From flat organizations to remote work: How do you lead a company today?

Leadership is changing. Not so long ago, a normal work culture was one in which there was distance between those in charge and their employees. There were boundaries, delineated by professional hierarchies, and leaders reigned supreme.

Today, the role of a leader has drastically expanded as society shifts its perception of success and younger generations let their workplace expectations be known. To boot, the titanic shift to a remote work model is posing new challenges for managers who now have to assert their leadership across the internet ether.

We asked our expert in The Lab, Ben Prouty — serial entrepreneur and CEO of the child education app Poncho — about the new view of authority, what it means to be a remote leader, and how companies can offer attractive career paths to younger workers.

How has leadership changed over the past decades?

When I was straight out of university, the previous generation — my dad’s generation — was in the management roles, and they all had the same management style. It was the corporate mindset of the time; old school, and very much hierarchical, as in, “I’m the leader and I’m making the decisions.”

I was quite junior [in my company], so maybe it was partially that, but I never got the sense that there was really a good opportunity for push back; an opportunity to challenge somebody’s style or way of leading…generally speaking, there wasn’t a lot of collaboration, and I’d say it was leadership by distance, and potentially creating a bit of a fear factor, which is almost the opposite of what we aspire to today.

So what do you think has been the main driver behind that change? Is it mostly a matter of figuring out that this is a more efficient and better way of leading, or is it rather that we have different social norms today?

I think we as a people, as society — our cultures, norms and behaviors outside of work — have evolved. Just like it’s happened within the workplace. The way we all interact with each other, it’s a more level playing field, more collaborative.

And I think informality plays a role, as well. Out on the street. I think a lot about formality; at my age, how I greet people and how they greet me. And a lot of that [formality] has been lost, for good or for bad, and I think that’s just extended into the workplace.

I imagine that a lack of formality contributes to a willing to contribute as employees worry less about getting shut down. But on the other hand, there is also this issue with an informality that creates insufficient boundaries.

Absolutely. And that’s something I struggle with as well because removing the traditional hierarchy is all well and good, but there are times where, frankly, you need boundaries and a little bit of distance. And you do need to retain some of fear. We can’t be all nicey nicey the whole time.

You always need to have that dynamic where you can switch it up a little bit as a leader. I think if you’re one dimensional and that’s all you rely on, then you’re just going to be trodden on all over. So have your A-game, which can be very informal and friendly. But yes, have them ultimately respect you. If they respect you, then when the time comes to start ratcheting up the pressure a little bit, they’ll deliver knowing that that’s not your default setting and that you’re not constantly in that mode.

What would be your advice to someone who maybe unexpectedly got promoted into a management position and now is meant to lead? Someone who’s never done it before and is now in this modern, progressive environment where the leadership role might not be sufficiently defined.

This happens often in startups, where people are pushed into leadership positions or management positions before they’re ready. For example they’ve been excelling in their original role, they’re the best salesperson on the team, but then the company grows and has to hire new people. Because that employee is excelling at what they were hired to do, they “get” to manage the incoming hires. They just get thrust into it. I’ve seen examples of 50% thriving and for the other 50%, it absolutely doesn’t work. And when it doesn’t work, it’s actually a complete disaster for everybody involved.

Often, the biggest issue for that person is they just behave as they did when they were on their own. They don’t make that total change of track. And that is required. As soon as you’ve got a leadership management position within the company, the main thing is making sure you’re taking time to listen to and spend proper one-on-one time with the people on your team. (That’s obviously not sustainable on a corporate scale, but certainly within a small startup, just take time to understand what they expect and want from you as a boss.)

And then the second main criteria is to be consistent. Consistency is critical. The worst thing you could do as a leader is to be erratic. Be consistent in your message, and what you expect. You’ll notice that people will respond much more effictively.

So if society has shifted its perspective on the roles between employees and leaders, how do you think we can make professional environments mirror a new ideal of what it means to lead at work?

I’m seeing and hearing about more examples of companies that are creating two different tracks. It seems to be an effective approach. They’re saying, look, you can either get on this track of broad management and cross discipline, and you’re going to go up this pay scale and this hierarchy of titles… or you’re going to go really deep and be the best salesperson, a real expert on this, but you’re also going to go on the same pay scale.

They go up in parallel and have different types of titles. But really the thing that they’re deciding is how broad they want their expertise to be and therefore what level of leadership responsibility are they prepared or willing to take on board.

It remains to be seen if this will be the perfect solution. But I think it’s a start. And I think if I had been presented with that early in my career, I would have liked the idea of having that optionality. Now it feels like different personalities can be rewarded and feel like they’re progressing in a matter of different ways by climbing parallel ladder within the business.

Another obvious, big shift is the remote model. People are working full time from home. Communication is mostly online. What advice would you give to leaders to stay in touch with everyone even though they might not see them everyday?

That’s a great question and I don’t think anybody has quite figured that out yet. I guess it depends on your leadership style. It was very interesting quite early on in the pandemic when certain companies and certain types of leaders, typically in the corporate world, were very much pro getting people back into the office. My read on that was that they needed that presence; it was essentially what gave them their leadership position, just being seen and being in the corner office like “I’m the boss and I’m wearing my suits and I’m here and I’m more senior than you.” The pandemic killed a large part of that traditional leadership culture.

But I think in that sense, it was much of a less cumbersome transition for us who work in the the startup environment, where we’re already collaborating a lot online anyway. As for leadership, I imagine that being thrown into a leadership role in a fully remote environment must be pretty tricky, especially if you have no prior experience.

Personally, I do lean quite a lot on leadership cues that are in person; having one-on-ones and sort of getting the team together in a room and reinforcing my role is what I tend to lead with. So a lot of that is lost online. But I don’t think there’s any sort of magic wand; you’re still going to need to do the legwork elsewhere to build that respect and get people knowing and understanding that you’re needed for certain things to be facilitated in an online world.

I believe where we’ll probably settle in the future is a kind of hybrid model. The in-person meetings is where you can truly take the necessary steps to fullfill that leadership role and build your credibility. It’s almost like accumulating leadership credits that you can then use when you’re forced to lead online and everyone is working more independently.

Photo: Welcome to the Jungle
Edited by Jordan Nadler

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