Maintaining a dynasty when your team has "aging" champions
Edition No. 24: A few brewed thoughts, two curated links, and one good read.
Hi folks,
Since you last heard from me a couple of weeks ago, it’s been a really busy as we continue to build products and refine the levers that make us hum at Stark. We published our first white paper on managing a modern accessibility posture and growing your teams’ accessibility maturity at any scale (I put together a short summary video here if you fancy). And I spoke on the Lumina podcast about: innovation and adaptation in an org, operationalizing accessibility, and more.
AND! Edition No. 24 is here as I said it would be — despite me actively being swallowed by a collective internet mission to try and find Kate Middleton (in hopes that the crown falls).
As for today’s newsletter topic? This one is near and dear to my heart. I’m a big sports nerd, but I’m also really bullish about doing right by your team members—especially in a startup when they’ve been around and held down the fort from the early days. Questions I asked myself, that you may find have stirred up for you too are: What does “aging” look like in a startup? How do you build a team that learns to continually win together year after year simply because they have shared attributes? How do you maintain that dynasty…
Massive thank you to
, , , and for helping shape my thoughts on this topic and bringing this post to life.Let’s dive in…
If you’re here for the first time, thanks for checking out Thoughts Brewed—a monthly newsletter sharing my learnings in startups, leadership, design, and life in general. And as with most things of mine, it’s without a filter.
One Good Read
Maintaining a dynasty when your team has "aging" champions
I’ve had the privilege to hire, and the unfortunate responsibility to fire, a decent amount of people throughout my career. And while I plan to give time at some point in this newsletter on each of those topics, one thing I don’t think we spend enough time discussing are the aging champions of a company.
I have an affinity for drawing parallels between managing a sports team and leading a tech startup. It’s become a running joke at the company. While the comparison might not resonate with everyone, the underlying principles of team dynamics, leadership, and performance management are universally applicable. In an early stage startup though, time moves much faster than in most other organizations — sports or enterprise.
Regardless of whether or not you follow sports, you know about the New York Yankees. Now, as a biased new yorker I’m not about to convince you of why they’re the best (they are). Instead, I want to shine a spotlight on the New York Yankee dynasty from the early 2000s. The "Core Four" were on the roster — Derek Jeter, Andy Pettite, Jorge Posada, and Mariano Rivera. To me (and what seemed like everyone who loved sports in general) it was arguably the greatest period in baseball history.
The guys were playing for an organization that set a pretty high bar for performance, and instead of moving into a downward spiral like most championship teams historically do, the Yankees seemed to be continually getting better with wins following their three-peat. The crux of their success? A steadfast commitment to nurturing their talent pool. But while the Yankees would win the World Series in 2009, that would come to an end.
No team is immune to the fact that anytime you have a dynasty you can bank on the aging. Legends retire, and if the coaches aren’t able to acknowledge or proactively address it, you go through a talent and experience gap with the organization struggling until the “new crew” are molded into an equally world class team together. Yes, the ability for a dynasty to continue is contingent on how willing you are to acknowledge the reality of a potential downfall and how proactive you are about addressing it.
As this became a topic of relevance for us at Stark, I spent time questioning: what does “aging” look like in a startup? Not aging in the literal physical age of an employee. I personally don’t care whether or not you’re 16 or 60—as long as you have a shared sense of vision, urgency, enjoy working in a team setting, and have a passion for your craft. More like: How do you mitigate a dynasty doomed, and instead create a team that learns to continually win together year after year simply because they have those shared attributes? How do you support your folks that have been with the company for a while (startups age like dogs!)?
Understanding why this occurs as a whole and for the specific individual is crucial.
Why it happens
Regardless of the reason, your job as a team member’s manager is to see what their stuck spot is in the process and seek to rectify it. In my experience, the various reasons for “aging” are…
Things get more complex than someone can deal with given what the company needs and the time period it needs it in, versus where their skill level is at. They can’t adapt quickly to the changes called for. In corporate companies, you often see the Peter Principle in action with employees getting promoted simply because years in work despite it being a promotion straight to their level of incompetence — making it impossible for them to adapt to that level of complexity, or change of difficulty.
People no longer get out of the company what was originally desired or promised. Maybe they don’t get to contribute as much in the weeds anymore. Other times people have a certain quality bar they want to contribute and when they no longer can (for a variety of reasons). Or they don’t feel they’re getting to do their best work. When either of these things happen? You end up in a funk, you can’t grow, and in some cases you start to regress. Ego or pride kicks in. Resentment, albeit unintentionally. I’ve been there as the employee. I think many of us have.
The unspoken reality that not everyone is capable of infinite growth in a particular role; some reach a plateau. And for startups, where agility and rapid growth are critical, recognizing and addressing that plateau is essential.
