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6 Leadership Skills for the Digital-First Era

April 22, 2022 Leadership
Lance Haun
By Lance Haun

Organizations that have transitioned or are in the process of transitioning to a digital-first operating model understand there is a lot of change management that needs to take place. The technology choices alone can be a real logistical challenge.

But it’s not all about technology, of course. From thinking about what your organization's real estate footprint looks like to how and when to bring people together, there's a lot to consider. One aspect that often seems to be left out is how leadership skills need to adjust to this new operating model. While they're progressive in many ways, some organizations are going into this major organizational shift blind, without adequately preparing the key people who will make or break these transitions: leaders. 

It was one thing for leaders to step up in a temporary situation. Expectations, from both organizations and employees, were low. But assuming that the best people leaders are capable of leading with the same effectiveness remotely over the long term is a major mistake. As people make decisions about the types of digital-first companies they want to work for, they’ll be looking for a sophisticated leadership skill set built for this new environment. 

Here are the six most essential leadership skills for the digital-first work environment:

1. Multimodal, Expert Communication 

Being a great communicator is a key leadership trait, but that communication has been typically limited to in-person interactions and email. It gave leaders a targeted set of communication skills to build and become experts at. 

In digital-first work environments, in-person interactions are much more limited. Even virtual one-on-one conversations happen less frequently. While emails are still relevant, there are a variety of short-form communication channels to manage that are different than an email. 

Digital-first also gives organizations a greater ability to give asynchronous communication a try, through pre-recorded video or podcast episodes. Speaking through a camera, microphone or computer instead of to a physical being is a new skill that every leader will need to learn in order to be successful in the future.

Related Article: A New Category of Workplace Technology Emerges: Employee Communications Management Platforms

2. Intentional, Proactive Employee Connection

Managers who like to "walk the floor" to get a pulse on employees have been around for a long time. While it’s a disruptive practice in many senses, it’s also a sure way to interact with employees and gauge what’s going on in their world. You might see someone at their desk when you show up to work — and still there as you leave. 

That visibility disappears in the digital world. Monitoring software or the practice of keeping a close eye on a person’s Microsoft Teams status can't compare. Instead, leaders must take intentional steps to connect with employees.

Figure out a cadence that works, of course. But also, make note of critical times where you would normally check in with an employee. For example, if a person had a particularly rough experience with a client, reach out to them instead of waiting for them to reach out to you. 

Related Article: How to Practice Ethical Employee Monitoring

3. An 'Always-on' Digital Technology Learning Mindset

The types of tools needed in the pre-digital world could be implemented slowly and deliberately. Organizations could offer training and onboarding to everyone to help them get the most out of every technology investment. 

In a digital-first environment, however, the advantage goes to organizations that not only pick technologies that are naturally user-friendly but also have workforces and leaders willing to jump in headfirst to learn. Technologies used for communication, collaboration and productivity may change more frequently in a digital-first world, and organizations will depend on leaders to drive that change among their workforce.

4. Tech-Forward Work Experience Investment

The front door to digital-first organizations isn’t an office building. Instead, it’s the digital experience that every employee gets and projects into the world. When an employee must use a webcam that looks like it was developed in the 1990s, a computer that constantly crashes or out-of-date software, their experience and the experience that they can deliver to customers is likely to be just as bad. 

For employees who attend a lot of virtual meetings, an upgraded webcam and microphone setup will make every interaction better for them and for clients. For almost every company, having an additional monitor is a productivity booster. Collaboration software, even if siloed in small teams, can help bring the team better efficiency. Leaders need to be willing to solve these new types of pain points the same way they would advocate for a better office experience.

Related Article: It's Time to Address the Coming Leadership Void

5. Radical Personalization of the Employee Experience

In the pre-digital era, employees had the same experience every day coming into the office. They generally parked in the same areas, worked in the same buildings, had access to the same amenities and so on. People’s experience working from home — or anywhere remote — is very different, which is why leaders must learn ways to personalize the experience in very different ways. 

An employee with a dedicated office and good self-management habits might need very little from a leader or the organization. Another employee with a shared space that constantly gets moved or juggled might need a different level of support from the organization. Unlike a centralized office, the day-to-day experience of work is going to vary wildly from employee to employee in visceral ways.

6. Empathy Tightly Paired with Accountability

We’ve worked in offices and other physical locations for decades. How we’ve built cultural norms and expectations in those spaces are established parts of how some people manage work. Undoing decades of ingrained habits is going to take time. Leaders have to be able to be empathetic during this massive change-management exercise. Deciding to transition to digital-first won’t be for everyone and could have people feeling dismissed or left behind. 

At the same time, new norms have to be established for this transition to succeed, and along with that comes accountability. In the same vein of radical personalization, everyone’s journey is likely going to be a little bumpy. And for new employees who join, their transition into a digital-first organization is also going to be an individual one. Having key milestones to hit while still personalizing the approach is critical.

Related Article: We Can’t Keep Blaming Technology for a Lack of Leadership Empathy

Building Digital-First Leadership Skills

Many leadership principles apply to digital-first organizations just as they do to any other organization. But having all interactions online makes some common tactics and norms out of date or ineffective. 

As companies move into this new way of operating, it’s worth thinking as much about helping your leaders adjust as it is about the technology or the employee experience. Building those leadership skills will help guide employees and the organization into whatever unknowns digital-first has to offer.


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