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Top 3 Reasons Annual Planning Sessions Get Off Track

4 min read

Photo Credit: iStock by Getty Images

Published October 14, 2014

Photo Credit: iStock by Getty Images

Picture of Jessica Wishart

Jessica Wishart
Senior Product Manager at Rhythm Systems

In their webcast last week, coaches Chris Cosper and Cathy McCullough shared the most common reason that CEOs fail to have successful annual planning sessions.  In their preparation, they fail to consider the potential obstacles to success.  They don’t ask what could potentially derail them or consider what (other than a list of Annual targets and priorities) they hope to get out of the investment of time with the team.

After looking at patterns from the hundreds of annual planning sessions our team has facilitated, Cathy and Chris identified three of the likely culprits that stand in the way of a great executive team annual planning session.  Getting this session right is so important because it is the foundation for all of your quarterly plans and the weekly and daily execution for your whole company for the next year.  


The way that our coaches help clients avoid these traps is by thorough preparation and what we refer to as a “SuperGreen” call to clarify the company’s unique situation and goals and look for blindspots that could get in the way during the session.  Here are some questions to ask yourself as you prepare for annual planning to make sure that you’re not being blindsided by one of these 3 common issues that could stand in the way of a great session:

1. Unaddressed People Challenges

  • Are there people on your executive team who are difficult to work with or with whom others on the team struggle to communicate and interact effectively?
  • Do you have new executive team members?
  • Are the roles on your team clearly defined and agreed upon?
  • Is the team healthy in that there is enough trust to candidly discuss important and potentially sensitive topics together?
  • Is each person on the team willing to put their personal agendas aside to support the decisions you make together in planning, even if those decisions are not what that person wanted initially?

2.  Significant or Hidden Barriers

  • Are systems and processes in your company that used to work simply not working anymore?
  • Have you (or any members of your executive team) outgrown your leadership capabilities?
  • Have you hit a ceiling of complexity and no longer know how to run the business most effectively?
  • Is your business so large or complex that you need to change your planning process or your process for cascading and cross-communicating your plans to departments or divisions?

3.  Elephant in the Room is Ignored

  • Is there something happening in your business or in your industry that your team is not willing to discuss?
  • Are there pet projects, people, or ideas that you are so passionate about that your team does not feel comfortable sharing their honest feedback?
  • Are there changes that everyone knows need to be made, but you just haven’t been able to pull the trigger on?
  • Does the pre-work you send out to your team before the session contain some themes that you need to further explore?

If you are feeling stuck by any of these potential roadblocks, consider bringing in a facilitator to help you navigate the session successfully so you can still have a great session and a great year.  For case studies on how our facilitators were able to head off each of these 3 reasons that annual planning can be derailed with our existing clients, please listen to the recording of our webcast.  

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