Part 1 of What Startups Need To Become Successful Companies: Leadership

Russ 🌹
You could
Published in
8 min readMay 13, 2017

Not all startups aim to become companies. But I’ve worked with many that do. I’ve seen a few companies do a lot of things right, and many more doing so much wrong.

What’s the difference? Aren’t startups and companies different words for basically the same thing?

But First, Some Background

I’ve had the pleasure and misfortune of interviewing with numerous software startups, and have worked with close to 20 in various projects and capacities. I’ve asked enough questions, and seen enough projects, to be able to identify blindspots and more importantly, where they are coming from and how to address them. I’ve even done it professionally, having been paid to interview companies that are being courted for acquisition and write up reports of the findings.

Not to say I’m an expert here, only that i’ve spent some time in the trenches of various trenches.

But We Will Always Be A Startup! It’s In Our DNA!

This is what I hear when people say that: “I don’t wanna grow up, I want to be a kid forever!” And of course you do. We all do. And we do well to keep some focus to what that was like. Sorry Peter Pan, but kids play games, adults pay for the house the games get played in, and the food on the table, and the heating, and the clothes….

Responsibility is not sexy. And we often struggle to do our best in delivering on that. Adults can still go to Disney World and have a good time, but they wouldn’t sell their house to do it. Given the same decision, a kid would likely be more interested in a ride on the monorail than where they’ll sleep for the next 10 years.

Kids are fast, and can easily outmaneuver towering adults in a game of tag or time-for-bed. But what adults lack in comparative agility, they make up for in distance. Their stamina, stride, and knowledge of how to best utilize their resources gives them a hefty advantage.

Startup vs. Company

The kinds of things that drive a startup, and the kinds of things that drive a company, are often very different. While both have employees and products, that’s often where the similarities end.

A startup’s primary goal is to get sufficient traction in the marketplace. This might mean enough users, or enough customers, or a certain amount of revenue. The idea is that, until those things are satisfied, everything is still just a guess. So this means cutting all sorts of corners and doing all sorts of things a company would never, and could never, do.

Conversely, a company has the things a startup wants. But it needs to keep them. It not only needs to keep them, it needs to have more of them. So existing resources must be maintained, and new ones acquired. But if you’re not keeping an eye on each, one can slip away from you.

Responsibility is not sexy.

What’s the best way to maintain what you have, and try to add more to it at the same time? By getting boring and responsible. Remember all those corners you cut as a startup? When you’re a company, it’s payback time.

Startups do it the fast way. Companies do it the best way.

Let’s take a closer look at probably the most important trait of them all.

Leadership

Leadership isn’t automatic. By far, this has been the biggest takeaway from my experiences with numerous startups, yet is probably the most important thing for a company to have.

To be a leader is a noble thing — we place a lot of emphasis, culturally and politically, on leaders. As such, there is all sorts of ego that comes into play when people come into positions of leadership. “I’m the CEO and the leader for the entire company” is a common utterance.

But what if I told you it is possible that you could be the CEO and not be a leader as well? In fact, many organizations, though by no means all, do have leadership. But it’s rarely coming from the CEO; instead originating from lower in the ranks.

It’s not that the CEO should not also be a leader; in fact they above all would do well to demonstrate such skills. But leadership isn’t automatic. It’s more than making decisions, or giving directions.

People aren’t cogs. They have emotions, skills, dreams and lives. For the typical startup, these things are set aside. To some degree this is out of necessity, but more often it reaches levels of neglect and ignorance, especially as time passes. A key driver of this is often greed. Instead of providing stability for their workforce, ensuring they have a job AND a life, a classic gesture is to drive people to burnout or illness, then replace them when they wear out. And when they are not employees but “independent contractors” this is all the easier, and much cheaper.

To be a leader is a noble thing — we place a lot of emphasis, culturally and politically, on leaders.

So leadership is not automatic, and it’s not cheap. It will consume time and money and the return won’t be obvious at first. But this is where successful companies do well — they play the long game. They pay employees to think about and advocate for their mission full-time. Decision making and praise is delegated down the chain of command, while responsibility and accountability comes squarely from the top.

