An Open Letter to Leaders

Dear Leaders (and Leaders-in-Training):
The days of top down, command and control managerial leaders are a thing of the past. Today’s leaders are vulnerable, collaborative, aspirational, and inspirational. Today’s leaders are globally connected and community focused. Today’s leaders are building empires and leaving legacies. Do you have what it takes to be a top leader in today’s fast-paced, constantly changing world?
So, what does it take to be an amazing leader? I’ll tell you what it’s not. It’s not about a title or position. It’s not about tenure or seniority. It’s not about intelligence or degrees. And it sure as hell isn’t about age. Amazing leaders can be found at any level of an organization. Wherever there is a group of people – in schools, non-profits, homes, Fortune 500 companies, governments and churches – leaders show up. Are you one of them? When people are searching for guidance, looking for direction, or asking for decisions to be made, do you step up and lead?
Great players (i.e. star employees, co-workers, etc.) don’t always make great leaders and that’s okay. Take Michael Jordan, for example. Perhaps one of the greatest basketball players of all time with 6 championship wins. As owner of the Charlotte Hornets his record is less impressive. Someone who is a great basketball player needs to become a different person to lead a team. Not everyone is up for the challenge. Are you?
If you have your mind on leadership and leadership on your mind, you’ve got to ask yourself if you are willing to change and grow into the person you need to be (which takes years of purposeful effort). Leadership is not a passive activity. You can’t just sit back and watch events unfold and have pleasant conversations over afternoon tea. You have to get into the arena and have tough, really tough, conversations and make gut-wrenching decisions that effect other people’s lives. Leadership is knowing that not everyone will be happy with your decisions, but you make them anyway, trusting that you are doing the right thing for your company. You have to be okay with being publicly criticized about the decisions you make. You will never be able to make everyone happy. Once you move from the sidelines into the arena, it’s a different game. You will be judged and judged hard. You will either thrive on the pressure or it will break you – there is no gray in the leadership world. You’re either in or you’re not.
Leadership ain’t pretty and yet it’s one of the greatest things you can do. Still want to be a leader? Then you’ve got to ask yourself:
  • Am I willing to go above and beyond what your job requires every day?
  • Am I a team player and consistently putting the good of the company and the good of the team ahead of myself?
  • Am I leading myself first by reading, exercising, journaling, meditating, etc . daily?
  • Am I teaching others how to think differently by asking powerful and purposeful questions ?
  • Am I role modeling the behavior of a leader?
  • Am I adding massive value to others and intent on making someone else’s life better?
  • Are people coming to me regularly for leadership advice and guidance?
Were you able to answer “yes” to all of these questions? Good. You’re on the right track. Did you discover that you still have some work to do? Great. It’s not going to be easy, but awareness is the first step. Now it’s about taking the necessary steps in order to develop influence and build your leadership skills.
It’s really difficult to move from the stands and into the arena. Most people are unable to withstand the stress and end up laying down their sword and climbing back into the stands. But that is the difference between mediocrity and greatness. There is pain in either path – the pain of mediocrity or the pain of growth. You get to decide. Greatness means picking up the sword and going into battle over and over again no matter how many times you get knocked down. True leaders are rare and the world needs more of them. People who are not satisfied with the status quo and who are unafraid of the ridicule they will receive. People who can withstand the pain, pressure, and loneliness of leadership.
If you feel the call to become an amazing leader than it is your duty to answer. You can not assume that others will rise to the challenge, because they won’t. Leadership is the ultimate test of vulnerability and perhaps one of the greatest gifts you can give to the people around you. When others are sitting back, resting on their laurels, when others are keeping their heads down and their mouths shut… Be bold. Be brave. Stand up and lead.
Don’t fear the fight. Fight forward,

Why CEOs Need a Chief of Staff and an Executive Assistant

c suite dream team

I’ve had a Chief of Staff (COS) for several years and the most common question I get is what does she do? Well, you’d have to ask her; I’m not entirely sure. Really. That’s the point right? I couldn’t tell you exactly what my Executive Assistant does either. What I do know is that I am able to focus on my 20% (sharing the vision and mission, leading the team, and making important decisions) because I have my COS and EA behind me. 

