The most wonderful time of year: Strategic planning ✨

Goodness me this last few years have been chaotic. I’ve probably forecast and reforecast more budgets in the last 24 months than I have in the entirety of my career leading to it.

Jessica Zwaan
14 min readDec 4, 2023

When you’re deep in the turmoil of the day to day, it’s easy to forget why we do this at all if we have to do it again so frequently; should we do away with being proper business people entirely and embrace the chaos? Or perhaps we should just stick with our plan, push through despite the headwinds and maintain some fragmented impression of strong leadership?

I like planning. Be it quarterly, annual, 3-year or even further into the future. I like planning because I think it works, but I don’t think it works because it all comes true. I think planning works because work (and living) is chaos. Spending time trying to understand what you want to come true (even if it never does, although it probably sometimes should at least) is a meaningful exercise to get under the skin of what you really want to do, regardless of what challenges you face.

Budgeting, forecasting, planning and goal setting are all predominantly internal-facing exercises. They’re opportunities for us to look inward and say, “Hey wait a minute, what are we all doing here together and how are we going to make it happen?” and that’s where the value really emerges. It means we should have fewer conversations with our teams when they are themselves faced with predictable challenges, and helps us deploy capital and resources without nauseating internal diatribe about ROI and sequencing. We already know what we know, so let’s do it.

But how do you plan when things feel… so… unplannable?

Knowing where you’re going

To take twee business advice from the Cheshire Cat (something I am known to do more frequently than perhaps I should admit), “If you don’t know where you are going, any road will get you there.”

Upon visiting my P&L no doubt

You should already have things like your mission and vision statements. There are lots of ways folks define these, but here is how I think about it:

  • Vision: What the world will look like when you change it the way you want to.
  • Mission: What you’re there to do. A big picture view of the world as you see it once you’ve implemented all the incredible products and changes you’re working on.

In this post you’re operating a lucrative Holiday Wreath business. 🎄

  • Vision: A world where every front door is uniquely festive.
  • Mission: One billion families with one of our one-of-a-kind holiday wreathes for every celebration on the planet.

In the context of annual planning this is an opportunity to connect your operational cadence to the year against this mission you’re hoping to achieve. Maybe it’s changed, maybe it hasn’t, but remembering where you want to go is the initial requirement.

From here, your strategic plan should offer a more forward-thinking view than the company goals you’re aiming to create, and it should cover more than one year. If you have something like this already (and if not I suggest your executive team gets together and gets somewhat clear on the long-term horizons) then take that and begin picking apart where you want to be at the end of this year. Break it down into some clear metrics and deliverables and work backwards.

The strategic plan says we need to be selling Holiday Wreaths for Christmas (done, nice one), Diwali, and Hanukah by the end of 2024. We plan to do birthday wreathes in 2025 (fancy — imagine!), so let’s leave that out of it for now but be aware that we should probably think about it getting into Q4.

End of 2024:

  • Shipped 1.2m Christmas Wreathes
  • Shipped 500k Diwali Wreathes
  • Launched our first 100k Hanukah Wreathes to ship end of 24
  • Successfully expanded to Australia and Japan
  • A team assembled to deliver Birthday Wreathes in Q1 2025

Knowing where you are

The real challenge is often not getting to this position. Many companies have ambitions which they know well into the future, but putting pen to paper and making them reality is a whole other kettle of fish.

There are three primary components of planning that I look at in my COO role: Revenue Plan, Operational Finance Model, Workforce Planning. All of them are inter-related and should be the output of your strategic planning initiatives.

Doing these things all at the same time is incredibly hard, and probably why things tend to fall apart or feel rushed. The difficulty is often not within the activities themselves, but rather within their interoperability. It’s easy to put a revenue plan together if you have no headcount or budgetary restrictions — oh, but wait, of course you do. Ok, so what’s the headcount plan? It depends on the budget. And, since we’re a startup we can’t just deploy cash endlessly, so how much actual cash can you bring in?

In other words — we’re all in this together.

Truly a bubushka doll of questions

Imagine you’re renovating a house while you also have a baby due to arrive in 9 months. A precious baby ‘Runway.’

You’ve just got your new keys, and you’re on Day One trying to work out what you need to do over the course of the next 9 months to get from a shabby do-er-upper to the vision of Pintrest inspiration you’ve imagined for yourself.

Now, what needs to be done? As much as you’d like to it doesn’t make any sense to go down to Ikea yet, you’re not even sure if you’re getting an office or a guest bedroom. So first you make a list of everything you’d like done. These are your ‘objectives’ before baby comes home.

You want to hire an architect and building contractor in, but you aren’t sure if you actually have the budget to do that. You don’t know what exactly needs to be done yet and their upfront costs may cut into your other priorities. And what comes first? Do you do floors or start painting? What if the painter goes over time and the floors can’t start…you’ll be paying by the hour so it’s probably best to just finish the floors first… but if you keep doing things one at a time you won’t even be done with the minor repairs before you go into labor.

