Issue 9: How a Chief of Staff Can Lead the Transition from Strategic Planning to Execution
How do you turn whiteboard planning into actual executable action?
Welcome back, aspiring and current Chiefs of Staff!
🏮 🧧 新年快樂 , Happy Lunar New Year! I, for one, am always happy that I get a “second new year” to celebrate when I inevitably want to update and revise some of my new year’s resolutions. One of my goals is to attend 1 (yes, 1 - it’ll be my first ever) musical festival this year. Any suggestions on which one I should go to?
In this week’s issue, I’m featuring guest author and partner to Ask a Chief of Staff, Elate (more on them at the end of the issue). Elate has worked with hundreds of Chiefs of Staff to turn strategic planning into actionable execution. They’ve seen what works and what doesn’t and, more importantly, they’ve seen how successful Chiefs of Staff are able to take what is written on the page and bring it to life in their organization.
If you want to learn more about the Chief of Staff role in strategic planning, make sure you sign up for our upcoming workshop: “What Role does a Chief of Staff Play in Strategic Planning?” It’s a great opportunity to hear from experts in the Strategic Planning space and share any challenges you might have at your organization when it comes to execution. Hope to see you there!
What can Chiefs of Staff do to take Strategic Planning into Execution?
To say that the market conditions from 2022 to 2023 have shifted would be quite the understatement. After years of continued growth and smooth sailing for many companies, 2023 has brought about more challenging market conditions that have forced leaders to rethink hiring plans, budget allocation, and overall go-to-market strategies. You’re probably no stranger to seeing the what seems like endless LinkedIn posts about layoffs and company downsizing.
While many companies have been spending the past few months planning for 2023 and what’s to come, the reality is that planning is the easy part. Ideating on potential initiatives, white boarding new ideas, or even just digging into a spreadsheet and modeling out numbers happens in a vacuum. The application and delivery of all those hours spent planning, ideating, and forecasting now becomes a reality. And for many companies, a reality that almost certainly won’t go as expected, especially in a year like 2023. Below are 4 actionable steps you can take to help ensure that your strategic plans are executed:
1️⃣ Get Leadership Alignment on Areas of Focus
As the calendar changes over and companies look towards the new year, there is often an unbridled sense of optimism and urgency about what lies ahead. With goals for the coming year laid out in front of them, Leaders are tasked with creating the momentum for their teams heading into the new year.
However, now more than ever, it’s critical that the momentum and energy through the new year is channeled in the right direction. And, although cliche, it starts at the top.
After spending countless hours in offsites working through strategic initiatives, finalizing budgets, and discussing goals for the coming year, leadership has to be aligned with one another on how that comes to fruition. Far too often, what gets discussed never gets agreed upon. Whether it be the dependencies that exist between different departments or the push and pull of resource allocation, if Leaders aren’t aligned on the priorities, then how can they expect their teams to be?
The Chief of Staff position is often the most capable, and even responsible for ensuring communication across teams. As a Chief of Staff, you should know what your principal’s priorities are and how they are aligned (or unaligned) with the rest of the team - if it’s the latter, there’s more work to be done to get your leaders on the same page. Gathering this ahead of time, you should be able to distill these down to 3 companywide priorities that will drive the offsite discussions on what the company is focused on executing on for the year. By the time to get to the company wide planning portion of a gathering, the priorities should already be laid out. The “What” should be established and now it’s a matter of the “How.”
To make a nautical analogy, the leaders of the company should all agree on the destination, but the operational work of how to get there will come down to the functional teams. Your job as a Chief of Staff is to hear out your leaders and make sure that if your leaders are all saying, “Antigua is the destination,” they are all in agreement that they mean the Caribbean island and not the city in Guatemala.
2️⃣ Empower Employees through Clarity
While a successful 2023 starts at the top, the follow-through comes from the teams across the business. One thing we saw across company after company in 2022 was priority fatigue. For many employees, it felt as though either everything was a priority or nothing was a priority - haven’t we all heard that as a Chief of Staff before?
In a year like 2023, where many companies will be asked to do more with less, laser-focus on the right priorities can make or break a successful year. This is why it’s so important that you don’t simply leave the communication of company priorities to your company kickoff or monthly all-hands meetings.
Instead, the Chief of Staff should be focused on providing a single, unified view of company priorities that can be referenced at all times by employees - not only for their understanding of where the company wants to go, but also, how their work ties into that direction.
Some things we can suggest to help communicate priorities effectively:
Establish a single source of truth (whether that’s a standing Notion doc or Slack channel) where announcements around company wide goals live
Clearly set the expectation that this is the one channel that all employees are expected to read and be up to date on
Reiterate priorities time in and time out. A former colleague once told me that they started every all hands meeting with a reiteration of the company mission and top priorities, so much so that it became a running joke to recite the slide from memory - it’s rote, but it works!
