Leadership in a Digital-First Environment

By Kayla Sheely

Leaders are an important part of an organization. Having a good or bad manager can make or break an employee’s experience at your company and can even add to the prevalence of quiet quitting.  

We sat down with Dave Ryan, Lead Link of Voice System Engineering’s UI/UX Circle to talk about leadership in this digital-first age.  
What would you say are the most important leadership qualities in today’s workplace? 

The ability to not micromanage is important and goes hand in hand with trust. Especially with being remote, you don’t know what people are doing all the time, and you have to be okay with that.  

You also need to be able to step back and let the people that report to you do their thing. Ironically, if you’re doing a good job as a leader, it almost looks like you’re doing nothing because your whole team is doing everything they need and you’re just there to help them when they get stuck.  
As a leader, how do you motivate your team? 

For me, a big way is calling out when my team does a good job – not being sparing with praise but being fair and honest with it. Another way is trusting people with projects that might be a little bit outside of their comfort zone. Part of having your team grow is giving them work that maybe they’re not sure if they’re ready for. But then also giving them support to know that even if they have issues or potentially fail, it’s okay. As a leader, I’m asking you to try this thing, and I’m going to help you out with it. 

Lastly, being clear with expectations, which is honestly something I’m still working on a lot myself. It’s important to recognize that everyone’s different, and you can’t assume that everyone’s going to approach stuff with the same mentality that you have about it.  

What has changed in your leadership style since going completely remote? 

I’m a little more hands on than when we were in person. I set up touch bases with everybody (which I didn’t have before) to check in and see how everything is going. Sometimes there is more chitchat, and other times it is more helping set priorities. When we were all in the office, a lot of this happened informally, so these weekly touch bases have been important for me.  

I’ve also really cleared out my schedule with a lot of the day-to-day technical design and coding that I used to do and delegated it to other people. At first, I felt like I was kind of being lazy and that it looked like I wasn’t really doing anything. But I’m still busy all day, helping people with different questions, helping prioritize, and things like that.  

And the other thing I’ve been recently encouraging is cameras on in our tactical meetings when all the UI/UX people are together. You can see how people are reacting to what you’re saying, and it helps bond with being remote.  

How do you think about leadership in the context of Holacracy? 

I’ve only been an official leader since VSE instituted Holacracy, but one thing I always liked about Holacracy that I latched on to early on is that it seems to have some systems in place to stop “managers” (Lead Links) from micromanaging. In a lot of ways, Holacracy feels like a pretty natural fit for me because I don’t want to micromanage. I want to be able to sit back and let everyone do their thing. Specifically, a Lead Link’s job is to clear the path for the members of the circle more rather than dictating what they’re doing – it’s to help them prioritize and help fill in the gaps. 

What are some pitfalls that leaders can get caught in? How would you recommend avoiding them? 

Recognize when you don’t need to talk. It can be tempting to feel like I need to say something to show that I’m involved. But sometimes you don’t – the people on your team have got it. You can maybe say something to support them, but sometimes it’s just adding noise and not necessary. I will often be the last person to talk in a meeting, and that’s intentional on my part. I want to hear what everyone else is thinking before weighing in.  

I think when many people first get into a leadership role, there can be a lot of new stress. Before you are in a leadership role, it’s easy to think “what does this manager do all day?” It’s hard to imagine the extra pressure that comes a leadership position. Suddenly you’re in charge of this group, and there can be a temptation to do a lot of the work yourself. You have to fight that instinct because you want to elevate your team to a level that everyone benefits from.  

Do you have any advice for leaders or aspiring? 

It’s perfectly fine to say “let me think about this” if you don’t have an answer right away. Don’t feel pressure that everything has to happen in a split second or off the top of your head. Sometimes it makes sense to ruminate on a question or issue. 

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