Quarterly Planning - What It Takes For It To Run Successfully

What is Quarterly Planning?

Quarterly planning is a process with a series of events where teams and stakeholders retrospect, prepare, plan, and prioritise work aligned with strategy for the next period ahead.

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These events happen over three levels: Business Leadership, Product and People Leadership, and finally the Team—which we will explore.

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In essence, the events create the critical feedback loop needed to make informed decisions about what to do next and help the organisation course-correct to where it wants to go.

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The key to quarterly planning is that it is done continuously, enabling the organisation to adapt and maximise value delivery to their customers. Would you keep funding an 18-month project that has delivered the necessary value in 9 months?

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Most quarterly planning follows similar events: you will start with goal-setting at the highest level, review how the last planning cycle went, then work with the delivery teams to plan and align to the goals—maybe even set their own OKRs—and then this is all played back to ensure you are all aligned. (The ideal situation would be to have everyone in the room at the same time. I intentionally discuss these events as remote or hybrid formats.)

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In the book Sooner, Safer, Happier by Jonathon Smart et al., this is known as the Golden Thread of Value, which talks about how you can follow the big goal to the delivery detail. The image below is an example of how TeamForm brings the Golden Thread of Value for all teams.

TIP: You can read more about connecting and monitoring your OKR and QBR to ensure value delivery here.  

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One key step to an effective quarterly planning cycle is to understand how we can use our existing measures to enable informed decisions. There are numerous options available depending on how you are working currently. To that end, let us begin by working out how you most likely monitor your progress and then look at some more options.

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How can you monitor your delivery during the quarterly planning cycle to improve delivery?

Let us begin with one of my favourite questions when working with leaders who are about to start setting the goals for the upcoming work: How do you know what your teams are working on and if they’re aligned to the goals this quarterly planning cycle? If, like many others I have worked with, you answered Excel, PowerPoint, or even JIRA, then welcome to the club. Having a partial view of what’s going on is a great start—although not the whole picture to value delivery.

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Now, how do you ensure you are reflecting the latest state of delivery?

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Again, if you answered with a steering committee, one-to-ones, or even sending an email out with a deadline to update the Excel file, then you are not alone. Wouldn’t it be great if this was done more often and was easily manageable? Critical to the success of delivering on your strategy is effective monitoring and reporting of progress. Where are your risks? Do they need to be escalated?

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Instantiating a series of weekly, fortnightly, or even monthly events to align is key to ensuring that you are not carrying too much into the next planning cycle and that blockers are dealt with sooner rather than later. Product/Outcome and People leaders should be able to gather the latest insights and then update relevant parties on progress. This event is not about monitoring status via RAG (Red, Amber, Green); it is best used as an open forum to discuss those items which have real impact on delivery. It is best to do this without judgement as the outcome is shared, rather than on a single person’s shoulders.

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We will now look at the three personas described earlier, the challenges they can face or that can creep in when you begin to use the quarterly planning cycle, and how you can help resolve them. Even if you are using quarterly planning processes, you may relate to some of the issues faced.

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Quarterly Planning for Business Leaders

When using quarterly planning, the pressure to deliver results often leads to rushed or ill-thought-out conclusions. A lack of insight or appreciation for how your entire ecosystem is impacted can stall delivery. In the 2024 edition of the Business Agility Report, we see that something as simple as not communicating the message clearly can lead to misalignment and hinder a team’s ability to adapt.

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"This ability to defer taking real decisions and instil diligence now only increases cost of delay and delivery later. The ability to Empower with Accountability is one of the slowest to establish across organizations. Needing a combination of factors to take hold, most leadership behaviours establish at about 3 years, but often take over 8 years to become mature. - Empowerment Takes Time (Business Agility Report 2024 (p24))”

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So what are your options during quarterly planning to help break the cycle of delay and disappointment?

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It may sound obvious but there are two things here:

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1. Enable leadership at all levels – Empower your people to make decisions without needing you to be present. In the book Turn the Ship Around by L. David Marquet, he emphasizes the importance of moving away from dictating actions and instead focusing on clearly communicating the desired outcome. By shifting from a follower’s mindset to one based on leadership, you can engage those around you to act with purpose, confident that they are contributing toward a shared outcome.‍
2. Communicate, communicate, communicate - Don’t assume an email has been read, a recording has been watched, or that people are fully engaged in a meeting. (I’ve done my fair share of what felt like a three-hour PowerPoint meeting, when a single slide and a 10-minute conversation would have sufficed.)

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Boldly state the vision, engage in communication, have regular check-ins and updates, measure and iterate, and—most importantly—lead by example and create the right environment to challenge and ask questions.

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These actions will improve messaging, enable your people to come together to solve real problems, and ensure that if the email doesn't quite get the message across, your regular check-ins will—especially if you are using meaningful OKRs to help monitor progress. (TIP: You can read more about connecting and monitoring your OKR and QBR to ensure value delivery here.)