Now as the one managing this, quite frankly, even with the best intentions, not catching it early enough ends up creating a ripple effect and turns into a mess. People bring their full selves to work after all. The challenge lies in honoring the contributions of long-standing team members while acknowledging that their current role may no longer align with the company's evolving needs.
There’s an emotional component to it as a leader that I personally haven’t been able to shake. And maybe that’s a good thing? Even the best, arguably only the best, develop such great relationships with their players. They create a space through sharing yourself to a certain degree without wanting to become a peer, or wanting/needing to be liked. And yet, when you have to say goodbye, there’s a pang that can’t quite be shaken. Especially considering that your aging champions, regardless of why it’s happening, are usually your original crew that have been committed for a long time and have a very different knowledge set about the company in particular compared to newer hires. It’s hard not for it to be emotional. And still you end up inevitably facing the question: “Do I figure out how to stick with this person or do I swap them out?”. And when the latter occurs: “How do I handle this situation while recognizing that this behavior is no longer enough (for what we need at the company now) and do so in a way that the champions don’t feel diminished or discarded?”.
A lot of managers don’t have a plan for when certain team members hit their plateau of talent. Hell, scenario planning (good, bad, plateau, doomsday) is a very difficult task that forces us to face potential realities that sometimes have us in the red. But any good coach has a playbook for a reason, including the swap of players, to ensure you stay away from the red for as long as possible. You see this in a number of sports—your “bottom” line, while they may “warm the bench” and not be the shining stars, are equally capable of running the plays and performing at any given moment.
Now it’s worth noting: You can utilize people at their ceiling capacity, but they won’t be someone who continues to be a champion. And unless you’re a late stage startup or corporate company, it’s very expensive and (in my opinion) not an option.
No matter how much preparation to grow into a role though, nobody is truly immune to the personal S-curve as well as the curve of organizational life that occurs when you’re in one for a certain period of time. Stay in a job too long? It flattens. Take another role or convert a job into another job and the curve starts back up again.
So the next question becomes: how do you know when someone should get re-potted versus when they need to be released? Or really…what the hell do I do with these team members?
Approaches to take with an aging champion
Recognition of stagnation
You want them to go out on a high note. So you end it ahead of stagnation.
Bill Walsh was head coach of the San Francisco 49ers and the Stanford Cardinal, during which time amplified the west coast offense. Bill was known for taking a champion and trading that player about a year earlier, once he determined the player was starting to decline. A major skill as a coach, he could spot the signals for when the decay in performance was occurring.
His proactive approach to team management and foresight when a team member's performance begins to wane allows for transitions that honor the individual's contributions while safeguarding the team's future success.
For those of you unaware: Bill Walsh was a coach that traded his 4-time superbowl champ for an unproven backup quarterback. He took risks, he had an alternate way to run a ship. He’s a hall of famer for a reason…
Repotting / Infusion
In every company there are cycles where someone burns out in a job if they’ve done for too long at a certain intensity.
Just as plants thrive when repotted, there are some individuals that can flourish when placed in new roles or projects. The strategy involves identifying opportunities for team members to apply their skills in new contexts, thereby injecting them with fresh energy and challenges, and/or infusing a veteran perspective into an alternate team.
In this approach, the chemistry of the group changes and helps the individual thrive as well.
Re-configure a group
I’m going to take a few different players and put some new ones together. In catalysis there’s a way in which you add something and the collective process gets better. The group collaboration can change based on catalytic behavior.
The mental models, personality, etc.
Take a group working together which got into some bad habits. Sometimes you see a mix of players that do things differently. Different connections and ways of looking at things certainly help as models. This doesn’t happen as much in an early stage like later stage, and can happen in later stage only because there’s much more specialization like you see at a bigger company.
You saw this with the Golden State Warriors when they brought in Chris Paul to try to make their second unit play better and well…now they’re playing better. He sets others up well to succeed because of how he collaborates. That’s his specialty. Now everyone has someone facilitating. That can come from teammates or a coach.
Know when it’s time to grow or go?
In sports, players and coaches go back to video reels to look at performance. It’s a continual reflection on the various ways in which we made decisions as individuals and a collective.
Teams in startups should do it as well. Quarterly Business Reviews (or QBRs) are a decent example of a framework designed to have teams stop at a certain target place to say “what did we learn about collaboration, execution, performance, etc”. You see these utilized often in sales when you service enterprise companies. For some they become just another meeting you have to get through but if you do it right, it’s a quarterly milestone with the power of reflection where learning occurs. Worth noting there’s a way to simplify this very early on in a startup. I’m someone who fundamentally believes that less process, from 0-to-1 and 1-100, is always a good thing.
The act (in whatever format that takes) becomes a very potent signal to the team. It says we want to learn from our experience and turn it into value. You do the same when you take feedback from customers, and any process along the way has that potential.
