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A quick guide to becoming an agile boss

Many organizations struggle to reconcile with the fact that ‘going agile’ involves a radical re-thinking of leadership styles. Interestingly, the Agile Manifesto’s fifth principle says, ‘Build projects around motivated individuals. Give them the environment and support they need, and trust them to get the job done.’ Such leadership requires a courageous new approach. 

A typical conversation I’ve encountered, more than once, is where a large organization’s CXO shares their intent to ‘go agile’. I respond by asking them how willing they would be to give up their corner office. This ask symbolizes how open the leader is to lead by example. As we see it, agility comes easy to those who are comfortable with the servant brand of leadership. This kind of leadership readily places employees at the center and expects to follow a serve-first mindset. 

In this article, we present a few questions that should help you identify your agility quotient, as well as some recommendations for becoming an agile leader.

1. Do you encourage and build authentic relationships?

Leaders want to effect progressive change. One of the most important factors to making an organization-wide impact is having meaningful connections. This involves connecting with people and helping them see and believe in your vision for the organization. 

If you have a distant relationship with your team members, via executive assistants or several levels of managers, perhaps it is time to reconsider your approach. You can build stronger relationships by moving closer to the teams. This could be a literal change; shifting your work space to your team’s table, if not near them. This could be non-physical too; seeking open and spontaneous conversations and cutting through existing hierarchies. 

We’d also recommend spending time with your team members without a pre-fixed agenda, attend showcases in the team zone, and lead retrospectives by opening up about your own vulnerabilities. Finally, it’s better for you to view workflows and project dynamics without them being airbrushed by your team because it’s closer to what’s actually happening on ground. 

2. Do you favour long term effectiveness over immediate efficiency?

A HBR article refers to how, “…the prospect of a fast-moving, adaptive organization is highly appealing. But as enticing as such a vision is, turning it into a reality can be challenging.” We’d recommend a shift in how you, as a leader, arrive at optimum business strategies. Our counsel is to do away with siloed efficiency where team meetings are where your department heads give you updates and take instructions from you and instead, suggest bringing your cross-functional teams together and turning meetings into a discussion, a debate, and a collaborative problem-solving session. 

However, leaders will have to also recognize if such an approach is appropriate for the business context. For instance, a crisis situation may call for a different approach when compared to business-as-usual. 

3. Do you actively seek and act on feedback?

Hierarchical organizations might not support honest feedback as one should expect. Assessments are usually top-down, annual events and not always open. We’d recommend that agile leaders  look beyond the ‘manager-reportee’ hierarchy and keep an open mind to learning from anyone in the team.

When encouraging your teams to share direct feedback to their bosses or sponsors – it’s important to observe non-verbal feedback too, and act on them. For example, does your team keep a 10 minute buffer in meetings with you because you’re usually late? If so, it might be an opportunity to act on this non-verbal feedback.We place a lot of emphasis on definitively showing teams that you’re listening and growing.

4. Do you encourage cooperation over competition?

Cooperation is key to a lot of desirable traits and practices at an agile organization. It leads to better trust, authentic connections, faster communication, knowledge sharing and collaborative teams. 

We’d advocate keeping an eye out for rivalry or competition in your teams. Notice if differences of opinion amongst team members is coming from a place other than genuine beliefs. In parallel, we also suggest exploring aspects of your own behaviour that might encourage a competitive streak which could be eating into intended innovation. Here are a few ways you could encourage people to come together and contribute to the common cause;  prioritize collective team awards over individual awards, evolve KPIs to encourage greater knowledge sharing and foster a culture where helping others meet their goals is celebrated.

5. Are you a changemaker?

For organizations that are resolving issues and evolving their way of working, change is to be anticipated. A lot of the time, the proactive changemaker is the agile leader. And, such changemakers are working against established operations, convention, silos of information, dynamic market conditions, crises and more. 

We’d urge you, the changemaker to actively alter course when you see yourself displaying inflexibility. You could start with an experimental approach to change-making – start small, invite the team to join in your experiment and move forward together. Keep your eyes and mind open to social, cultural and technological progressions. And, these changes could take any form, from leveraging solar power to infrastructure as code.

6. Are you actively eliminating motivational debt?

Organizational agility survives when leaders are coherent and intentional. This growth mindset is motivated by clear goals and aligned strategies of approach. If your style of leadership is more instructive than persuasive and does not build understanding or consensus – then you are creating motivational debt. 

For instance, do you have the practice of taking your team into confidence and discussing their work with them? If your team members are unconvinced about a task, do they have the freedom to approach you and clarify the requirement? 

Here are a few suggestions that agile leaders should keep in mind to reduce motivational debt: During remote meetings, keep your webcam on and show your team that you’re listening. We’d also suggest not requesting a special ‘progress report,’ but viewing project statuses along with the rest of the team. It can be valuable to walk your own project wall and share more information from your side, such as the board’s expectations of you, or your own goals and challenges. Help your team recognize the real-world impact they’re having, and motivate them.

A quick look at the agile leader’s checklist:


It’s critical to understand that agile organizations aren’t built in a day. Being agile is much more than applying some techniques to run software projects – it requires a commitment to adaptive leadership, a focus on delivering value fast, and a different understanding of what your organizations’ portfolio should look like. 

“Agile leaders have the ability to cleave through this ambiguity, to focus on a decision when everyone else is floundering, to clarify direction when everyone else sees confusion. This requires an ample supply of thought and analysis, but probably an even greater supply of guts.” – Jim Highsmith, Executive Consultant, ThoughtWorker

If your organization happens to be hierarchical, use that structure to lead by example and demonstrate the change you want to see. Build an agile team by being an agile leader. 

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