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Thoughts on how to become a better leader, and avoid being a bad boss.

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The Power of the Pen: 6 excellent books on leadership development

From over 1,000+ leaders all over the world, here are the six most-recommended books if you’re looking to become a good leader. We all have that one book — the one that shaped who we are as leaders. For some of us, it may have been more than one book. For others, perhaps we’re still on the… Read the full article...

The 3 Ways Leaders Can Influence Company Culture

  How do you help create the positive workplace culture you’re looking for? Start here. “How do you actually influence company culture?” This is the big, hairy question I often get asked by CEOs, managers, and employees alike. I recently posed it at the end of the piece, The 3 Key Elements of Company Culture — And Why… Read the full article...

The Bad News Advantage: The importance of giving difficult feedback

Why sharing bad news makes you a more effective leader. Sharing bad news is a good thing. As a leader, you might not think it, at first. But it’s true. Leaders who are honest about the bad — just as much as the good — are better leaders. But it’s not just me saying this. Research proves this. In… Read the full article...

How to respond to the negative feedback that’s most-frustrating to hear

Here are some sample responses to the 3 types of negative feedback that are most infuriating to hear. The feedback we receive can sometimes feel like bullshit. I recently spoke with a CEO who told me she received feedback from an employee who proclaimed, “This company doesn’t care about parents.” The employee then proceeded to gripe… Read the full article...

The 5 ways to improve your self-awareness as a leader

The most overlooked element of a successful leader is self-awareness. Here’s why and what you can do about it.   A few months ago, I asked Ben Congleton, CEO of Olark, what he wished he’d learned earlier as a leader. No, he didn’t mention learning a new business development hack, nor did he talk about the… Read the full article...

Improve your leadership through actions – not words

If you’re looking to improve your management style, consider how action-oriented your leadership style is. The quickest way to improve your leadership skills is to live this phrase:  “It’s not what you say that matters — it’s what you do.” I observed the truth of this old adage, firsthand, about six years ago. At the time, I wasn’t CEO… Read the full article...

The 2 most common excuses that keep you from getting honest feedback

Take a closer look: You may be unintentionally cutting yourself off from the honest feedback you want to hear. I was on the phone with a CEO the other week. He wanted my advice on how he could cultivate a more open, transparent company culture for his team. This CEO seemed to be already doing a… Read the full article...

Six tips to rock your one-on-ones

Quick, handy best practices to have effective, productive 1-on-1 meetings with your team One-on-ones with employees are one of the most underrated tools for managers. If done properly, these meetings can be an incredibly effective way for managers to receive feedback, gauge employee satisfaction and productivity and even offer some insight into how team members… Read the full article...

The 3 Key Elements of Company Culture — And Why They Really Matter

Let’s look past the buzzword and define the key elements of organizational culture. “Culture” has become the ultimate buzzword these days. Everyone wants to “improve their company culture.” I see the word frequently littered across the headlines of countless articles, book titles, and conference talk topics. Leaders also seem to talk about it all the… Read the full article...

The 8 best questions to ask during a one-on-one meeting

What should you put on your next one-on-one meeting agenda? These one-on-one meeting questions should be a part of every manager’s toolkit. That one-on-one meeting is scheduled on your calendar this week. So, what should you talk about? As a manager, executive, or business owner, this is one of the most recurring and perplexing situations… Read the full article...

The 25 best icebreaker questions for team-building at work

Our most popular get-to-know-you questions for work, based on four years of data. If you winced at the word, “icebreaker,” I don’t blame you. Get-to-know-you questions and games tend to feel cheesy. We’ve all been victim to a terribly trite icebreaker with coworkers that made us roll our eyes. I know I have. However reluctantly, you… Read the full article...

How cereal improves employee engagement

As unlikely as it sounds, breakfast cereal can be the ultimate team-builder and way to boost your team’s morale. The executive director of a prominent nonprofit called iMentor Chicago reached out to me the other week. Her name is Halleemah Nash. “A question I asked my team a few months ago really caught me off guard,”… Read the full article...

Top 19 Leadership Lessons from AMA with David Heinemeier Hansson (DHH), CTO of Basecamp

  /How do you structure your day as a leader? Favorite leadership books? CTO of Basecamp and Creator of Ruby on Rails, David, shares his answer to these questions and more. What kind of leader is David Heinemeier Hansson? We were lucky enough to find out his management style, leadership lessons learned, and more during… Read the full article...

7 ways to prepare for an effective one-on-one meeting with your manager

Got an upcoming one-on-one meeting with your manager? Consider a few of these tips in preparation for it. Many managers say flat-out that their biggest frustration is when employees are not prepared for a one-on-one meeting. Yikes, really? Over the past four years, I’ve heard countless managers, CEOs, and business owners say a version of this… Read the full article...

Want to improve your management style? Screw the Golden Rule

Here’s why “Treat others the way you want to be treated” doesn’t work as an effective leadership strategy. “Treat others the way you’d like to be treated.” This is The Golden Rule we all learned growing up. As a manager or CEO in a company, you’d think it would make sense to follow it too.… Read the full article...

