Setting your team up for distributed heavy lifting
Thoughts Brewed: Edition No. 16
Hey everyone,
Happy Summer! Last post I wrote was on the need for a tech ethics board and I mentioned that something top of mind was giving away lego blocks as leaders. Let’s dive into the thoughts I’ve brewed on how you set yourself and team up for what I call “distributed lifting” (or shared responsibilies) in an organization…
Setting your team up for distributed lifting
I originally wrote this from 40,000 feet (~12,000m) in the air, headed toward the first bit of normalcy I’ve felt in over a year. My 5 year old (or 5 ½ as she’d remind you) is napping next to me -- ha! Suck it future jet lag. My Google Docs trying to reconnect in the air, I was reminded that despite sitting in a tube in the air flying as they communicate to other planes in the air, Google docs is struggling to keep the wifi connected. I question why the limitation exists; is it intentional on the airline’s doing, lack of resources for this issue by the company, a strategic one, or the point in which we reach the limitation where technology and physics collide? There was a constraint and limitation, and I genuinely want to know why.
Another time…
Fast forward to March 2021 and I couldn’t help but wonder why my to-do list was 5x the size as everyone else's already large to-do lists. I had developed a bad habit of front-loading my to-do list for the week, with so much being piled into Monday. I had my hands in everything helping wherever I could and a core of my time still being spent in Design, despite being pulled in so many other directions.
I’ve always been someone that had a million things going on in my head at any given time. And I’m someone that loves having something to do, something to get my hands dirty in. I’ve recently taken the time to acknowledge that my brain is like a Ferrari with the brakes of a tricycle. Building a rocket ship in the making, there are a number of things that can go wrong at any given time. One thing I promised myself though was that I would always do my best to build the team with intentionality. That takes a lot of work, but the outcome is so deeply worth it. A healthy and high performance team, a place where people are challenged to do their best work, and a mission headed for success that nobody wanted to turn down. And every step of the way, I’ve found myself more and more proud of our ability to do just that.
Absolutely toast from fundraising followed by hitting the ground running post-hiring, I ended 2020 in an absolute blur. Probably because it was company building, fundraising, dealing with a global pandemic, and homeschooling a 5 year old — all at once. I still haven’t really put down on digital paper anything about the fundraising experience.
I kicked off 2021 with rest and an initial task to start my executive coaching. I was no longer just the founder of a team clearly onto something. I was now the CEO of a company supercharged by our first investment round and rapidly scaling the team and business. And quite frankly, I wanted to make sure I didn’t suck at it. To date, I’d argue hiring an exec coach will always be a top 3 investment I made while building Stark.
There were things that I had questions about and that I needed answers for. for. But I knew I didn’t necessarily want direct answers that told me what to cook and the exact recipe by someone else who had done it. What I needed was someone to talk to me about how cooking happens elsewhere—ideally in kitchens completely different to mine. I needed to learn about the art of cooking and the different approaches. Of course, it was up to me to decide on the ingredients, make the meal, and present it. I just needed an expanded mental model of not just how to cook, but how to cook at a Michelin star level.
In fact, I needed mental models for quite a few things in this kitchen, because one thing was certain: this kitchen was growing and more people were coming to us for some Michelin level dishes. So off to the races we went covering any topic that was relevant or top-of-mind, with each week being different. Some weeks it was about how to concretize policy, others about the conversational dance with customers and investors to make sure I knew when to listen, and the different ways to respond to yield the best results.
But something funky was happening toward the tail end of Q1 2021.
Things were continually getting pushed back. I was working more to avoid becoming a knot in the workflow. I realized when designing a major integration that it's super hard to go from the highest altitude (like top level strategizing) to a more narrow vertical like designing and code, and still be productive or helpful. I realized a few things about actively zoning out for hours on whatever I was designing: those hours turn to days and weeks.
Doing so was completely taking away from higher priority tasks that need to be done by me—which sit at higher levels of thinking. I was exhausted—removing so many of the healthy habit time design blocks I had set in place. And if you know like I know, if those aren’t there, it’s a one way ticket to downfall.
I needed to stop designing. And I remember sitting on the couch, my brain running at super speed about the major shift that would happen. Benedikt sitting across from me, I looked up and said, “So my job shifts to making sure everyone has what they need to do THEIR job properly?! WHERE’S THE MUCK TO GET INTO?!” He laughed and replied “Yes!”. And I laugh now knowing the muck is very much there, it’s just different.
