illustration of a person standing in the middle of a tornado

The phrase “transformational change” pops into my head a lot. We’re certainly being forced to make massive changes these days. But, truth be told, transformational change was on my mind well before I’d even heard the word “coronavirus” or knew you could make a face mask using coffee filters.

Not only because many of the customers my teams build for are evolving in some pretty dramatic ways (agile at scale, anyone?) but also because my organization has just come through a massive change ourselves. Having been at the forefront of this, I’ve learned a few lessons that can help leaders in any industry guide teams through times of transition – whether they’re choosing change, or adapting to new circumstances.

First, let me set the stage. My teams have traditionally made software that our customers install and maintain on their own servers. And we still do that today. But like many other tech leaders I’ve spoken to, we recognize that the future is in the cloud – i.e., the hosted “software as a service” (SaaS) model. So in addition to shifting our entire business into cloud-first mode, we have to be prepared to help our customers navigate the transition from server to cloud when they’re ready.

Chances are, you’re eyeing a similar change on the horizon, or, if nothing else, are eyeballs-deep in the sudden shift to working from home. Given the uncertainly around how long we’ll continue to work remotely and the added challenge of having kids, partners, and roommates around, our teams need us to step up more than ever. Here’s how.

Lead with courage and compassion in equal measure

Change breeds fear. A common reaction to fear is to build conspiracy theories. Accusations fly fast and thick. “The customer support team is lazy”… “Sales teams don’t sell enough”… “Product teams just don’t have a product ready”… “It’s all stupid politics!”

Leading with courage requires calling bullshit on blame games, and leading with love requires understanding why people are playing them in the first place. We tend to assume the worst when we don’t understand the reasons behind whatever change is afoot. When the finger-pointing starts, that’s a sign that people can’t see that there’s a shared goal. As a leader, it’s your job to peel back the layers of misinformation and explain how the change will help everyone accomplish more.

Photo of a mountain climber

As a leader, you also need to acknowledge the disruption your teams are experiencing. This can be hard. Still, it’s the best way to calm their fears and help them adapt.

Illustration of people leaping over abstract shapes

Can’t stop, won’t stop

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Courage can overcome your own misgivings, but you need love to help others overcome theirs. At the end of the day, you all play for the same team. But if people lose sight of that, competitors will kick your collective ass.

Embrace the chaos, but manage the rate of change

From a distance, Africa’s great wildebeest migration appears to run like an elegantly ordered transit system. When you look closely, however, you see the truth: it’s utter chaos.

So is large scale change.

As long as you’re moving in the right general direction, it’s ok to adopt a mindset that values progress over perfection. In fact, that’s probably the most prudent (and sanity-saving) thing to do.

Photo of a herd or wildebeasts

With the server-to-cloud transition I led, there were countless deliverables needed from pricing and packaging to product capabilities and more. Trying to answer every question in painstaking detail before we started delivering anything to customers would have delayed us by weeks or even months. Instead, we chose an incremental approach in which problem discovery and solution were centralized in one team. They cleared the path for other teams that focused on keeping current customers happy and landing with new customers. This way, we could both manage the rate of change and make progress on several workstreams that ran in parallel.

To be sure, the sudden switch to remote work has been chaotic, partly because it wasn’t possible to make that change incrementally. We can, however, give our teams continuity in smaller ways. Don’t let rituals like retrospectives or team lunches fall by the wayside – it’s easy enough to adapt those to a remote work context. Keep checking in, keep talking with team members about their career growth, and keep offering words of encouragement.

Learn from others, but be true to yourself

8 people-first leadership stories that inspire

Leading change can be lonely. Especially when you’re the one with the unpopular opinion, the one that is convincing others to look in a different direction. At those times, it’s wise to ask for help. Over the past year, I’ve spoken to dozens of tech leaders, many of whom have led teams through a similar transition.

While I learned a number of valuable lessons from them, it also made me understand how unique my teams’ strengths are. Not that we’re perfect. Far from it. But while we grow and learn and make mistakes, we also need to have the conviction to be ourselves and not just copy what others do. Within the context of being stuck at home while also trying to work, this is true at the individual level too. Working on the couch in sweatpants is calming for some, de-motivating for others.

Photo of a group of meerkats

At an offsite a while back, we went through an exercise in which we all wrote down the one big thing we dreamt of doing over the coming year. I wrote: “Start a movement.” Granted, leading my teams through a major change to our business model and dealing with all the downstream effects on how we build products wasn’t exactly what I had in mind. And leading them through a complete upheaval of the way we work, forced upon us by a global pandemic? Didn’t really see that coming, either.

That’s the thing about massive organizational change: it has a way of choosing you. (And not the other way around.) If you respond by resisting it, you’re sunk. But if you choose to embrace it, you’ve got a fighting chance at navigating it successfully and leading people on a journey they’ll think back on as an adventure.

Leading through change and embracing the mess