The (not so) new leadership: Context > Control

Many leaders still see their job as directing the activity of the people working for them, setting up detailed systems designed to remove the variability from human behavior and achieve predictable outcomes.

This approach to management stems all the way back to 1911, when Frederick Winslow Taylor released his opus, Principles of Scientific Management. His techniques were responsible for dramatically increasing the output of industrial era factories by limiting the freedom of employees to make decisions, instead creating detailed scripts to drive very specific, management-prescribed, behaviors. By creating a system that forced every employee to conform to standards in every situation, Taylor ensured maximum compliance, which at that time equaled productivity.

But that was a different time, and those employees were doing repetitive tasks in a factory. Today’s workers are asked to navigate rapidly changing markets and produce results in all kinds of situations, so compliance, at best, comes with many caveats. But many managers still use those techniques today. You see the issue.

Today, the most successful companies adopt a context > control philosophy to management. At VNN, it looks something like this:

  • Leadership’s job is to create context
    • Establish long-term vision, short term milestones needed to move toward that vision, and set any hard guidelines outside of which employees may not go (the goal is to make these as broad as possible)
    • From there, avoid making decisions wherever possible
    • Instead, ensure that everyone within the organization has the appropriate context to make their own decisions. Ensure everyone is aligned to where the organization is going, and understands their role in achieving the vision.
    • Then align some more (HT Patrick Lencioni).
  • Individual employees’ job is to use good judgement
    • Each employee is empowered to make the best decision for every situation in which they find themselves, based on the context provided by leadership

This way, the people closest to the situation, the ones best equipped with the most information about the situation–namely the employees–are the ones making most of the decisions. Meanwhile, leadership spends most of their time answering questions, providing feedback, coaching, training and generally ensuring that the decision makers (employees) have the context needed to make decisions in the moment that are aligned with overall company priorities.

Doing this admittedly requires humility on behalf of the leadership, as they need to embrace the fact that they cannot keep up with the pace of business on their own, and empower their team to help them make critical decisions (and then support them when they decide things different than you would). But I’ve found that if you empower your team, and expect them to step up, they do.

When they do, the rewards are many. In addition to better serving customers (by ensuring the person they’re talking to is empowered to help them without checking with their boss), this approach has proven to lead to a more engaged and productive employee base, and a greater level of innovation throughout the organization.

I remember the moment when I realized we had implemented this effectively at VNN: I had given feedback to an employee that I didn’t think a project he was passionate about would work, but I also let him know that, as always, my opinion was context and it was his decision, within the parameters we had constructed. He decided to go forward with it, busted his ass on the project around his core responsibilities, and it’s now one of our most successful business lines. I had to eat some humble pie on that one, but there’s no question that VNN would be less successful if I had dictated that particular decision.

What was a radical philosophy as recently as a few years ago, what I’ll call “context > control,” is quickly becoming mainstream. It’s not there yet, but organizations like The Ready, Whole Foods and Google are all leading the way, and VNN is working every day to do the same.

Many leaders still want to control every aspect of their organization. But the companies that let go of that control, democratizing decision making and embracing the full capabilities of their employees, will outpace those who centralize decision making and look to control results.

They already are.


In a future post I’ll detail exactly how we went about implementing this approach at VNN, and the structures we use today to ensure everyone has the appropriate context to UGJ (Use Good Judgement, which we stole from Netflix like any good artist).


It’s also worth noting that the above is nowhere near the leading edge of management. Recognizing the futility of pretending to control the future, some companies have gone so far as to eliminate the annual budget entirely. We still have a budget, but I must say this is very intriguing.

Do Less, Better

Inspiration sparks the best ideas, creative process crystalizes them, and perspiration makes them come to life. Three parts of the value creation chain.

We startup founders are excellent at the perspiration part. We push and push, optimizing for a constant state of busyness, checking off more boxes than we did yesterday. Eliminating more gaps in our schedules in favor of “GSD” (getting shit done).

In doing so, we feel productive. We’ve been conditioned to “do more, faster“. And that’s not wrong, but the question is at what cost?

Inspiration and creativity require one thing: Space. The very thing that our quest for productivity would have us eliminate. We’ve been sold a line that we must hustle ad infinitum, and bought it wholesale with little awareness of the implications.

Nothing happens without perspiration. It is the core characteristic of successful founders, and foundational. But successful founders get that part, and then go too far.

