? 

I get them to write down what they’re doing every minute of every day for five days. 

And yes, I truly mean every minute. 

You know when you went on Instagram at 11:23 for a quick scroll while sipping your coffee, and then 38 minutes later you were still scrolling? Yeah, I want to see that. You know that 20-minute meeting that turned into a 90-minute meeting? I want to see that, too. When you’re answering emails, I want to know what they were about. What was the outcome? Were they necessary? Why or why not? 

I also want to know if you took breaks. Did you go outside for lunch? Did you meet friends? Did you exercise? All of this is invaluable data.  

And no, it’s not a popular activity (by Day 3, I usually get a text message saying something along the lines of: “how much longer do I have to keep doing this?”) But as the expression goes, what doesn’t kill you makes you stronger. And those who see this homework assignment through to the end definitely get stronger once they see the results. 

It’s incredibly eye-opening to see, in black and white, how you’re spending your time every day. 

More often than not, my question for people at the end of this exercise, once I’ve had some time to look over their data, is this: where in your schedule is your thinking time? Where is your time to focus on ‘Future You’?

The truth is that when we create space for reflecting and imagining and strategizing, everything changes; this is by far the number one thing I hear from clients once they’ve gotten into the habit of setting aside daily thinking time.

They also say things like: 

“I have more energy.”

“I’m getting opportunities I’ve never gotten before.”

“It makes me feel alive knowing I’m moving toward my vision.” 

I wonder – is anyone likely to say any of these things after spending all afternoon attached to their phones, answering a seemingly endless tidal wave of calls, texts, and emails? 

I don’t mean to suggest that social media is all bad, mind you. The technology we have at our fingertips today is amazing, and it comes with many benefits. Those who play at a whole other level, however, got there because they knew the importance of being intentional with their time. And sometimes, that means turning off your phone for a while.  

People often tell me I’m creative, but I don’t think I’m creative at all. I think I just have good habits; habits like writing down ‘five crazy ideas that might just work.’ Most of them don’t, but some of them turn out to be my biggest offerings. All because I started putting down my phone once a day. 

This idea was initially a bit of a tough sell for Kevin Cassidy, the founder and owner of a leading commercial asphalt paving company in Haverhill, Massachusetts.

Now, Kevin is an incredible guy. He built his $10-million company from scratch, and he has a team that loves and respects him. He has a brilliant business mind; he’s one of those guys who sees opportunities everywhere. But for a long time, he wasn’t accountable to anyone. When he first came to me for help, he said he needed some focus and direction. He had reached a certain point in his career from relying on the skills and habits he had cultivated long ago, and he didn’t know how to get to the next level. 

After reading the data supplied to me by Kevin from his five-day self-tracking adventure, I realized he had the same problem a lot of my clients had. He had no thinking time baked into his schedule. 

After some back-and-forth, he agreed to start turning off his phone between 3 o’clock and 4 o’clock every day. This would be his time to focus on Future Kevin, and nothing else. 

Like any coach worth his salt, of course, I wasn’t going to let him off that easy. A few days into his challenge, I texted him around 3:15 and asked if he had a minute to chat. He said “sure”, so I gave him a call. When he picked up, I responded: “What the hell are you doing?” He groaned. “Busted,” he said. 

A couple of days later, a package arrived for Kevin at his office in Boston. In it, he found a lockbox and a note. It read: “Kevin, you’re to put your phone in this lockbox and lock it up every day from 3-4 o’clock. Take the temptation away.” 

He’s been a devoted undertaker of dedicated thinking time ever since, and he’s the first one to say what a blessing it’s been in his life.

Change can be really uncomfortable. But it’s the only way we grow. And change is only possible when we commit to it, in a lot of little ways, every single day. 

Takeaway Tip:

Ask yourself: How much time do I invest in my future vision every day? How much time do I invest with my phone off every day?

Then, start with 20 minutes a day. 

Turn your phone off, ask yourself a question you don’t know the answer to (example from a client: how can I make an extra $1,500 a month without leaving my apartment?) and turn it into a research project. Alternately, look back at your answers to the 10 essential questions from Chapter 5 and choose one to work on.

Where are we going?: The first call

I moved to an invite- and referral-only business model a few years ago, and it was one of the hardest professional decisions I’ve ever had to make.

