How should you engage in strategic planning?
1. Plan to Plan
Strategic planning is a serious exercise that requires planning and commitment. Planning to plan is a key first step in the planning process.
First, you should decide who will attend the planning session. Start with the key management team. These are usually direct reports to the owner. If you are at an early stage, everyone in the company may feel like a direct report to the owner, so ask yourself who the leaders are. Who will manage functions as the company grows? Who performs those key functions now? Of course, owners should all be present in most cases.
You may want a facilitator or management consultant to attend as well. Some people ask their outside accountant or lawyer to attend, but this can be expensive and can be limited to sessions where you may want their direct input. Some people like to include a secretary to make a good record of the meeting and decisions made. This could be an administrative professional from your office who is discreet, or you can hire a temp just for this meeting.
2. Decide Where to Plan
Offsite is best. You want the team to be as free of daily work distractions as possible and away from the general staff (who may need to know the results but don’t need to see the sausage being made).
For the first session, I recommend a two-day offsite retreat with everyone staying overnight and bonding over a meal together in the interim evening. After that, one-day sessions held two or three times a year or a two-day session once a year are fine.
Make sure the location has plenty of power, comfortable seating, and a whiteboard or flipchart or screen to project a computer screen. The location should be comfortable, free of distractions, and a place where work can get done (like a big table everyone can sit around).
For the two-day retreats, a big Airbnb house with enough bedrooms for everyone can work well, or a hotel with rooms for everyone and a meeting space can work as well. For one-day sessions, conference room rentals are ideal. Make sure there is coffee and drinks and snacks and generally plan to eliminate all the little things that people will worry over and distract from the work.
3. Decide When to Plan.
It can be hard to choose dates when all the key players will be free and able to attend. On regular workdays, they may feel they cannot leave work completely unattended by any management. On non-workdays (if you have those) there will be family time and events to contend with.
This planning is important, though, and deserves priority. Close for a day if you have to. Train other employees to at least handle things for a day so you can all be away. Set the schedule to help (see no. 4 below). But make time to get this done.