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Where Did "Why" Go?: The Role of Critical Evaluation in Strategic Planning

Guest post by: Joe Evans

Article Overview: This article explores the importance of critical evaluation in strategy planning and asking, “Why?”.

Where Did "Why" Go?: The Role of Critical Evaluation in Strategic Planning

Why? It is an inquiry we don’t make often enough. “Why?” is the simplest form of a question, yet when it is asked, it cannot help but be thought provoking. “Why”, “what if” and other forms of critical evaluation promote discussion and lead to improvement in our decision-making process. Even so, we all too often elect not to use these words from of our repertoire. Instead, they are often replaced by, “sounds good to me” or some other form of passive acceptance. We should reflect on the importance of this elegantly simple but powerful trigger for critical thinking and make sure we do not allow “why” to become part of a forgotten business vocabulary. This article explores the importance of critical evaluation in strategy planning and asking, “Why?”. Our life lessons and common sense should be applied within our business lives, day in and day out; never left at the door when we get to the office. Just think about it. Whether it is selecting which grade of gasoline to buy or trying to determine what the difference is between the regular and the “extra strength” brand variation that costs $.75 more -- we use critical evaluation in our lives constantly and are good at it. Where we are less proficient is leveraging this skill to its fullest potential - all the time. To do so we just need to program it into the decision-making process to occur systematically so we benefit from our cognitive talents in all aspects of our lives.


Our strategic planning process should be leading us through a critical evaluation framework that drives better decision making. The process should automatically be challenging the status-quo of the organization in order to drive better performance through a constructive current-state critical evaluation.

• We’re losing market share. Why?
• Our costs containment strategy is not working. Why?

Exploring such questions ultimately leads to more questions to contemplate. “Is the status quo the right answer?”

The strategic planning process should structure critical evaluation and drive questions about current problems in the business or organization and provoke innovation and creativity channeled into addressing performance. Likewise, the strategic planning process should also challenge our collective ideas for the future state vision.

• Is this the right next move? Why?
• We’re not closing new business. Why?
• Are these ideas worth pursuing? Why?
• Is changing it a good idea? Why?

Propagating Mediocrity

Critical evaluation challenges us to think and improve. All ideas need to be challenged in order to weed out potentially risky or harmful strategies and operational tactics that could have long-term detrimental impacts on the business. Ask, “Why?”

Many times our instincts tell us that something just doesn’t feel right. Do we stop to analyze why, or think about the situation and try to determine what it is that is bothering us about it? Most of us will mull it over until the bothersome element begins to crystallize in our minds and we can then take appropriate action. Conversely, we can sometimes go with a spontaneous “gut feel” - another over-used skill that can get us into trouble. If our gut is sending us a strong message, shouldn’t we in turn be asking ourselves “why”?

This is as true in conjunction with our day-to-day routines as it is in strategic planning. Too often we “accept” mediocre suggestions without truly using critical evaluation to poke at the notion. It is just as damaging to excuse oneself from the decision process by deferring to weigh-in with an opinion or looking away when faced with the opportunity to evaluate data and impact a decision. Stepping forward to contribute is a valuable leadership trait and organizations need leadership.

Critical evaluation is our filtering mechanism to protect us from poor choices. Mistakes will still be made, but with our filter working at 100%, some poor choices will be avoided and bad ideas stopped. The filter is our protection from simply accepting and blindly trusting in consensus or the person speaking the loudest. 


In our business world, we not only have the obligation to filter - but also to question, challenge and improve. Despite Enron’s “ask why” tagline, it’s clear that the question wasn’t being asked and answered enough. If only the risky decisions had been averted and the unethical behavior questioned. Instead, a company has disappeared off of the map, and many lives were damaged or ruined. Many bad ideas and poor decisions can be effectively filtered out through systematic critical evaluation.

The Power Duo: “Why” and “What If”

The same is true for seemingly “good” ideas. During strategic planning, good ideas can be made better when challenged and defended. Without critical evaluation applied, how do we know it really is a “good idea”?

Consider the current disaster unfolding in the Gulf of Mexico with the sunken BP deep-water drilling rig. It would seem logical that “actionable” contingency plans would have been in place for the “what if” scenarios. Unfortunately for the Gulf States and BP, whatever contingency plans that may have existed prior to the explosion and massive oil spill, have failed to have an impact thus far. The company would have benefited from more “what if” planning. Better yet, what would BP’s situation have looked like today if better planning efforts and controls had been in place to begin with? Could the disaster have been avoided entirely and lives saved?

The planning process for our business must force such evaluation to take place, systematically. When a thorough planning process is followed, future-state vision and key outcomes go through a critical evaluation and are reviewed against the same evaluation criteria we should be applying to our current-state result.

• Are we satisfied that this the best it can be, at least for now? Why?
• What if we’re wrong on our assumptions?
• What are the scenarios we should plan contingencies for?

Why this and not that?: The Refinement of Strategic Key Outcomes

Good leaders become great by asking, “why?” They test for weakness in concepts, the conviction behind the ideas and the depth of analysis behind the suggestions.

Our strategic planning processes must provide that same framework for critical evaluation. It must help us select amongst the options available in formulating strategy and provide us with guidance that is true. A good planning process is like a compass that helps us find “true North” and avoid getting lost in the woods.

The planning process should serve us in the identification of the best strategic options. As part of the process, it should aid in the relative valuation of potential strategic outcome choices and help us to prioritize our options from greatest to least beneficial.

Timeframes and Decision Gates: Analysis Coupled with Action

A structured planning process is required to pull us through to the planning conclusion, keeping us from getting lost along the way. To do so effectively, the process must couple the required critical evaluation with the necessary rigor to maintain momentum and take action. Analysis paralysis would likely result in the absence of a process built around established timeframes and decision gates. In strategic planning, at a minimum, we need to take action based on:

• Competitive analysis
• Return on Investment data
• Contingencies / mitigation plans
• Fully vetted assumptions

Established timeframes and decision gates within the process allow deferring taking action on our ideas until the “last responsible moment”. At the same time, the process continues to drive progress towards the goal of completing our planning effort. Once we’ve reached the decision point, our choices will be based upon a superior body of analysis and more thorough understanding of our options.

The Rewards of Critical Evaluation

Our economy needs businesses to thrive. To do so, we as business leaders must continuously strive to mature our organization’s strategic decision process and planning acumen. Our business cultures must encourage free thinking and reward those who constructively challenge, innovate and participate in making our models more successful by asking “why”.

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Article Tags: business vocabulary, critical evaluation, critical thinking, passive acceptance, strategic planning
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