You’ve Gotta Plan to Plan

Does your leadership really have a shared vision?

Often, I find that when members of a management team or partnership have heartfelt disagreements over important business decisions – and disagree to the point where they can’t even understand each other’s point of view – it is because they have different ideas of the ultimate goals and direction of the company. They each think they know where the company is headed, and they think everyone knows.

But they actually have different visions of the future. This is because the team has not taken enough time to engage in strategic planning together and to create and commit to that shared vision that allows for better communication and unconditional positive regard for everyone’s views.

To avoid this, take the ownership and management team offsite for a one- or two-day retreat for strategic planning no less than once a year, and as often as once a quarter. A one-day retreat must be focused and can be done more frequently. A two-day retreat builds in time for team building and bonding, and unstructured conversations that can be magical. How often you do either is up to you, so long as you do at least one per year.

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.

4. Set the Agenda.

The content of your strategic planning sessions will change over time. Early in the company’s life, you will begin by focusing on big issues like a vision statement or mission statement, development of the business’s product and service offerings, deciding what your competitive advantage is (are you focusing on price, quality, or service?), looking at competition and perhaps a marketing plan. You will also take time to set up the long-term exit strategy. An agenda will keep the meeting moving and give people an opportunity to get their thoughts together before the meeting.

You can also build time into the schedule to allow managers to call back to the office and handle any important or urgent questions from staff. Take breaks between topics to allow people to stretch and refresh their minds. Take a lunch break but have lunch brought in if you can, so you don’t break your rhythm too much. If you have planned a two-day retreat, make a plan for dinner (go out together or cook a meal together at the Airbnb). Limit day two to half a day and have lunch together before you head home.

On the agenda, identify who will lead each session, and who will take notes. The leader’s job is not to present, it is to facilitate the discussion, ensure everyone is heard, and build consensus. The leader should sum up conclusions clearly and set any action items and responsible parties.

Each discussion topic should end with a decision and assigned actions – and the leader states those clearly so that the secretary can record them and so that anyone in the room who does not agree that the summation was accurate can speak up. The goal is to build a shared vision and consensus.

One person (like a consultant) can lead all sessions, or you can have different people lead each session. In general, I don’t like the head owner or CEO to lead all the sessions – too much power at the front of the room stifles discussion and innovation. In fact, the owner or CEO should try to speak last and get the benefit of everyone else’s ideas before weighing in, where possible.

5. Assign Homework.

Often, these planning sessions will involve finance, and so tasking the CFO/controller/treasurer with bringing current financial statements is an example of homework that is often needed.

Depending on the topics to be discussed, you may have other homework to assign. Any data you predict the group will need to make decisions on any topic should be assigned to someone for homework. Sometimes, the homework will be presented by that person at the start of a topic, and sometimes they will just have the information prepared for reference during the discussions.

Often, during the discussion of a topic, the group will find it wants other information or data in order to make a decision. No worries – add that topic to the agenda for the next meeting and assign gathering that needed data as homework for someone.