My job would be to get the team to see where things are going extremely well and repeat that, properly allocate, take notice of where we are making mistakes so we can course correct, and continue to build out the broader Big Ass Vision. In this specific case recently, it would be to help one of our designers learn how to truly shift into a lead role. What I needed to remove was the ambiguity and nervousness that would inevitably come if I didn’t make this move.
You see, when you hire high-performing people, there’s never a problem with being able to move fast or wear multiple hats. However, once it’s no longer the “norm” it becomes less efficient, and you start to tap into a region of the brain that treads on threat. Not because there’s anything fundamentally wrong or unhealthy about the company at that moment, but because the brain recognizes it’ll end up trending in that direction. We weren’t at that point, but for many companies, the first point of growth is the first opportunity to introduce this issue.
Not in this company. I needed to just rip the bandaid off. It felt counter productive to do anything else, and that was emotionally and cognitively heavy. I needed to swiftly act on three key things:
Scale myself as a CEO → To prepare these next major milestones and years ahead, and be able to ensure 1 and 2 happen successfully.
Scale the team → Step back and simultaneously put capable folks into roles where they had the opportunity to lead and succeed.
Scale the company → Focus on higher level thinking in my own work time.
In doing this, along with a few shifts to general processes, the company would become the most stable possible solely because the team would officially share the heavy lifting.
Scaling the team and setting them up to lead
After designing for almost two decades along with spearheading the design ofStark for a few years now, I needed to step back from it. This was a tough decision emotionally for me as a designer-turned-CEO, but certainly not a difficult decision. I was so grateful knowing I had the ability to share my recipe for leadership and design thinking with a teammate that was very capable of growing into and excelling in the role. And I loved knowing my role is to take our big vision and focus on designing the broad strokes that set our team up for success. Not just from a strategy or product stan/dpoint, but also ensuring our teammates are getting max value and success out of their roles, too.
When anyone first joins, they’re promised an extremely challenging, rewarding, and safe place to do (hopefully) the best work of their careers. How do we put them, by default, into what I consider a circle of success (I’ll dive deeper into these pillars in another post)?
Awareness → Choice → Responsibility → Empowerment
“Give a good idea to a mediocre team, and they’ll find a way to screw it up. Give a mediocre idea to a good team, and they’ll find a way to make it better. The goal needs to be to get the team right, get them moving in the right direction, and get them to see where they are making mistakes and where they are succeeding.”
FYI: This direct quote is from Daniel Coyle in Culture Code, but he borrowed it from Ed Catmull at Disney and expanded on it. Something something “great artists steal”. Anyways...
In order to enable and empower the team I needed to use any opportunity to share my principles for thinking and decision making, so that they could make their own daily decisions accordingly.
One way to do this is by kickstarting weekly 1:1 meetings with, who you deem as, your direct reports. You can and should follow this weekly (if you need it) or bi-weekly meetings with each of those reports together in what’s considered an LT (Lead Team) Meeting. Your direct reports are those designated to oversee a particular discipline; in our case, this is: technology, design, marketing, and community.
When putting processes in place, we actively work to ensure what we do for one applies to the whole, and what we decide on now is something that has the ability to scale. We do so knowing good and well that as a company with a Kaizen mentality, we’ll revisit these every x-months. But the practice of understanding how a single atom can impact the entire nucleus is important.
As an organization grows it’s very likely and common that even more info doesn’t get evenly distributed. You can even think of this as a really peaky bell curve. You’ll typically find this in the likes of Amazon, for instance. Your job as a leader is to build a high functioning and high performance team and set of processes to work against that bell curve peak as much as we can.
Nassim Nicholas Taleb has a whole ass chapter on the dumbness of the Bell Curve that explains my stance on this much better:
"…because the bell curve ignores large deviations, cannot handle them, yet makes us confident that we have tamed uncertainty. Its nickname in this book is GIF, Great Intellectual Fraud.” —Nassim Nicholas Taleb
I thought the whole concept was a fraud and counterproductive to the way companies could and should maximize on the ROI that is hiring (and innovation).
So I re-defined the ideal organizational bell curve.
The goal I wanted to make sure of was that whatever processes were put in place ensured that while those at the end of the bell (think: support,) may not receive as much information as those at the top (think: CEO, executives, board, etc.), that the little amount received was nothing but quality and efficiency—ensuring they could share in the distributed lifting and feel that circle of success, too.
We want to make sure we distribute as much info as possible to as many as possible but of course there is a limitation. Think: part time employee or contract. Validating my argument that consultants are more harmful than good (another post for another time).
