Why is it so hard to learn new stuff?

We say we want to improve only to find ourselves back in old habits and ways of being wondering how we ended up here.

Recently I’ve been working on improving my Spanish and I find myself struggling. I do pretty well for a while and then a waiter will say something I’ve never heard before, a new accent will make the words tricky to discern, or the speed of someone’s speaking overcomes my ability to translate in my head. 

In English, I have a sizeable vocabulary, I can write poetry, make metaphors, and even make clever puns. In Spanish, a 3rd grader has a more advanced vocabulary than I do. I celebrate navigating the grocery store. I rejoice in understanding simple sentences. 

The experience is humbling and it’s HARD. But I’m committed so I keep going. 

This is no different than what it takes to improve your leadership or get better at communicating. You don’t know the vocabulary of good leadership, you don’t know how to navigate listening to people when they talk. 

You have an old language you’re familiar with, a mother tongue of habits and skills you’ve relied on to get you to where you are. 

But in order to learn a new language, to improve as a leader, to serve your team and vision in a new way, you have to let yourself be humbled, to slow down, and to be willing to look foolish and make some mistakes. 

Otherwise, you’ll just end up speaking your old language and never discovering what a new place, people, or language can hold.


Why some leaders aren’t meant for your business

Sometimes leaders think that someone who disagrees isn’t a leader.

But this isn’t true.

You and I can both be on a hike together.

We can both be responsible for getting this small group to our destination.

We can both show up as leaders.

But if one of us wants to go to a different spot, then we’re no longer on the same journey.

We are leading but not together.

This doesn’t mean I’m a leader and you aren’t.

It doesn’t mean if I don’t convince you to follow me I’m not a leader and you are.

Two leaders can lead powerfully and still go different ways.

If you’ve got a great leader on your team.

But they have a different direction.

Get clear on what it is.

Inspire them to lead.

Even if that means it leads them out of your team.


Why leaders won’t follow you

A lot of my clients decry that there are no leaders in their companies. 

They wish people would take more responsibility. 

They wish they would take more initiative. 

But of course they quash any leadership they don’t agree with. 

Creating leaders is one thing. 

Empowering them to make choices is another. 

And letting them make choices you don’t agree with is something else still. 

If you want to create leaders that will follow you, you have to generate trust. 

You have to enroll them. 

You have to really hear out their points of view. 

Otherwise, they either won’t follow you or won’t be leaders. 



At the end of the day as a leader all you have is your instincts.

You might have data, research, a high level view, and some experience, but a lot of times it comes down to gut.

That can be hard to admit.

You want people to agree with you. To believe your arguments. To be right.

Because it feels like you’re being wrapped in data, information, and feeling of trust. 

But in truth you’re totally naked. You have some data and some experience but mostly gut. 

You think the customer wants this not that.
You think the market will go here not there.
You think that this feature will work better than that one. 

It’s ok to say: This is what I think, I might be wrong, but it’s what my gut tells me. I’m open to being challenged but I might go with my gut anyway. 

No one can argue with your gut.
They can challenge your thinking.
Challenge your data.
And it may change your mind.
You gut might respond.

But at the end of the day.
It’s your instinct.
You can be humble and choose it.
And be willing to sit with whatever shows up. 


The Work of a Life Coach

This is my work. Though it doesn’t look like work at all.

Recently, I took a client out to the desert to talk about leadership, life, sex, purpose, the challenges of growing up, and what it means to increase your capacity. 

We wondered at ancient sandstone formations, shared deep secrets, and revealed our hearts and dreams. 

It was a powerful, intimate weekend that both of us will remember for a lifetime. 

This is why I’m a coach. Not simply to improve sales numbers, or increase team engagement, it’s to have life-changing conversations with people who deeply care about their lives and work. 

It’s not work you clock into and out of. It’s work you have to live 24/7, even when that means revealing that less than marketable parts of yourself. But that’s who I am. 

I’m not a 9 – 5 coach. I’m a 24/7 365 person who stands for possibility. And I ask my clients to be the same. No front or back of stage. All on stage. Being proud and intentional about what shows up. And humble and reflective when what shows up isn’t what you’re proud of. 

