The 2 Things Leaders Can Do Right Now To Prep Teams for Transformation

When it comes to transformation, an organization's biggest asset is its people. That’s where the Design Sprints and think tanks are firing, and where the change agents and early adopters exist. But without a cultural baseline of trust, vulnerability and curiosity, there’s little chance you’ll be able to activate your talent for the work ahead in your digital transformations strategy. 

Why? To state the obvious, if your teams feel a sense of mistrust and/or are afraid to fail, they won’t step outside of the box, and that’s exactly where you need them to be during a transformation. 

Herein lies the importance of psychological safety – a topic that absolutely deserves a place on your reading list, and from where I want to pull two key behaviors that should be applied within the context of any transformation.

1. Demonstrate vulnerability to build trust with your team

If you read that line and immediately assumed this is already true of your relationships, I’d caution you to reflect a few moments longer. 

Are you and your fellow C-suite leaders regularly sharing failures and learnings openly? Is the executive team owning missteps and errors in a shame-free, blame-free way? 

If the answer is “no,” then I’d wager your staff doesn’t feel agency to own their mistakes either. This is a “practice what you preach” moment. If you’re asking teams to step into uncharted territory, they need to know they’re safe to try, fail, learn, and try again without the fear of losing their jobs. And that attitude starts from the top. 

When I coach leaders, I encourage them to fold this self-reflection exercise into the same conversations where finances, operations reports and KPIs are being discussed. Ask every leader to share something that went well, somewhere they fell down, and what they learned from it. Then ask them to take the same exercise back to their teams to encourage them to feel more comfortable talking about trial and error (and to show that their leaders expect error to happen). 

In order for this to work, it cannot be one-way. Every member of the C-suite starting with the CEO needs to be prepared to own their misses and reflective moments in a “public” way. Because if it’s not happening at the leadership level, it most certainly isn’t happening anywhere else in the organization. 

2. Foster Curiosity and Enhance Digital Transformation Employee Experience.

Transformation requires divergent thinking. When’s the last time you hosted a speaker or organized a team outing on a non-work-related topic? Sometimes the greatest catalyst for change happens after exploring ideas and topics seemingly unrelated to the task at hand. Analogous experiences are wildly effective at pulling us out of our bias or conditioned ways of thinking.

Here’s a good example: a client of mine specializes in helping adults finish their degrees after having started and stopped the traditional learning experience many times (due to becoming parents, balancing education with work, mismatched learning environment, etc.). Our task was to better understand the experience of learning to identify barriers to completion, reasons for drop out, and so on. 

To do that, we each participated in our own learning experiences. I chose knitting after having given up 10+ times and swearing it off with the declaration that I was unteachable. I signed up for a small-group class and showed up to our first lesson a bundle of nerves, feeling intimidated and resigned. Then I imagined how so many of my client’s students might feel after returning to education for the Nth time. This analogous experience resulted in insights that were completely applicable to the problem my client set out to address.  

It’s in this spirit that I insist you engage your staff in divergent thinking. Start a book club with surprising topics (rather than boring business titles). Ask everyone to take an online course with the intention of reconvening to talk about learnings and reflections. Organize a monthly learning lab on a new topic. The options are endless!

Doing this builds a culture of curious, divergent thinkers, and that’s exactly the type of mindset you need when heading into a transformation. 

So, my advice to any leader considering this major change – or wondering why their current efforts are at a standstill – is to ask yourself if vulnerability, trust, and curiosity begin with you and your executive team. Be honest with yourself. Your transformation depends on it.

If your organizational health checks out, you can proceed to the next pre-transformation step, which is all about building a killer transformation team.