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There are some anti-patterns to be aware of. Not all of these occur at once, and if—like me—you’ve been guilty of applying any one of them, now’s your chance to stop, make a change, and take a step toward better delivery.

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Things to consider for Business Leaders

Outputs over Outcomes

What is the difference between outputs and outcomes? Let’s take a look at an example. A team is tasked with selling 100 reams of paper. The team sells 100 reams and celebrates meeting their goal—high fives all around. However, after delivery, it turns out the customers actually wanted high-quality pre-printed paper, not recycled blank paper. The result? While the team delivered on the output metric, it was the wrong metric and guidance, leading to a loss of customer retention and, therefore, customer value.

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A more effective approach would have been to focus on outcomes, such as:

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• Decreasing the number of returns to the warehouse by 20%
• Improving customer satisfaction and repeat orders by 10%

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By measuring only the output and not the outcome, you encourage busy work that may not align with the overall goal. Who wouldn’t want their bonus if all they had to do was sell 100 reams of paper? Output goal achieved—but at what cost?

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Measuring the number of things delivered is an anti-pattern. Anyone can game a system to show improved output. The goal should be to ensure an outcome or need has been met. As discussed in this post, there are useful exercises to help align your goals to outcomes.

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Questions that Business Leaders ask

• What problem are we trying to solve?
• What do our customers need?
• What measurable business value should this work create?

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Relying on the Wrong Metrics

Anyone can pick a number and a target, but an ill-thought-out metric will lead to the same problems as relying on outputs over outcomes. The goal of metrics in quarterly planning is not just to count deliverables but to provide enough information for informed, data-driven decisions.

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For example, if you ask for 20 new features in the next month, how will you monitor this? Story points? Lead time? Number of tickets closed? You should be able to determine how you will validate success. Is it increased revenue? Improved NPS scores? Or are you setting arbitrary targets like delivering 20 features worth 80 story points? The issue isn’t the math—it’s whether those 20 features are valuable and aligned with business goals.

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You want to ensure a meaningful balance of qualitative and quantitative metrics to understand which levers you can pull and their impact on the work. At the C-level, consider some of the insights in this article on measuring the unmeasurable.  

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Relying on the wrong metrics can be costly. But understanding what your metrics truly show gives you the advantage to pivot when necessary and make data-driven decisions. A valuable exercise would be to map all the stages of delivery and identify where your system becomes impaired. For more information, click here.

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Questions that Business Leaders should ask

• If we get X what are we leaving out this quarter?
• Does this Org Unit / Business Unit / Team have capacity and how do we know?
• Are the plans aligned to the organisations north star?

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Quarterly Planning for Product/Value and Capability Leaders  

Value Leads (Product Managers, Chapter Leads) play a crucial role in running a successful quarterly planning cycle. They help create clarity around business goals and enable their teams to deliver actionable plans by unblocking the path to realising value.

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The roles focus on product and customer needs, people and career growth, training, and other opportunities—creating a healthy tension between business needs and people needs.

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To avoid impacting the effectiveness of quarterly planning at this level, here are some common practices that can lead to failure—and how to address them.

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Things to consider for Product/Value and Capability Leaders

Focusing Too Much on Tactical Details Over Strategic Alignment

Using the quarterly planning process described earlier, you can start to align the work with overall business goals and ensure future work is directly connected to these priorities. There will be trade-offs; however, using the strategic goals helps to align and set the right focus. Your next steps will be to create the right actions and outcomes, which not only help with prioritisation and planning but also ensure you can monitor progress effectively.

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Most businesses use some form of Objectives and Key Results (OKRs). If you are unfamiliar with how to begin, I have added some great getting-started links below:

• ‍https://www.soonersaferhappier.com/old-training/quick-learn-outcome-canvas
• In the following checklist, you’ll also find some great questions to ask to make sure your OKRs are as good as they can be: https://www.soonersaferhappier.com/post/okrs-a-checklist
• If you’re unfamiliar with the background of OKRs, here is a simple overview of how it was introduced to Google in the '90s: https://library.gv.com/how-google-sets-goals-okrs-a1f69b0b72c7

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Failure to Identify and Manage Risks Early

C‍‍‍ommon issues that present themselves include:

• Not addressing resource constraints or team capacity issues
• Not resolving dependencies early enough
• Lack of cross-functional collaboration or communication

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Ensuring you have the right regular forums in place to discuss some of the common risks identified above—early and often—will help to prevent the often-seen “just get it done” approach. The aim here is to be able to make the best decision given the data and context you are operating in. To that end, you should be having regular updates from your team leads or product leads to understand when you should support them in resolving risks early enough.

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Questions to ask‍

• How often are we meeting to discuss dependencies, risks, or blockers at the (team, leads, business) level?
• Are the right people in the meeting to help with the challenge?
• Should this challenge be escalated? What other options are available to us?
• What is the risk to waiting/doing nothing vs. taking action to resolve?

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Monitoring your performance

You should be having regular review sessions to identify any concerns or issues with the process itself. I am a firm believer that the process you start with should not be the same process you have 6, 12, or even 18 months later.

