This evening, about five hours ago, I was talking to a peer – a very close friend, a confidante, and a fellow coaching consultant. He said these very true words, “You can get a lot of things wrong in your business and survive… but if you don’t get leadership and loving and developing your team, you will fail miserably.”

This is a hard truth. And, to state the obvious, it’s good to talk about what is true – even when it’s hard. It’s good to be talking about what is real and what really impacts your team and your business.

I could write not just 1,000 words but 100,000 words on the challenges we face as leaders, but I think this visual does a great job of capturing the top challenges to leading right now.

Let’s unpack these one at a time:

Maintaining a healthy work-life balance is the first challenge to leading in the digital age. In today’s world, being a leader never stops. I’ve felt this tension for decades. I felt this years ago when I was a junior officer in the military in the early 90s, when I was working for a fortune 100 company in the mid-2000s, as a senior leader for a software company about a decade ago, and even working for a big church up until a few years ago. Maintaining the balance has been a challenge for a long, long time. Without question, this challenge has only intensified. It feels like people have access to you 24/7, and it’s so hard to have boundaries. At my worst, for many decades, I was probably getting about a D+ on this. Now, with a lot of personal self-development and boundaries, I may be at a B. But I want to get to an A+. I want to be available to my work people; I want to be freed up for my family. I want to lead by example, showing my work ecosystem that I am not tethered to work 24 hours a day; but I also want to support the needs of those within my work ecosystem. In short, the world doesn’t stop; but what am I doing to ensure a healthy work-life balance? This challenge is a tough one, for sure.
Leading through influence – and not relying on your title or position. This used to be so backwards for me. Particularly in the military, and even when I worked for a fortune 100 company, it was less about influence and more about title and position. Nobody would say that out loud; but our actions, words, policies, and behaviors reinforced that our title and position mattered more than anything else. In the old days our title was the “most important thing.” That’s not true anymore. It probably never should’ve been true. But today, the questions are, “Do you see leadership as influence? Do you see people around you – whether they are above or below you on the org chart – being able to have as much impact and influence as you do?” This is the world we operate in. I think it’s a great thing. But do you recognize it as a “great thing” as a leader? Furthermore, do you embrace it? And, being fully honest, do you recognize it as a challenge that you are currently facing? Because if you are in charge or responsible for something (i.e., a team, multiple departments, a P & L), then you are responsible for outcomes. And if you are responsible for those outcomes, you need to be incredibly tuned in to those influencers – even if they are people who may not have positional authority. You and I both need to recognize this and embrace it. For years, I probably got a C+ on this, and I’ve gravitated maybe to a B+; but I want to get to an A+. There’s still room to grow for me, without question.
Communicating effectively in a visual interactive world that demands immediate application. This is a tough one. It’s as tough as it gets. Everybody, I don’t care what generation you are in – Gen X, Y, Z, or the next generation – has an attention span that has shrunk exponentially. If you can’t communicate with impact and with immediate effectiveness, then you are behind the power curve. This is a challenge for every leader. I don’t even know what my grade was for the first number of years I was leading in the workforce, but it wasn’t a great score. And as each year goes on, this becomes more and more and more of a deterrent to success. I probably think about this one more than any of the other five challenges to leading in this era. As leaders, we have got to get our arms around this. If we’re not having on-target and effective communication (that is attention-grabbing), we are missing the boat.
Building agile, collaborative teams that harness the superpowers of each individual. Gone is the day of “everyone should walk, talk, and dress like me on this high-powered Fortune 100 sales team.” Today things have changed in a good way; we embrace diversity and agility. We embrace different personalities, temperaments, skills, strengths, and gifts. Today, we are like a League of Justice, with all the different superheroes that come together to be an effective body, unified by a common purpose. To be candid, it’s hard to embrace all the differences, diversity, agility, and collaborative efforts that need to take place. It takes work and effort and time, and patience. And yet, it’s so worth it; but it’s hard to do and takes incredible intentionality. It takes predictable rhythms and repeating rhythms to dive into this mindset and to create the space for this kind of teamwork. I would say I was at an F+ on this many years ago… particularly when I was in the military. It was bad. My collaborative nature was almost non-existent. I’ve gotten better, quite a bit better – maybe getting into an above-average grade. But I still have room to grow.
Leading virtual teams with ingenuity in a remote world. Frankly, I don’t know anyone that’s not dealing with this. I have a team of consultants and coaches, and we are spread all over the country. I am coaching and consulting multiple executive teams across the country. Their executive teams and their subordinate teams are spread throughout the country and around the globe. Everybody is dealing with this remote world. EVERYBODY is trying to tackle the question, “How do we lead with effectiveness when people are spread out in different locations, time zones, cultures, and subcultures?” This one, like #3, keeps me up at night. This is probably my second biggest obstacle; but if we don’t dig into this, how are we going to lead a high-performing team?

All of these five can feel insurmountable and overwhelming; but we’ve got to start with at least recognizing that these are real challenges that we face. Then we can start to develop a helpful course of action to remedy them. When we acknowledge them and start having a conversation about them, we can make a lot of movement. We can start to take steps towards being better leaders. We can be GREAT leaders, even when it’s hard to lead in this very challenging age.

Leadership Challenges in the Digital Age