The Chief of Staff role, most commonly seen in the military, government, and hospitals, has been making it’s way onto the corporate scene more recently. Entrepreneurs, high growth start-ups, and complex corporations are all starting to see the benefit of having a Chief of Staff, well, on staff. So what exactly does a Chief of Staff do? The Chief of Staff (COS) role is probably one of the most misunderstood positions, right next to that of Executive Assistant. Let’s break these two roles down.

A recent article explains it well:

As a company grows and becomes more complex, hiring a chief of staff can be a smart move. In the political arena, the COS is a leader and trusted advisor who takes responsibility and delivers results for the president or governor. In the corporate world, the COS understands the company’s sensitivities, customers, and team members who make it all work.

While the COS concentrates on troubleshooting and paying attention to the daily needs of the company, he makes room for the CEO and COO to spend more time strategizing and focusing on the growth of the company.

Another way to look at it is that the COS focuses inward. They manage the needs of the CEO, Executive office, and company, such as overseeing employee satisfaction, recruiting, brand and reputation management, training, communication flow, and maximizing the CEO’s reach. While a COS may often have a focus area (such as recruiting, technology, or business development), they will more often then not be the “filler” or as I like to call it, the “fixer” position. They will take on any special projects that do not fall specifically to any other person or department in the organization. This might be an internal audit of the company’s operations, setting up a new recruiting platform, or establishing a Foundation in the CEO’s name. The work is varied and strategic. A high powered COS maximizes your reach, attends meetings on your behalf, keeps projects on track and moving forward, ensures communication is flowing between all parties to successfully achieve your priorities and goals.

Where the COS is strategic in nature, the Executive Assistant (EA) is more tactical. While the COS is managing the company, the EA is “managing” the Executive. This can be everything from travel arrangements, meeting prep and follow-up, event planning, extensive calendar management, research, and assisting with personal items. A high powered EA knows the names of everyone in the room, and details on them and their families, they can throw together an event in a week and ensure it is flawless, they anticipate needs, know what you know, and take care of all the details behind the scenes so you, the CEO, can simply show up and lead.

There are, however, a few caveats to consider. A high powered EA may often be serving in the capacity of a Chief of Staff, just as a Chief of Staff may be fulfilling some of the functions of a Executive Assistant. Depending on the structure, size, and complexity of your organization, it might be the same person. And, because the corporate Chief of Staff role is still being developed, one CEO’s Chief of Staff is really an EA (more tactical), while another’s serves as a Vice President (more strategic).

Now, I didn’t hire a COS, my COS started as my EA over seven years ago and grew into the position, taking on more and more projects and leading alongside me as my companies grew and became more complex, as we added new teams, new divisions, and new projects. About a year ago, the workload was such that it necessitated our search for, and eventual hire of an Executive Assistant. 

So what do the COS and EA roles have in common? They are both force multipliers. They take your vision and make sure it is carried out. They both lead and assist a CEO and typically only report to the CEO or another senior C-Suite Executive. Strategy and tactics combined, they are the ultimate C-Suite Dream Team. A great COS and EA will work together to get things done before you even know you needed them. 

With both a COS and EA on staff, a CEO can not only be extremely focused on only the most important issues each day (thanks to the support of their EA), they can also be in two places at once (thanks to their COS). Let me give you a couple of examples of how the CEO/COS/EA relationship works in my organization:

  1. When I am on my one-on-one coaching calls each week (which my EA has scheduled, often rescheduled, and then prepared any documents or notes for me), my Chief of Staff is meeting with potential talent or future business partners for our company. My EA has ensured we are both in our meetings when we need to be and then is asking us for feedback and follow up items so that nothing is forgotten or missed.
  2. This weekend we hosted a full-day seminar, called Quantum Leap, for high school students (and some parents). My Executive Assistant planned and organized the entire event, arrived early to set up, and ensured that the day went smoothly, so all I had to do was show up and be totally present while teaching these high schoolers. My EA also made sure the students had everything they needed and checked in with them during the breaks. Meanwhile, my Chief of Staff was giving tours of the office to current and future business partners and making connections with and for some of the adults who were there (sounds like we may be launching an internship program next!).