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Taking the time to understand the root causes of what is and isn’t working can lead to better delivery and outcomes for you, the teams, the business, and ultimately your customers.

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Start with some simple metrics and ranges, such as Lead Time, Cycle Time, Throughput, along with eNPS (employee Net Promoter Scores). Use these as a guide in discussion with the teams to understand what could be improved. Why does testing take a long time? How can we make this process better?

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Questions you could ask during any meeting

• Who is available?
• Who wants to grow / do something different?
• Do we have the right skills for now? Or should we delay, hire, train, and have someone ready for next quarter - or even two quarters from now?
• Are these features consistent with the OKRs / Strategic vision?
• Do I have evidence / feedback from customers the market needs this?

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Quarterly Planning for The Team

Welcome to the engine room. So far, we have explored communication and direction, helping to align the teams with the outcomes for the next delivery cycle. It’s almost time to start working on those items. Some of the best practices encourage everyone to provide input and help steer the direction for the next quarter—how you will be measured and who can help you get there.

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As a valued team member, let’s look at how you can have an impact on delivery as we explore the following issues that can arise and the actions you can take to get back on track.

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Things to consider for the Team

Dependencies and blockers

During quarterly planning, you may realise that you have a need from another team or are a key part of delivery for another team. This is where you need to have your goals on hand and have key people in the room to discuss what gets done first!

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It is ideal to remove dependencies where possible to improve the flow of delivery. Often, you will find your team or organization is not set up in an optimal way for the strategic goal. The Team Topologies approach to team structuring finds ways to ensure your value teams are supported in the right way. Read more here.

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‍As an example, Team 1 is dependent on Team 2, who are not even focussed on the task at hand this quarter.

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It is often vital to bring transparency to the issue as early as possible. The sooner you can resolve any potential delay during this planning stage, the better it will be for improved decision-making, managing your risks appropriately, and possibly accepting the trade-off in the short term if it can’t be resolved.

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What can lead to this issue arising starts with planning and can be as simple as not inviting the right people into the conversation early enough, or if the right people are “too busy,” we may have found your blocker. For more details, click here.  

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Questions to ask‍

• Are the right people in the meeting to help with this challenge?
• Could someone else with authority help to make this decision?
• Should this challenge be escalated? What other options have I/we exhausted?
• Does this align to the overall goal this planning cycle?
• Can it be prioritised between us?
• Would it help if someone was able to sit with the team to help development?
• What teams are dependent on us and who are we dependent on?

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Feedback

One of the most critical actions you can take is to ensure you communicate early and often the status of development. Ensuring you have a regular cadence or communication channel to bring to light problems or even acknowledge the help of others to resolve challenges.

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Too often, the reason most challenges stack up is not the lack of effort but due to the lack of communication between people. Having a more proactive approach may cause short-term upset, but in the long term, it will enable better delivery and improved ownership.

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Questions to ask‍

• How can we gather feedback and measure usage/satisfaction?
• Which goals align to this feature?
• How can we actively promote our latest delivered item?
• Have we taken too much on this planning cycle?

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Other key considerations to running a successful quarterly planning cycle

People

Having explored all the vital roles, it would be remiss not to tie this all back to the people. Now is also a suitable time to check in and make sure your team is happy to take on these items. If there are any upskilling opportunities (raised in career conversations), make sure you haven't overcommitted to delivering too much too soon, to avoid finding yourself in the same place as the last delivery cycle.

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Questions to ask

• Who has been stuck on this piece of work for too long?
• Is there a challenge beyond next quarter that would be worth upskilling our people on this delivery cycle?
• Given what I now know, what is my real capacity this planning cycle? And who has public holidays/leave coming up?
• Did we commit to too much last quarterly planning cycle?

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Tooling

Imagine having to manage all of that in Excel, and you only have a piece of the data puzzle. TeamForm can help your organization resolve these problems and improve visibility for all. By capturing where people are allocated, what skills they have, and supporting your quarterly planning process for future quarters, TeamForm also gives you some indication of the financials, enabling you to balance delivery against costs.

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Questions to ask

• Is there a better way to planning?

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Closing the Feedback Loop for Continuous Success

In any quarterly planning process, the most critical step is closing the feedback loop. Throughout the article, it has been stressed many times that for successful quarterly planning, having regular chances to review where you are at all levels is vital.

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While reviewing performance, assessing outcomes, and setting future goals are important, the true value of quarterly planning comes from listening, iterating, and continuously refining your approach to work.

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By actively gathering feedback from all levels—whether business leaders, product managers, chapter leads, or teams—you ensure that each cycle is more effective than the last, allowing the business to pivot quickly, maintain alignment, and drive continuous success.

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Finally, by looking after the needs of the people over the next planning cycle, you’ll keep employees engaged and highly motivated to do their best work and delight your customers.

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Questions to ask

• Given our last quarterly planning cycle, what can I do differently to make this planning cycle even better?
• How can I engage those around me to support quarterly planning and make it more effective?