Why should we ask less of our leaders or of ourselves? 

If this is an adventure you want to go on. Let me know. And if not I hope it inspires you to take an adventure of your own.


Manager vs Director

Some companies hand our director titles like candy, but few really understand the distinction between a manager and a director. So here are some simple guidelines. 

Managers focus on doing things, directors focus on how things are done. 

To the manager, the day is filled with tasks done in a certain order. The focus is efficiency and a willingness to get in there and do stuff or help other people do stuff. 

To a director, the day is filled with understanding how things are done and how they might be done better. They are trying to make tasks happen but they are also looking at what should be happening and how it can happen better. 

Managers focus on projects, directors focus on visions

To the manager, the project is the largest unit of focus. The work needs to be divided up, procedures need to be followed, and people need to be motivated. 

To the director, the vision is the largest unit of focus. This is how things could be. Let’s figure out how to get there. The vision may be their own or part of a larger vision or work in coordination with several other visions, but it’s not just about doing the work it’s about changing the way things work. 

Managers focus on small time scales directors on larger ones

Managers focus on the next 7, 30, and 90 days. They live in the week month and quarter. They manage priorities, they motivate people, and they keep things running on time. 

Directors focus on the next 30, 90, 365, and 1800+ days (5 years) They live in how things will shift in the future. They see over the horizon to what’s coming and they make decisions that will shape what that future is. 

In truth, anyone can be a director. The hardest part is the shift in focus and the shift in identity. If you’ve been a trusted team member for a long time and you’re great at getting things done, learning to shift into thinking about how things happen and what’s coming next is a challenge. 

You no longer get as much done. At least not in the way that you used to. Instead of doing, you create. Instead of managing, you envision. It’s a leap beyond a simple upgrade in skills and it’s a powerful one if you have the courage to make it. 


Where are they right?

In the book Thanks for the Feedback, the authors talk about how most of us receive feedback. 

Someone gives us feedback overtly “You’re giving too many details in the all-hands meetings” or covertly [You interrupt your director and they sigh and cross their arms], and then we filter it for if we agree or disagree with what’s been said. Often we disagree or disagree in part and dismiss the feedback outright. 

A lot of leaders listen to everything this way. 

Do I agree or disagree

  • with that choice
  • with this assessment
  • with this response to a customer
  • with this response to a developer
  • with this feature choice
  • with this order of priorities

The result is often that the leader is always right. And I can assure you it’s not fun to work for a leader who is always right. 

A better way to listen to feedback is to ask:

  • Where are they right? 
  • or
  • What exactly is the feedback I’m getting right now? 
  • or
  • If they want to be good at their work why would they choose or respond like that? 

If you assume benevolence and then seek for the gold you just might find some. 

And if you discover that the feedback is malicious or the choice careless you can always adjust your response as needed.


Where do you have leverage? 

This isn’t about manipulating people. It’s about understanding where you have power in the world and in your relationships. 

Leaders tend to think people will agree with them if they’re right, or if they predicted the future the last time, but while this may get compliance it rarely leads to enrollment and enthusiasm. 

You’re much more likely to get people to follow you if you can learn what they care about and speak to that directly. 


What’s the difference between an employee and a leader?

What’s the difference between an employee and a leader?

You might say it’s responsibility or scope of work, but very often the biggest difference is mindset. 

An employee thinks about their work as a series of tasks to get done. 

Those tasks are clearly defined and their job is to complete them to the satisfaction of their manager or boss. If something isn’t working they might do their best to fix it, but if it’s outside the scope of their job they might also just tell their boss and wait for a solution to be offered. 

A leader thinks about their work as a vision that needs to get created. 

They think about what they want to happen, they assume it’s possible, and then they work to figure out how to make that happen. They have conversations, invent new ways of doing and thinking, ask tough questions, and overcome obstacles in order to bring their vision into a reality. If something goes wrong they accept and adapt as needed. 

Most of us would prefer to lead teams of leaders. 

And yet so many leaders treat their teams as employees. Leaders want their team to do what they would do. So they direct, control, and limit. Worse still they treat their teams as obstacles that need to get fixed, falling into their own employee mindset. 

