Planning Team

Garbage in; garbage out! A company’s real investment into planning is people. Putting the right people – those with an objective and analytical mindset – on the task is the only path to a successful outcome.

Think about strategic planning as tax season for most general managers and analytical players in a fast-growth company. Commitment to developing a strong plan enables a company to focus all resources solely on executing flawlessly during the planning period. Conversely, a lack of commitment to planning leads to lack of confidence in the plan. This results in poor forward momentum and waste of organizational resources many times over throughout the planning period because outcomes that could have been well-developed during planning will be reworked. To be clear, I am using the term planning period to frame the time window that the planning exercise is intended to shape, not the window of time when the planning exercise is performed.

So, a company should put its best analytical minds on the task. Every company is different, and employees are different further. Thus, sticking to the don’t rinse-and-repeat principle, proposing a one-size-fits-all planning team structure wouldn’t be optimal. Broadly speaking, planning needs a few critical roles and they have specific responsibilities.

Role 1: Strategic Planning Lead

Strategic planning requires a quarterback. This is NOT the CEO. This is one of the areas that a CEO must delegate because it requires deep attention to operational details and analysis. However, this role must have the complete backing of the CEO. This role must demonstrate two very important characteristics:

Objective & analytical mindset

The Planning Lead has to have strong business acumen around strategy and all business functions, an analytical mind, and a good handle on operational pitfalls that can occur if planning is poorly executed. The role also should have past experience running planning efforts, without which the company is risking its time and resources (and the company’s future itself) on someone learning on the job. The Planning Lead is accountable to:

  • define the planning approach that is tailored to the company’s needs
  • choose the right individuals who need to be involved throughout the various stages
  • structure the underlying internal and external analyses required to reassess strategy
  • moderate all idea development, assessment, reviews, and decision-making to ensure the plan is comprehensive and cohesive


The cultural relevance and complexity of strategic planning is often underestimated. Planning can lead to poor results that range from tactical ideas cobbled together, on the ineffective end, to a land-grab for budget by various teams, on the harmful end. Strategic planning will not make everyone in the organization happy because it is meant to be a disciplined, trade-off exercise. The path to make choices cannot be a split-the-pie-evenly or a command-and-control CEO mandated approach.

Tough trade-off choices have to be made throughout the planning exercise. These have to be made based on objective assessments of internal performance, analytical understanding of the market, and a realistic mapping between investment and the resulting impact. The strategic planning lead, with the executive sponsor’s support (see below), has to make these choices prior to group reviews and agreements. In other words, the strategic planning lead should not behave as a project manager. Checking boxes or simply aggregating information, based on input from strong personalities involved, will result in an ineffective planning output.

The planning lead should be an independent thought leader, who can stand firm and balance all the information available to arrive at the most optimal outcomes for all organizational stakeholders (investors, employees, customers, vendors, and partners).

Role 2: Executive Sponsor

In a small- to mid-sized company, this is the CEO and / or CFO. The CEO is accountable to the board for the company’s strategy and operations, and the CFO is accountable for the company’s financial forecast. Both of these aspects are outcomes of strategic planning. Executive Sponsor is the dispassionate referee in this exercise. The primary role of the executive sponsor is to:

  • stay fully engaged throughout the exercise by consuming and understanding all relevant analyses and findings, and actively police all participants for objectivity
  • bring holistic perspectives around market dynamics and investor interests to the table
  • lean into senior executives that own and manage teams to remain objective, and engaged through out the process
  • be maniacal about the importance of translating the strategic plan into operational plans, and holding functional teams accountable to execute on it

If the executive sponsor is not fully engaged, decisive about making decisions based on objective findings, and advocating adherence to the planning approach, the exercise is at risk of not driving the necessary organizational changes to grow further.

Role 3: Analyst

In this context, an analyst does not imply someone who slices and dices data. This role epitomizes the insightful or strategic maturity level of the Objective & Analytical Culture. An effective strategic planning exercise in a small- to mid-sized company does not need more than one full-time-equivalent analyst for the duration of the exercise. This role remains joined at the hip with the planning lead and executes on direction from the planning lead.

Role 4: Objective Business Leader

This is the hardest role to find the right people to engage in a small- to mid-sized company. Everyone is busy and many hires are functional operators, not cross-functional ones. Strategic planning requires a team that can put the company-first hat on. This implies that each participant thinks about the whole rubrics cube and not just their favorite color. So, the specific individuals tapped to get involved is situational.

During one of the recent planning exercises that I supported, the company brought together every department lead into the exercise. This is a very common occurrence. However, the Chief Technology Officer was the only one who asked the hard questions, challenged groupthink, and brought a prove-it-to-me attitude to the exercise. The other department leaders were almost exclusively disengaged until it was their turn to talk about their own functions when they spoke mostly about their spending plans with limited details on how those plans would really drive growth. Inclusiveness creates a comfortable collaborative feeling in the short-term; however, it does not have any relation to the quality of the planning outcomes.

This role is the all-important conduit between the plan and the rest of the company. These individuals have several key responsibilities, including:

  • Help execution and synthesis of assessments laid out by the planning lead
  • Dedicate mindshare to consume all assessments and develop cohesive hypotheses on strategy development and identification of strategic initiatives
  • Apply critical thinking to work through various investment trade-offs to ensure that the final plan is in the best interest of all organizational stakeholders
  • Translate strategic initiatives into detailed operational plans

This maybe obvious; but, none of the responsibilities above are functionally focused. In a small- to mid-sized company, strategic planning cannot be along functional silos. The individuals stepping into this role should operate at a high objective & analytical culture maturity level.

Who are the right picks for this group?

On this front, companies often swing to the extremes of over-inclusion or under-representation. On one hand, including key players from every function with responsibility for any topic that might be impacted by strategic planning might seem appropriate. Alternatively, the executive sponsors might try a command-and-control approach by only including a very small group based on seniority or organizational position.

There are several challenges with over-inclusion. If too many individuals are involved, what does each person bring to the table during the planning exercise? A small- to mid-sized company doesn’t need an army to develop a strong plan and passengers complicate the exercise with an abundance of tangential discussions, and misaligned strategic thinking and planning experience levels. Additionally, attempting to spread the work across many functional supervisors and senior executives is highly inefficient. It will diminish the quality of the output because it is challenging to dovetail small pieces of work completed by many individuals.

The command-and-control approach is fraught with risks as well. The biggest risks are 1) lack of analytical involvement to work through key planning deliverables, and 2) lack of organizational adoption of the plan because the right analytical minds aren’t involved in developing the plan.

Optimally, the company must apply a work-based staffing approach, to build the planning team. Planning at a small- to mid-sized company needs a small swat team, which is very hands-on. The company is best served by choosing a handful of individuals who can influence up, down, and across an organization and bring a critical thinking and analytical mindset to the process. Unless senior executives are very hands-on in terms of designing and performing analyses, and ideating and detailing strategic initiatives, they are better off serving as Executive Sponsors. Planning is a complex exercise and it requires the core team to be comfortable with creating and consuming details.

To conclude, staffing for planning is more about quality than quantity. A small, objective, and influential group of thought leaders are the most optimal candidates for the four key roles on the planning team.

Published By

John Oommen

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