How to Plan a Successful 2024 Strategy: Expert Advice

Strategy leaders enter a critical phase every fourth quarter as one year winds down and another one approaches. This is when past achievements intersect with future ambitions, requiring careful planning and insight. 

We sat down with Joe Krause, Vice President of Customer Engagement at AchieveIt, to gather expert advice on effective preparation for 2024. Here is Joe’s perspective on key trends affecting 2024 planning and top tips on how to run the planning process.

Trends that are shaping the industry

Organizations didn’t pause strategy in 2023

2023 marked a shift in approach for strategy leaders compared to the COVID and post-COVID years. 2020, 2021, and 2022 were characterized by uncertainty. Many organizations felt it too risky to engage in new strategic planning during this period due to the rapidly changing and unpredictable environment.

However, as 2023 dawned, a new theme began to emerge. “Most strategy leaders that were on a pause unpaused themselves in 2023 and started to actually create their plans,” says Joe. They realized they needed to shift focus from short-term operations back to long-term strategy. Organizations needed to elevate their thinking, anticipating future needs and positioning themselves for success.

In 2023, excuses for postponing strategic planning had faded away, giving way to a more forward-looking approach. “People are now a little bit more comfortable betting on the future,” says Joe.

Transparency is imperative in 2024

Transparency in strategic planning and execution is an emerging trend that will leave its mark in 2024. Public-facing organizations, especially city and county governments, are changing how they share their plans and progress both with the public and their stakeholders. 

The increasing use of public-facing dashboards highlights the transformation towards greater openness. In the public sector, a substantial number of institutions currently utilize these dashboards to cater to the increasing demand for transparency. Citizens and stakeholders are more insistent than ever on understanding the progress made towards planned initiatives. 

While some states, like Florida, have a legal obligation to transparency, others are quickly adopting it as a best practice. The essence of this trend is to communicate the “how” and “what” of strategic plans. Instead of simply pledging to take action, companies and organizations are progressively concentrating on showing how they’re executing their plans. 

This goes beyond merely highlighting accomplishments. Being transparent involves openly acknowledging where difficulties and challenges lie. As Joe puts it, “It’s not just sugarcoating the good stuff. It’s showing where the difficulties lie and making sure that people understand you’re being fully transparent about them. Because if you cherry-pick what you’re putting on the dashboard, people will see through that pretty quickly, and you’ll lose trust and faith.”


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Actionable Strategy Tips for 2024

Make time for a 2023 retrospective

As the year comes to a close, Joe emphasized the significance of looking back at what 2023 brought and seeing what can be learned from it.

The outcome of your retrospective will largely depend on the plans you made at the beginning of the year. It also depends heavily on the regular status updates your team has throughout the year.

It’s a time to delve into the year’s strategic plan, examine all the updates made, and assess what worked and what didn’t. The retrospective process can be time-consuming, lasting up to a day, but it’s an investment worth making. You can tack it onto an existing meeting, but this might dilute its impact.  

Ideally, this meeting should occur sometime after Thanksgiving and early in December. It should be an in-person discussion, preferably with the entire leadership team present. It might be tempting to wait until January for your annual retrospective, but in reality, the year’s insights and lessons are already apparent by December. Joe advises against waiting until January as this is a notoriously chaotic time of the year.

Committing to a December retrospective allows for a more thorough evaluation of the year. Your end-of-year retrospective may miss some last-minute end-of-year details, but it’s worth taking that risk to make sure the retrospective happens as planned.

A well-conducted 2023 retrospective sets the stage for a more insightful and effective planning process for 2024.

Organize a 2024 planning retreat

Joe emphasizes the importance of scheduling a planning retreat to set the stage for a successful 2024. Many organizations overlook this vital step, but it can make a substantial difference in shaping your strategy for the new year.

Ideally, this retreat should occur in the last few weeks or months of 2023. It’s an opportunity to reflect on the past year and apply the lessons learned from your retrospective to your plans for the upcoming year.

Planning retreats typically span a day or two and have the full leadership team present. Having a specific agenda with clear deliverables is crucial. The goal is not to create an exhaustive, detailed plan in these few days, but rather to establish a strong foundation. Successful planning retreats typically end with a plan that’s 75% complete and focuses on critical aspects, including:

  • Primary objectives for the year
  • How you intend to measure them
  • What actions you will take to achieve them

This high-level framework sets the direction for your organization’s efforts in the coming year. While finer details, such as project initiatives, budgets, and specific tactics, can be developed later, the retreat should ensure that you have a clear vision and a roadmap for the year ahead.

Crucially, the retreat should have a defined endpoint. Joe warns against the common practice of perpetual planning, where organizations keep scheduling meetings to discuss their plans without setting a firm deadline for finalization. Having a specific completion date, perhaps by January 15th, ensures that you don’t drag your planning process into the new year.

Another valuable suggestion from Joe is to have an external facilitator guide the retreat. This impartial facilitator can help streamline the process, keep discussions on track, and encourage candid exchanges. By not being part of the organization, they remain objective and can ensure that the retreat is effective and productive.

Choose AchieveIt as your retrospective and planning partner

At AchieveIt, we’re here to help you reflect on the past year and prepare for the challenges and opportunities of 2024. Our services encompass both critical aspects of your journey: retrospectives and planning.

AchieveIt helps evaluate your yearly plan, examining the items you entered the year with, how many were completed, what remains outstanding, and how effective your deadline estimations were. This retrospective analysis delivers invaluable insights into your planning process and execution.

During your planning retreat, our expert consultants will guide your team through a one or two-day intensive session to plan for the upcoming year. What sets this process apart is our AchieveIt software. While your ideas and strategies take shape, they are concurrently entered into our software, ensuring that your plan materializes in real-time on the screen. This approach sets you and your team up in the best position to monitor and report on your progress going forward.

For further information and to discuss how AchieveIt can aid your organization’s success, contact us today.

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Meet the Author  Chelsea Damon

Chelsea Damon is the Content Strategist at AchieveIt. When she's not publishing content about strategy execution, you'll likely find her outside or baking bread.

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