Leadership Lessons to Help You WIN

Leadership Lessons

For the last 20+ years, I've been focused on leadership.

It's changed my life in many ways, including climbing the corporate ladder from a first-year accounting student to CFO.

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The Background

After an undergraduate degree in business and a Master's in Accounting, I realized I knew little about leadership.

I also knew the way you climb the corporate ladder is through your people, not through your work.

The people on your team need to believe in you and lift you up. They need to want to see you succeed.

What it meant was I spent the next 20+ years studying good leaders:

  • Books
  • Courses
  • On the job

I looked for good leadership and tried to understand what made good leaders stand out.

Below are 24 lessons I codified that helped shape my leadership style, which I share with young leaders on my team:

It is not about you anymore

You've already been promoted. Let go of the spotlight.

Get the roadblocks out of your teams' way and let them shine.

You need to listen more and ask good questions

Not like you're thinking about what you're going to say. Like you care.

Learn to ask great questions, the first two:

  • What's on your mind?
  • and, What else?

Never stop learning. Ever

A-players don't want to work for someone they've outgrown.

The easiest way to prevent it isn't to hold them back, it's to outpace their learning:

  • read
  • courses
  • seminars

Raise your expectations and your empathy

People respond well to challenges, and they respond better when the person who challenges them cares about them.

This is a Mentor Leader. Be it.

Give your team credit, and take the blame

When things are going well, praise your team publicly and when things go wrong, own the problem.

They know you have their back when they see this and will go to war for you.

I do this by email.

If things go well, I'll email the shareholders and cc my team praising their work.

If things go well, I'll do the same taking the blame for the problem.

Learn the golden rule of leadership

Don't lead people the way you prefer to be led. Lead them the way that they want to be led.

Every person is different. Adapt your style to your people and don't expect them to adapt to you.

Leave your assumptions at the door

When you have a meeting with one of your team, don’t go in with expectations.

Seek to understand, and then, if needed, to be understood.

Your team is not you

There’s a reason you were the one who was promoted or hired.

Don’t expect the same of your people as yourself.

Expect of people what they’re capable of.

Believe in people more than they do

Your expectations may be higher than they have for themselves. That’s okay.

Share your belief in them and help them make it a reality.

They will be your teammates for life.

Get used to uncertainty

You aren’t a line player anymore.

Your schedule isn’t set from the moment you punch in until you punch out.

As a leader, you deal with curveballs. With fires and challenges.

Get used to it.

Have the hard conversations early

Don’t shy away from them.

Weak leaders do that. Instead, try this:

  • I expected a,b, and c
  • What I saw was x, y, and z
  • It made me feel like _______
  • Can you explain what happened

Make it about the behavior, not the person.

Fight for your people

Some people think it is okay only to review salaries when their team asks.

Unfortunately, women and many minorities are less likely to ask for a raise, and it is not right to ignore this fact.

Do your research and fight for your people.

Extend trust and respect without a need to "earn it"

When you require someone to earn your trust and respect, you limit your relationships.

You may get burned if you extend it quickly, but it's a much happier way to live and doesn't have a ceiling.

Get outside and go for a walk and talk

When you do, leave the agenda behind and connect with the person.

What are their:

  • hopes
  • dreams
  • aspirations

How is their home life? Family life? Mental health?

The best colleagues spot the best colleagues

They also spot B-players, and if you don't cull your B-players, you will lose your A-players in time.

Make the hard choices and cut quickly.

Invest in your people:

  • Personally
  • Professionally
  • and, Financially

If you consistently tick all three boxes, you will have your teammate for a long horizon.

You need to fire fast and hire slow

If someone isn't a fit, you need them off the team quickly, before the chemistry can be poisoned.

Likewise, unless you're sure someone is a fit, you cannot add them to your team.

Involve your team in hiring

The more people who meet new colleagues, the more likely they will fit.

The number one rule is you cannot say "yes" unless everyone says yes.

If someone has a reservation, don't make the hire until it has been explored and put to bed.

Hire people you want to spend time with

If you're looking to climb the leadership ladder, you're spending more time at work than at home.

Make sure you spend that time with people you like, so it's enjoyable.

Ask yourself: would I have this person over for a BBQ?

Only ask people to do what you have done or would do

Nobody wants to work for the person who asks them to work overtime and come in on weekends unless you're with them.

Lead from the front, not from the back.

It is a marathon, not a sprint

Not all decisions need to be made right away, and some don't even need to be made.


  • Decisions that make themselves
  • Decisions your team can make
  • Decisions that need you

Slow down. Listen. Be more patient and reflective.

Paint a picture for people

Your team needs to know where they're going.

You need to learn how to communicate your vision to your people to get them bought in and rowing alongside you.

Go to Toastmasters and learn.

Learn to see the forest and the trees

Some people are good at detail.

Some people are big picture thinkers.

As a strong leader, you need to be able to zone out to 10,000 feet and get down in the mud and figure things out with your people when required.

TGG Podcast

This week on the Growth Guide Podcast, I talk about why Money is Not Evil.

Society teaches you Money is Evil. It's the biggest lie they tell us.

Most of us are conditioned to believe money is evil and it creates two problems:

  • A scarcity mindset
  • An aversion to wealth

Money is simply a tool and it’s what you do with it that matters.

The different ways society teach you money is evil are:

  • Cartoons
  • Childhood stories
  • Lessons from our parents

I have two sons. I see this on TV, in the media, when they watch cartoons or movies. And, there's no way I'm going to let them think money is evil or they don't deserve it. It's our job as parents to teach them.

To hear more on why Money Isn't Evil: Listen on Apple and Spotify or watch on YouTube:

video preview

Last Word 👋

I love hearing from readers and I'm always looking for your feedback.

How I'm doing with the Growth Guide. Is there anything you want to see more of or less? Which aspects of the Newsletter or Podcast do you like the most?

Hit reply, say hello, and let me know what you think of my Leadership Lessons and what would you add?

I'd love to chat with you !

All my best,


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The Growth Guide

Welcome to the Growth Guide where I simplify psychology, success and money by sharing advice from millionaires, expert authors and my life to help you grow: Personally, Professionally and Financially. Join 26,000+ readers!

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