With the way we glorify the hustle as founders and leaders, is it really a surprise that true inspiration and creativity have become so rare? Why everyone is just the “AirBnb for pet crates” or the “Uber for luggage”?

Scaling value while also scaling variability

Scaling a business, we’re told, is about establishing processes, procedures and workflows, to ensure that the value that you created when you were small persists as you grow. The goal being to ensure that every experience your new customers have is of the same value as the experiences your early customers had. To do so, it seems, you have to eliminate variability to prevent substandard customer experiences.

But variability drives innovation. Without random variation, single celled organisms never evolve into human beings, and nobody even has the luxury of thinking about scale. Variability is the singular engine driving adaptation, growth, and increasingly, in the rapidly changing world we live in, survival.

So can we scale both value and variability? Should we?

You simply can’t replicate the chaos that permeates an early stage startup as a company grows, and you shouldn’t want to. We all have enough grey hairs from that time. But if we convince ourselves that there is a “right way”, then our teams will hew ever closer to that. Then, innovation stops, people get caught up in dogma, and the company struggles to meet evolving expectations in a dynamic market.

Even though everyone in the company is doing everything “right.”

What if we aimed instead to scale not only the value creation that we cultivated at a small size, but also the variability that helped us find that value creation in the first place?

As an example, what if instead of a “right way”, we instead scaled a “default way” for our teams (HT: Aaron Dignan), while also giving them autonomy to deviate if it made sense? If we did this, our teams could do what had been proven effective in the past, but they could also change things if they thought it was for the better. They might be wrong, or they might be right, but either way the organization would be smarter having conducted the experiment.

Might we be able, this way, to scale customer experiences better than the ones we first had success with?

The case for the startup psychologist

Cofounders are effectively married, so why do we not invest in couples therapy for startups? It works.

There is no more fundamentally important relationship inside a company than between its cofounders, and no area in which things can get more royally screwed. By extension, that applies with only a very slight reduction to the founding team and/or leadership team, the group of people with varying functional areas who through their relationships guide the direction and success of the company.

Market, strategy, culture, all of these things are important. But none of them can overcome bad relationships within the leadership of a company.

So why do we, as founders and investors, not invest in nurturing and securing those relationships? And in the rare cases where we do consciously, why do we expect success from people without any professional expertise?

We rely on board members, usually business leaders all, and the founding team itself to fix these matters. This is like handing a drill to Mike from Accounting and asking him to fix your cavity. He’s not trained in dentistry, so you don’t hand him a drill.

A board and founding team are not doctors in psychology (much less do they possess the required dispassion to do the job with objectivity), so why in the world do we so unquestioningly trust them with managing the psychological dynamics of the leadership team, the single largest lever in our organizations?


I’m piling on here, as it is definitely encouraging to see groups like Freestyle Capital investing in the mental health of their founders. This is critically important and they are pushing the envelope, far, to do even that, but it’s about more than the mental well-being of the individual. We need to go farther, and invest in the mental well-being of the leadership team (if not the organization).

Innovation in the fight game

Ducking a superman punch to open the fight, Donald Cerrone grabbed at Conor McGregor, wrapping up the shorter striker’s arms in a clinch.

The fight prior, Holly Holm leveraged the clinch dozens of times in a 15-minute contest on her way to a win against Raquel Pennington, illustrative of just how frequent this technique is. By tieing up all four arms the fight grinds to a halt. The fighters push and grind against one another, trying to establish an angle to strike while avoiding being taken to the ground.

But McGregor changed the sport of MMA last night in Las Vegas when, his arms tied up in a clinch, he crouched and launched himself shoulder-first into Cerrone’s cheekbone. McGregor shouldered his opponent’s face thrice more before Cerrone finally backed away. By then his nose was broken, and the fight was over 20 seconds later. Cerrone never landed one strike.

“I’d never seen anything like that before,” Cerrone, a veteran of over 50 professional fights, said afterward. Joe Rogan, who sits cageside for nearly every UFC event, agreed.

Nobody had. Shoulders were irrelevant in the thousands of fights and perhaps millions of clinches prior. But this morning, fighters around the world began drilling shoulder strikes in the clinch, and we’ll see more shoulder knockouts to come.

Innovation is obvious in hindsight. But every “industry standard” practice has a beginning, before which that practice seemed as weird as jump-punching someone with your shoulder. Or jumping up and throwing the ball down, rather than shooting it up into the hoop.

Someone always has to go first.