Makes sense, doesn’t it? Why wouldn’t a CEO want both a COS and EA on staff? If you are a CEO with multiple divisions and complex business systems, an entrepreneur with several companies and business ventures with multiple stakeholders, or a founder in a high growth start-up, you need an Executive Assistant and a Chief of Staff. Your day will run smoother, you will be able to serve your company at a higher level, and you will be able to maximize your vision, reach more people, and ultimately grow and scale your company bigger and faster, all while maintaining your sanity (at home and at the office).

Want to learn more about these two roles and how to implement them successful into your organization? Email my Chief of Staff at You can also check out two webinars we did recently: One that explains the various positions, along with other administrative roles, and one that specifically discusses the difference between the EA and COS positions (email Hallie to purchase that webinar).

Do you have a Chief of Staff? How do you define the position in your organization? How do you see these roles evolving in the future?




Fall in Love With Your Vision. Date Your Model.


I mentioned last week that I have been diving deep into my organizations and I’m still asking questions, making changes, challenging our previous way of doing things, and generally breaking shit. I’m relentless. Here’s the thing, though, I would rather be disrupting my own organization, than allowing the competition to do it. I will always be one step ahead because I refused to rest on my laurels. One thing is for sure – as I’ve been getting really granular and digging in deep on every little part of the organization, the big vision has never been more clear.

Sometimes you really do need to go small, in order to go big.

As a business leader (really, a leader of any sort of organization – your church, your family, a committee at the office, your fitness group, etc.) your vision is critical for the overall success of your organization. Without a vision, what is it all for? Leaders must be communicating the vision constantly (every four minutes) and it should be so consistent that anyone in the organization could be asked, “What is the company’s vision,” and they would all be saying the same thing. Is this happening in your company or on your team? Does everyone know why they are coming to the office each day (other than for a paycheck)? If they don’t, that’s on you. Change it now.

Consistency is really critical here. My five organizations have shifted focused, had multiple divisions, closed a couple divisions, changed models and compensation structure, gone through re-branding, etc. But despite all of those changes, the North Star, the vision, hasn’t wavered. I am just as committed today, as I was ten years ago, to build a business where personal growth is the foundation for transforming the lives of my employees, their families, and our clients. I fell in love with my vision and so should you.

So, while you need to stay true to your vision (for the sake of your staff, your overall brand, and the consistency of your leadership), I would definitely encourage you to date… your model. Here’s what I mean. If you’ve got your North Star, your vision, in your sights, then it will be up to the model to get you there as quickly, as efficiently, and as profitably as possible. There are going to be thousands of ways to do that. Think about it – if you want to lose weight (your vision) how many different programs are out there to help you achieve that goal? Pretty much endless! Hell, all you have to do is eat less and move more! You can chose a model, let’s say intermittent fasting, then after 60 days realize you don’t have as much energy as you used to, so you move to a low carb, high fat eating plan with 3-5 HIIT workouts a week. Great. Still on the path towards your vision, the model has just changed.

Your model for any goal and ultimately for your vision should be flexible, nimble, and ever changing. If you get stuck on a model, then you’re often unable to see what might need to be changed, adjusted or completely thrown out. If you get stuck on a certain model being the only way to achieve your vision, then you may never achieve your vision at all. For example, if your vision is to see a sunset, but you’re running East then, no matter how hard or how fast you run, you’re never going to see it! If something isn’t working, make a change. Direct your energy towards the right activities, the right models. That does not mean your vision changes, your vision should be the guiding force in determining when or how to adjust your model. The why (your vision) doesn’t change, your how (the model) can and should. Sometimes the tweaks are minor, like adjusting an intake form and follow-up process. And other times your model may change drastically, like reorganizing an entire team or division, eliminating a product offering, or changing your company name. Regardless of the size of the change or how your model shifts based on these changes, the vision must stay in the forefront of your mind.

