Navigating the Challenge of Chasing Deliverables: A Chief of Staff's Perspective

Being a Chief of Staff is a rewarding journey filled with opportunities for growth and impact. However, let's not sugarcoat it—some aspects of the role can be challenging. One such challenge is the constant follow-up with the leader's executive team to ensure timely deliverables. It's a task that can feel like walking a tightrope between diligence and diplomacy, but there are ways to make it smoother.

Embracing the Challenge

Firstly, it's crucial to accept that you can't control other people's actions. If a team member misses a deadline, it's on them, not you. Setting this mindset early on can relieve some of the pressure.

Strategic Follow-Up Plan

Developing a follow-up plan is key. Consider sending the initial request three weeks before the due date and a final reminder one week prior. This structured approach allows for timely interventions without being perceived as overly intrusive.

Leveraging Relationships

Forge strong relationships with key individuals within the executive team who are responsible for actioning requests. Whether it's an operations role, another Chief of Staff, or an Executive Assistant, having allies who understand deadlines intimately can streamline the follow-up process.

Communicate Effectively

When deadlines are missed, communicate transparently with the executive. Let them know you've received other deliverables and will proceed unless their input is received by a reasonable date. This approach maintains accountability while keeping the lines of communication open.

Patience and Persistence

Chasing deliverables can initially be a repetitive cycle. However, consistency pays off. Over time, the executive team will come to expect and appreciate the rigor you bring to the table.

Empathetic Approach

Approach follow-ups with empathy. Acknowledge the shared goal and emphasize that you're all working towards the same objectives. This mindset fosters collaboration rather than tension.

Balancing Priorities

Remember, chasing deliverables is just one facet of your role. Don't let it consume all your energy. Maintain a balance and prioritize other strategic aspects of your position.

Join the Conversation

You're not alone if you're grappling with this aspect of the Chief of Staff role. Share your tips and experiences in the comments. What strategies have worked for you? Are there any common pitfalls to avoid? Let's engage in a dialogue and support each other in navigating this challenge.

Being a Chief of Staff is about more than just chasing deadlines—it's about driving excellence and fostering a culture of accountability and collaboration. Together, we can master this aspect of our role and continue making meaningful contributions to our organizations.

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