How are you possibly going to manage all of this?

Like renovating a house, moving a business from here to ‘there’ (wherever that is) is an intricate web of budgets, deadlines, status quo, and sequences of events. You have to address all of these one at a time, and then go back and make sure the plan locks into some kind of sensible arrangement. But if baby comes early, or the painter is slow, you need to have a contingency plan because — honey — life is chaos.

To get started on all of this you have to take a very real, critical stock at where you are today.

  1. People Operations: A thorough review of your current organisational design and the performance, skills, and current concerns about those in place. Where are your critical roles? Who in your team may be a flight risk?
  2. Business Operations: What are your current company cadences you need to fit with, are you operating quarterly OKRs or goals? Calculate and examine how much time is required during each of these periods and how much genuine “working time” you have Q on Q.
  3. Finance: What are your current liabilities including offices, software, and statutory operating expenses (tax, etc)? Do you have any significant cash cliffs, investment requirements, or risks which should be factored into your planning this year? 👉 Build this into a Operational Finance template with departmental tabs and a revenue model (linked below and added a contact for if you’d like to build one of your own, Tomi at Whereby)
  4. Revenue: How has your revenue team performed to date? What is your average deal size, payback ratio, and ideal customer behaviour in the market right now? Look at behaviours across your various cohort of customers to get a detailed understanding of how you’ll need to perform within the forthcoming year. If you’re working across markets and jurisdictions have an understanding of how those will model into your plan.
  5. Product: What technical debt are you forgetting about? Make a list of which product features are launching or launched recently which may need to be revisited. Understand the market your product is operating in and what may have changed that requires cross-company awareness; competitor launches or acquisitions, market dynamics, and consumer behaviour.

Begin building your Operational Finance Model (now, small companies will likely use a sheet for this, some may use Google, some may use a tool like Pry Financials.) I’ve made a “baby budget” for those of you out there who want to see how you can build these things together.

If you’d like a copy of this, ask for comment access.

Plan for the best (and hope for the worst?)

“…there are known knowns; there are things we know we know. We also know there are known unknowns; that is to say we know there are some things we do not know. But there are also unknown unknowns — the ones we don’t know we don’t know.”

– Donald Rumsfeld

You only know what you know.

  • Known knowns: Things you’re aware of and understand, such as how long it takes you to hire a new employee.
  • Known unknowns: Things like consumer trends you’ve observed but can’t yet pinpoint how to address in your product.
  • Unknown unknowns: I’m trying hard to not use the example we’re all thinking of…but it’s Covid. Covid is the perfect example.
  • Unknown knowns: This is probably the most nefarious of the four. Things you and your team think you understand when, in fact, you don’t. Or things you’re totally unaware of but which are happening in your midst. An example of this is a consulting client I worked with a few years ago who started working with a new payment provider, totally unaware that payment provider was planning on stopping servicing a geography the company worked in. The payment provider would have warned with them, if only someone had taken notice of the “German Support Update” email.

When planning, you need to focus on what you know and build from there. My advice, prudently perhaps (lawyer after all) is to budget for the worst case regardless of your aspirations. Always have a Case A and a Case B, make the worst case scenario a known known. Why? Because 2022, that’s why.

If you have your Operational Finance Model built out with your starting financials and fixed costs for the year, I suggest you first build your revenue model. As I mentioned, I always suggest you build two “versions” of this which you can tab back and forth between: Base Case (worst case scenario, if all of our metrics fall at the bottom of what we expect) and Target (where we’re hoping we’ll land consistently). Note that this will be adapted and adjusted throughout the planning process as team projects, budgets, and resourcing comes to light. Start with the revenue you can predict, and then add the revenue you want to add or build in with new products, launches, and expansion. I’m not a revenue model girl, and my experience is mostly supporting CRO/CCOs to build them — so I’m not going to wade in too deep here. A nice little primer is linked.

Remember: this is an operating model, so should take into account payment lags for received revenue — we are not building a recognised revenue model here!

Critically ask yourself: What kind of numbers do we need to hit, and what does our funnel look like, to reach our revenue goals?

The model I linked is very very basic and is also built for a kind of imaginary e-commerce-SaaS-hybrid monstrosity which is designed purposely to not reflect any company, while also nudging you to understand how it may work for you. Please do not @ me if you think it’s nonsense. It is. It is very simple nonsense for you build out. It is not a template you should start filling in without deep critical understanding of how it works. That’s by design, I think it’s very important your operations team has a nuanced understanding of how all of these things work together — which only really comes from understanding and building these things from scratch more or less.

Action Plan

You should now have an understanding of what your revenue needs to look like throughout the year, and should be able to work with Marketing, Product, and the People team to define how to resource the team and bring on these customers. This step involves the identification of strategies to close gaps and contradictions, plans to implement the projects, and measures for assessing progress. Consider things like recruiting, training/retraining, restructuring, project planning and technical debt, changes to your stack etc. I like to do this together in a room over the course of a day or two, with each budget holder having a clear line of sight into the considerations of others to build accountability and cross-functional emapthy.