In fact, when models are shifting and there are multiple changes in the organization, then it is more critical than ever to be sharing the overall vision of the company. You may need to up your vision sharing from every day, to every hour. You must make sure all of your leadership team members and division leaders are also communicating the vision and how each team member’s individual contribution fits into the overall vision. Change is difficult, especially when people feel like it’s just change for the sake of change. Change often requires extra work, learning a new system or process, or shifting job responsibilities. If the vision is clear and a team is bought into it, then they will not only withstand the model change, but come out on the other side stronger and more committed to the company and vision then ever. Dating is hard. It’s up to you to guide your team through the dating phases of building your vision, while ensuring they never forget their love of and commitment to the vision.

What’s your vision? How many iterations have you gone through on the way to fulfilling your vision?



Enthusiasm is Everywhere. Endurance is Rare.


I’ve spent a lot of time over the past few weeks taking a deep dive into my companies. I always tell my clients that you have to inspect what you expect, and I’m no different. It’s an exercise that I am committed to doing at least quarterly, though likely more often than that (you’re welcome team!). So, I’ve been inspecting and asking questions and restructuring job descriptions and eliminating unnecessary or less effective systems and processes. It doesn’t mean that what we were doing before was bad, simply that we can (and will) do better.

This is all part of being a leader and building a business to be able to scale. I see a problem, break it even more and then put it back together again. And just when I think I’ve solved all the problems and I can breathe for just. one. second., another problem in another company pops up and I break it even more and then work with my team to put it back together again. This is one of the core cycles of a business leader and it can be exhausting and exhilarating at the same time. It takes a rare breed to be able to build a business and the talent who are able to keep up with the leader’s intense drive are just as rare.

And yet, people like to talk a big game. There are a lot of people who have big goals and dreams and like to tell everyone and their mother (and post it on every social media platform too). Or you have those people who are the perpetual students, learning, taking classes, reading the right books, signing up for every conference, taking notebooks full of notes, and then… nothing.

You see, enthusiasm is everywhere. You see it on New Year’s Eve or on milestone brithdays or after coming back from a great conference. Millions of people are ready to take on the world, to change the world, and again… nothing. We don’t have any shortage of enthusiasm in this world, let me tell you that. Great ideas. Accumulation of knowledge. Good vibes everywhere. But what does a big idea and a positive attitude amount to? Absolutely nothing if you don’t take that knowledge and execute.

Enthusiasm is everywhere (just like goals are). It’s endurance that is rare. How many people do you know who had an incredible New Year’s resolution to change their life? I see those hands raising! How many are actually still invested or committed to that goal? Did they start slacking off? Allow themselves to cheat? Get distracted by a squirrel? Allow other things in their life to become more important? Did they lose sight of their why? All of those things may be true, I’m not discounting that. But you can either have reasons or results.

And how does one achieve results? Grit, grind, persistence, never giving up, endurance. I’ve told you before and I’ll tell you again. Building a business is hard. It’s much easier to go back to phase one or two where you are generating all the income based on your own entrepreneurial efforts. It’s easier to be so involved with the company that you know every single person’s wants, needs, and goals and can personally help each one achieve them. Building a business is hard and it requires endurance. It’s not for everyone, but those that can survive the 5-7 year grind are the ones that will reap the rewards.

