Reflections from co-creation of Digital Stategies : Learnings on the three Cs (Part 3 of 3)

Over the past couple of years, I’ve had the privilege of co-creating digital strategies a good variety of companies, each unique in size, complexity, and industry. As I reflect on these experiences, several key insights stand out that I'd like to share. Below reflections are in way an attempt to be comprehensive but read them as additional inputs to your current repertoire of learnings.

To begin with, my recent work reaffirmed much of what I discussed previously in the two articles

1. What – Digital Strategy as Platform Ecosystem

and the

2. How – Three Cs to accelerate the flywheel of Digital Transformation, ?

Building on this foundation, I’ll dive deeper into the nuances of the three Hows — Congruence, Culture, and Capability —withe some practical tips on what worked and what did not.

1. Congruence: The Alignment Challenge

Achieving alignment among the board, management, senior leadership, and Digital/IT teams remains the most challenging—and the most critical—aspect of digital strategy. Once alignment is achieved, progress flows more smoothly. Here are some key learnings:

a. Organization Context: Context is king—without it, even the best strategies can fail. Leaders must stay attuned to the organization’s pulse and understand when to push forward and when to hold back. For example, advocating for aggressive digital investment during a period of declining revenue is unlikely to succeed. Conversely, aligning your strategy with current organizational priorities, such as improving customer service, can enhance buy-in and momentum.

b. Senior Leadership Mindset: Early-stage alignment meetings with senior leadership aren’t just about presenting frameworks and showing the Art of Possible —they’re also about understanding the decision-making patterns of key stakeholders. Senior leaders often filter innovative ideas through their "mental model of success," that have worked for them in the past. Tailoring your approach to resonate with these models can accelerate buy-in. This requires emotional intelligence to navigate the complexities of leadership mindsets effectively. Typically, these mental models will have bias on one or more enablers e.g., Talent (who will drive this); Execution (What are the failure modes); Collaboration (How will cross functional teams come together); Comprehensiveness (Have we thought through everything) etc. It is important to bring more details to the table depending on the leader’s mental model.

A common use case in many organizations is expanding distribution reach. Traditionally, business leaders have focused on growing their networks by opening new dealers, retail locations, or branches, depending on the nature of the business. Presenting the concept of a Digital Dealer or Virtual Branch as an enhancement and support to these existing network expansion efforts is likely to gain more buy-in than framing it as a replacement for the current approach. This complementary positioning ensures alignment, reduces risk in the mind of stakeholders at the same time drives the digital agenda forward.

c. Cross-Functional Collaboration (Structure and Incentives):

The involvement of cross functional teams in the strategy creation process goes a long way in their commitment to the success of the same. At the same time, for long-term success it is especially important to align structures and incentives. Initial enthusiasm fades very quickly without formalized frameworks and aligned incentives as sooner than later people will get pulled into their line priorities / what their respective managers value. For instance, in a manufacturing company, a digital initiative aimed at reducing R&D cycle time is highly dependent on collaboration with the shop floor. However, if incentives are misaligned—e.g., if only the R&D team is rewarded—the initiative may receive lukewarm support from other critical teams.

2. Culture: The Key to Long-Term Success

Conscious long term effort in culture building plays a pivotal role in the successful execution of digital strategy. Here are some learnings:

a. Skill Building: Behavioural shifts are driven by belief, and belief is rooted in knowledge and skill. Investment in awareness and skill-building goes a long way in driving digital evangelism and adoption. This includes not only technical tools but also learning the ropes of Agile, Design Thinking and other supporting skills.

b. Getting them invested: What gets reviewed, gets improved. One of the approaches that I have seen working well is to initiate a dedicated review of digital programs by the CEO with Business Heads on adoption, outcome tracking and debottlenecking (This is beyond the standard steering committee). This creates a positive cycle of senior leadership getting ‘invested’ in the success of the programs at the same time a positive stress on the project teams to drive adoption and outcomes.

c. Balancing outcomes and efforts: All digital programs should be outcome-oriented, with a clear link to business strategy. However, it’s equally important to balance outcome tracking with input/effort challenges. Very few programs are successful from day one. Digital initiatives often follow an "iceberg" like model, where the visible results are only a fraction of the total effort. Leadership messaging is key during challenging phases—embracing a startup-like mindset of realignment, reflection, and pivoting is critical for success.

3. Capability: Building Sustainable Digital Infrastructure

a. Architecture Principles: The importance of digital architecture is often underestimated by many business and digital teams. Many a times in the mirage of speed one makes sup optimal architecture choices rather than considering long-term architectural impacts. Solutions developed with this mindset often fail within a few years, leading to costly rebuilding cycles. Sustainable solutions must be rooted in the organization’s long-term architectural vision with alignment to clear end state. This target architecture must establish key guiding principles, while also being regularly updated to reflect current realities and evolving technologies.

For instance, trying to solve analytics issues without first addressing master data management is merely a temporary fix. While short-term solutions might produce accurate reports, they become unsustainable without robust data governance. Similarly, failing to establish an API ecosystem from the start can lead to a tangled web of integrations, which are difficult to manage and hinder operational agility.

b. Security and Privacy – Investing forward: Security and privacy needs lot more forward investment. Neglecting these aspects during the design phase is akin to letting weeds grow unchecked around your crop. The total cost of remediation after security audits or breaches is exponentially higher than the cost of prevention. Unfortunately, securing budget post-breach is often easier than securing it for prevention. Digital leadership must work to make management aware of this and advocate for proactive measures.

c. Digital Talent - Outsource vs Inhouse: Having the right talent is essential to executing the digital strategy and roadmap. While there’s a growing preference to build in-house digital talent wherever possible, it’s important to consider the organization’s current context and maturity level. A balanced mix of in-house and outsourced talent is often the best approach, tailored to the specific needs of the organization. For instance, many companies hired data scientists in recent years as a trend, but only a few were able to keep them engaged or provide a clear career path. Cross-functional agile teams, with the right blend of in-house and outsourced talent, alongside digital and business teams, represent a sustainable model for long-term success.

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