strategic planning

The pitfalls of strategic planning (and how to overcome them)

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  • Strategic planning

Think about the planning that goes into a cross-country trip. While it's exciting to see where the road takes you, even the most spontaneous travelers have a destination and expected travel timetable in mind. 

So it goes with strategic planning. Whether your horizon for strategic planning is next month, next quarter, or next year, it's essential to define the actions today, next month, and next quarter to impact your desired destination and outcomes. 

"I find that many folks confuse strategic planning with tactical execution," says Mark Kelly, CEO of NewEdge Growth. "Too often, we get consumed with what we're going to do tomorrow, that we never raise our head above the trees to see if we're headed in the right direction.”

Let's take a look at some of the most common challenges and pitfalls of strategic planning — and how you can avoid and overcome them. 

Common challenges of strategic planning

There are four main challenges when it comes to strategic planning: lack of ownership, poor communication, lack of alignment, and slow adoption. It’s important to understand what’s at the core of these planning challenges before we dive into solutions.

Lack of ownership 

An effective strategy requires cross-departmental and cross-functional feedback from across the organization. However, to avoid creating a disjointed strategic plan, someone still needs to own the final compilation, documentation, and execution of the strategy. 

Kathleen Booth, VP of Marketing at, notes that one of the biggest disadvantages of strategic planning is lack of ownership and follow through, and that achieving the goals that are defined during the strategic planning process requires clear focus and a commitment to priorities. “In my experience, this is best achieved through an OKR (objectives and key results) framework where each objective and key results has an individual owner responsible for ensuring follow through,” says Booth. 

Poor communication  

Effective collaboration is one of the most critical and challenging parts of the strategic planning process. Still, it can be tough to gather all the necessary inputs you need, especially as your organization scales. Business disruptions like COVID-19 can inevitably make strategic planning and communication more challenging, especially without digital collaboration or whiteboarding tools. 

Lack of alignment

Even the most well-executed strategic plan won't be useful without strategic alignment. Yet a staggering 40% of executive leaders say their enterprise accountability and leadership are not aligned on strategy execution, according to the 2020 Gartner Execution Gap Survey. And this lack of representation from across the organization is one of the primary planning challenges.

As Charlotte Laing, Head of Marketing at Metrikus and AirRated, explains, "There must be input from all parts of the organization, at all levels, so that you can understand the landscape, the challenges, and the direction that makes the most sense.”

Slow adoption 

Let's say you've avoided every pitfall to this point and achieved buy-in on a rock-solid strategic plan for your organization. What happens if no one puts it into motion? 

Fast-growing companies often face near-constant changes to tasks, roles, teams, and strategies—with innovation at the forefront of it all. All too often, this translates into strategic plans that have taken weeks to finesse becoming obsolete soon after their inception. If your teams are slow to adopt the plan, it will quickly become outdated and irrelevant to everyday processes and priorities. 

Ways to avoid strategic planning problems 

Don’t worry. While there are definitely challenges to strategic planning, there are also plenty of solutions to those issues. Here are a few for you to try at your own organization.

Build and simplify business strategies visually 

There are many ways to build, visualize, and evangelize your business strategy. Some leaders swear by tools like GOST (Goals, Objectives, Strategies, Tactics) to create a structured strategic plan:

  • Goals: What goals are you trying to achieve? A strategic plan without goals will only result in spinning wheels.
  • Objectives: It's important to align clear objectives to your goals, and those objectives should be SMART (Specific, Measurable, Attainable, Relevant, Timebound).
  • Strategies: Set by the departments. For each objective, identify three methods to reach those objectives.
  • Tactics: Set collaboratively by the department and individual groups and the strategy owner. For each strategy, set three tactics to execute during the timeframe. "This gives you a direct line of sight to how you impact the outcomes of the business and allows you to track your progress throughout the year," said Kelly.

With these strategies and tactics set, you can roll it all up into a comprehensive master strategy document that's easy to understand and aligned company-wide to the business's desired outcomes.

Create a living, breathing strategy document 

Effective execution doesn't necessarily mean rigid execution. The "perfect" strategy document is a flexible one that can evolve. 

As you execute your strategy, market conditions might change, or some new information might inform one part of your strategic approach, but this doesn't mean your strategy needs to be abandoned. "When something comes up that alters your strategy, alter your plan," says Laing. "Don't hang on to sunk costs because it was perfect before: recognize that the equation has changed and move forward."

Use resources with scaling in mind

Speaking of flexibility, a strategic plan that can scale with company growth should be the goal of every forward-thinking business leader. In fact, according to Gartner, organizations that are able to successfully unlock capacity to execute new growth strategies increase profitability by 77%. As you build your strategic plan, consider how you'll use resources as you scale. Hopefully, your strategic plan results in growth and scale, but without starting with the goal of scale in mind, it's tougher to move a strategic plan past the pilot phase. 

Design and conduct training effectively

Strategy shifts can cause disruption and discord, or they can infuse new energy into your business. To ensure the latter happens, be sure to schedule education and training sessions to ensure your team and your new strategic direction are set up for success. Designing and conducting training sessions is a lot of work but will help avoid endless rounds of revisits to your company strategy. 

Don't rush it—use data and analysis to build a solid plan 

Strategic planning needs to incorporate data that instills confidence—a plan based on intuition alone can lead to wrong decisions. During times of uncertainty like COVID-19, data is harder to leverage as many older baselines are not relevant. The solution is to test data quickly and let the data guide the decisions you make regarding your target market and priorities. 

"A common pitfall is relying on older data that's not adjusted for a new reality. Past intuition is great, but data needs to help lead the discussion and decision," said Alon Waks, CMO, Advisor, and Consultant of Flywheel Consulting. "We're all writing a new playbook."

Collaborate and communicate 

Throughout the strategic planning process, make sure everyone's on the same page. Your team should be included in every strategic decision, no matter how small—and that doesn't mean just communicating the change, either. Set up a 30-minute call or meeting to discuss the proposed change and develop a new plan together. Hold it in a breakout room, assign a moderator, and record the session for those who can't attend in-person. "Not only will you end up with a team which is more on board with the strategy, but usually you'll make a better decision, too," says Laing. 

Effective collaboration and communication during the strategic planning process also ensure greater buy-in once the strategic plan is finalized and published. "Folks will feel they had a voice in where the company is headed," says Kelly.

Follow up and review after executing a strategy

No strategic plan is ever final. As you execute against your plan, it's important to review the results, iterate, and optimize. But don't jump the gun: Establish clear KPIs aligned to your company goals, and then set a realistic expectation of when you expect to see results. And make sure to budget time for reactive tasks. This way, you can act on new ideas and also clearly see when priorities need reshuffling.

Strategic planning is no easy task, and that's why it's so easy to fall into these common pitfalls of planning. However, with the right tools and a bit of forethought and strategic planning, you can beat the odds and execute strategic plans and shape your organization's future.

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