But endurance is rare. It’s rare to find an individual who will sacrifice a salary for an opportunity for growth. It’s even more rare to find a business that survives beyond it’s first year! It’s rare to find talented individuals who are ready, willing, and able to run along side you (sometimes pulling you along!) for years and years, struggling just like you are day in and day out. When you do find those individuals, your focus as a business owner is to build a moat around your key people such that if you lost them it would be devastating to your business, or at the very least leave a big whole for a while. Sure, everyone is replaceable (even you), but those key hire replacements would take years to find. Build a moat and keep those people on your island through equity, vested interest, higher salaries, and bigger opportunities to constantly grow.

We all talk about the grit and grind it takes to build a business, but I’m not talking about being gritty enough to muscle through a tough project. I’m not talking about the daily grind. I’m talking about mastering the boredom of singular focus. Enduring the daily grind, for not just months, but years. You literally have to up your threshold for mental and emotional pain. In order to build a big business there is no way in hell you can be the same person in year two that you were in year one. Not if you want your business to survive and thrive anyway.

So, how do you build your endurance muscle? Practice. Lot of practice. Lots of failure too. Lots of trial and error. Some more practice. A big dose of drive, a dash of insanity, and another sprinkle of failure.

But in all seriousness, you need to get real clear on your why and then start playing mental games with yourself (no, I’m serious!). You really have to decide who is going to win the battle of wills. You or the voice in your head telling you to give up, that you’ve done enough. And then the endurance part kicks in. You may be battling yourself like this for years, but on the other side of endurance is success. If your why is strong enough, you can withstand any how.

You get to choose how you show up every day. You get to choose what actions you take every day. Some of them are going to be uncomfortable, and boring, and routine, but if you can get over that, then you can get on to success. It’s like the people who always give me a story about why they don’t work out. It’s because they hate it. They’ll never love working out like I do or enjoy fitness like all the Instagram Fitspos do. Let me tell you something that may be a shock to you. I don’t like working out. I don’t like getting up at 3:45am. I don’t look forward to my training. 90% of people don’t like working out and I don’t blame them! It’s hard and it’s uncomfortable. But those same 90% LOVE the feeling they get afterwards – feelings of pride, accomplishment, joy, fulfillment, success, etc. That. That is what people are after when they work out and that is what people are after when they build a business. But the only way that happens is if they ENDURE! Endure the pain, the struggle, the sweat, the tears, the long days and even longer nights.

Enthusiasm is everywhere. Endurance is rare.

I don’t give a shit about how excited you are to work out, start a business, write that book, etc. What I care about is your execution and endurance. That’s where the magic happens. That is where “over night successes” are born. That is where you will ultimately find fulfillment.

Got endurance?

5 Things I Wish I Knew Before Starting a Business


As I’m gearing up to teach Quantum Leap for High School in a couple of weeks, I can’t help but reflect back on my own high school experience. The first part of high school for me was rough. I was 100 pounds overweight, failing classes, and partaking in some light drug usage (a model student, I know). But high school was also one of the most transformational times of my life. It was then that I took a stand on my future. I knew that I was made for more and refused to live in mediocrity any longer. It wasn’t easy, but I stopped with the drugs, I lost the weight, and I ended turning my grades around enough to get into UVM’s guaranteed admissions program.

College was great and I really discovered my entrepreneurial spirit there – selling out house parties and flipping cars. After making a decent amount of money doing that, I decided to invest into my first piece of real estate with my brother – a pre-construction condo that just a few years later sold for a $65,000 profit. I graduated from college and took my first step on the corporate ladder as a financial controller. But within, a year, I had maxed out. I always showed up and worked hard, yet my bosses would tell me to slow down because I was making them look bad. I cannot NOT be growing. It was at that point, I knew I needed to step off the ladder and do my own thing. That was when I got into real estate.

But here’s the thing. My decision to get into real estate wasn’t because I had a deep love for buying and selling homes; it was to build a company that I owned, where no one could put a limit on my thinking or my growth.

Fast forward, 10 years later, and I not only own one business, but five thriving organizations. Have I arrived? Have I accomplished all I want to? Hell no. I’m just getting started. But I will share with you a few pieces of wisdom (that I wish I knew before starting a business) that I’ve acquired over the past ten years of grinding through the joy and pain of building a business.