At the same time we want to make sure the info they receive is quality information in a way that helps them do their job well. Does this change once you get to the size of Amazon, Microsoft, etc? Absolutely. The goal isn’t to stop a curve, it’s to make sure it’s not peaky! Peaky Bell Curves create pesky behavior. Say that 5x fast…
Scaling the company
During a very long walk on the Friday following the execution of the decision to shift out of design and designate a Product Design Lead, I was thinking about the move we made to the team and my role just days prior. And how I felt immediately relieved because it offloaded so much of what had become sludge to me, and allowed me to take on so much critical strategy, customer, and fundraising related work. I found myself with "less" to do but so much critical stuff to fill my to-do list with! Part of what made me realize I needed to make this move was that my to-do list was 5x the size of everyone else's. Doesn't mean their lists were small AT ALL—mine was just way too large. So offloading has been brilliant.
At times, I feel like I've delegated nearly everything. What is my role then? My role is to keep others growing and help them find ways to delegate. We’ve started to build parallel teams, and with that, establish leads of said teams. My Direct Reports updating me weekly and discussing whatever is top of mind, we’d now work together to continually discuss:
How to make their daily work more optimized
The different ways we can enable the folks of individual contributors they lead to confidently and efficiently increase not just the volume of projects but the scope and complexity of said projects.
The people stuff. Projects are managed and people are lead. Be it a Chief Technology Office or a Product Design Lead, you’re in the business of people and it’s your job to make sure they have a well rounded circle of success.
Give away your lego blocks, people. Just make sure you share the strategy to the tower building.
Scaling myself as a CEO
I kept asking myself what has led to positive non-incremental change for me over the course of the last few months? What actions remove the need for 100 decisions but, instead, get me to a single decision needing to be made? I needed to pinpoint that so I could keep repeating it, and then establish mental models around why they are successful and how they can be applied elsewhere.
A few things stood out most:
Reading
Writing
Thinking
I know. You were expecting some grand wisdom, right? Me too. But alas, it always goes back to the fundamentals, and it’s the discipline to stick to those fundamentals that requires hard work.
In adding those mission critical tasks to my to-do list, I felt guilty for one of those things being reading and learning what I need to in order to now scale myself and help others on the team do the same. It's not any different than what I have been doing technically, but the idea of carving out dedicated time each day or week to read all that I need to learn was an absolute kryptonite in that moment—from aspects of the business I’ve not experienced yet to helping others execute on that growth.
Realistically, I won’t know 100% of what I need for this next phase, but I have the capacity, the coaching, the team (+ extended team of investors), intelligence (IQ and EQ) to do it. And I need to unlearn that while the team may be actively working on direct things for the company (design + engineering + marketing), part of my job is to learn, in the same way that I write.
I need to learn the trade of my new craft.
One of the key challenges I’d come to face more and more is to decide what the most important things are to focus on though. As a CEO, you will always be time poor while running a startup and there are a million things that could be done. Deciding what to focus on and what the most critical items are is a key success factor. The less day-to-day tasks you have, the more you can focus on what’s most important and take that time for strategic learning and thinking.
I spend 1 hour per week with my exec coach discussing things that are top of mind, recent or upcoming events at the company, and how I’m personally navigating the waters. With that, like I mentioned, we discuss the frameworks to thinking about and executing on these topics.
Every day I have two (2) 1-hour blocks in my cal for reading, writing, and learning. And not everything I read is directly related to Stark.
I subscribe to ~5 newsletters that I read religiously—almost all business, leadership, or mental model related.
I shuffle between ~4 different books at any given time (a mix of business, history, science/med, novel, memoir, etc).
I try to write down thoughts from things that occurred during the week, topics that are top of mind or relevant, or debriefing things I’ve learned through coaching or my own self-work.
I’ve worked extensively on understanding how to read and learn. And how to do so in a way that links learning to a spectrum of areas it can apply. And because what I focus on is key, it’s almost always something that can be directly tied to what I’m working on. This has absolutely impacted time optimization in the best ways as well.
On the topic of writing: Writing doesn’t necessarily…spark joy. But to me it’s the most effective method, with compounding interest, in an effort to expedite the research I conduct toward the validation or debunking of my hypotheses on any given core focus.
And then there’s the self-learning. What I’ve managed to do (as a byproduct of being a founder, mother, partner, human, and individual with anxiety) is self work. There’s a lot of toxic behaviors that many founders often bring into the team dynamic which could end up being the fruit that poisons the tree. Understandable too, with founders building up teams straight out of college when they’ve barely learned about themselves. Although it feels unnatural to what you want and need to do, spending time unlearning a lot of what we’ve been raised with benefits not only you, but your team. Realistically, not every founder cares about this, but on this team, there’s a high intention to take care of the people.
