A company's prior experience with strategic planning is an important piece of assessing their readiness to become a strategic planning client. The most basic question that can be asked is whether the company has any prior strategic planning experience or not.

Strategic planning is as much art as science. If the company hasn't been through the exercise before it will take some time to educate the leaders. Chances are some of them have been through something like strategic planning in a prior life at another company. There may be some residue from lackluster prior experiences. Or, we might be able to start with a clean slate, without having to deal with the baggage of past failures.

The basic premise is that it doesn't matter whether a company has experience or not. Those with and those without experience can be equally successful in constructing and executing their next strategic plan. But knowing what experiences they've had will help us go about the planning process in a way that makes it more relevant and ultimately more successful.

If a company doesn't have any prior experience there are a few things I'd like to know.

Has the company ever set goals that were shared with every employee?
Have they celebrated a success together such as hitting a sales target or staying "accident free" for a record number of days?
Do they write things down? Are team members held accountable to written plans? Are sales quotas tracked month after month? Are meetings run with an agenda and are followup items sent out to attendees after the meeting?
What happened the last time someone was held accountable? Was it messy and confrontational or orderly and constructive?
Are team decisions usually based on numbers and data or does the team usually talk about perceptions and base arguments on anecdotes?

If a company does have prior experience with strategic planning here is how I would expect those questions to be answered.

Yes, when we did planning before every employee received a very summarized copy of the plan that showed how their job or department was expected to contribute.
Yes, we have celebrated both big and small things in the past. And people knew those celebrations were coming because we talked about the goal and tracked progress until we crossed the finish line.
Someone is always taking notes when we make decisions and those notes conclude with action items. When we get back together we make sure the action items from our last meeting were completed. We also don't expect people to show up at meetings without an agenda.
The last time we held someone accountable they weren't surprised by the conversation. They pretty much knew they had been coming up short and we were able to constructively talk about suggestions for getting things back on track.
We like to see numbers. We know they aren't everything, but seeing them helps us understand if the stories we are hearing are systemic. Sometimes we hear things or "feel" a certain way, but the data just doesn't bear it out and we can see where emotion is getting the better of us. At other times we see things in the numbers that cause us to go out and solicit stories so we understand what is driving the data. It's a two way street.

Just to be clear, we almost never see all of these answers in one company. Sometimes companies are very data focused but horrible at holding people accountable. Sometimes they are great at throwing celebrations but terrible at communicating how the celebration fits into what the company is trying to achieve long term. But we also run into companies that haven't done strategic planning before that have very good answers to these questions.

The point is this, the questions are the same regardless of the company's experience level with strategic planning. The answers tell us whether the basic disciplines and tools are in place to make planning worthwhile. There is generally a good bit of housekeeping that needs to be done to insure that planning on a company-wide scale has a good chance of success. Smart questions are a good place to start.