The Art of Startup Leadership: How the Best Projects Come From Empowered Teams

You saw the need for a meeting, and you scheduled the meeting. You also determined the time of the meeting and who should attend. All of those decisions showed elements of team leadership.

But not the ones we revere.

No, to be a real leader, we’re told, you need to own that meeting. This means driving the conversation, maybe even immediately steering it toward the idea you’ve been mulling over for the past few days.

You need to listen, sure, but not in some passive way that shows your weakness. The business world is dog eat dog, and the internal hierarchy of job titles isn’t enough to defend you from usurpation.

So you must take center stage, be way out in front so others follow. You must lead with brilliance and boldness like those who have changed the way we see the world, people like Nelson Mandela.

I always remember the regent’s axiom: a leader, he said, is like a shepherd. He stays behind the flock, letting the most nimble go out ahead, whereupon the others follow, not realizing that all along they are being directed from behind.”

—Nelson Mandela

Wait, what?

While many see this as a condescending simile (yes, I see your reasoning), the concept of leading from behind is one worth thinking about how to do—especially in the context of startup team leadership.

Let’s say your startup is growing up fast, and as the leader navigating this crucial period of growth you’ve helped free your team from the facade that a flat organizational structure can work. But this bold step forward often means an erroneous step back into the horrendous aforementioned advice churned out from those superpower publishers of the traditional business world.

It doesn’t have to be that way.

Leading from behind is talked about but not often painted, and it’s a concept pretty much ignored in the startup world. It’s a great idea, but what does it look like? How can leaders leverage the concept into something real that benefits their growing company and allow teams to produce the best projects?

And then there are the larger questions, questions that cast a critical eye toward ingrained assumptions:

-What if the conventional representations of team leadership have been way off?

-What if the language and imagery we typically associate with leading—being dominant and out in front while rallying others to catch up—isn’t the best way?

-Might the pressure to always be out in front make it impossible to stop and consider alternative ways of leading your team?

Where it comes from

Paying homage to Mandela, Linda A. Hill, a professor at Harvard Business School, helped put the idea of leading from behind into the minds of business leaders.

For now and into [the] coming decade or so,” she wrote in 2010, “the most effective leaders will lead from behind, not from the front.”

She went on to say, “It’s a concept whose time has come.”

For Hill, and indeed for those who have long embraced the concept, the realities of modern business have made this happen. She breaks these realities into three primary categories:

1. “The psychological contract between companies and employees is changing.”

People are seeking more meaningful work, and they’ll increasingly sacrifice pay or other perks in order to feel fulfilled and valued. This is especially true in the realm of startups, where company culture tends to be more progressive (unlimited vacation, remote work, etc.) and the company mission often places a great priority on its ability to make positive social impact.

2. “Innovation—not simply incremental but continual breakthrough innovation—will be a key driver of competitiveness.”

As much as society highlights the lone solitary genius, most discoveries are a result of collaborative, team-oriented processes. If Hill is right, and continual breakthrough innovation becomes the key driver of competitiveness, modern team leadership must evolve accordingly. This means startups who stay competitive will be those who replace the top-down patriarchal approach with a process more akin to workshop facilitation circle processes—where each participant feels valued, equal, and not just safe but actually empowered to share their best ideas. 

3. “Leaders can encourage breakthrough ideas not by cultivating followers who can execute but building communities that can innovate.”

Original thinking is created, not executed. The traditional model of team leadership by setting the course must therefore be transformed into leading by building communities of creators. As a startup, it can be easy to remain in “go mode” all the time. To “feed the fire” as Patti Sanchez put it. But in doing so the big picture of fostering long-term innovation for your team—a process that demands a form of team leadership built with equal parts patience, vision, and empathy—falls by the wayside.

Hill’s final lines are just as important now as they were six years ago:

Those who are exceptional at leading from behind are likely to be different than those who excelled at leading from the front. And this raises the question: are we identifying and developing the leaders who can tap the power of collective genius?”

Using crickets and crumbs

Jim Everingham, Head of Engineering at Instagram, recently wrote about how the observer effect impacts team management. In essence, in a hierarchical relationship, a leader’s very presence (and certainly their presentation of ideas) changes how the team shares, discusses, and ultimately decides on which ideas to pursue.

This is expected, and can certainly be a good thing. But for Everingham, it makes the most sense to use your power to empower your team so that it can produce the absolute best project result. Through being hyper-sensitive to the way his role of “head of engineering” can impact the process, he leads through a blend of Socrates-style questioning and empathic listening.

To apply this form of team leadership, let’s head back to our original example of setting up a meeting. You did all the work to set it up, but you also realize this:

Meetings are not opportunities to handpick the audience you want to watch you shine.

So how do you take a step back and lead from behind?

You take time before the meeting, even just 10 minutes, to think about the crumbs you’ll drop when a question you ask related to the overall goal is met with crickets (silence).

If your goal, for example, is to decide which position you most need to hire for, you could open the meeting not by laying out that idea you’ve been mulling over for all to see, but by asking something like:

Where do you think we have the most need? Why?”

Then, as Everingham, puts it:

If no one has any immediate ideas and all you’re hearing is crickets, you have the option to open the box very slowly and carefully. You can drop a breadcrumb to lead the team to a next conclusion they can use as a jumping off point — a hint that doesn’t give away what you think they should do. But the more breadcrumbs you drop, the narrower their thinking will become, so you have to be careful and thoughtful about what you reveal.”

This flips the traditional model. In many cases, a leader may ask the initial question not so much because they really care but because they want their team to think they really care.

As the question hangs and the crickets chirp, the traditional team leader then bypasses the crumb stage altogether and leaps right in, dropping their own idea:

Well, here’s what I think we should do.”

Boom.

This is what produces the best project results, be it hiring, engineering or otherwise. It’s at that pivotal moment where what Hill refers to as a team’s “collective genius” is buried under the rubble of roles. In this situation, the leader thinks they are leading, but in reality they’ve simply pulled ahead by pushing their team down.

A better solution is to drop crumbs that, through specificity, can lead the conversation to its next level:

Okay, well let’s break down each department’s need. First up: marketing. Throw out a few challenges we’re having here.”

This “crickets and crumbs” approach to leading from behind can work regardless of which industry you’re in or how fast you’re growing. But to make it work you must tap into your own leadership skills while simultaneously allowing your team’s ideas—which are likely better ideas than you have—to shine.

To give it a go, remember it in these three steps:

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See also:

Listen Like a Lion

An Ocean of Ideas, a Team Without Nets

-Illustrations: Bully