Empowering Teams and Transforming Challenges into Opportunities

Barry Snyder: Software Engineering Executive | Strategic Thinker | Inspiring Leader | Eternal Optimist. Connect with Barry on LinkedIn.

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Q1: Describe a project or achievement you're particularly proud of and how it reflects your skills and strengths.

In my tenure at a leading financial services firm, I assumed leadership of an organization encompassing 21 technology teams. This transition presented me with significant challenges, ultimately leading to a transformative period for the organization. Under my leadership, we evolved from a struggling organization to being one of the higher performers in our division.

The transformation was grounded in addressing three primary challenges:

1.        Cultural Shift: I shifted the organization from an operational focus in a continuous firefighting mindset to a modern engineering culture focused on efficiency, quality, and innovation. This shift was instrumental in enhancing performance, building trust with our partners, and encouraging a forward-thinking approach within the teams.

2.        Improvement in Associate Morale: Morale was notably low at the outset. Leading by vision, inspiration, and empathy, I achieved a 21% shift in morale within my first five months in the role.   This was a significant uplift from being one of the lowest to reaching levels comparable with the company's highest benchmarks.

3.        Modernization and Trust Building: Setting measurable outcomes was key to success.  Working with enterprise architecture, product, and my teams, we set metrics for measuring our modernization journey. Our efforts yielded a modernization shift from 9% to 64% over 18 months. Concurrently, I worked in close collaboration with my business partners, transitioning from a position of low confidence in IT to one of being a trusted partner.  

The transformation was not just organizational but also personal for myself and the associates I led.

Over time, I saw a dramatic, positive shift in how the associates engaged in their work.  In the beginning, everyone was drained from firefighting and an overwhelming amount of toil. As the culture and technology shifted, morale lifted with engineers doing what they love to do best – passionately solving business problems with code.  

This change underscored the impact of my leadership approach, which emphasizes vision, inspiration, and measurable outcomes.   Coupling my leadership approach with empowering teams to make decisions, enabling them by removing obstacles, and including them to understand the impact of their decisions fostered a high-performance environment in which they could succeed.

Change is not easy, especially in a heavily regulated work environment such as financial services.  The world is in constant flux; new technologies are constantly being introduced, and business priorities could change on a dime.  This requires a dose of mindfulness, inspired innovation, and continuous improvement—an example of one such situation.

Around 14 months into my tenure, I was faced with a 9% dip in associate scores after a series of challenging business events that, while successfully navigated, impacted morale.  Digging into the scores, I realized the leadership on the ground was not being fully empowered or enabled to make decisions on the ground.

Inspired by a working session with one of my leaders, I replaced status meetings with a series of working sessions with my leaders and their direct reports with an ask to cascade.  

The focus was, instead of telling me my status, to bring to our session a problem we would work on together.  

This fostered a culture of empowerment and learning at all levels while arming my leaders with the knowledge to enable point decisions by leads on the ground. At the same time, I formed an extended leadership team to give voice to team managers and tech leads across the teams, where I encouraged everyone to speak out. 

These efforts were aimed at empowering managers and leaders at all levels, ensuring they felt included, heard, and capable of driving positive outcomes. The associate score not only reset to its prior score but reached beyond by a 14% increase.

My leadership philosophy is rooted in empathy, engagement, and authenticity. Learning from many inspiring leaders throughout my career, I've realized the importance of being true to oneself and leveraging one's unique strengths to foster a supportive and inclusive environment. This approach not only lifts team efforts but also drives meaningful and impactful work.

In summary, the journey within this role was a testament to the power of transformative leadership, where challenges were met with strategic and empathetic responses, leading to significant organizational and personal growth.

Q2: What unique perspectives or approaches do you bring to your field of work?

In discussing my approach to leadership and innovation, I reflect on my core strengths: inspirational leadership, innovative problem-solving, and a deep commitment to my team. While the concept of servant leadership is widely discussed, my interpretation goes beyond simply serving the team. It involves empowering and enabling team members to make decisions and grow, thereby aligning their objectives with the organization’s strategies and objectives.  In short, create and grow leaders.

There is always an opportunity to improve, but this cannot be done by one person.  

In every leadership role I have been in, I saw opportunities to raise the bar and improve overall performance. This is where inspiring teams to continually improve via vision and my investment into their own growth, comes into play.  But what you don't measure you don't improve.  I couple objective, evidence-based metrics on targeted outcomes with my leadership.  These measures are not used for individual performance evaluations – which can undermine the purpose of these metrics – but creating a psychological safe/no-fault environment to continuously improve and drive overall organizational performance.

An example of where this came into play.  I was digging into a demo with one of my tech teams that led to a brainstorming session.  I realized the team was dismissing ideas that did not have the wow factor or were startlingly innovative.  As I did my routine of demos across sprint deliverables, I recognized this was endemic across the teams.  Everyone sought that perfect, innovative idea versus building upon existing ideas.

A staggering amount of innovations originate from bad ideas.  I took it upon myself to build a fun and engaging approach to showing how bad ideas can be fostered into great innovations.  I conducted a workshop for my leaders and then expanded this across their teams.  The core idea is to encourage everyone to share every idea they could imagine, no matter how bad it was, and then build upon them together.  This was not only a fun exercise for everyone but fostered psychological safety in brainstorming ideas, teamwork, and inclusion.  After these workshops and shift in culture of innovation, the metrics measuring ideas to production code showed an overall increase.

