By Kumar Dattatreyan

Collaboration and Servant Leadership values are crucial for success in modern, agile work environments. When traditional, hierarchical organizations attempt to change into modern, flexible, and nimble organizations, applying these values often involves navigating complex situations without clear-cut answers.

I recently facilitated a leadership workshop where we explored the values of collaboration and Servant Leadership, and while everyone agreed that these were worthwhile and necessary to support real change, how people would navigate these changes proved to be a problem.  While it is easy to agree with the premise of collaboration or the promise of Servant Leadership, the group found it very hard to put into action.  This article presents a series of dilemmas at both executive and team levels to illustrate the challenges of embodying these values in real-world scenarios.

1. Collaboration in Agile

Collaboration in agile goes beyond simply working together. It involves breaking down silos, fostering cross-functional teamwork, and ensuring that diverse perspectives contribute to better outcomes. However, collaboration can sometimes conflict with other priorities such as speed, efficiency, or established hierarchies.  

I've found that exploring scenarios like these in working sessions with leadership makes it easier to imagine how an individual faced with a dilemma would or should manifest these values. The debate and conflict that arises are both healthy and constructive.  There are several techniques that you can use to facilitate them, but that's a post for another day!

Read them and think about how you would respond, keeping Collaboration as the central theme to adhere to.  

Executive-Level Collaboration Dilemmas

1. Strategic Alignment vs. Departmental Autonomy Dilemma: As CEO, you're implementing a company-wide agile transformation. Do you: 
1. Mandate a standardized agile framework across all departments to ensure consistency and easier cross-departmental collaboration? 
2. Allow each department head to choose and adapt their own agile approach, potentially creating inconsistencies but addressing specific departmental needs?
2. Collaborative Decision-Making vs. Individual Ownership Dilemma: A major market opportunity has arisen that requires a quick response. As the CEO, do you: 
1. Convene your executive team to collaboratively develop a response, ensuring buy-in but potentially missing the market window? 
2. Make a unilateral decision to seize the opportunity quickly, risking potential resistance from your executive team?
3. Cross-Functional Integration vs. Specialized Excellence Dilemma: As CTO, you're restructuring the IT department. Do you: 
1. Create cross-functional teams that blend different IT specialties, fostering collaboration but potentially diluting specialized expertise? 
2. Maintain separate, specialized teams (e.g., security, infrastructure, development) to deepen expertise, but risk creating silos?
4. Collaboration vs. Individual Ownership
   Dilemma: As the CTO, you are restructuring the IT organization into a collaborative, shared decision-making framework.  Do you:
1. Entrust this critical decision to the experienced Product Owner/Manager, ensuring clear accountability and potentially faster decision-making, but possibly missing out on specialized insights?
2. Implement a collaborative decision-making process, leveraging diverse expertise for a potentially more comprehensive solution, but risking slower decision-making and unclear accountability?

How you approach these dilemmas calls for a close examination of where and how you want your company culture to change.  Please spend some time going over these scenarios and comment below with your thoughts.  

Team-Level Collaboration Dilemmas

1. Consensus-Driven Development vs. Technical Leadership Dilemma: Your team is divided on the technical approach for a new feature. As the Scrum Master, do you: 
1. Facilitate extended team discussions to reach a consensus, potentially delaying the project but ensuring team buy-in?
2. Defer to the most senior technical lead's decision to move forward quickly, risking team resentment?
2. Pair Programming vs. Individual Productivity Dilemma: Your team has a tight deadline for a complex module. As the team lead, do you: 
1. Enforce pair programming for all tasks, promoting knowledge sharing but potentially slowing down initial progress? 
2. Allow developers to work independently to maximize immediate productivity, potentially creating knowledge silos?
3. Cross-Skilling vs. Specialization Dilemma: As a Product Owner, you notice that user stories often get bottlenecked by specialized skills. Do you: 
4. Encourage team members to cross-train and take on diverse tasks, temporarily reducing efficiency but increasing flexibility? 
5. Optimize the process for specialization, potentially increasing short-term efficiency but maintaining dependencies on specific individuals?

All of these dilemmas are real and potentially things you have faced or will face. Answering these questions will help reveal your transformation goals. What are you willing to give up to gain a competitive edge over your competitors?  

2. Servant Leadership

Servant Leadership in modern work environments empowers teams, facilitates their success, and prioritizes their growth and well-being. However, this approach can sometimes conflict with traditional notions of leadership, organizational hierarchy, or short-term business needs.

The following scenarios/dilemmas illustrate the difficulty in making these behavior changes actionable.  Read on and think about how you would respond:

Executive-Level Servant Leadership Dilemmas

1. Empowerment vs. Strategic Control Dilemma: As CEO, you're setting the company's strategic direction. Do you: 
1. Empower your executive team to collaboratively develop the strategy, potentially leading to a more diverse but less focused strategic plan?
2. Develop the strategy yourself and present it to your executives for implementation, ensuring a unified vision but potentially reducing buy-in?
2. Employee Well-being vs. Shareholder Value Dilemma: As CEO, you're facing pressure from the board to cut costs and increase short-term profitability. Do you: 
1. Prioritize employee well-being by maintaining current staffing and benefits, potentially disappointing shareholders?
2. Implement cost-cutting measures including layoffs to boost short-term profits, risking employee morale and long-term innovation?
3. Transparent Leadership vs. Organizational Stability Dilemma: As CFO, you've identified potential financial challenges in the coming year. Do you: 
1. Share this information broadly within the organization, promoting transparency but potentially causing anxiety and turnover? 
2. Limit this information to the executive team, maintaining stability but going against principles of open communication?

Team-Level Servant Leadership Dilemmas

1. Individual Growth vs. Team Performance Dilemma: A team member wants to take on a challenging new role that they're not fully prepared for. As their manager, do you: 
1. Give them the opportunity, prioritizing their growth but potentially impacting team performance? 
2. Assign the role to a more experienced team member, ensuring smooth performance but limiting the individual's growth?
2. Team Autonomy vs. Project Guidance Dilemma: Your team is struggling with a complex project. As the Project Manager, do you: 
1. Allow the team to work through the challenges independently, promoting learning and autonomy but risking project delays? 
2. Step in with a solution based on your experience, ensuring the project stays on track but potentially undermining team autonomy?
3. Servant Leadership vs. Traditional Authority Dilemma: Your team is resistant to a new company policy that you believe is beneficial. As their leader, do you: 
1. Advocate for your team's position to upper management, supporting your team but potentially being seen as undermining company decisions? 
2. Focus on getting your team to accept and implement the policy, maintaining organizational alignment but going against your team's wishes?

Conclusion

These dilemmas illustrate the complex decisions leaders face when trying to embody the values of Collaboration and Servant Leadership in agile environments. The scenarios are two ends of a spectrum, and the likely answer will vary.   There are no universally correct answers; the best course of action often depends on the specific context, organizational culture, and long-term goals. 

By regularly engaging with these types of dilemmas, leaders at all levels can develop a more nuanced understanding of how to apply agile values in their daily decision-making. This ongoing process of reflection and adaptation is itself a key aspect of agile leadership.

The goal is not to find a perfect solution but to thoughtfully consider the trade-offs involved in each decision. By doing so, leaders can create more collaborative, empowering environments that are better equipped to navigate the complexities of modern business.

Reach out if you'd like to have a conversation about this or a related topic.  I'd love to hear from you!

 Check out my YouTube interview with Glenn Marshall on this topic