Outline all of these on a project plan for the year, and map their associated costs within your newly born Operational Finance Model. From here you should have something that is beginning to resemble an annual plan and budget.

I like to set the high-level overview and let the team plan for each quarter with 2-week sprints (OKR planning, performance changes, offsites, key strategic launches). The high level plan should offer clarity on projects and deliverables for a one year horizon, and then for teams to “fill in the gaps” on a quarterly basis in their goal and sprint planning. This means you will have visibility into one to two large launches ahead of time each quarter, but ensuring you leave room for things like sudden customer requirements, technical debt, resourcing challenges etc.

⚠️ A word of warning: do not fully book your team. 100% utilization is a myth we have invented to make ourselves feel efficient, and if you do not leave time for the unexpected (or even the unknown knowns like maternity leave, learning and development, or decision fatigue) you will find yourself consistently failing to meet your deadlines.

Move from clarity into reality

Communicating the plan and ensuring it is understood at the deepest level of the team is the part we often forget. We’re so excited to have our shiny new financial model, newly signed off budgets, and ambitious goals — that we forget to sit and and walk the whole team through it.

The folks who haven’t been in the room for all of these conversations have roles in this plan which must be understood, and the necessary communication, marketing, and coordination has to occur to get everyone on the same page.

One thing I suggest we avoid going forward, and perhaps we’ve all already learned from the pain of the last two years, is to make it clear to your team that this is a plan, and plans sometimes fail. They change, adapt, and exist only in clarity on the day they’re shared (and sometimes even not then) before collapsing into the nuance of human understanding. Make it clear to everyone that you’ll do all we can to stay on track, connected and aligned, but that things will inevitably feel like we’re drifting off course (or wildly flailing in a new direction) from time to time.

Finally, you’re into March 2024.

Your plan is launched, your budget is tracking, and your team are focussed. But what’s this? A Canadian wildfire burned your wreath forest into ashes. Do we cling to our plans, ignoring the potential plans literally going up in smoke? No. Duh. We have to monitor, reevaluate, and revise. Things happen to change our plans, and they happen often.

When I was younger in my career I used to spend a lot of time wistfully longing for a perfect world in which roles were clear, strategies unchanged, and crisis avoided. But the only certainty is that these things will never eventuate. Now, I try to look for two things only:

  • Was this crisis unexpected?
  • Was this crisis irrational?

If it was expected, hopefully you had a plan or can learn why you should have. If a crisis is unexpected, you can learn from that lack of preparedness.

If it was a rational crisis, it means it makes sense. Maybe it was unexpected, but it was something you could have prepared for. This is something like “three members of our sales team resigned in the same quarter because we should have revised our compensation structure earlier.” It wasn’t expected, but on reflection it makes sense. From here you can ask yourself if you were we right to not have a contingency plan. We can’t have one for everything, so was this worth the investment into preparing for it’s eventuality? Sometimes we realise we should have, and you learn and move on. I don’t mind these so much.

If a crisis is irrational, it means it doesn’t track a logical path. Someone in your team exiting in a dramatic fashion, going to the press, leaking your internal secrets. Someone contracting a highly-transmittable virus and it spreading across the globe. Governments behaving in ways we’ve not experienced before. Unexpected, also irrational. They’re the black swan events that surprise you in ways that keep you up at night. These really bother me even today.

Things are unexpected, but they can also be irrational. Irrational things happen. They happen to us all. We cannot both plan for all of these events and not be frozen in bureaucracy. We need to look to build workplaces that are prepared for rational crisis, but not be stymied by the reality that irrational circumstances will happen. It’s how we deal with them that matters most.

Ok that’s all from me, folks. 👋

Download the Financial Operating template here: If you’d like a copy of this, ask for edit access.

EDIT: A few weeks ago I posted this blog and I mocked up an operational financial model from a few templates I had, which included work that various teams I’ve worked with have contributed to in the past. I never intended to pass this work off as my own, but of course that’s how this has come across and I want to make sure I make it right. Deeply stupid and inconsiderate of me, and I want to make it clear right here and now that everything I share is the work of many and never just myself.

For this reason I want to specifically call out the team at Contact and Whereby, and specifically Tomi Oludemi: who contributed or inspired large parts of the formatting of this model and bravely raised this egregious oversight to me. Tomi is an incredibly talented Operational Finance leader and I want to make sure I put her name front and centre if you’re looking for any support building financial models of your own (reach out or ask me for an email intro, she’s great and will absolutely build you a model of your dreams).

I’ll reach out to some of the other folks who’ve built parts of docs I’ve shared to ensure their name is also published wherever I’ve missed their credit (and I apologise in advance for those oversights!)

Rest assured, the actual figures are not confidential, but the absence of care and courtesy on my behalf is none less embarrassing and thoughtless.

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Jessica Zwaan

G’day. 🐨 I am a person and I like to think I am good enough to do it professionally. So that’s what I do.