As 2022 comes to a close, strategy and operations leaders are beginning to turn their attention to 2023. From overseeing strategic planning offsites to setting Q1 OKRs, the strategic planning process is in full swing. 

One role often tasked with bringing the company’s strategic vision and direction to life is the Chief of Staff. If you aren’t familiar with the Chief of Staff position, we shared a bit more about the Chief of Staff role and learnings from guests that joined us on Season Two of Aspiring Ops. 

On Season Three of Aspiring Ops, we had the opportunity to meet with current Chiefs of Staff to get their thoughts on the strategic planning process, and their approaches to communicating company goals to employees. 

So as we close the books on 2022 and get ready for 2023 company kickoffs, we wanted to share some of our learnings from leaders in the Chief of Staff position, including how they think about the strategic planning process and what comes after your leadership team offsite.  

Thinking of Strategic Planning In Bets

Let’s start with Ben Miller, Chief of Staff at Ladder, and how he and his team think about the strategic planning process, as well as the connection between their company culture and how they build their plan. As a high growth company fresh off their $100M Series D, Ben shared that he and Ladder think of their strategic planning in terms of bets. 

For many companies, strategic planning can be a process of simply going through the motions. 

But the strategic planning process can be so much more than just a financial exercise of modeling a proforma that maps out your company’s expenses and revenue targets. The process of building your plan can help define the culture and create momentum for the company heading into 2023. 

Here at Elate, we recommend creating an identity for your strategic planning process. 

• How do you propose, review, and finalize company objectives? 
• Do those objectives tie into bigger themes? 
• How do you cascade goals and targets to employees to help share how the work they’re putting forth connects to the larger vision? 
  

It’s the idea of connecting long-term vision with tactical execution in a way that creates alignment, transparency, and a sense of purpose. Ladder’s structure for thinking of strategic planning in ‘bets’ helps define the culture they are building at the company. 

Providing Clarity and Creating Alignment 

For Céline Felan, the Chief of Staff role not only comes with the responsibility of helping to build SugarCRM’s strategic plan, but also how she continues to provide clarity and drive alignment across the company. 

As she shares, “In the end, it’s making sure we’re all clear on what that common goal is, and making sure we’re clear on what everyone’s roles and responsibilities are.”

The advice from Céline on providing clarity in the Chief of Staff position is applicable to so many different facets of the role. So often the Chief of Staff is tasked with flexing between every part of the company and serving as the connective tissue between leadership and employees. The ability to provide clarity and understand the meaning of a priority or goal for every department is critical to success. 

This skill set is on full display in every step of the strategic planning process. From the company’s strategic planning offsite with the leadership team  to rolling out OKRs to employees, the Chief of Staff has to provide clarity and drive alignment along every step of the way. 

Reinforcing Direction through Communication  

As Amy Liu, Chief of Staff at Smarthop, has come to learn, decisions aren’t made in a vacuum. Priorities that are agreed upon and set during your leadership team’s strategic planning offsite have to be shared and communicated across the rest of the company. 

As she shares, “If you just have a group of 10 people that know what the priorities are, then you’ve fundamentally failed. (Leadership) might think these are the priorities, but the organization is running in a very different direction.” 

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From her experience running and leading strategy sessions at Smarthop, Amy understands how critical it is in her role as Chief of Staff to communicate the decisions made by leadership with the entire company. 

And it isn’t enough to simply share your company’s strategic plan once in a Powerpoint presentation. The process of creating alignment and visibility comes from creating the channels and cadence for regular communication with employees. 

Unlocking the Impact of Your Strategic Plan through Communication

Far too often, we find that strategic planning is a “set it and forget it” activity done at the leadership level once a year, and then communicated to the rest of employees in an annual company kickoff to start the new year. Even while companies track their KPIs and results throughout the year, they don’t think of their strategic planning and execution process as an opportunity to continue engaging and aligning team members.

Done right, your company’s strategic planning process that begins in Q4 can serve as a growth catalyst for how your team not only achieves, but exceeds the plan you originally put in place. 

Here at Elate, we have the opportunity to work with leading strategy and operations leaders at high growth companies. For many, the idea of strategic planning is taking a new form. 

The planning process still entails the process of building a plan in Q4 with high-level company themes and goals that tie into your company’s long-term vision. But rather than a static document shared once a year, strategic planning is becoming an ongoing, dynamic process that can serve as the blueprint for continuously engaging employees, communicating direction, and taking action on new opportunities as they are presented. 

However, this can only be achieved if the strategic plan itself is something communicated to employees and reviewed regularly by leadership with an established operating cadence. 

So as you head into your 2023 planning and company kickoff, don’t just go through the motions when it comes to building your plan. For the Chief of Staff at a high growth company, the strategic planning process can help create momentum for your company, but that momentum can only be sustained through constant communication and clarity that can be provided by the Chief of Staff.