A CMO's Guide to a No-Plan, Plan

Amidst uncertainty, marketers must balance coherence and adaptivity in annual plans. Use tools like compression, simplification, workshops, role clarity, collaborative spending, and regular retrospectives to thrive. Embrace uncertainty, shape success.

A CMO's Guide to a No-Plan, Plan
Original art by Madison Van Rijn

Happy Q2 to those who celebrate!

Question: how are your annual plans turning out?

If you’re in a big corporate organization, many thousands of analysts, managers and directors around the world gathered data and built their recommendations for the year ahead. PowerPoint slide after PowerPoint slide are beginning their annual journey from raw data, to insight, to budget request – until senior leadership review requires that they be re-written from the ground up.

At this point, those plans should be well on their way toward coming true.


Or…did we not anticipate the impact of AI/LLMs? Or two of the largest bank failures in history? Or [insert gigantic, unexpected upheaval]?

Economic, climactic, cultural and societal uncertainties are making 2023 plans feel more like March Madness brackets. Bets placed at the end of 2022 are showing up in a world that looks very different from the way it did just a few months ago – and we still don’t have a good way to predict just how much more change we might see.

Whether you like it or not, we’re all playing business on expert mode now, and we need new skills.

The challenge is not to figure out how to eliminate planning – intense, thoughtful consideration of the future and what we intend to do about it is essential.

Instead, the task is to manage the tension between two, equally valuable outcomes: on one hand, we need predictable coherence between our strategy and our tactics; on the other, we need adaptivity, flexibility and responsiveness. We cannot settle for a tradeoff. We must have both.

Thankfully, we have an abundance of time-tested tools that can help marketing leaders do just that. We’ll cover six of these tools in this post. They fall into two general categories: 1) tools that create more coherence, and 2) tools that create more adaptivity.


  • Compress: Aim to compress strategy or vision into catchy, memorable, tweet-length (or shorter!) statements.
  • Simplify: Use simpler documents for planning. Ask teams to write their strategies, plans, requests in Word documents, not PowerPoint slides.
  • Workshop: Make plans with the people implicated (AKA the people who have the best data about the situation) by facilitating planning workshops.


  • Clarify: For leaders, over-spend your time clarifying roles for teams, jobs and individuals (in that order). Under-spend your time reviewing or providing feedback on plans and tactics. Use outcomes, not outputs, to get this done.
  • Spend Together: Facilitate monthly or quarterly spending meetings, where representatives from all teams can bring ideas (and provide feedback to each other) for approval. Apply all the other tools described here to help make this more effective.
  • Retrospect: Frequently pause to blamelessly look back on what’s working and what’s not, to help decide what to do next.

Let’s break each one of these down. We’ll define each, give a path forward, highlight a few pitfalls worth avoiding, and if we’ve got ‘em: show some examples.


Aim to compress strategy or vision into catchy, memorable, tweet-length (or shorter!) statements.

A lesser-known skill of great leaders is the ability to encode meaning in short, memorable statements that drive action and accountability. Take this example from Eugene Wei, writing about his experiences of this phenomenon at Amazon with Jeff Bezos:

Compress to impress — Remains of the Day
One of the funniest and most implausible things in movies is the grand speech by the general, usually the film’s protagonist, in front of thousands of soldiers in the moments just before a critical battle. Examples abound, and the punch lines lodge in the memory, from Henry V (&quo
“One year, when our primary goal was to grow our revenue and order volume as quickly as possible to achieve the economies of scale that would capitalize on our high fixed cost infrastructure investments and put wind into our flywheel, the theme was ‘Get Big Fast Baby.’ You can argue whether the ‘baby’ at the end was necessary, but I think it's more memorable with it than without. Much easier to remember than ‘Grow revenues 80%’ or ‘achieve economies of scale’ or something like that.”

Compression allows strategic coherence and adaptivity to live together in a large, complex team environment, simply by helping important ideas travel further with less “signal loss” along the way.

How to do it?

Instead of just trying to make it work, we recommend a “hack” to make this easier for every team and leader to pull off with aplomb: try expressing strategies or plans as a series of tradeoffs between two equally good things.

