You're probably wondering what I'm talking about 😂

This is one of the many dichotomies of leading a company, or a team, or really just being a leader of any other human in any situation.

How do you be a patient and kind leader that invests in the growth of your team, while also ensuring the business gets the best outcomes possible in the shortest amount of time?

How do you shoot the gap between being endlessly supportive and being overly ruthless?

I don't have all the answers, but I think at the core, it has to do with being realistic about what your team members are capable of - and what kind of environment it takes to help them thrive.

Clear Standards

Many times, when I find myself disappointed with someone's performance, I also find that I dropped the ball on setting clear standards and expectations somewhere along the way.

As the leader, you must understand: what you tolerate, you endorse.

Sounds simple enough, but in practice it just unearths more questions:

Where's the line between setting clear standards and micromanaging?Are you spending time building systems to build guardrails for B-Players when you should really be spending time recruiting an A-Player to replace them?Would your life be easier if your team was better?Are you standards realistic, or are you going to fire someone in pursuit of an ideal that might not be achievable? Is the grass really greener on the other side of that hiring process?

These questions are where the real work lies, and it's very situational...but at least as of today, here's how I think about it:

Outcomes vs. Containers

I tend to bucket my team members into two categories:

Category One: People who can thrive when given an outcome.Category Two: People who need a specifically architected container in order to thrive.

The "Outcome People" reduce management overhead and pull outcomes forward.

The "Container People" increase management overhead, but are frequently required on a team in order to move work forward.

The "Outcome People"

I'm not an idealist. I'd love to sit here and tell you that the only people who deserve to be on your team are "Outcome People", but it's not always possible. They're rare, they're often expensive, and you need to make sure that you and your company are worthy of attracting them - which is tough to do, especially in the early days.

But wow...when you get one, do everything you can to hold on to them.

These are the ride or die team members. The people you can truly build with. The ones that you can shorthand a conversation real quick, say "please make this go", and rest easy knowing that it'll SLAP when it's finished. Those people get raises, they get equity, and they make you money (if you structure things right) because they're also generating upside for the business.

Hold onto those people at all costs.

The "Container People"

You gotta get good at managing people like this, too. In the early days, you'll probably have a team full of them (but hopefully not one of your co-founders). You're gonna have to build systems, guardrails, SLAs, SOPs, processes, feedback loops, 1:1s, all that stuff.

Without it, the net quality of work coming out of your company will trend towards mediocre. You have to build the rhythms that allow you to hold the standard in many places at once.

It's a mandatory skill.

But there's a limit. Eventually, you'll be spending so much time managing processes for the "Container People" that you'll realize it became a huge part of your job.

And then you'll have the moment of reckoning:

Outcomes > Containers.

Can People Change?

Yes, of course. In fact, "rate of change" is one of my most important subjective criteria when I think about how someone's role can evolve on my team.

A "Container Person" can develop into an "Outcome Person" - but it's hard, and it requires some baseline attributes that (in my opinion) can't be taught.

There's an aptitude component to it - you simply have to be smart enough to learn, and driven enough to put effort into the learning process, in order to do it.

There's a psychological mastery component to it, too - you've gotta be willing to make independent decisions based on incomplete information, knowing that you risk being wrong and hurting the business.

And most of all, you have to be good at being right:

Leaders are right a lot. They have strong judgment and good instincts. They seek diverse perspectives and work to disconfirm their beliefs. (from Amazon's Leadership Principles)

Which brings me to my last thought on this topic:

Choose Your Leaders Carefully

As your company grows, you're going to need leaders to run teams of people.

If you remember nothing else from this post, remember this:

If your leaders aren't "Outcome People", you're in for a world of hurt.

If you're staffing a leadership team, it's because the size of your business has exceeded what you can physically do by yourself. You need more simultaneous outcomes than you can personally create.

It's a vulnerable position, if you think about it. If your leaders can't get outcomes, you fail.

The leadership team is where you need to be ruthless.

Your leaders need to be able to get outcomes in a chaotic and ambiguous environment. They have to make decisions without being micromanaged. And they need to get it right a lot more than they get it wrong.

Hire accordingly.

MV