Now here’s the tough bit of the topic because I recognize there’s many reading this that aren’t managers but instead the individuals who directly report to us: Every CEO or manager or leader (I don’t care what fancy title we’re given) I’ve talked to has some version of “removing” the bottom 10% on a somewhat-annual basis. And that’s the job. Each stage company has some version of this. Very early stage startup, and the turn over is the highest typically. Later stage startup, and this becomes an annual occurrence you just don’t really notice it given the larger number and distribution across teams. Only when there’s a reduction in force (aka RIF) do you feel the impact of people truly leaving the company and it’s because it happens en masse. And while it does indeed seem harsh, doing so (when done right) ensures companies get to do right according to what their employees and the company needs.
For those of you frustrated by this, the likelihood is that you had an asshole manager, or maybe someone not truly ready for the role and the very difficult balance that comes with it, or you’re at a company that doesn’t culturally prioritize the important balance between fiduciary duty to the company’s needs and the promise we’re responsible to hold by giving you the most challenging, rewarding, and successful place to work. And to the managers: no matter the reason why, saying goodbye to folks is never easy for either party. Give yourself grace, too.
There’s something to be said about respect and not keeping a team member when you can no longer provide them with a great experience or ability to grow as a professional anymore though. And in saying goodbye, the team immediately feels and notices the increase in performance and velocity because of it.
Learning occurs after the experience in the same way that courage comes after the decision. My hope is that in doing so, you (much like myself and my team) learn what’s needed to continually recharge, repot, or release your aging champions so that no matter where they land they can help build a dynasty.
Two Links
Patrick Collison on craft, beauty, and the future of payments
“the best people consider themselves craftspeople in their domain. And they really, above almost all else, want to work with the best other people. And so I think it may almost be true that even if from a customer facing standpoint, craft was not valued by the market. You actually might still want to build an organization that index is very heavily on this because you just want the best people for other reasons. And now as it happens, I think customers do in fact value it and I think the evidence is broadly consistent with that. But yeah, I think it's very hard to assemble groups of the best people if you don't take the practice of the work super seriously.”
Generative UI Failure by Per Axbom
“The door is wide open to claiming that users will in many cases use voice, text, keyboards and eye-trackers in the future to ask AI assistants to navigate and fetch content for them under their own supervision. Something that could mean volumes for accessibility without requiring any new interfaces at all for existing websites. But a unique, individualised UI for each user, generated without supervision by any designer, is an extreme take with very little foundation in feasibility or desirability.”
This post from Per Axbom is critical to the accessibility space and technology industry as a whole. I found myself wanting to describe everything so great about it, and why a post like this needed to be written. It is both a beautiful articulation and a painful surfacing of dated thinking a number of individuals traverse earth with — selectively ignorant to the reality of the world.
But instead of going on, I'll just say: do yourself a favor and read it.
Few Brewed Thoughts
→ Time and focus married ensure the ability to set then execute on goals
One of the first steps in Management 101 is getting agreement on what the goals are and how we’re tracking them. Given the amount that happens in a startup, it’s an incredibly difficult task mainly because it relies on hyper-focus. A way we open our weekly meetings now is with the review of: “How are we tracking with these goals? Are we on target?" And the answer is either “Yeah, and here’s the proof of it” or “nope, here’s why, and how we’re course correcting…”.
Nat Friedman emphasized how you learn more per unit time because you make contact with reality more frequently. Time is the denominator. And without a deep understanding of the problem statements and focus to solve them, you waste the ability to optimize speed, and lose time — a most critical resource in a startup. There’s a post in there somewhere about shared urgency — another relevant and recent topic for me…
→ There’s a special kind of organizational “Moore’s Law” you experience specifically in enterprise sales.
The more people in an org, the more people get involved in decision making, the more complex the process becomes, resulting in more people who don’t understand it, and the more work you need to do in order to untangle it and make more money from them as a customer.
→ What are the various ways to measure how much [an improved] writing culture impacts a company's success? And what is the stage to double down on it?
The correlation between successful companies and having a writing culture is undisputed. At Amazon, writing's the only tool employees can use to sell their ideas internally and then bring them to customers. Nothing gets done without a doc written. I don’t fully subscribe to that approach, but I do think there’s a fine line between rigid and flexible that we haven’t quite hit yet. I’m also aware that my thoughts now are directly tied to the stage we’re at. And yes, if this feels like an incomplete thought it’s because I’m asking myself the question in real time. Any thoughts there? Please share.
Too much process causes slow progress, or whatever 50 cent said.
As always, thanks for reading! I appreciate you. If you found it insightful, please give it a share on the socials. If you have any questions, go ahead and AMA by dropping a comment or pinging me on Twitter. If I don’t have the answer, we’ll deep dive together and I’ll more than likely turn it into a post.
Until next time…
This was really insightful. One of my new obsessions is trying to figure out how to mature an eng org, but I haven’t thought about whether anyone has or is approaching plateau and how to address that with grace, and actually find opportunities there