The world doesn’t need more workers. We need more leaders. And we need leaders who touch, move, and inspire others to lead. 


Leadership Design: How To Design a Better Boss

I’ve had over 30 jobs in my life and that means I’ve had 30+ bosses, leaders, and managers to deal with. I’ve worked for almost every kind of boss you can imagine: the boss who shouts orders, the boss who seems to care but fails to back you up, and the boss who is a genuinely compassionate person. 

Over time I began to realize that all leaders, like apps or buildings, have a certain design. Some of the ones I worked for had a leadership design that made doing work easier and my office life enjoyable. While others had such bad leadership design that not only was it hard to do good work, it made me not want to work at all. 

When I became a coach and started coaching the kind of people I used to work for, I started to wonder what might happen if you applied design principles to leadership. 

Could you design a better boss?

Here’s what I found:

Leadership as a Function of Design

Adobe identifies 4 golden rules of User Design¹:

  1. Place users in control of the interaction
  2. Make it comfortable to interact with 
  3. Reduce excess guessing and thinking
  4. Make the experience consistent

These are all great standards to create a positive user experience. But they are also great standards for good leadership design. 

1. Place users in control of the interactions:

Most founders, CEOs, and Senior managers I coach try to control the people around them. 

They think, “if I can just get them to do what I want them to do then I’m a good leader”. The result is that they end up bullying or pressuring their teams to work as they do. But great leadership isn’t about creating clones, it’s about inspiring people to bring their best selves to work.

If you want to create a good user experience, you must work to let the users have enough control so they can do what they want while also creating the right kind of boundaries so they don’t get lost or confused. This is exactly the same for great leadership.  

If you give your team clear boundaries, goals, and expectations while encouraging them to do their best work, come up with creative solutions, and feel responsible for what they contribute, you’ll have a team that is committed, focused, and inspired. 

2. Make it comfortable to interact with.

If you were scared to use an app, you would never open it, if you were afraid that your coffee maker would kill you, you’d buy a new coffee maker. Good design means a design that is helpful, unobtrusive, and comfortable. 

But most leaders don’t get this. They don’t understand that fear is the #1 motivation that exists in the workplace. They don’t get that people are afraid to be honest because they might get yelled at or fired. They don’t get that people are afraid to take risks because they’re worried their boss won’t have their backs. 

Great leaders understand what’s at stake for their teams and work to make their teams comfortable in working through challenges together. 

They demand respect by setting clear expectations and standards, but they are also open to challenges to their thinking, direct feedback, and radical candor. These leaders understand that if the team trusts their leadership they will work better together especially when hard choices have to be made. 

They don’t let fear go unchecked, instead, they choose to be responsible for the impact of their leadership and they use that responsibility to inspire the team to work together. 

3. Reduce excess guessing and thinking

I’ve worked with leaders that think out loud so often that their teams don’t know what strategy to follow. I’ve also worked with leaders who keep everything so close to the vest their teams are shocked when they suddenly change directions or tell them they’re very disappointed in the work they produced. 

The problem is the same in both cases, the team doesn’t understand what the leader wants. 

Great design might challenge the user to think harder or come up with a creative solution, but they never ask the user to do more guessing or thinking than they need to. 

Great leaders also challenge their teams to come up with creative solutions and do inspiring work. 

4. Make the experience consistent

The last principle of both user design and leadership design is consistency. Great leaders have to ensure that the consistency is both inward and outward. The company culture is being reflected in a way that individuals feel comfortable and at ease (rather than walking on eggshells) and the mission is being consistently utilized.

When leaders are all over the place, it makes for a bumpy ride for the team members. One that prohibits successful work and instead projects the leader’s needs over the company’s.

I’m not saying that the environment has to be cold and heartless, or that the leader should act without emotion. I’m saying that the general goal of both the business and the company culture should be at the forefront of the decision-making and execution within the business.


The goal for leaders today is to get results. However poor leadership design leads to poor morale and experience for the do-ers in the company. As a company continues to grow, the leadership should do so as well. I have no doubt that the design elements listed in this article will continue to play a role in a good leadership design. Placing the user at the front, making it comfortable, reducing guesswork, and being consistent are the ways to design a good boss.