The consistent reality of my various CIO, COO and CTrO has been that time has been my constant enemy and this amplified when multiple Executive Sponsor roles are layered onto a busy schedule. Once you become comfortable in a state of being time-poor, task-rich, you quickly realise that the culture you foster and the team you build around you can make or break the transformation's success.
The reality is that successful transformations survive and thrive based on a culture of fearless communication. When your touch points are limited to weekly check-ins and steering committee reviews, you needed need transformation leaders who won’t hesitate to speak the truth, especially when it’s bad news. Fearless leaders who communicate openly are not just an asset, they are the only real mechanism a sponsor must ensure that the unfiltered ground truth reaches you in time to make key decisions.
Almost a decade ago I was asked to take over a global ERP enables transformation spanning Professional Services, HR and Finance that implemented a new operating model and a shift to a new outsourced share service centre. On arrival what I found was 5 workstreams operating in silos, a culture of faking it before with each workstream desperately not being the first domino to drop, with each Programme Director being in clear realisation that they were failing. Instead, fearless leaders, what I found was a culture of fear, fear of a CFO with an intolerance of bad news.
In transformation, being blindsided with a false narrative renders the Executive Sponsor ineffective, leaving the problems that aren’t addressed to snowball into bigger challenges, ultimately threatening the entire initiative. The Executive Sponsor needs fearless leaders that play a critical role in surfacing problems before they grow. Without leaders who feel empowered to openly communicate challenges and risks, you’re left with a skewed view of reality, and that puts your accountability to the CEO and board in jeopardy.
When an Executive Sponsors become unwilling or unable to hear anything but good news, they inadvertently create an echo chamber. This stifles dissent and constructive criticism, both of which are essential for navigating complex transformations. Transformation Leaders need a safe space when the update Programme Sponsors and Steering Committees, the challenge is that many Executive Sponsors come to the role without the understanding or experience to understand that the initiative they are accountable for is never a straight-line journey.
Those who choose to only listen to good news create an expectation among their teams that bad news will not be tolerated, leading to a suppression of early warnings. This culture of denial ultimately results in small, manageable problems escalating into avoidable obstacles. Steering Committees are only effective when as the Executive Sponsor you have created culture of openness, when potential risks or challenges are raised, being able to show that your team has identified issues early and has actionable responses will demonstrate that you’re in control. It reflects that you’re not just measuring progress through milestones, but also through proactive risk management.
The 1-2-1s the Executive Sponsor holds with his Transformation leads creates the opportunities that create the conditions for that fearless culture. It’s in these conversations that you can set expectations that transparency is not just welcomed but required. By nurturing an environment where bad news is seen as an opportunity to adapt rather than a failure, you empower your leaders to speak up, innovate, and solve problems before they escalate.
Fearless leaders are the most available and dependable team members because they take ownership of the transformation journey. They understand that their proactive involvement is crucial to navigating uncertainties and keeping momentum. Empowering leaders to make decisions without micromanagement fosters a greater sense of autonomy, which in turn leads to higher engagement and willingness to step up when issues arise.
Encouraging fearless transformation leadership means that executive sponsors need to embrace a mindset where bad news is viewed as an opportunity. A “good news only” culture pushes people to suppress insights, distort progress, and create a parallel reality, all of which contribute to failure. Instead, executives should seek a balanced view of the transformation journey. This involves recognising successes and milestones but also diving deeply into what isn’t working and addressing obstacles collectively, without judgment.
To break free from the “good news only” trap, executive sponsors must visibly demonstrate that they value transparency and honest dialogue over sugar-coated updates. This means not just asking for the truth but rewarding those who bring it to the forefront, even when it’s not what they want to hear. Open forums for discussing setbacks, genuine curiosity about what’s not working, and demonstrating empathy for those raising concerns all help signal that speaking up is not just accepted but expected.
Fearless transformation leaders stand out because they act with integrity, maintain focus on the mission, and are willing to speak up even when it’s uncomfortable. They become the most available and reliable members of a transformation team because their focus shifts from protecting themselves to ensuring the overall success of the transformation effort. This kind of commitment creates a resilient, adaptive team dynamic that is essential in a complex and evolving landscape.
In transformation, only fearless leaders, armed with the courage to openly communicate both wins and setbacks, can help you steer effectively through uncertainty. When your performance is measured in the boardroom and limited touchpoints, fostering this fearless leadership isn’t just about enhancing team dynamics, it’s about safeguarding the very success of the transformation for which you’re accountable.
How are you creating and open culture and fearless leaders? Let’s Connect!
Building coalitions isn’t always smooth sailing, but with the right strategies, it can unlock unmatched potential.
Transformational success is rarely about technology or processes alone, it’s about aligning culture, leadership, and operational goals to drive meaningful change.
Let’s take your transformation efforts to the next level, reach out directly at shaun.taylor@rckpm.es for a more in-depth conversation.
About Shaun Taylor
Shaun is a seasoned C-level transformation executive with a proven track record in strategic growth, operational optimisation, and value creation, he specialises in helping c-suite leaders navigate complex transitions. His expertise lies in large-scale and private equity-backed businesses, where he has secured complex transformation and operational successes that have deliver measurable outcomes.
Through the RCK Programme Methods, he brings a structured approach blending agile principles with deep operational insight to align technology, operations, and strategy to achieve sustainable success. Whether it’s Cost Transformation, Value Creation, Enabling ERP-enabled change or building coalitions that foster cultural alignment, Shaun and the RCK team ensure your transformation efforts are not just implemented but delivery the results you have committed.
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