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.

Conclusion

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.

¹https://xd.adobe.com/ideas/process/ui-design/4-golden-rules-ui-design/

 

Leadership: The Secret Existential Crisis Entrepreneurs Never Talk About

At some point in your journey as an entrepreneur, if you’re lucky, you’re going to face an existential crisis. It’s something few of us talk about but many of us have faced. But if you know it’s coming and you’re prepared, you can get through it with as little pain as possible.

You see . . .

When you start a business or side hustle your work is about two things
Doing great work and/or providing a valuable service or product
Finding customers and helping them understand the value of what you have to offer

These two things are not small, easy, or simple to figure out, but they are at least straightforward. Your work needs to be good and you need customers who see that…

But as you grow and get more customers, offer more complex services, and start to hire people to support you or do some of the work for you, your role begins to change.

You go from being a person who does great work to being a person who creates great work.

And this transition is challenging. Doing great work is simple, you sit down and do your best. Creating great work is more complicated, you are planning, leading, and assuring that great work is getting done.

The skills are different, the former is about keeping track and executing. The latter is about defining and communicating what is good, and then making sure “good” is happening.

I remember when I worked as a house manager at a music venue and the boss asked me to come downstairs. “What’s wrong with this picture?” I looked and everything looked fine to me. “It’s too bright in here,” she clapped back in my silence. “Oh?”

“How dark should it be?” She groaned and lowered the lights. “I can’t tell you everything, you’re just going to have to figure it out.”

I felt discouraged. What she was saying was somewhat helpful. Most places lower the lights at a certain time of night. It increases the vibe, encourages people to buy drinks, and makes it feel less harsh when you come in from the night. But it’s not something I had ever thought about before.

It was good she wanted to teach me, but this was the WORST way to do it. Instead of helping me learn and giving me some guidelines, she just got mad at me. What was OBVIOUS to her was NOT obvious to me.

This is essentially a failure in leadership and it’s something I see founders, entrepreneurs, and owners do ALL the time with new team members.

It all starts with What Can’t They Just!

Often when I listen to founders and entrepreneurs complain about their team members at some point they’ll say Why Can’t They Just . . .
Send me the updates I need
Answer this email
Make a decision on their own

The underlying assumption is that other people SHOULD think like you think. They should be capable, they should be leaders, and they should know what you know and act how you act.

But if your team simply duplicates your skill then
You need more skills
You’re not hiring the right people

The best people bring new ideas and talents to the table. The best people approach problems differently. The best people create things but not the way you will.

The hard thing for most leaders is that they don’t understand how to get good work out of people who are different from them.

So they expect what they would produce and then get upset when they don’t get it.

Next Level Leadership

This isn’t really leadership it’s cloning.
So if you want to be a better leader you’re going to have to let go of this strategy.

The question you should ask yourself is how do I get the best work out of the people I have?
NOT how do I get them to think like me?

The reason why this is so hard for most leaders is that it requires a shift in identity.

You start with the identity of I’M GREAT AT DOING THIS
to I MAKE OTHER PEOPLE GREAT AT DOING THIS

And that shift in identity is hard.

It’s why so many founders end up writing code, getting on sales calls, or micro-managing people on their team.

They don’t trust what other people do and they are unwilling to let anyone else be better than they are.

So as you grow your business get ready for this.

At some point, YOU’LL HAVE TO LET GO OF ALMOST EVERYTHING THAT MADE YOU FEEL CONFIDENT IN YOURSELF WHEN YOU GOT STARTED.

It’s a key initiation as a leader. And a threshold you need to cross if you want to truly become a great leader.

 

Your Urgency Is Made Up—2 Steps to Being a Better Leader

Most of what you think is urgent isn’t urgent.

You don’t need to reply to that email.
You don’t need an update on that in the next 10 mins.
You don’t need to solve that problem on this call.

After working with hundreds of leaders I’ve noticed a pattern.

The most important and hardest problems never get dealt with.
Instead, what’s urgent gets dealt with instead of what is important.

And often why something is urgent is because the leaders think it’s urgent.

Partly this is due to how much founders and entrepreneurs have to get done.
Hell, it seems like we’ve ALL got a lot of things to get done.

The impact of this is that everything seems urgent.
Because you’re behind.
On everything.

So what’s the antidote?

It has two parts:

1) Space

Almost every leader that I’ve coached does better when they have space to step back and reflect. They begin to see the big problems and start dealing with them.

But creating space requires courage, it requires boundaries, it requires commitment.

If you want to be a better leader get ruthless with creating space.

2) Start Distinguishing Fear From Urgency

The other thing that makes leaders get urgent is if they’re anxious. They are worried that something is going to go wrong so they go looking for it. And like a dog hunting for a bone, they won’t give up until they’ve found something.

If you can simply notice when you’re afraid, you can work with your fear. It requires emotional intelligence and honesty, but it’s life-changing.

That’s it. If you just do these two things your leadership will get better and your urgency will go away. Ok maybe not completely but it will get less.

And the result will be a more grounded trustable version of you.

 

The Art of Leadership

Many people think about leadership as a process or a method.

If I input X then I can get my team to give me Y. And that might be true if the people you were leading were simply robots; easy to program and decode.

But the nature of leadership is that it’s messy humans leading messy humans. Humans who have deep-seated fears, hang-ups from the past, and dreams about the future.

So many leaders try their best to squeeze their teams into a box they want them to be in. They talk about leadership like a big chess game or a mass propaganda campaign. For a long time, that kind of leadership was effective, but the smarter and more powerful human beings have become, the less effective that style of leadership has become.

This is why I often talk to my clients about the art of leadership.

When you see leadership as an art you can begin to see the constraints of your team like the colors in your palette.

You can begin to see the uncertainty in the market place as the distortion your eyes create when it looks out on a landscape.

You can begin to see each challenge as an invitation to create art, inspiration, and possibility.

But this can only happen if you let go of the machine of leadership and the x=y mentality.

If you paint by numbers 1 may equal red, but if you paint as an artist 1 can be any color you want, so long as it invokes purpose, beauty, and serves the people you long to change.

Leadership as an art can be intimidating because what’s right gives way to what works and who’s in charge gives way to who’s committed.

But people are done being treated like machines. Especially the kind of smart, talented, caring individuals who you want to lead.

This is why when you take on the task of leading with art not only does your life get easier and more interesting, the people around you also become better at being who they already are.

 

Why I Make My Bed in Hotel Rooms Now

When I worked as a roadie I never made my bed in hotels. Sure I would pick up trash and try not to leave the room as a total disaster (something I wasn’t always effective at), but I never made my bed.

After all, I thought, they’re just going to strip the sheets anyway.

Then I noticed how it made me feel.

I noticed that when I left my room, I felt a bit sad, a bit like a slob, a bit like I don’t really care about myself or my bed.

So I started making it. No military corners or tight lines, but I’d place the pillows in a good place, pull up the comforter and fold it over.

As I sat there and looked at my bed, it felt complete.

Leadership at times is like this, it’s making a bed that someone else will simply mess up.
It’s being something and creating something in the face of that very thing being undone.
Right now as our world is going through so much, you may see this great being undone as a reason not to lead.

When in fact, it’s when we need your leadership the most.