Leadership means doing what is best for the organization and the people in it; collectively and individually. By setting people up for success, the organization is setup for success. People will eagerly give their best when you try to do what’s best for them.

But We Are A Flat Company!

No company is a pancake. Each organization, no matter the makeup or purpose, has at least two levels. Flat companies simply do away with extra levels and keep it to a minimum. But there is still leadership to be found in both, even if much of it is done collaboratively and collectively. If there isn’t, that’s a sure sign of neglect. Every village needs it’s elders.

Not Convinced Leadership Matters?

Head on over to the startup graveyard, read through some of the reasons for failure, and draw your own conclusions. By my count, a handful directly cite leadership as a source of failure, while many others cite reasons that are tied to leadership.

Leadership isn’t automatic.

What Does It Take To Be A Leader?

It takes a lot of skills and vigilance, many of which may be entirely new to you as concepts. But put simply it’s a lot of trial & error, with a hefty dose of resilience.

There are three key metrics I feel every leader should keep an eye on: Mission Success, Organizational Success, and Individual Success.

Mission Success: The product or service is doing it’s thing for people, and they’re happy. That translates into things engagement and retention for most companies.

Organizational Success: In delivering on the mission, the organization is happy and healthy. Resources are not overloaded, surprises are few, and there’s lots of communication going on. The mission is championed by the organization, and likewise the mission direction is influenced by it.

Individual Success: Staff pickup engaging work with achievable deadlines without having to sacrifice their free time to deliver it. Their voices are given regular forum, and their dreams are tracked and opportunities for achieving them (or coming closer to them) are made available where possible.

If you’ve been keeping track, that’s three metrics for (at best) two eye balls — and each metric is itself broad, with numerous sub-metrics.

So how are you supposed to stay on top of so many things, when you’re at least one eyeball short of being a triclops?

You Try (And Care)

People make mistakes, and you will too. But if you think you’ve already got this leadership thing down, think again. Even after you’ve read everything there is to read on leadership, or gone to every conference you could find, or feedback you’ve gotten from your staff, or simply have years and years of experience to reference; You must be willing to grow as a leader, which means admitting you’re not as good today as you could be tomorrow.

I know for some, this will be a hard truth to stomach. It’s more palatable to see ourselves as powerful beings in control of destiny, than as mere mortals who are making mistakes along the way. Humility goes a long way, and mistakes will always happen.

As far as books go, Turn The Ship Around! is by far my favorite. If you’re clever, you can probably find my review for it somewhere among the other 671 5-star ratings.

But there’s one more thing that leadership offers. It is the defining essence of many leaders we’ve come to look up to in society, and the hardest thing instill on others.

Vision

Martin Luther King jr., Mahatma Gandhi, Abraham Lincoln, Steve Jobs and Elon Musk all share this characteristic. A vision of the future, of what could be, that to many seems to push the boundaries of possibility. But it’s more than just another idea for them — They embody it. It’s a significant part of their life and of their psyche. There is nothing more important to them, than their vision. So much so, that the first two gave their lives in pursuit of this vision, instead of pursuing a simpler life of comfort.

Vision doesn’t need to get us to another planet, or start a new democracy. It just needs to picture a new reality, identify how it’s going to get there, and have a good reason why. What constitutes a good reason? Something that benefits society, or at least a good portion of it. Profit can be a side effect, but it can’t be the vision itself. Visions based on greed will ultimately collapse and represent footnotes in history.

What Does This All Mean?

Companies with strong leadership are inspired and inspire others. They give interested compasses a magnetic north, and help them get there, or where ever their compass wants to go.

Leaders continuously identify and do what’s best for their mission, their organization, and the individuals that deliver on it.

Stay Tuned!

If you liked this write up, please recommend and comment below!

We’ll cover the trials and tribulations of management in part 2 of this series.

Are you looking to be a better leader, or better yourself some other way? We can help you make such tough changes.

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Russ 🌹
You could
Editor for

Developer, designer, writer and psychology enthusiast. Creator of WillYou DidYou.