Top 13 Leadership Lessons from AMA with Amir Salihefendic, CEO of Doist

As the CEO and founder of a bootstrapped, remote company with over 13 million customers, Amir shared his leadership lessons learned with our online community. Every few weeks, we invite one of our 1,000+ members from all over the world in Canopy to participate in an “Ask Me Anything” (AMA) session. It’s an opportunity for us… Read the full article...

Watch: Stop Feeding Shit Sandwiches — the worst method of giving feedback

In this 5 minute lightning talk given at Disrupt HR, I share the worst way to deliver feedback – and what we should do instead. Ever catch yourself feeding a shit sandwich? You know, when you layer your feedback good-back-good. I happen to think this technique is the absolute worst method to give feedback in the… Read the full article...

Top 5 Leadership Lessons from AMA with Valentina Thörner, of Automattic

In our leadership community in Canopy, Val shared her expertise leading a world-class, remote support team in our first ever AMA. Here are the top 5 leadership lessons learned from it. In our leadership community, we recently kicked off a series of “Ask Me Anything” (AMA) sessions, featuring members we respect and want to garner more… Read the full article...

How to fire someone with grace, dignity, and respect

The “right way” to fire an employee doesn’t exist — but we can all get closer to it by keeping these 6 things in mind. A few months ago, I fired someone. Ugh. It was gut-wrenching. I’ve fired people before – but it doesn’t matter how many times you do it, it always feels downright terrible. This moment… Read the full article...

Company culture: a lesson from albizia trees — what happens when growth is “tall and fast”…

Nature can teach us a lesson about company culture “Did you hear that noise?” I was in Hawaii last week walking along the Manoa Falls Trail, when our guide who was taking us through stopped us. We all shook our heads, “no.” “Okay, well that’s good,” he said. “If we had, it would have been the… Read the full article...

Why we dismiss negative employee feedback

Three fallacies that get in the way of taking constructive feedback. Here’s how by recognizing them, we can overcome them. My stomach dropped. My face flushed. I thought to myself: “No way that’s true!” and “No way that’s me” Those were my physical and mental reactions when an acquaintance gave me some feedback a few years ago. (She… Read the full article...

Close the loop: The critical principle of good leadership

You can’t just make the call if you want to be a good leader — you’ve got to explain it. Leadership is about making the call. Or, at least that’s what we seem to think. We seem to think leadership is about making the complex decision. As captain of the ship, you survey the seas — what your board is… Read the full article...

How to repair the trust of your team as a leader

One in three employees don’t trust their employer. As a manager, here’s what you can do about this significant leadership weakness I recently came across a 2016 study conducted by Edelman where they’d surveyed 33,000 people in 28 countries. From it, they discovered: One in three people don’t trust their employer. One in three people… Read the full article...

The power of assuming positive intent

My greatest leadership weakness, and how I’m learning to overcome it My parents were in town last week. During one conversation we had, my mom shared an opinion that I strongly disagreed with. And as I responded to her, she said this to me: “You’re getting defensive.” Throughout my life, I’ve heard this quite often. Getting… Read the full article...

Anonymous employee feedback breeds a culture of distrust

The pitfalls of anonymous employee feedback aren’t often talked about. Here’s how it can backfire. As the CEO of Canopy, I often get asked about my opinion on asking employees for anonymous feedback. Is it a useful approach? Would I recommend it? My answer is the same each time: I hate anonymous feedback. I hate… Read the full article...

The Bad Boss vs The Good Boss

How to avoid becoming a bad boss — “The Boss You Don’t Want to Be.” “People leave bosses, not companies.” We’ve all heard this truism in corporate leadership discussions. But how many of us have lived that statement? How many of us have left a bad boss? How many of us know what it’s like to work for… Read the full article...

8 things leaders of remote companies do differently

If you’re thinking of going remote, here’s what successful leaders of remote companies do Earlier this month, I spoke with a CEO who’s looking to transition her company to become remote in the upcoming year. I could tell she was hesitant — perhaps even nervous about it. She’d never run a remote company before. She asked me:… Read the full article...

The 10 qualities of a good leader

What I’ve observed from effective leaders and tried to keep in mind as a CEO these past few years “This is somewhat terrifying.” I remember thinking this when I became the CEO of Canopy back in January 2014. Sure, I’d started two companies beforehand — but one was with close friends, and the other was by myself. With… Read the full article...

Don’t let worry become a leadership weakness

Worry is a natural byproduct and characteristic of a leader. Here are five ways to cope with worrying as a leader. The other week, I interviewed Jason Fried, CEO and co-founder of Basecamp. I asked him what he wish he would’ve learned earlier as a leader. His response? Worry less. I smiled when he said this.… Read the full article...

Don’t want to be a bad manager? Stop feeding Shit Sandwiches

One of the most popular methods of delivering difficult employee feedback is, well, shit. Here’s why and what you should do instead I recently ran into a friend who mentioned how she uses the Shit Sandwich to deliver feedback. If you’re not familiar with it, the Shit Sandwich is a technique for delivering feedback popularized by… Read the full article...
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