Hold town halls and office hours with your leaders that allow employees to ask honest questions about the priorities of the company
3️⃣ Establish (Or Evaluate) Your Operating Rhythm
An operating rhythm of your organization is the frequency, structure, and process for reviewing the strategy and execution of that strategy over the course of the year. For each company this will look a bit different, and should take into account the culture of your company.
A good operating rhythm should set the pace and regularity for how your leadership team goes about reviewing the areas of focus you set for the year, discussing areas of opportunity and potential risk, as well as the cadence for how often you meet to do so. It might include things like all hands, company wide gatherings and offsites, quarterly business reviews, OKR planning, town halls, and more. The company size and stage will play a critical role in determining the frequency for how often you meet as a leadership team. But once set, again, ensure your leaders are committed to the process.
For companies who already have strong rhythm in place, ensure it stays an area of focus, but don’t forget to revisit it and have the rhythm evolve as both the internal and external landscape change. Many companies saw a huge change in the way all hands were run once we moved into the world of remote/hybrid during the pandemic. Just because things have been done a certain way, it doesn’t mean that it can’t be improved. Take a look at one of our past workshops on Maximizing All Hands and Offsites.
For a more detailed looked into establishing your company’s operations rhythm, we would highly recommend reading this article co-written by On Deck and Josefin Graebe (former Chief of Staff at Lime and Uber): Build Your Team’s Operating Model on These 4 Principles
4️⃣ Capitalize on the Momentum of Your Company’s Strategy
Over the past few years, we have seen a shift in the way companies go about Strategic Planning. Rather than a static, manual process that feels more like checking a box, Strategy and Operations leaders are evolving their process to be more dynamic, combining real-time insights with engagement across all areas of the organization.
After the offsite and plane rides back to home offices, don’t let the enthusiasm from the planning sessions fade to the distance. As a Chief of Staff, assign follow up actions to each department. Maybe that’s have them come up with 3 goals for the next quarter that contribute directly to a company priority. Maybe that’s asking for feedback by a certain deadline on the priority action plans. Whatever that plan is, call back to things that happened during the planning phase so that employees can see a direct correlation from their projects to company priorities.
For example: let’s say one of your company priorities this year is to expand to [x] new geographic locations. During the initial planning and brainstorming phases, Tom (your Sales VP) was adamant that Boston was going to be the new hot spot for your product and was convinced that it would sell like hot cakes there. As a follow up, you can ping Tom to say, “Boston sounds like a great expansion location and leadership agrees that it’s a great place to start for Q1. Can you get your team to come up with an experiment you can run this quarter to test if this will be a success? I’ll follow up with you end of week and present it to the rest of the company. Looking forward to what you come up with!”
This interaction accomplishes a few things:
It makes Tom feel heard and seen
It empowers Tom to figure out how to get this done and in turn, empowers his team to think about how they can contribute to company priorities within their function
It establishes a clear deadline for follow up
As a Chief of Staff, you’re often balancing the 10,000 foot view along with the “in the weeds” approach and this same balance applies to the company and employees as well. Listening to your employees’ excitement and tying that back to company priorities will help create forward facing momentum as those priorities are executed on.
More about Elate:
From working with hundreds of Chiefs of Staff, the team at Elate has seen that when done well, this evolution can serve as a competitive advantage on how an organization delivers on the objectives.
If you’re interested in learning more about how Elate is partnering with Chiefs of Staff across leading companies like Seismic, Paystand, Jobvite and so many others, reach out to our team today. We’d love to share more!
Open Chief of Staff Roles:
I’ll be sharing a few of the roles that I’m working on each issue. If you’re interested in any of these positions, reply to this newsletter with a copy of your resume and I’ll follow up!
Soma Capital - Chief of Staff to Aneel Ranadive (Managing Partner)
Early stage fund, focused on B2B / SaaS
Location: Miami (or willing to relocate)
Preferred Qualifications:
Meticulous attention to detail
Technical background preferred (engineering or compsci, deep understanding how products are built especially software)
Strong writing skills
Serna.bio - Chief of Staff to the CEO
Industry: BioTech, $11M Seed, 7 person team
Location: Remote, East Coast time zones required
Preferred Qualifications:
BioTech background OR VC/banking/finance background
Aspirational future founder
Experience with fundraising (board prep, pitch decks, investor calls)
Structure driven, highly organized, excellent async communication
Masterschool - Chief of Staff to VP Growth
Industry: EdTech, $100M Seed
Location: Remote, East Coast time zones preferred, some travel to Tel Aviv
Preferred Qualifications:
Former founder, entrepreneur, growth hacker type mentality
Has taken products from 0 to 1 multiple times
Understands marketing functions
EdTech background
Additional Chief of Staff Related Reads:
Build Your Team’s Operating Model on These 4 Principles
6 tips for making a career change, from someone who has done it
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👋🏼 Until the next issue,
Clara
PS: I’m going to work hard to keep all the content in my newsletter free so that it’s accessible for everyone, but if you want to help support my writing endeavors, you can buy me a matcha 🍵 Special shoutouts to Laura, Aly, Kelly, Trish, Eva, Amanda, and Meg for supporting the last issue!