Some examples we’ve seen:

  • Growth even over Profit
  • Retention even over New Users
  • Mobile even over Desktop

This is a pretty simple exercise, but there are two pitfalls to avoid:

Pitfall Number One: Good Thing Even Over Bad Thing

"Run profitably even over Go out of business"

When an obviously bad outcome comes up, this is usually an indication that there are big problems in the business that are worth solving. But a tradeoff between a good thing and a bad thing isn’t high-quality strategic thought.

Think of it this way: on the right side of the “equation,” the goals trying to identify something truly valuable that the team will actively NOT to pursue over the next while. If and when "bad things" come up, use them as a source of inspiration for process optimization, automation, or waste-elimination.

Pitfall Number Two: Wordy/Boring

"Flawlessly execute our three big bets (launching our new product; expanding to the next city; improving customer service) even over Optimizing existing operations"

Instead: Big bets even over Existing ops. Write down what the big bets are, and what "existing operations" means, in other documents. The goal with compression is to make something catchy and portable that simplifies decision-making. Adding more noise in an attempt to qualify the signal makes the strategy less portable, and ultimately less useful.


Simplifying documents for planning is a key step towards coherence and adaptivity. Instead of using fancy PowerPoint presentations, ask teams to write their strategies, plans, and requests in Word documents. This makes planning easier. It makes adjusting plans easier, too.

How to do it?

  1. Encourage brevity: Limit the number of pages for each document, forcing teams to be concise and focused on the most important aspects of their plans.
  2. Use full, narrative paragraphs, not bullet points: Get teams to think deeply about what they’re recommending. They’ll have time to do so, because they’re not worried about design.
  3. Create a company stylebook, and spread it around: Use this as a tool to help folks focus on clear writing, rather than jargon or overwrought “professionalized” tone. Use straightforward words and simple sentences.

Check out Working Backwards for more.


  1. Over-simplification: While it's important to keep plans and strategies simple, avoid oversimplifying to the point where essential details or context are lost. Remember: paragraphs, not bullet points, and say what you really mean.
  2. Too much time on narrative, not enough time on facts: This isn’t a “who’s the best writer” competition. This is about communicating persuasively without visual support. Focus on facts and logic.

An example we’ve seen:

It’s no coincidence that Jeff Bezos’ annual letters to shareholders are around 6 pages of singlespaced text, are narratively structured, and contain real Business Facts in support of Amazon’s strategic moves. We tend to have leadership teams read this letter and then read their own strategy documentation, and then compare the experiences. How long did it take? How much did you take away? Which do you prefer?


Facilitating planning workshops with the people implicated in the plans (those who have the best data about the situation) builds coherence and adaptivity, mostly because it means plans will be built on real customer knowledge, and they’re much more likely to be achievable in the real world.

How to do it?

  1. Gather the right people: …not just the “most important people.” Invite key stakeholders, subject matter experts, and doers, outside thinkers, and contrarians to participate in the planning workshops.
  2. Set a clear invitation to participate: Why are we coming together? What will we achieve? What’s in bounds, and what’s out of bounds? These questions are more important than the overall agenda. Consider them carefully.
  3. Get commitment: end any planning workshop with a dedicated moment for each team or implicated party to share what they promise to do as a result of the session. Push for concrete action.


  1. Dominating the Conversation: Ensure that all participants have an opportunity to contribute to the discussion. Build your programming to include facilitation techniques that actively involve everyone in the room.
  2. Vagueness or insufficient prep: It’s easy to throw some ideas on a post-it note and call the workshop a success. Don’t let this be your standard. Be sure that participants are able to bring good data into the session, and that they have templates, tools and time to deeply consider their next actions.

An example we’ve seen:

This is from a team that was able to compress a months-long strategy development process into a single, two-day workshop. A big bonus: the actual output was better. Focus, people!

This is a two-day workshop protocol that we created for annual planning, and it's pretty straightforward to pick up. Review the work on the team's plate. Look back to identify some strategies (use the "Compress" method from above!), and then use those strategies to focus on the most important work to do. Then, run World Cafe to get some collective wisdom on the way forward.


