Humility and Fierce Resolve
I pulled out my notes on Good to Great to find a quote or two for yesterday's blog post on self-awareness. Inevitably I found other quotes meaningful to me. They speak for themselves and since my drafts queue is full of half-finished ideas, allow me to simply share them with you below. You'll find my brief comments in italics. The title of this post refers to the two key qualities found in all of Collins' Level 5 leaders.
Management and leadership is not about those doing the managing and leading, but rather about those being managed and led.
... Level 5 leaders have ambition not for themselves but for their companies ... Level 5 leaders want to see their companies become even more successful in the next generation and are comfortable with the idea that most people won’t even know that the roots of that success trace back to them. As one Level 5 CEO said, “I want to look from my porch, see the company as one of the great companies in the world someday, and be able to say, ‘I used to work there.’ ”
I pulled out my notes on Good to Great to find a quote or two for yesterday's blog post on self-awareness. Inevitably I found other quotes meaningful to me. They speak for themselves and since my drafts queue is full of half-finished ideas, allow me to simply share them with you below. You'll find my brief comments in italics. The title of this post refers to the two key qualities found in all of Collins' Level 5 leaders.
Management and leadership is not about those doing the managing and leading, but rather about those being managed and led.
... Level 5 leaders have ambition not for themselves but for their companies ... Level 5 leaders want to see their companies become even more successful in the next generation and are comfortable with the idea that most people won’t even know that the roots of that success trace back to them. As one Level 5 CEO said, “I want to look from my porch, see the company as one of the great companies in the world someday, and be able to say, ‘I used to work there.’ ”
The hardest thing a manager has to do is let someone go. It is always gut-wrenching for both parties. To be great you must relentlessly focus on the long-term ambitions of the company. As a result tough decisions become necessary and obvious.
Letting the wrong people hang around is unfair to all the right people, as they inevitably find themselves compensating for the inadequacies of the wrong people. Worse, it can drive away the best people. Strong performers are intrinsically motivated by performance, and when they see their efforts impeded by carrying extra weight, they eventually become frustrated.
When it comes to product, Squarespace's Anthony Casalena embodies this lesson more than any founder I know.
Good is the enemy of great. And that is one of the key reasons why we have so little that becomes great. We don't have great schools, principally because we have good schools. We don't have great government, principally because we have good government. Few people attain great lives, in large part because it is just so easy to settle for a good life.
Only rocket science is rocket science and only saving lives is saving lives. The rest of us should remember that work is just work. Don't overthink it. Focus on your family and choose work that is deeply meaningful to you. The rest will follow. For me that means choosing to help grow teams creating innovative software that has tangible and meaningful impact on the lives of the individuals who use it.
When [what you are deeply passionate about, what you can be best in the world at and what drives your economic engine] come together, not only does your work move toward greatness, but so does your life. For, in the end, it is impossible to have a great life unless it is a meaningful life. And it is very difficult to have a meaningful life without meaningful work. Perhaps, then, you might gain that rare tranquility that comes from knowing that you’ve had a hand in creating something of intrinsic excellence that makes a contribution. Indeed, you might even gain that deepest of all satisfactions: knowing that your short time here on this earth has been well spent, and that it mattered.
You Deserve
You deserve to surround yourself with a team that has the right culture, one capable of moving with urgency to solve problems that create new opportunities. You deserve to be part of a team that enjoys helping each other become increasingly successful.
You deserve to work with folks with little tolerance for politics and posturing because it undermines the culture that can drive success. You deserve leaders that welcome mistakes but hate needless surprises.
You deserve the trust and freedom to speak candidly and honestly, and count on your colleagues to do the same. You deserve teammates that feel a huge obligation to hold themselves personally accountable for everything one does. Teammates that take responsibility when something goes right and when something goes wrong.
You deserve to surround yourself with a team that has the right culture, one capable of moving with urgency to solve problems that create new opportunities. You deserve to be part of a team that enjoys helping each other become increasingly successful.
You deserve to work with folks with little tolerance for politics and posturing because it undermines the culture that can drive success. You deserve leaders that welcome mistakes but hate needless surprises.
You deserve the trust and freedom to speak candidly and honestly, and to count on your colleagues to do the same. You deserve teammates that feel a huge obligation to hold themselves personally accountable for everything one does. Teammates that take responsibility when something goes right and when something goes wrong.
You deserve leaders who provide creativity a nourishing environment largely free of the constraints of time and capital. In return, you deserve an org that never uses creativity to create excuses.
You understand that every penny of cost or expense of a business is paid for with customer revenue. You deserve to be compensated richly for teamwork and performance, and understand that the cost of paying an underperformer to leave is demonstrably less than the cost of keeping them around.
You deserve a team that knows that nothing is more important to the right culture than the customer, no matter what burning fire comes up.
