Leveling the playing field with extroverts

Earlier this week I was watching Deb Liu, the CEO of Ancestry.com , talk on Lenny’s podcast.

And she starts to talk about how extroverts have a natural advantage in the workplace. But that introverts can also develop strategies to effectively compete.

But when you hear her strategies, it is almost like she is saying… “introverts need to do their best to mimic the playbook of extroverts and over time they will get better at it.”

She recommends things like ‘speaking up’ and marketing the results of your group.

If you click on this video below it starts at the point where she is talking about this stuff.

And it resonated a lot. In fact it touches many of the things that triggered me to develop the systems that I now use today.

But I came to a bit of a different conclusion than her. I realized that if I could set my own rules then I could pretty much completely level the playing field without having to force introverts to practice being more like extroverts.

And today i’ll explain more about what I mean.

So why are introverts disadvantaged in most corporate review systems?

If you look at how most larger companies work you will typically see a pretty standardized performance review system.

You will be reviewed by your manager, but you will also be calibrated against your peer group. This is for example the system that was in place when I was in Wayfair back in 2017.

If I was say a 'level 7’ than all of the level 7 employees in the tech organization would be calibrated against each other by the folks that are more senior to them. And they would be bucketed into one of three groups: high performers, on track, and low performers.

Having taken part in some of these review sessions I can tell you that I barely knew a lot of the folks that I was casting a vote on. Rather I knew most of them more by their reputation.

Perhaps someone told me that they were good or bad, or perhaps a project that they’d done had been a big success. And so I cast my vote based on this limited information as well as whatever their manager said during the session.

In such a system it is extremely important that you market yourself very well in the organization. Because it is probably the thing that influences how you are bucketed in these sessions more than anything else.

You could have done amazing shit and worked your ass off, but if you’ve kept it quiet and only your manager really knows it.. than you are more likely to be screwed.

Because unless your manager does an amazing job representing you, the group will simply bucket you based on the limited information that they have.

How I learned this the hard way?

So in the early part of my ‘corporate’ career since about 1999 I would say that I was innately pretty good at marketing myself.

Why? Because I was a pretty outgoing guy that got along with pretty much anyone. I organized social events and could communicate the things I was doing pretty effectively to the wider company via these ‘informal’ channels.

And so the whole corporate thing came pretty natural and easy to me during those early years.

But then my health started deteriorating and particularly my voice felt a lot more strained and weaker. It was a gradual thing that got worse and worse over the years… starting from my late 20’s.

The effect was that it slowly converted me from more of an extrovert during my younger years to more of an introvert by the time I was in my early 40’s.

And this hit its absolute low point with a major health event that happened to me in 2014. For awhile in mid-2014 I could barely talk above a whisper and felt like a hermit because of some neurological symptoms I was facing.

So I needed to learn the new rules of the game of being an introvert. It was a shitload harder!

I couldn’t rely on networks of informal relationships that I used to develop almost effortlessly. Rather i needed to try to market myself in other ways. Ways that felt more forced.

And despite my efforts to improve, I would say that i still was not that effective at it. So when I looked above me in the ‘corporate world’ I saw folks that I thought I could easily beat in structured/strategic thinking and getting shit done.

But they could run circles around me on the relationship building side. And that was far more important.

This was not a status quo i was going to accept. I was gonna create my own rules to the game. Ones that favored my natural advantages.

This is why I developed the systems I use today

So i was always a very ‘systematic person’ but I would say that I started to develop the system I use today in early 2021.

The company I was contracting for was using Clickup and it was like a match made in heaven.

I started organizing everything I do in a tree-like structure of spaces/folders/lists/tasks. And had kanbans for literally everything I did.

I also had a very big scope and we wanted to do things quickly, so I was hiring loads of freelancers off of Upwork. I think I had like 30+ at one point doing all kinds of stuff from data analytics to product management to engineering.

So I developed my ‘everything is a task’ system to be able to manage that. And realized that in order for the system to work well I also needed them to use Clickup like i did.

To achieve that i established rules like the fact that any work that was done needed to be reflected as a comment on the task. And they needed to keep their clickup inbox clean at least once a day to keep the flow of communications smooth.

Things just started to work very smoothly… even as I was juggling more simultaneous scope than I ever had in my career.

Plus I added additional part-time clients so that at one point I had three different clients and my own side hustle startup at the same time. But i was staying on top of it all relatively easily using these systems I’d developed.

At my high point I counted that I was managing 50+ people directly (mostly contractors) and staying on top of it better than almost anyone that was managing only 7.

I knew exactly what they were doing, what progress they’d made, and when they were going to finish it. Plus if they got blocked I knew almost immediately and would unblock them within 1-2 hours.

I realized… this was game changing shit. There wasn’t anyone out there that I knew of that could manage this much shit as well as I could.

This system consistently outperformed any team i’ve had exposure to

Now fast forward almost four years during which time I’ve stress tested this system in all kinds of teams and scenarios while peering into many different organisations through my contracting.

Anytime I found a flaw, i tweaked the system to plug it.

These days I typically go without any recurring meetings and have almost no meetings at all. I’m able to find and onboard freelancers to do almost anything within 24 hours.

And by testing and vetting folks quickly I find competent people in a week whereas a traditional company would typically spend 3-6 months.

I have no management middle layers. No politics. And I respond to team members when they get blocked almost real-time.

I’ve also found that the folks that I like working with always stick with me and end up liking it.

I get loyalty not by perks or paying them more… rather I get it by being fair, transparent and being a solid overall leader. Folks tell me things like “Ken… I learned a lot by working with you.”

And that makes me proud. Because I get this more now than I ever have at any point in my previous career.

As level a playing field as I have ever seen

Now to come back to my main point in this article.

As I reflect about the hundreds of people i’ve worked with these past four years, I do not think that the extroverts had any real advantage.

Rather in many ways I would say that they were disadvantaged:

• There were no meetings so there was no forum for them to utilize their charisma and relationship building skills.
• If they tried to build a relationship with me, they typically found that it fell flat. I’d respond to their messages asking if they could have a call with me with a response like “please just update your clickup cards and I will respond.”
• Their interactions with team members was all via tasks and comments on those tasks.
• They were evaluated purely on the tasks that they got done and not at all based on their relationship building. No 360-degree feedback or any of that garbage.
• Executing these tasks well did not rely on having relationships. Whenever they needed the support of a team member they just tagged that person and knew that our process was such that they’d get the support they needed quickly.

Basically an introvert could feel that they were finally fighting on a level playing field. And so I noticed that the types that enjoyed working with me the most were exactly that…. introverts.

Like a band of X-men.

And as Wolverine once said.. “We work as a team, and we fight as a team. All of us. Let's go.”

P.S.

If you're interested check out my new podcast "Million Dollar Ideas". Where me and my partner, Usman, break down four startup ideas we're thinking about each week.