How to Plan With Usefulness, Agility, and Innovation in Mind
You plan when you’re the dumbest. I don’t remember where I originally heard this, but the idea behind it has stayed with me ever since. And it’s so true; when you’re in the stage of developing the plan, you’re the least informed around how the work will go.
This doesn’t mean that no degree of planning is helpful — quite the contrary from my experience — it means we should plan with this in mind.
Some organizations I come into are leaning too much into planning, and some organizations are plowing through each day, quarter, and year without taking the time to strategically plan and feeling the effects of it. It’s a balance. Ideally, your planning should allow you to take action with less friction, whether that’s through clarity of work and timelines, mitigating likely risks, or organizing the work being done so it’s easier to understand.
In this piece, I’m going to walk through how I approach planning for a project, and how that differs from annual or quarterly planning, and how to get the most out of the process.
I hope you find it useful! As always, reach out if I can answer any questions.
Planning Principles
Before we dive into planning for specific, I wanted to share a few quick guiding principles that your planning should accomplish, regardless of the specifics you choose to deploy:
Understand, or identify, your highest priority objectives. One of the most consistently important steps in business planning is knowing what you’re aiming for. We should always be able to answer, “What are we optimizing for here?” or “What are we hoping to achieve with this again?” Without clear, prioritized objectives, your / your team’s efforts risk becoming scattered and misplaced, and before you know it the project has undesirably morphed into a distant version of what it started out as.
Understand how different trajectories impact your finances. Money is the lifeblood of every business, and every decision you make sets your business on a particular trajectory; each path comes with financial implications and/or tradeoffs. This backbone is something that needs to be considered and treated as such in your planning. If your plans are focused less on driving revenue this quarter or year, is that viable for you? If not, how can you keep the purpose and goals of your plan but still set goals to have that equate to revenue? There’s no right path inherently, but your planning should take financial implications into strong consideration.
Planning should be a catalyst to action, not a hinderance.?Often, planning becomes a crutch for overthinking or a black hole where great ideas go to die. Effective planning is not about creating the perfect spreadsheet or project plan that nobody uses; it’s about setting the stage for consistent action. A good plan provides you with clarity, confidence, and direction so you can execute with less friction than if you didn’t have it. It’s easy to think that creating the plan?is the goal, where in reality the goal is to achieve the outcomes of the work.
Planning For the Year Ahead
Unlike project planning, annual planning has a slightly different purpose and will have you zooming out more than you would for a single project.
For even more specifics than what’s below, I’ve found success with the annual planning model from the Entrepreneurial Operating System.
In my experience, the most effective annual planning I’ve consisted of included:
A thoughtful agenda that considered our ultimate goals for the meeting, shared in advance with everybody in attendance (likely only key members of the leadership team) with permission to suggest adaptations prior to the call. The agenda also included any pre work, mostly coming to the table with some existing thoughts, and was clearly communicated to all involved.
An analysis of our previous year and goals. Before we look to the year ahead, it’s helpful to look back to the year that just happened and ask ourselves: how was it? How’d we stack up against what we set out to do the year prior? I find this helpful not only to ensure we’re aligned on how we did and discuss what we want to carry with us to next year, but also to get accustomed to taking goals seriously and get reps in measuring success of the goals we set.
Revenue goals. When I’m business planning, the most clear and actionable sessions I’ve been a part of often started with revenue goals and worked backward from there. At a minimum, you should set a revenue goal for the year ahead, but I’ve also set three and five year goals to help fuel the one-year goal and found it helpful to know at least where we’re striving to go longer term. How do you set them? There’s no perfect formula, but you should combine the knowledge you have around what contributed to your revenue from this year, and make an ambitious goal around what you think you can do this year. This may look at setting other goals around pieces like conversion rate, new eyeballs, sales, or other components that need to be in place in order for the revenue goals to be hit.
Objectives & Key Results (OKRs) or some other measure of success. Lastly, and as mentioned above, I find it helpful have some stepping-stone goals between now and your revenue goals you just set. How will we know if we’re on the right track? Sometimes this can simply be revenue milestones, but often times it also includes what needs to happen in marketing, sales, and operations, in order to achieve them.
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Planning For the Quarter Ahead
Ideally, planning each quarter shouldn’t feel like you’re reinventing the wheel. In fact, it should feel like a direct result of the annual and longer term goals you’ve already set.
In my organizations, quarterly planning often includes:
And that’s it. It’s typically done in a day and shared with the wider team (if applicable) the same day.
Planning For a Big Project
Planning for a project applies the same principles as annual or quarterly planning, but introduces some new steps because the scope is much more narrow.
It’s similar to annual planning in the sense that we always want to identify the ultimate goal behind the project and the role its serving, and we want to map out the steps that we feel confident will get us there.
The ultimate goal of the planning should be to increase the likelihood you actually complete it, and come away with the answers to the questions you came in with.
More than revenue, it’s helpful to map out the milestones and work in between, who’s owning what, and what timeline we are on.
The size and importance of a project will often dictate the amount of planning I’ll dedicate to it. If I’m running a quick test or making a two-way door decision that benefits from speed, I’m typically not going to do a lot of planning; I’m just going to take action.
On the flip side, I’ll spend more time mapping out major projects with a lot of moving pieces.
There are plenty of ways to do this with free tools, and I encourage you to do what’s most useful for you and your organization. In case it’s helpful, I’ll link a free project planning template below in addition to a step-by-step walkthrough to set up a simple but powerful work management system in ClickUp.
Free Resource: Complete Project Planning Template in Google Sheets
Free Resource: ClickUp Project Management Setup Walkthrough
I hope you found this useful!
I aim to make these genuinely useful for you and I hope you took away at least one useful nugget.?If you’re looking for additional support in building your business thoughtfully, please don’t hesitate to reach out via my?contact form, or at [email protected].?If I’m not the best fit for you, I’ll do my best to point you in a better direction.