5 Strategic Planning Pitfalls and their Antidotes

Thank you @SmartBrief for featuring this blog on December 21!

Strategic planning work is some of the hardest work we do with groups. Over the years, we have discovered some consistent dilemmas groups experience in planning – and their antidotes. Read on before you jump into strategic planning for next year!

  1. People have differing titers for plans and strategic planning.

Some people really need a plan in order to move forward. They want it in writing, in black and white, and they want to know exactly what their part of the plan is in order to feel successful. Others have very little need for the plan – they believe that what must be done, will be done, and are confident in their ability to push forward without much clarity or documentation.

Due to this phenomenon, when groups come together to plan, one group tends to be checked in when the other is checked out, and vice versa.

The antidote: Structure your planning conversations to invite differing engagement styles within your team. Strike a balance between having specificity about what will be done tomorrow, with forming the “gist” of your directional push. Details can always be added and documents that clarify roles can be created after the group session once the direction and big picture focus is clarified. 

  1. Thinking forward is different than thinking backwards.

It is often easier to analyze past actions rather than “blank slate” future actions.Too often, groups trying to think about the future end up entangled in their notions of what is possible based on what has worked in the past. While relevant, this can be limiting.

The antidote: Provide context from the past (what do we know for sure, what have we learned) and then think expansively and openly about what is necessary and possible tomorrow. Inviting challenging questions and provocative ideas to the process significantly helps with the work.

  1. The words hold us hostage.

It is natural and human to get too literal when we begin to put words to paper in a planning process, which can slow us down. Groups do not typically wordsmith well together.

The antidote: We have found that delegating refined writing of concepts and ideas is much better done post-planning session by 1-3 people with a knack for using words well. This can then be offered to the group for reactions and edits prior to making “final.” Too much time in a group meeting parsing words will drive some people crazy and they will mentally check out. Let the group do the heavy lifting of imagining the future, aligning around direction and priorities, clarifying intention and purpose, and challenging each other’s thinking. Let fine editing and ultimate word choice wait until after the meeting, driven by competent experts.

  1. It is tempting to over-plan execution, rather than over-executing plans.

People often enter a planning process with the expressed concern that “this will not be actionable and we will fail to actually implement it back at work.” As a result, an inordinate amount of time goes into attempting to plan for how to implement the plan back at work. Predictably, back at work, the day-to-day whirlwind of business as usual takes those well made plans and has their way with them, leaving people feeling frustrated at the time spent preparing for execution.

The antidote: Invest in teaching leaders how to drive execution on strategy plans day-to-day in their area of responsibility. Managers, Directors, Executives, and Front-Line Leaders should understand how to integrate long-term priorities and intentions into their regular work. Planning at its best results in new context, prioritization, and vision that allows day-to-day work to be executed in sync with the directional push, not separate and distinct from it. Over-communicate the plans and priorities you craft in strategic planning sessions so that everyone, at every level, understands how what they do today connects to where you are going tomorrow.

  1. People enter strategy planning sessions with no previous thought.

Senior executives are often the ones who engage in planning off-sites to drive the company forward. Do not ask them to show up on the planning day(s) without giving thought to their opinion about where the company has been and is going.

The antidote: Prime their thinking with document review, reflective questions, market analysis, and other advance information that facilitates them showing up to the planning session ready and willing to add value with their thoughts and opinions. We pay leaders for the quality of their thinking – give them advance notice so they can bring their A thinking to the critical conversations about “where are we going.”

Investing time and effort into thinking together and co-creating plans for the future is a critical move for sustainable organizational effectiveness. Do not short-change this critical investment by falling prey to these common pitfalls. Planning together is critical to execution and success in creating buy-in, clarity, energy and hope. Doing it well is the hallmark of the best leaders out there.

Jim Morris