Over-index on clear roles for teams, jobs, and individuals (in that order), and actively under-manage the reviewing and revising of specific plans and tactics. By focusing on outcomes rather than outputs, your teams will have to make better decisions and adapt more effectively to changing circumstances.

How to do it?

  1. Define clear objectives and expectations for each team, with an extremely logical connection between their work and the overall strategy. Even if this is obvious to you, write it down.
  2. Unless this kind of thing already exists for a team, break down the team's objectives into individual roles and the expectations you have for how the role contributes to the overall team objective. Don’t get down into task-level detail.
  3. Set up regular check-ins with your teams to monitor their progress, discuss any challenges they may be facing, and provide adjustments to objectives, expectations, and roles as necessary.


Too much worldbuilding, not enough doing: It’s easy to obsess over organization charts. It’s fun, too! We love this kind of work. But remember to use simple formats. Text is best. Complex visuals can seem helpful to support your message, but if you feel the need for this kind of support, you probably need to think more about the basics of your structure. Focus on teams. We cannot say this enough.

An example we’ve seen:

We love seeing formats that show a team’s overall process (flow across the top), the individual deliverables necessary to the process (boxes with all-caps text), the skills needed for those deliverables (bullets), and the individuals/leaders that contribute. This is enough – and it shows how the handoffs are intended to flow.

Spend Together

Spend control is an incredibly powerful lever for adaptivity or rigidity. Facilitate monthly spending meetings with representatives from all teams to push adaptivity, collaboration, and transparency. These meetings offer a platform for teams to present their ideas, give and get feedback in the context of the overall budget, and get support for their work.

How to do it?

  1. This is a meeting that deserves a rigorous agenda. Here’s a rough outline: share current business results; each team shares what they want to do;
  2. Allocate time for presentations: Give each team representative an opportunity to present their ideas and initiatives, ensuring that everyone has an equal opportunity to be heard.
  3. Encourage constructive feedback: Foster a culture of open dialogue, where participants feel comfortable providing feedback on each other's ideas and suggesting improvements.
  4. Make data-driven decisions: Base approval decisions on data and evidence, rather than personal biases or opinions.

Some examples we’ve seen:

We love this memo from Microsoft's history on Shrimp and Weenies. It's not 100% the same thing as what we describe above, but it's a phenomenal guiding policy for distributed spending across the company in a time of distress.


  1. Dominance by High-ranking Employees: During spending meetings, ensure that everyone has an equal voice, regardless of their position within the organization. Avoid situations where high-ranking employees dominate the conversation, leaving others hesitant to share their ideas.
  2. Lack of Clear Criteria: Establish clear criteria for evaluating and approving ideas during spending meetings. This helps maintain transparency, fairness, and consistency in decision-making.


Regularly pausing to reflect on what's working and what's not is essential for adaptivity and continuous improvement. By conducting blameless retrospectives, teams can learn from their experiences and make informed decisions about what to do next. “Doing less” with planning means you have to do more with ongoing learning.

How to do it?

  1. Make them regular. Not just at the end of the project: Set aside dedicated time for retrospectives. This should be biweekly such as monthly or quarterly.
  2. Use structured techniques: Utilize structured retrospective techniques – don’t just wing it. We love "What worked? Where did you get stuck? What might you do differently next time?" method, to guide the conversation and ensure you cover all the bases while staying clear of too much negativity bias.
  3. Focus on improvement, not blame: As a leader, it’s your job to keep the retrospective discussions focused on areas for improvement, rather than assigning blame for failures.


We cannot emphasize this enough: do not do them only at the end of the project: Conducting retrospectives exclusively at the end of a project leaves no opportunity for learning and applying improvements during the project's lifecycle. Instead, schedule regular retrospectives throughout the project to identify and address issues in a timely manner, allowing for course correction and continuous learning.


As we navigate this ever-changing landscape, it's crucial to strike the perfect balance between coherence and adaptivity in our planning processes. By embracing these six time-tested tools, you can foster a dynamic, (actually) agile organization capable of responding to unexpected challenges while maintaining a clear strategic direction. So, buckle up and embrace expert mode with confidence and resilience – let's shape the future, one well-planned step at a time.