If you are leading any digital transformation effort – from a “simple” website redesign, to a much bigger reimagining of business operations – you are inevitably leading a change management initiative. The case for such a transformation is likely clearer than ever, given the rapid shifts propelled by the pandemic and other recent events. Yet any project that promises big change attracts diverse stakeholders: those who love what you’re preaching, those who hate it, and those who fear it but are persuadable. 

This is all hard work. But it’s needed more than everand, fortunately, successful examples abound! In one of our recent gatherings of senior leaders across the mission-driven sector, we talked with Kellye Rogers, Portfolio Lead & Director of Core Innovation at Capital One, to learn specific strategies and best practices for managing the challenges of digital transformation. She’s led successful digital innovation projects for organizations including Twitter, NBC Universal, Time Inc, and 

Kellye’s experiences, and our own work with mission-driven organizations, point to six hard-won lessons for anyone tasked with managing or informing a significant innovation or digital upgrade within their organization.

Remember your vision—especially when things get rocky.

If you’re building a product that’s going to change the world, you’re in a kind of temporary professional marriage with your project team. Things will go wrong, and there will be days when you can’t stand each other—it’s inevitable! Just as in any marriage, you have to keep asking: “What’s the vision we’re committed to together? Why are we here?” 

In prior work in the healthcare sector, Kellye struggled to get two teams of developers and experts — both hung up on technical minutiae — to move beyond differences and focus on the needs of end users. By inviting in a patient to talk about her lived experiences with medical technology, they realized that the technicalities bringing them apart were actually irrelevant to the patient experience they all sought to improve. 

In healthy relationships, partners also know it’s vital to make time to celebrate the successes and small victories. When you savor the good moments, you build goodwill and shared experiences that allow you to work through the rough patches with somewhat less friction.

Talking with end users? Be as humble as possible.

Every organization has front-line staff members who are closest to your beneficiaries: service agents, case managers, customer service professionals, etc. Empower these people to connect you with the stories your team needs to design and implement effective solutions for real-world problems.

At the same time, in talking with these individuals, the last thing you want to do is come in acting like you’re the expert! You build trust with frontline staff by being completely humble and extraordinarily curious. When you are really listening to what they have to say, they will gladly share their stories with you. (And if you implement what they’re asking for, you know they will adopt it.)

Have team members check departmental identities at the door.

For real: consider literally having team members take off their departmental badges and hang them by the door! For a past client, Kellye had members of her project team physically remove their departmental identities before every team meeting. This simple act was a powerful reminder that everyone’s purpose in the room was to improve the lives of beneficiaries and clients, not to worry about narrow bureaucratic mandates.

Put the visionaries in the same room as the detail people.

We tend to valorize leaders with the bold vision for transformational change. They’re your unstoppable champions, and they’re vital—we hope you have at least two on your team! At the same time, visionaries tend to gloss over the details. So don’t be afraid to put them at the same table as those whose superpower is obsessing about the tiniest details. Together, these two groups of people can power your project through all kinds of practical barriers.

Don’t waste energy trying to convert the cynic.

You may be tempted to try and change the mind of the most pessimistic member of your team, but don’t waste your time. They’re a bit like a bucket with a hole in the bottom: you’ll never fill it up! At the same time, don’t write your cynic off completely; they’re actually a valuable asset who can guard you against over-engineering, and indulging fluffy needs and pet projects. The cynic wants to be a cynic—it’s what they do best!  So, use them strategically to fight against ideas and features that you know won’t work.

The best products have the least ego in them.

As your project moves forward, stakeholders grow attached to specific features or platforms, and will want to leave their mark on the final product in specific ways. Yet it’s not about any one person’s beliefs – it’s about the bigger group of people whose lives will be changed by your digital transformation. To cultivate this humility and flexibility, remember that nothing lasts forever. As good as your new product or service may be, it will eventually be followed by a decommission! Opportunities for further improvement are continuous and never-ending.