I have found that when I lead from a position, anything is possible, measure the impact of delivered outcomes, and foster psychological safety with empowerment, the teams you lead innovate in unexpected ways.

My leadership style is about more than just directing; it's about investing in people and recognizing that everyone brings a wealth of experiences and knowledge to the table.

This belief extends to seeing potential beyond the primary job role, encouraging team members to apply their diverse skills to solve problems in innovative ways.  For my leadership style, this is the root of innovation as driven by diversity.

Q3A: How have you adapted or innovated to meet new challenges in past roles?

In a previous role at a prominent enterprise in the housing financial sector, I led the developer tools and open-source teams. Upon interviewing engineers, the biggest complaint was about the open-source governance, which would take three to nine months to approve the use of roughly 80% of open-source products.  In an agile environment, this is a significant impediment to productivity.

On digging into the process behind the governance, it was discovered the governance process involved multiple handoffs between five different governing groups, resulting in a lengthy approval time, slowing productivity and heightening the risk within production.  Teams would either bypass open-source options, spend the extra time to build the base capability internally, or take on the risk of using the solution with the intent to refactor at a later date.

Recognizing the inefficiency and the frustration it caused among engineers, I sought to automate the governance process.

After an analysis with stakeholders – with a focus on engineers as the customer – I formulated a vision of on-demand access to production safe open-source.  I spearheaded an initiative to find a more efficient solution.  The original idea was to have a repo with preapproved open source that was under continuous scanning.

Our breakthrough came when we discovered a vendor who offered an automated solution that aligned with our goals. By implementing this tool with our own internally built scripts, we automated 26 governing policies.  The solution realized the vision of open-source on demand but in real-time.  As open-source components were drawn from the public domain, they were vetted against the policies, ensuring compliance with technical, security, and legal standards with a delay in seconds vs months.

This innovation not only eliminated the backlog but also empowered developers by giving them immediate access to the open-source resources they needed, thereby significantly accelerating software development cycles. The success of this project was evident when we received a standing ovation from the developers during a presentation of the solution at an internal meetup, highlighting the profound impact of our work on their efficiency and job satisfaction.

An unexpected bonus was the steady decline in high-risk open-source products in production.  Where 26% of open-source components in production had a CVE number of 9 or higher, within three months, the number was reduced to 11%, and in another six, we were below the industry standard by 4.6%.  By cleaning the polluted workstream, we cleansed the dam.

The experience underscored my approach to tackling new challenges by thinking creatively, engaging stakeholders, and leveraging technology to find win-win solutions that address inefficiencies and empower individuals to perform their best work.

This approach not only solves immediate problems but also fosters a culture of innovation and efficiency that benefits the entire organization.

Q3B: How have you adapted or innovated in past roles to meet new challenges?

In my role overseeing enterprise DevOps initiatives, we faced the challenge of managing a complex DevOps pipeline that incorporated 31 different tools. The sheer volume of data generated by these tools made it difficult for any individual or team to effectively analyze, digest, and determine the necessary actions to optimize our processes. The situation was compounded by the need to constantly adjust and refine our approach, a task made even more daunting by the conflicting opinions of external experts we brought in for guidance.

Despite fine-tuning our enterprise DevOps platform, feedback collected through monthly surveys and direct conversations with team leaders revealed that we were only meeting the needs of about 30% of our teams. This was a concerning statistic, and upon further discussion with engineering teams and product leads, it became clear that the multitude of variables in software development made comprehensive analysis and optimization a near-impossible task with our current methods.

Recognizing the limitations of traditional data analysis in this context, and with machine learning starting to emerge, we decided to explore its potential to address our challenges.

We had previously experimented with machine learning in a research and development capacity to understand how it could support DevOps. Inspired by these explorations, we took the innovative step of applying TensorFlow, an open-source machine learning framework, to analyze our DevOps pipeline data.

This approach marked a significant shift in how we managed our pipeline. I shared our experiences and insights at the 2017 All Day DevOps conference, which I also detailed in a YouTube video to reach a broader audience interested in the intersection of machine learning and DevOps.

One of the most compelling outcomes of this initiative was the ability of our machine learning model to identify a decline in code quality and delivery practices in what had been one of our star projects.

This decline was traced back to the departure of key team leaders, a change that traditional monitoring methods had failed to flag as a significant risk. Thanks to the predictive capabilities of machine learning, we were able to recognize and address this issue proactively, enabling the team to realign with best practices and maintain their high standards of quality.

This experience underscored my belief that innovation requires a willingness to look beyond conventional solutions to solve problems. By engaging closely with our customers to understand their needs, and by considering every challenge as a software problem amenable to creative technological solutions, we were able to significantly improve our DevOps processes. This journey highlighted the importance of customer obsession, adaptability, and thinking outside the box in driving meaningful innovation.

Connect and Collaborate with Barry Snyder

Are you impressed by Barry's experience and expertise? Do you see potential synergies or opportunities where his skills and experiences could be a great fit? 

Please reach out and connect with Barry on LinkedIn. He is currently exploring new opportunities where he can apply her extensive knowledge and innovative approach. 

Whether for collaboration, a potential role, or exchanging ideas, your engagement could open doors to exciting new possibilities. Let’s support each other in building a more connected and forward-thinking professional community.

— Bill

Bill Fox 
Connect with me: LinkedIn | billfox.co
Pioneering Leadership from Within | Unlocking Organizational Potential