What to expect from a Strategic Clarity Session

A number of people who enquire about a Strategic Clarity Session ask what it actually involves. The name is clear enough in principle, but the format is specific, and it helps to know what you are walking into before you commit two hours and £480 to it.

Before the session: the questionnaire ¶

Three to five days before the session, you will receive a written questionnaire. It has seven questions. They are not warm-up questions. They are the hardest questions in the session, asked in advance so that the two hours of live conversation can be spent on structure and framework rather than context-setting.

Most clients find the questionnaire takes between forty-five minutes and ninety minutes to complete properly. If you find yourself writing one-sentence answers, you are probably moving too quickly. The value of the session is directly proportional to the quality of the preparation.

During the session ¶

The session runs for two hours. The first thirty minutes are spent reviewing your questionnaire responses together, clarifying anything that needs clarification, and agreeing on the specific decision or problem the session will focus on. The middle hour is the working section: Oliver uses a structured framework to examine the decision from multiple angles, surface the assumptions that are doing the most work, and identify where the real uncertainty lies.

The final thirty minutes are used to build a decision framework specific to your situation. This is not a generic tool. It is built from the specifics of your questionnaire and the conversation in the session. You leave with something you can use.

After the session ¶

Within two business days of the session, you will receive a written summary: the key points from the conversation, the framework as discussed, and any follow-up questions or considerations that emerged. The summary is designed to be useful without Oliver present. You should be able to share it with a colleague or return to it in three months and still find it actionable.

The session is designed to be useful on its own. Some clients book a second session six to eight weeks later. Some move into a longer engagement. Some do not, and that is a fine outcome.