Why organizations struggle with operationalizing strategy

One of the recurring trends I’ve observed across multiple industries and at organizations that differ in both structure and size is the difficulty of delivering on strategic initiatives.

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One of the recurring trends I’ve observed across multiple industries and at organizations that differ in both structure and size is the difficulty of delivering on strategic initiatives.

These enterprises invest in bringing in top talent, both at the leadership and contributor levels and invest in strategic planning, identifying key initiatives to deliver. Most of the time, these initiatives are well thought out, with a good ROI. Yet, trying to bring them to life becomes a real headache.

In this blog post, we’ll take a lived example and explore the challenges faced, what worked, what didn’t, and how to move forward.

The premise: A promise of a brighter future

As each team is heads-down, busy trying to keep the lights on in an organization with decades-old infrastructure, a buzz is in the air. The company has just come up with its vision for the future and is investing funds to modernize itself and be a leader in the industry once again.

You would expect the mood to be effervescent, with smiles on everyone’s faces as they embark on an exciting transformation, but there is nothing of the sort. Instead, people are anxious and concerned, and the mood is dim.

While leadership brainstorms—crafting communication plans and ways to improve engagement—teams on the ground feel misunderstood and stressed out as the pressure to deliver on these new initiatives intensifies, and demands for day-to-day deliverables continue.

The divide between leadership and delivery teams grows, with no one seemingly knowing how they got here, or how to move forward.

The leaders’ lens: Stepping in to address challenges

To leaders, delivery was progressing at a snail's pace, which was surprising as the organization had certainly delivered more complex work in the past. Teams kept raising concerns about experiencing difficulty coordinating work between themselves, and confusion reigned on what priorities were for delivery. In order for the organization to deliver on its commitments, help was urgently needed.

To address these concerns, the solutions seemed self-evident. Management decided to centralize decision-making—they brought in more leaders, adopted new tools to improve visibility, and altered the organizational structure to get leaders more involved in the day-to-day work. After all, many of these leaders were hardened veterans with past experience leading teams to achieve tremendous results—success was guaranteed!

Reality sets in

However, delivery did not improve as time went on. Leaders had visibility, but with fragmented updates—initiatives would turn from green to red overnight with no prior warnings; risks were raised, but often lacked context to accurately assess the impact, and leaders were involved more than ever. As a result, this just added to the frustration on both sides—management didn’t see any material improvement in delivery, and teams were even more disheartened than ever.

The little initiative that could

All was not lost, as one initiative was steadily making progress. Sure, it was hampered in the beginning by endless debates around its requirements—and missing critical roles for successful delivery—but the teams working on it were determined to get it delivered.

These teams understood the ethos of this strategic initiative. They were able to talk directly with the business to get end-user feedback. They also clearly articulated the required outcomes, the target date for delivery and why it mattered, and the nice-to-haves versus the must-haves.

With this information, the product, technology, design, and delivery teams worked hand-in-hand, and:

  • Product owners were able to get a prioritized list of all the enterprise-wide initiatives from leadership. With this knowledge, they were able to have tough conversations with key business stakeholders about which features to deliver.
  • Technology talent was invited to requirements and provided critical insight around what could actually be delivered—they openly discussed technical challenges, and worked with business stakeholders to identify new solutions. While these new solutions were different from what the business initially had in mind, the team was still able to achieve the desired outcomes of the initiative.
  • Designers were given opportunities to raise concerns around accessibility and process flow—they shared best practices, as well as what worked and what didn’t from an end-user perspective. Their designs helped the whole team visualize the experience, and make changes as needed to deliver on a solid user experience.
  • The Delivery team orchestrated it all behind the scenes. They provided insights around a sustainable pace of delivery and facilitated conversations within each team around balancing the ability to keep the lights on while delivering on this strategic initiative. They also established bridges between teams and kept conversations going to ensure continuous alignment between teams. They facilitated conversations so that all teams felt like one team during the full duration of the initiative, working together with a common purpose.

The Delivery and Product teams played another critical part throughout the process. They shielded teams from the noise above and created alignment so that all teams were aligned on how the strategic initiative was progressing. They kept leaders informed, and at bay, reaching out to them as needed to remove impediments and to provide feedback.

In retrospect

While I would love to say that the enterprise reflected on what happened and made significant changes, the reality is that, unfortunately, little is done in retrospect. And this was no exception. Everyone congratulated themselves on the delivery of the initiative, and it became the success of the entire enterprise, celebrated as the achievement for that year. But then, things went back to the way they were—another reorganization, another new tool, and the continued thought that solutions will come from leaders.

Learning from the past

The biggest lesson I carry with me is that an enterprise that solely relies on its leaders to manage and solve delivery issues is doomed to fail.

Leaders are important, however, as well-documented in L. David Marquet’s Turn the Ship Around!, teams on the ground have all the knowledge and expertise to deliver successfully and efficiently. What they need from leaders are:

  • A clear understanding of the vision, strategic outcomes, and why they matter
  • Consistent communication about the shifting landscape and how it impacts them
  • How initiatives rank in comparison to one another
  • Facilitate the creation of direct communication channels with the business and, if possible, with the end user
  • Support to solve the challenges (The solution should be driven by teams and supported by leaders, with leaders acting as sounding boards and coaches to their teams. In my opinion, this includes decisions to get new tools or implement new processes.)
  • Commitment to look into concerns and risks raised by teams that they cannot solve themselves, and transparency about the outcome of that work
  • Genuine care about the well-being of the team
  • Dedicating time to be fully present in meetings, asking questions that help the team think differently about issues, and providing feedback as part of the inspect and adapt process

Moving forward

It’s difficult to change the culture within an organization. It’s also difficult to take a step back and create an environment where teams can solve their own challenges and coordinate delivery with one another—it takes a lot of skill, commitment, and time.

When you partner with an organization like Rangle, our leaders in design, product, technology, and delivery will work hand-in-hand to deliver on client outcomes. Our teams come in with an approach of meeting the client where they are, and helping teams progress at a sustainable pace that works for them. This is a great way to enable a strong collective mindset within organizations. I have seen Rangle’s success time and time again. It’s not easy, but when everyone is rowing in the same direction, you’re bound to get to your destination.


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