How many times have you flown to an exotic, offsite location to do strategic planning -- only to find that no meaningful prep had been done, and the agenda was just a few hastily jotted-down bullets in somebody’s notebook? Did you drink a little too much one night and miss the secret, early morning round of golf where the real decisions were made? Did you end up spending valuable time in shouting matches with higher-ranked executives?

This kind of meeting can destroy your chances of success. A meeting like this won’t surface all the critical information, and you’ll end up making uninformed, gut-based decisions. So this is not how Rally does meetings.

In the first week of October, our executive team gathered for an offsite in Colorado Springs. The first two days of the offsite included an extra 25 people from around the company to provide context, so the executive team would be ready to do some good strategic thinking.  

It was a beautiful location, and the weather was great. This did help move us out of our regular way of thinking in the office.

In a typical offsite, there would have been a series of short presentations spread over several hours. But that sort of meeting is exhausting, and depends more on good presentation skills than anything else. So the meeting we had was designed completely differently, with 7-8 parallel tracks of information-sharing.

Preparation is Key

What made this meeting work?

Months of prep. Our product marketing team had spent a ton of time doing deep competitive analysis, understanding segments, competitors, forces, factors, and trends. They did SWOT analysis on each of our offerings. We started refreshing all of this content back in August and continued right up to the first day of the offsite.

This kind of preparation is real work. The Agile movement has often been criticized for failing to specify how this work should happen -- somehow the Product Owner just “knows” all of this stuff. The reality is that as you scale Agile to a multi-product company, this work has to be done, just as it does in traditional organizations.

How much time do you spend preparing for a meeting? For something as important as strategic planning, you should spend a lot. But for senior product people, diving into this material is a key part of their job anyway. Having the offsite on the calendar for a specific date helped motivate them to shift away from customer visits, blog posts, and pricing and packaging concerns for a little while and consider the more strategic side of their jobs.

Because of this prep, they were able to walk into the meeting and speak confidently and in-depth about our markets and our position, and propose longer term strategies. This had a dramatic impact on the conversation had by our executive team -- and it improved the level at which they’re able to converse day-to-day.

Planning Rule of Thumb

Ryan, Rachel and I spent a lot of time planning the meeting. Jean Tabaka’s rule of thumb is to spend about twice the length of the meeting on prep, which in this case amounts to about 50 hours (spread over several months.) This seems about right, given this is a meeting of 35 senior people; the opportunity cost is enormous, but the benefit of getting it right is even greater.

Even physical preparation is important. For example, I traveled to the venue the day before to set up, and spent three hours getting the room set up correctly.

How about you? Are you walking into your strategic planning meetings with nothing but a hastily-drafted agenda and 100 MGs of PowerPoint slides, hoping things will work out?  

Don’t wait to plan your next strategic meeting. Need a guide? Let us help.

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