On a Management SLA
What if you published a management SLA for the whole company to use?
Team members would have transparency into the company's management philosophy and know what kind of leadership and commitment to people is valued. New managers would know what was expected of them. They'd know upfront the gaps in their management skills that need development. The company's organizational ambition and its commitment to developing internal leadership would be clear.
Organization design's primary purpose is to provide a framework for unleashing your team's creativity. Whether you choose hierarchical, holocratic, flat, or something else, you want roles and expectations clearly understood and easily communicated. A management SLA provides a base level of consistency across all the company's teams, regardless of function, and outlines a clear set of leadership criteria that all teams can checklist against.
What if you published a management SLA for the whole company to use?
Team members would have transparency into the company's management philosophy and know what kind of leadership and commitment to people is valued. New managers would know what was expected of them. They'd know upfront the gaps in their management skills that need development. The company's organizational ambition and its commitment to developing internal leadership would be clear.
Organization design's primary purpose is to provide a framework for unleashing your team's creativity. Whether you choose hierarchical, holocratic, flat, or something else, you want roles and expectations clearly understood and easily communicated. A management SLA provides a base level of consistency across all the company's teams, regardless of function, and outlines a clear set of leadership criteria that all teams can checklist against.
What might your SLA include? Perhaps frequency and content of one-on-one or performance reviews. Perhaps the need for a strategy offsite or regular team social events. Perhaps the role of team meetings or stand-ups. Whatever works for your org, if you can't write it down in a simple, digestible form that demonstrates consistency across the company, you have work to do.
When I drafted a management SLA at Squarespace and handed it off to HR to run with, the org was growing fast and new team leads were emerging just as rapidly. These team leads deserved a framework they could lean upon, and all team members needed to have a consistent experience in regards to feedback and professional development. Going forward this will help senior management evaluate team leadership across the org.
In scaling a company the most important question is what is the least amount of process and structure necessary to achieve our goals. You have to intrinsically understand the business AND the org AND the people in order to create an environment for people to do their best work. I chose the language of an SLA because it was language our engineering and customer care teams understood. By making it public, the SLA makes it safe to speak up when your manager isn't providing you the support you deserve, while also guiding the curriculum of any leadership and development programs the company is creating.
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.”
On One-on-Ones
Every one-on-one is a personal development opportunity.
It is a manager's responsibility to be regularly available for (and not to miss) a one-on-one and a team member's responsibility to show up and own the agenda. The meeting is owned by the employee because it is her professional development we are focused on. We're not here for a status update – email can handle that fine – but rather to open the pathways that lead to repeat success, removing blockers, and providing a safe environment to nurture not-fully-baked ideas.
My expected agenda is straightforward. First, focus on success. Discuss your wins since we last met. How have you moved the business forward? Be sure to have shared any necessary KPIs or project updates one day prior to meeting face-to-face. Second, air your blockers and frustrations. The most valuable data I can capture is how the org and, more importantly, I am preventing you from being successful. Third, and this is the fun part, what do you want to spitball? Use me as a sounding board to think through ideas, no matter how zany, before you are ready to present them to the team. Lastly, discuss the needs of the team and how you can contribute to addressing them.
Every one-on-one is a personal development opportunity.
It is a manager's responsibility to be regularly available for (and not to miss) a one-on-one and a team member's responsibility to show up and own the agenda. The meeting is owned by the employee because it is her professional development we are focused on. We're not here for a status update – email can handle that fine – but rather to open the pathways that lead to repeat success, removing blockers, and providing a safe environment to nurture not-fully-baked ideas.
My expected agenda is straightforward. First, focus on success. Discuss your wins since we last met. How have you moved the business forward? Be sure to have shared any necessary KPIs or project updates one day prior to meeting face-to-face. Second, air your blockers and frustrations. The most valuable data I can capture is how the org and, more importantly, I am preventing you from being successful. Third, and this is the fun part, what do you want to spitball? Use me as a sounding board to think through ideas, no matter how zany, before you are ready to present them to the team. Lastly, discuss the needs of the team and how you can contribute to addressing them.
Frequency should not be dictated by a recurring event on the calendar, though bi-weekly is a good pace and you should never go four weeks without a one-on-one. Sometimes you need to meet weekly, other times monthly. If I reserve the proper amount of office hours each week, my team members can pull the one-on-one as needed. I recommend booking an hour. It's better to use ten minutes and leave time over than to only book 30 and find yourself not getting all the face time you deserve.
I like to keep a shared Google Doc for each team member. It's easy to add a new agenda to the top of the doc, and to take notes during the meeting for reference. Obviously, it's also convenient for noting items that need to be covered at the next meeting. Notes and follow-through are critical in all meetings, big and small.
I'll discuss my role in providing you feedback at these meetings in a later post. You should never have to ask for it.
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.