Strategic Planning Facilitators

Strategic Planning Facilitators

By Ian Richardson, Managing Partner, Richardson & Richardson Consulting LLC

Inspired by Thursday Process with guest Paul Azad, Service Tree

Strategic Planning Facilitators

When an entrepreneur or group of leaders sits down to consider strategic planning, a lot of time it starts with problems, beliefs, and desires. I remember the first time my I.T. company approached the topic, myself and some of the more senior staff were having a “water cooler conversation.” We were wondering why we were making some of the same avoidable errors. We all confused, and a little bit anxious, around those errors and the semi constant stream of customer complaints that was leading to our team needing to perform rework. There was not a small amount of frustration floating around the office, and even some finger pointing, both internally and outside of the organization at the “cause” of less-than-ideal outcomes.

Myself, as the owner and person who held the bag of “risk” if we failed, I was a bit scared. What if we couldn’t get it “right?” How was I going to get new customers if we kept failing to execute successfully for the ones we had? I didn’t know the first thing about strategic planning, but from what I had read, heard, and seen, it sure sounded like something that could help. I knew I didn’t want to have to figure out how to do it myself alongside the myriad of other balls I was currently juggling day to day. I simply wanted to get to a place where my business would run itself day to day without me having to be involved in every little decision and action. In walked the concept of a strategic planning facilitator, someone to help and guide us through the process. I’m grateful I found one and wanted to explore the topic with you today.

The benefit of strategic planning facilitation

Strategic planning is one of those topics that can mean different things depending on who you ask. It might mean having a quick brainstorming session, figuring out a high-level plan of action, dividing up some tasks, and running forward fast. Other times, it might involve a bit more time and people in the room – you may be examining each part of the business intentionally to figure out what needs improvement, what needs additional resources or systems, and what simply needs to be understood better. I can’t think of a better time to be in business than today – there is a multitude of options, systems, processes, and resources, most widely available, for someone looking to perform strategic planning in their business.

Regardless of whether you’re trying to tackle a “fast plan” or a “deeper dive” – It can be a difficult thing to both participate in the planning process with your employees and peers, as well as lead that process according to a pre-designed structure and format. Shifting from “facilitator” to “participant” is to put it politely, really damn hard. My friend Paul Azad, CEO and founder of Service Tree, a ConnectWise Manage plugin that helps automate incident management scheduling, came onto the Richardson & Richardson webinar series The Thursday Process and shared his thoughts on the topic in the video below. He found that by having the right people from his team in the room and being “one of the team” versus “leading the team”, it became the team’s plan, versus “Paul’s” plan. Teams have a tendency to buy into collaborative efforts and support them more enthusiastically versus being “told” what to do.

Final thoughts around strategic planning

Strategic planning can be a bear of a topic to tackle, much less get started and have it become engrained into your company culture. R&R has created a large library of resources around the topic hosted at our blog that you can use to get started.

If you’re struggling with creating a strategic plan, figuring out how to effectively present it, or getting alignment with your team on the need to invest in the effort, Richardson & Richardson can help. Check out our case studies for stories of organizations that we’ve assisted with similar issues and download our white papers for deep dives on tools you can use in your organization. If you’re wondering where to start, book a complimentary session with one of the Richardsons today to come up with a plan on how to move forward.


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