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How to Empower Your Middle Management for a Successful Digital Transformation

Digital transformation is no longer an option for most organizations, it’s an inevitability. While eager executive teams and frontline employees may be enthusiastic about change, a common challenge emerges at the middle-management level. Often referred to as the "frozen middle," directors and VPs are prone to struggle when it comes to adapting to a product-led operating model. To their credit, they’ve risen through the ranks for a reason, but the tools that got them to this point aren’t going to get them to the next level. So, what will?

This article explores strategies to unfreeze the middle and empower these crucial leaders to support a shift to a product-led operating model and, ultimately, through a successful digital transformation.

Recognizing the Frozen Middle

Most of us are familiar with the term “frozen middle” – a phenomenon that occurs when middle managers aren’t quite sure how to be effective in their roles and, as a result, become stuck in inaction. This is a pretty common occurrence among companies transforming to product-led operating models because the middle managers are being asked to lead, work, and measure success in completely new ways.

And can we really blame them for being frozen? To date, they’ve excelled in their careers working one way, but now we’re asking them to revamp the way they do things without much direction on what they need to do it well. It’s kind of the ultimate “who moved my cheese” moment. That’s why it’s so important for organizations to give middle managers the support they need to understand what a transformed world will look like and how to get the org there.

Strategies to Unfreeze Middle Management

My Tuckpoint team is made up of digital transformation experts who specialize in operating-model transformation, which is a long way of saying that we address this specific challenge a lot. We try to spare our clients the time and heartache of this phenomenon by planning preventative strategies to get out ahead of it. That said, you may be reading this already in the throes of transformation already struggling with these exact obstacles. Don’t worry, there are still methods you can implement that will help right the ship and activate your middle managers. 

Here’s what it will take:

1. Transparent Communication

Addressing the elephant in the room is essential. As a leader, you’ll need to be open and honest about what’s required to transform and how management roles might look different. New ways of working may demand reframing or even abandoning familiar practices. Providing support and clarity is crucial in alleviating their concerns. When you do this, you start to normalize some of the fear they’re likely having over these shifts.

2. Redefine What "Good" Looks Like

Expose middle managers to successfully-transformed companies by organizing ride-alongs and go-and-sees in orgs that have embraced change successfully. Being a peer observer in an agile, product-based organization can reshape their perspective on quarterly business reviews, planning, and other processes they need to own. When you redefine what "good" looks like, it provides them with new tools and insights, and helps them understand what’s expected of them.

3. Coaching Support for Middle Managers

Coaching models often focus on individual product teams, but the leaders of these teams are equally important and frequently forgotten. We assume the leaders will just figure it out – surely they know how to show up in a completely different way, right? Not exactly. Middle managers should be coached on reading roadmaps, creating Objectives and Key Results (OKRs), and navigating the complexities of leading product-focused initiatives. Ensuring their skills align with the transformed organizational structure is crucial for success. And if they don’t currently have those skills, it’s your job as the leader to figure out how to help cultivate them.

4. Talent Strategy Alignment

When an organization transforms to a product-led operating model, the entire way it hires and builds its talent also shifts. Many middle managers may have never hired product folks before and will need guidance on identifying suitable candidates who align with the organization's new direction. We can’t just expect them to be great at it from the jump. Training them on effective hiring, support, and growth strategies for product-focused roles is essential to bringing in the right candidates for the job (and the future).

5. Incentive Structures

The existing or traditional incentive structures your organization has in place probably won't align with the goals of a product-led organization. When you transform, it can be hard for middle managers to get behind the change because their bonus structures and performance-based incentives are tied to old ways of doing things, not the new ways. As a result, there’s a direct tension between what they’ve been evaluated on before and what they need to be doing in the future. To overcome resistance and help alleviate the fear of losing bonuses tied to old ways of working, freeze or bridge performance incentives during the initial stages of transformation. Once middle managers are comfortable with the changes, redesign the incentive structure to align with the new organizational objectives.

Empowering Middle Management for Success

When you’re dealing with this phenomenon, it can be really easy to blame the lack of progress on middle managers. But it’s leadership’s responsibility to give them the support they need to understand what a transformed world will look like and the tools to get there. By acknowledging their concerns, providing support, and laying the foundation for success, organizations can empower these leaders to play their crucial role in shifting to a product-led operating model. 

Ultimately, recognizing the importance of the middle and investing in their development ensures a more seamless and effective digital transformation journey (and I know that outcome is something every leader is on board with). 

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