You deserve to be part of a team of such character.
On Walking and Talking
My most productive one-on-ones don't take place in the office. They happen on the streets of Manhattan, where two miles at a brisk pace gets the blood flowing, clears the brain for creativity, and lowers defenses. On the sidewalk bullshit seems to melt away and real connections can be made.
My most productive one-on-ones don't take place in the office. They happen on the streets of Manhattan, where two miles at a brisk pace gets the blood flowing, clears the brain for creativity, and lowers defenses. On the sidewalk bullshit seems to melt away and real connections can be made.
Walking for a meeting focuses you to get to the point quicker. Undoubtedly this is because exercise is relaxing and a change of scenery is liberating. It is far too easy for the noise of an open floor plan and the limited confines of conference rooms to start sucking the life out of you. The best part is that a walk requires you to step away from a screen and leave your phone in your pocket.
I'm also a huge fan of the walking interview for these very same reasons. The casual and friendly nature of a walk is one of the fastest ways to get past the mutual sales mode of an interview and size someone up.
October in New York is almost over and it's going to be chilly soon. Go take a walk while you can still enjoy it!
On Heartbreak
If you’re going through hell, keep going.
Two choices, same message, both true.
“If you’re going through hell, keep going.”
“It will all work out in the end. If it hasn’t worked out, it’s not the end.”
Goodbye, Squarespace
Twice in my career I've taken leave and found it difficult to return. The first time, when my son was born. The second, this past week. I was on Cape Cod for our annual holiday and felt really, truly present for my family in a way that I don't feel often enough. It also happened in Brazil when we went for the World Cup, so this has been a summer of reflection about what kind of dad I want to be and what kind of relationship I want my family to have with me.
“Even when change is elective, it will disorient you. You may go through anxiety. You will miss aspects of your former life. It doesn’t matter. The trick is to know in advance of making any big change that you’re going to be thrown off your feet by it. So you prepare for this inevitable disorientation and steady yourself to get through it. Then you take the challenge, make the change, and achieve your dream.”
Twice in my career I've taken leave and found it difficult to return. The first time, when my son was born. The second, this past week. I was on Cape Cod for our annual holiday and felt really, truly present for my family in a way that I don't feel often enough. It also happened in Brazil when we went for the World Cup, so this has been a summer of reflection about what kind of dad I want to be and what kind of relationship I want my family to have with me.
When I joined Squarespace four years ago next week, Lila was four and Remy was weeks old (Kiki wasn't even an idea). All parents know that the one constant with your kids is that whether they are filling you with joy or driving you up a wall, it all goes very, very fast. Lila starts 3rd grade next year and is closer to a teenager than a toddler. A friend reminded me recently that work is a rubber ball and family a glass ball. The work ball can bounce. I am making the choice to go take care of my precious glass ball.
I am a builder, and Anthony and I have certainly had a productive four year relationship. From 24 employees to nearly 400. From modest revenue to double digit growth multiples. From a handful of engineers to marketing, HR, business intelligence, customer service, QA, dev evangelists, to a Super Bowl ad and beyond, all the pieces are now in place. I did my job: I built an organization and worked myself out of a job.
Of course, when you have an amazing product, it's much easier to be a successful businessman. I'm most proud of how we brought all our disciplines together – product, marketing, customer service – to deliver the unparalleled customer experience that drives our growth.
Next Adventure
Being a manager and being a founder's lieutenant have a lot in common. In my philosophy both are necessarily selfless and often unfortunately thankless. You elevate your people by putting their needs first, by devoting yourself to helping them meet their goals, by helping to define their ambition, and by providing them the support and coaching they require to be their best self. You derive your satisfaction from seeing others succeed, giving away the credit and the ideas, and sometimes taking the blame.
I love coaching people, and have a solid track record helping young companies frame their ideas and build their foundations. I've become a more active investor and advisor over the past 18 months and I plan on digging deep to help a few early stage companies cross the chasm. I've already got my first two projects lined up. If my nose for investment opportunity matches my ability to build and scale nascent businesses, then perhaps I have found my next calling.
Thank You Squarespace
Thanks first and foremost to Anthony, who has taught me so much, most importantly the power of focus and saying no. He turned this type-a multi-tasker into a rank-ordered list lover. To my team, who repeatedly showed me what passion and ingenuity were capable of and whose development and success fill me with pride. To my peers on our leadership team, who each challenged me to be my best self and taught me valuable lessons that will pay dividends in my future endeavours. And lastly to my friend John, who always returns my focus to the glass ball. Squarespace has been a wonderfully life-changing experience.
I'm long Squarespace. The team is remarkable, the product pipeline strong, and the leadership we brought in is what gives me the confidence to depart. I'm a proud shareholder that can't wait to see the company scale new heights.