How to prepare for a strategy working session
A two-hour working session can be genuinely useful or it can be an expensive conversation that goes in circles. The difference is almost always preparation. Not elaborate preparation. But the specific kind of thinking that happens before the call, not during it.
Send materials before, not during
The most common mistake is treating the session itself as the place to share context. If the first thirty minutes of a two-hour call are spent explaining the background, you have lost a quarter of the time before the real work starts.
Send whatever is relevant at least 48 hours in advance. That might be a one-page summary of the situation, a financial model, a draft of the decision you are considering, or a set of options you are weighing. The format matters less than the fact that the other person has had time to read it and think about it before you speak.
Write down the question you most want answered
This sounds obvious. It is harder than it sounds. Most people come to a strategy session with a general topic rather than a specific question. 'We need to think about our pricing' is a topic. 'Should we move to annual contracts, and if so, what is the right price point for our mid-market segment?' is a question.
The more specific the question, the more useful the session. If you cannot write down a specific question before the call, that is worth noticing. It usually means the real work is to figure out what the question is, and you can say that at the start of the session.
Know what a good outcome looks like
Before the session, decide what you want to walk away with. A decision? A framework for making the decision? A list of the things you still need to find out? A second opinion on a conclusion you have already reached?
These are different outcomes and they require different kinds of conversation. Being clear about which one you want helps the session stay on track and makes it easier to evaluate whether it was useful.
The sessions that work best are the ones where the person coming in has done enough thinking to know what they do not know. That is the preparation that matters.