As a leader, being able to have people learn their patterns is an absolutely essential piece to ensure they act from greater awareness. But that starts with you. You can’t teach what you don’t know.
One thing I’ve managed to embody extremely well is discipline. With discipline comes a natural ability to understand your position in the greater mission and, with that, the role you play toward your colleagues in carrying the tree trunk. Your teammates need to understand that in moments that are scary, feel like complete shit, uncertain, long winded, and tap into their uncomfy patterns, you of all people will root deeper into the ground to ensure everyone can hold steady—and everyone will follow suit. Why? Not because of fear, but because they understand you act from a place of vulnerability, humility, and strategy.
“If we want people to fully show up, to bring their whole selves including their unarmored, whole hearts—so that we can innovate, solve problems, and serve people—we have to be vigilant about creating a culture in which people feel safe, seen, heard, and respected.” ― Brené Brown, Dare to Lead
You’ll know you’ve become so disciplined and put in the good self work to the point that you’re dangerous, when you’re able to confidently and powerfully quote Brene Brown.
In any company, but specifically startups, you have profit inflection points disguised as a crisis. If you take on something that’s a problem and get the solution right, it accelerates your probability of getting closer to profit. And the ability to do so happens when solution-oriented people have the right information so they can figure out what needs to be done.
This starts and ends with you, CEO.
How do you set your team up for distributed lifting? Share your frameworks with me!
Stuff around the web
A few features and relevant things in my day to day worth celebrating…
Interviewed by the Economic Times: Thrilled to have been interviewed as an expert on a topic we focus heavily on with accessibility adherence—inclusive design.
Featured in the Wall Street Journal: I was interviewed by the WSJ as an expert in the space to share some thoughts on the Wix Accessibility Wizard, and what makers and teams must account for when building accessibility tools.
White House news: Executive Order adding Accessibility to DEI (now DEIA) was passed for the Federal Workforce by President Joe Biden. Big win to move the needle in the space.
What I’m reading…
How the Word Is Passed by Clint Smith
What was your educational experience in school when learning about the history of slavery in the United States? I’ve come to realize that my education barely scratched the surface. And as I look back on my undergrad education, as I dropped into pottery and history classes deviating from my typical Bio major, it was an extended version of the K-12. And without a Black man or woman teaching it, the likelihood of it being anything other than that was very low.
I recommend listening to the audio book of this if you can. It is heavy and heartbreaking, eerily poetic, both justice and historical recounting, and painfully educational.
The Great Game of Risk Played in Category Creation, and Why the Winning Strategy is Aggression
“The first company to reach a prospect frames the buyer’s lens for a long time. The features that matter, the price point and pricing model, insufficiencies in competitors' offerings. Each subsequent bidder for the business must either conform to that mental model and spar for position within its confines, or exert enough energy and spend enough money to challenge and subvert the first framing. That’s a tall order, and exactly the position a startup should wish upon its competitors.”
How Pixar Uses Hyper-Colors to Hack Your Brain
"You'd imagine you were seeing a specific red, not projected on the screen but as a neurophysiological response to stimulus. And if you pick the precise wavelength, “you could actually cause someone to perceive a color that they could never otherwise see. Like, there's no natural way for you to have the perception of that color.” That color wouldn't be onscreen. It wouldn't be anything a projector could cast or a computer could generate. It'd be a function of pure cognition, different for every viewer, existing only in the mind, then fading to nothingness. Which is true for all colors anyway, when you think about it."
Worth thinking about…
The other day Tyrone V. Ross, Jr. (CEO of Onramp) asked: Can you gift children struggle? I got to thinking about how it relates to my own kid. The duality that comes with this for many folks that are reading this is, I imagine, loaded. Me included. Though I don’t come from much, I’m now extremely privileged and so too is my daughter.
But it begs the question: By removing a core of adversity (which we know has drastic negative health impact on us) and selectively injecting it, does that set the child up for so much more success in the end?
Is this applicable to adults in teams as well? In sports there are a myriad of ways to do this, but where and how does this apply in business?
Ask yourself: How do you build a practice around gifting continuous struggle, in a well-oiled and healthy moving team, while not breaking the spirit and culture of it?
As always, thanks for reading! And if you have any questions about the topics I’ll be covering, go ahead and AMA by replying to this email or pinging me on Twitter. If I don’t have the answer, we’ll deep dive together.
I appreciate you. And until next time…
the graphics are pretty!
... but, seriously. the best thing about distributed is that you can do it anyway you'd like... and even the breakdowns on time can change.. there's no reason that you even have to stick with 30 or 60 minute intervals... there is no fucking spoon!
:)