Seven Common Mistakes in Strategic Planning

Seven Common Mistakes in Strategic Planning – Virtual CFO

Strategic planning can be critical to the success of a business. As a Consulting CFO, I have been engaged in many strategic planning sessions over the years and I find that there are common mistakes leaders make. Here are some examples and ways to mitigate the challenges.


  1. Using an internal facilitator who does not know how to lead a planning session.Oftentimes it makes sense to bring in an outside qualified consultant to run the session. Facilitating is a skill in itself that an otherwise talented CEO or management team may not have. Additionally, an outside consultant may have more of an objective point of view and encourages people to speak their minds.
  2. Not clearly stating objectives. Without stated objectives and some level of structure, you run the risk that the session will wander. Starting off with clear objectives will help guide the session and ensure people stay on task.
  3. Failure to have an atmosphere of trust and openness. It’s important to brainstorm as a group, in an atmosphere of trust and non-judgment. Sometimes it is the craziest idea that really changes things. If you don’t have an environment where people are free to speak their minds, you may miss out on great ideas.
  4. Getting too granular. The purpose of the strategic session is to set major goals and the strategy for reaching them. Digging into tactics at this point dilutes the strategic purpose, can end up redirecting the conversation into the weeds and increase the risk of having too many action items (that are never completed) rather than a strategic few (that are completed).
  5. Misconception about the word “strategy”. People often don’t have a common reference about what “strategy” is, as it can mean different things to different people. From my view point, vision is what you want to be and where you want to go. Strategy comprises the big steps you take to get there.
  6. No follow-up on ideas from strategy session. Once you’ve done the hard work of going through a strategic session, and pulling in executives from their busy schedules, it’s important to move forward and implement the action items that came out of the session. The most common failure of strategy sessions is lack of execution. Management has its annual “walk in the woods” and nothing changes. I strongly recommend assigning action items to individuals and setting up a mechanism for follow-up and accountability. Quarterly updates are a good idea; progress reports and follow-up need to be more frequent.
  7. Ensuring the right attendees are present. There are two points of view: one says it should be a small group of people because it’s easier to get things done, but a bigger group, with more participants has a greater chance of more good ideas and buy-in. As the group gets bigger, the facilitator’s role becomes more important. It is important to include people from different disciplines and perspectives, including sales, finance, operations, marketing and other big areas in the company.

In the end, it’s critical to have these types of strategic sessions, but being prepared, having the right framework, facilitator and attendees are very important.

Carter Freeman is the Managing Director and Consulting CFO for the Denver office. You can reach him at

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