Issue 35: When Your Annual Planning as a Chief of Staff Meets Reality
Now that it’s February and your plans have been put into execution, how do you ensure progress while accounting for flexibility?
Welcome back, aspiring and current Chiefs of Staff 👋🏼
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This week’s issue is guest authored by Claire Podulka. Claire is Chief of Staff at digital product innovation consultancy TXI, where she supports the organization in delivering engaging experiences and custom software to companies ranging from startups to Fortune 100s. She serves as a trusted advisor to senior executives and owns organizational results for a team of 70+, ultimately making TXI more effective, sustainable, and transparent. Prior to joining TXI, she spent the majority of her career in education and led content development as managing editor for ThinkCERCA, an award-winning EdTech literacy product.
How Do You Re-Evaluate Your Annual Planning?
So, those annual plans you spent countless hours meeting and negotiating and communicating about back in December… how are they playing out for you?
If you’re like most of us, you’ve got a month of reality behind you now and those plans are starting to look - well, a little off.
Remember, the plans may be off track, but planning is essential. All of those conversations were not time wasted! You gathered new perspectives, built on one another’s ideas, gained more context, and created rapport. But to ensure that you’re still aimed successfully at the right goals, you have to continually check in not only on progress on your existing plans but what’s changing around your plans, because the two move dynamically with each other.
The exact approach you use for annual planning isn’t important here - use what suits your organization. My current organization uses EOS, which prescribes a 1-Year Plan and goals broken down into quarterly Rocks. OKRs are also pretty popular among Chiefs of Staff. There are plenty of looser and more homegrown frameworks, too, but they all boil down to the same thing: Set some measurable goals for the year. Determine your strategies for reaching those goals. Break the strategies down into more discrete tactics. With those three steps complete, you’ve got your plan.
As you execute your plan, though, you’ll notice that things are changing. The first thing to do is accept that reality. As they say, the only constant in the world is change. The question is, when your beautifully crafted plans meet the bumpy road of reality, what do you do?
💡 Step 1: Identify what’s changing
The first step, simple as it sounds, is to identify what exactly is changing, how it affects you, and whether you have any control over the change.
Sometimes, the change is external. For example, two huge players in your market merge, a revolutionary new technology takes the world by storm, or interest rates spike. (Not that any of us has experienced any of those lately…) Sometimes, the change is internal. For example, a key staff member leaves, a vendor fails to deliver, or a major customer’s timeline accelerates.
To combat the sense of overwhelm that can happen when a lot is changing all at once, create a document: I like a simple table in Notion, but a Google sheet or even a running Notes doc can work. It’s adapted from a simple risk register. You want to capture:
What’s changed
What impact it is likely to have on your work
How severe the impact will be
What, if anything, you can do to prevent or control the impact
It’s essential to take a broad and honest view of the situation. If you identify Change A but fail to note Changes B and C, then any adjustments to your plans aren’t going to be sufficient. For that reason, I recommend that you, as Chief of Staff, take a first pass at the change identification and then share it with your broader leadership team or other relevant folks so they can add their perspectives, too.
🌾 Step 2: Adapt your plans to the new reality
Now that you’ve got the lay of the land, it’s time to decide what you’re going to do about it.
First, remember that “nothing” is often a totally appropriate answer to that question. If something is changing that isn’t likely to have any serious impact on your work, then you don’t need to act.
But if there’s a change happening in the world or at your organization that necessitates a change in plans, don’t be afraid to adapt. There’s no shame in saying that you didn’t appropriately plan for the contingency between two internal initiatives, for example, or that you didn’t anticipate a competitor beating you to a feature launch. The problems really come when you stick your head in the sand and don’t respond to the change once you’ve seen it.
Gather the people who are closest to the work or most affected by the change. They’re the ones with the relevant perspectives that you need now. Provide what you’ve learned about what’s changing and seek their input. Depending on the situation, it may be best for them to own the decision-making or simply to provide suggestions or feedback on your decision. Whichever you’re asking for, make that clear so folks know how you want them to show up and what their role should be.
📝 Step 3: Communicate the changes
With your revised plan in place, you need to communicate about it clearly. Start with the people most affected - those people you already sought input from. Make sure to close the loop with them first: Thank them for their inputs, explain how you used them to make a decision, and get them aligned with the new direction and what they need to do to make it successful.
Once you’ve talked with the people closest to the work, it’s time to expand outward.
When sharing how you’re adapting the plan, remember to always include the why so your audience knows that you’re changing with intention, not because you forgot the previous plan or because you’re just a chaos agent. And remember to take ownership: it builds trust to take clear accountability of a change, and it erodes trust even more quickly to sweep the previous decision under the rug or pretend like nothing is changing.
That’s the “what” of the communication, but the how is equally important. Over-communicate changes in direction, which means not just repeating the message multiple times but in multiple formats. I tend toward the approach of publishing something in writing, often with a Loom video, for asynchronous consumption, followed by an opportunity for live conversation. This gives your audience a chance to come prepared with an understanding of the key messages plus a chance to ask questions and engage in conversation live. If the change is large enough, you might even want to schedule a Town Hall for people to come together and ask questions as a follow up.
This seems like a small detail, but it’s important to bear in mind: Remember to update your documentation with the new information and rationales, and keep the old documentation around for some period of time (I might recommend a week or two for minor things, a quarter for larger things, and longer for huge, company-altering decisions) so that folks can look back to understand the history, context, and reasoning.
(Note from Clara: When we created updates in documentation, we would create a drop down toggle in Notion and label it ARCHIVE and drop the previous documentation in there. That way people can follow along for historical documentation and reference the previous versions easily.)
🧽 Step 4: Rinse and repeat
Remember, change is constant. Maintain regular rituals around tracking internal progress and monitoring for external changes that might affect your business. And continually communicate about what’s changing and why to keep everyone in your organization aligned. You might even want to build updates to your annual plans into your Rhythm of Business so that there is time set aside for if/when plans change. If there’s no change needed for the plan, everyone gets some time back, which is always appreciated.
As you get into that flow, you may find that you want to spend less time on big-band annual plans and focus more on continuous planning. But that’s a whole other topic, and for that you want to look to the ever-insightful John Cutler.
📖 In Conclusion
If you find yourself a month - or even many months - into your annual plans and realize the world is changing, don’t panic. As a Chief of Staff, you know and accept that change is constant, and you can adjust accordingly. Identify what’s changing and how it affects you, adjust your plans accordingly, communicate the changes, and continue to monitor. With this approach, you’ll help your organization sail through those changes instead of being battered off course by them.
🎥 Upcoming Events and Workshops:
February 6th: NYC Happy Hour (In Person) [Registration Must be Approved to Attend]
February 13th: 6 Levers to Reduce Tech Spend with Tropic
February 15th: Feedback as a Catalyst
February 27th: Defining the Chief of Staff Role
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Additional Chief of Staff Related Reads:
How To Survive The Chief of Staff Role: Delegate
What is a Chief of Staff and when and why would you hire one?
The Chief Factor: Who You Work For Matters Most
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