One of the most common skill sets we see amongst strategy and operations leaders is an ability to simply get things done. This high degree of execution is often what allows someone stepping into a Chief of Staff or operations role to thrive amidst ambiguity and a constantly shifting list of priorities.
However, this focus on driving execution can sometimes create a project-based or tactical mindset for a strategy and operations leader. The danger in this mentality is that a leader can lose sight of the long-term vision and focus too much on the short-term work to be done.
From what we’ve seen, the best strategy and operations leaders need to find a balance of strategic and tactical thinking. Whether it be in the strategic planning process, owning one-off initiatives, or even scaling departments from zero-to-one, it’s essential to have the complete picture of what the company is trying to achieve.
For our recent guest on Aspiring Ops, Matt Groetelaars, his unique background in go-to-market strategies and enablement helped him bring together this balance of strategic and tactical thinking. More importantly, Matt’s background helped him to challenge stakeholders at Twilio and Segment when it came to setting the direction and prioritization of key initiatives.
On this episode of Aspiring Ops, Matt shares his journey to the Chief of Staff position at Twilio, and how he helped drive clarity for his executive team and employees by focusing on the problem to be solved. Matt also shares how his previous experience stepping into strategic planning at Segment shapes the advice he provides to new Chiefs of Staff looking to understand how to introduce strategic planning to a company for the first time.
Matt’s journey from Segment to Twilio is a unique one, full of advice that can help any Chief of Staff, regardless of where they are in their own journey.
Not only does focusing on the ‘why’ in the Chief of Staff role help align strategic direction with tactical execution, but it also helps shape the narrative for aligning team members internally. Matt’s enablement background was critical in his ability to evaluate and craft the messaging conveyed to employees.
“One of the big things you do as a Chief of Staff is help craft the narrative for all-hands calls, email announcements, or change management in general,” says Matt. “If you’ve forced your stakeholders to be clear and articulate to you why this needs to be solved now and why it needs to be solved in a certain way, then that helps really kill two birds with one stone. When it comes to communicating and getting the organization bought in, you can really help refine and hone-in on the crystal clear message for ‘Why are we doing this?’”
We’ve heard time and time again about the importance of creating clarity in the Chief of Staff position. Yet, Matt’s advice is especially valuable, because it helps provide a philosophical approach to the position, as well as practical steps to put that approach into practice.
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