It meant saying no to people that I might have known for a long time, but with whom I wasn’t a ‘perfect fit.’ Sure, it may have been good enough, but if I’ve learned anything in my career, it’s that ‘good enough’ always gets in the way of being great.

Nowadays, my decision to work with a new client pretty much comes down to one question: do I genuinely enjoy this person’s company? I’ve come to realize that if I wouldn’t enjoy having lunch with someone, then we’re probably not a good fit to work together.

This doesn’t mean, of course, that we must be best friends in order to work together. But we do have to be a good fit. The truth is that I’m not the right coach for everybody and that’s okay (hot tip: any coach who says they’re the coach for everybody is lying.) In this way, working on an invite- and referral-only basis is all about honouring both the client and myself.

All this to say, when I get referrals (as I often do, thanks to my amazing clients), I always make sure to kick things off with a one-on-one phone call.

The goal of this call is two pronged: it helps give them a sense of what I do, as well as gain some clarity on their own vision. And it helps me get a feel for whether their challenges are something I can authentically support. At the end of the phone call, we should both have a fairly good sense of whether or not we’re a good fit.

Ideally, the prospective client will also walk away with some answers to questions that they have never asked themselves. They will be equipped with a compass they didn’t have before. That’s why I call this session the ‘Strategic Focus Game Plan’, because when we actually sit down and create a map of where we want to go, it’s game changing.

In this chapter, I’m going to share with you some of the questions I would typically ask in this 45-minute session. While you’re reading, I want you to actually set quiet time aside (with your phone off) and answer the questions for yourself. Grab a cup of coffee or tea, take out a pen and paper, get comfortable, and go within.

Imagine it’s two years from today, and we’ve bumped into each other in the street. You say to me: “Oh my God, Shawn, the last two years have been off the charts – beyond my wildest dreams.” What does that reality look like to you, personally and professionally?

What are your top three business, health, and relationship goals for the next 12 months? Get specific. (Example: if your goal is to lose weight, don’t just write ‘lose weight.’ What are the habits and behaviours that will help you get there?)

Top 3 Business Goals:


Top 3 Health Goals:


Top 3 Relationship Goals:

To accomplish these goals, how are you acting differently than how you’re acting right now?

How is your team acting differently than how they’re acting right now? (If you’re a solo entrepreneur, your team might be a contractor, your family, etc.)

What do you want more of, and what do you want less of? (Less stress? Fewer headaches? More time off? More saying no to the wrong opportunities? Etc.)

What are you still tolerating? (This is one of my favourites. Identifying what you’re still tolerating is the quickest path to change.)

What are your top three opportunities and your top three challenges right now?

What are your top three strengths? (These are the things you’re really good at, and that give you energy.) This is no time to be humble.
What is one habit that, if you committed to it, it would change everything?

What progress have you made towards your vision?

At the end of this session, it’s pretty clear to me – and to the person answering the questions – if we would be a good fit or not. If I get the sense that we would be, we can talk about what coaching might look like for you. My coaching style is unique in that I don’t follow a script or a program. I show up to every call for you, to help you stay on top of your vision. That means that my sessions with one client may look very different from my sessions with another.

In writing about this, I’m reminded of one of my clients in Boston, who came to me through a referral. At the onset of our first phone call, he was already set to pull the trigger. He said he had heard about me from a friend, someone he had a lot of respect for, and he had his credit card in hand. He was ready to start working together. Today.

“Whoa, slow down,” I said. After all, we don’t propose marriage on the first date.

I asked him to answer some questions for me before we made anything official. Then, I encouraged him to consult our mutual contact one more time, just to make sure my services were what he was looking for. (When choosing who you want to work with, I’m of the opinion that ‘slow’ is the way to go; when coaches say, ‘you have to sign by 3 p.m. today’, that’s a big red flag for me.)

We ended up being a match, of course, and I’m now thrilled to call this awesome guy a client. But we never could have figured that out were it not for that one critical session.

Those 10 essential questions, and the immense clarity they provide, will set the foundation for change in your life – if you’re open to receiving it.


Takeaway Tip:

Block out 45 minutes in your calendar, take out a pen and paper, and answer the 10 essential questions.