  1. INVEST INTO TALENT SOONER. Do you want to be self-employed or own a business? The difference is people. That’s the only way you’re going to build a business. People, the right people, will always be your best investment. No one succeeds alone. And even if you hire people thinking they will fulfill your current need or are too afraid to pay a certain amount of money, then you will be left with sub-par results, and even worse, you may be cleaning up a mess after they leave. Take the time to learn how to recruit and hire the right people, how to train them, and how to keep them.
  2. READ. READ. READ. Most people read about 1 book a year after graduating from their last formal education. CEOs read about 60 books a year. If you want a 51 to 1 advantage over the next guy, read one book a week. Reading (okay, or listening to books on Audible) opens your mind to new ideas, new perspectives, and new ways of thinking that, when implemented, can change the trajectory of your life. Whether you are reading to escape to the halls of Hogwarts, reading to go deep into your spiritual subconscious, or reading to learn the communication skills needed to take your leadership to the next level, just read. The more you pour into yourself , the more you have to give to your team and family.
  3. THE IMPORTANCE OF MENTORS AND ROLE MODELS. You (your income, your knowledge, your attitude, your success) are the average of the five people you spend the most time with. What does your inner circle look like? If you are the smartest or most successful person in the room, then you’re in the wrong room. Is it time to find some new friends, new people to surround yourself with? If you’re looking for a mentor in your life, all you have to do is open Instagram, pick up a great autobiography from your local bookstore, or attend a conference. It’s about finding the people (who you may know personally or not) that are truly living the life that you want in those six important categories (financial, business, career, personal, physical, spiritual). It’s about following what they do and then implementing it. It’s easy to intellectually understand what successful people do, but very few people (except for the successful ones) actually execute on that knowledge. And that’s the key.
  4. SUCCESS IS A STATE OF MIND. We must clearly define what success looks and feels like to us or we will never find it. Once we’ve defined it. Live it. The most common mistake we make in life is looking outside of ourselves for something we should (and can) find inside. Success is no exception. Just as the source of true happiness lies within each of us, success also comes from within. Success is the result of a very specific attitude. We must choose and define what success looks like and feels like to us. Is it knowing that we gave it our all, regardless of the outcome? Is success hitting a certain financial goal? Is success having a family and not working outside the home? Do you know what success looks like to you? If we can’t define what success looks like in our mind, no matter what we have we will never be satisfied. And if we can’t define what success looks and feels like then we can feel like we’re working our asses off and never getting any closer to “success”. That’s because we keep moving the target or don’t even know what target we’re trying to hit! Success is a state of mind. Get clear and then get moving.
  5. THE KEY TO HAPPINESS IS NOT MORE MONEY. A lot of people believe that money is the key to happiness. People strive their entire life for more and when they get it, they might feel a certain way, but only momentarily. Money or what money can buy doesn’t really give them the feeling they were after. Money itself is just a piece of paper or a series of digits in your bank account. Happiness is happiness. Money is money. Happiness, like success, is a mindset. You can choose to be happy, regardless of how much money you have. And I know you know those people who have all the money they could ever want and are still miserable. However you choose to live your life, money just exacerbates that feeling or attitude. If you are an incredibly caring and generous person, then with money, you will give even more. If you are an asshole, then with money, you will be an even bigger asshole. Money won’t change you. It will expose you. Find joy and happiness within and any external rewards are just icing on the cake.

I have learned a tremendous amount over the past ten years and I’m learning more every day of just what it takes to succeed in business. There are millions of people with big dreams, then they get distracted by the next big dream, the next shiny object. It’s the people who make a decision, a commitment, to mastering the boredom (and say no to every damn shiny object that comes their way) who will succeed. Enthusiasm is everywhere, endurance is rare.

Are you thinking about starting a business? What’s holding you back?