Strategy Retreat Conversation Starters

If our organization were a living thing, what would it be right now, and why?

What's one word you hope people use to describe us five years from now?

If we could only keep three things we currently do and drop everything else, what should they be?

What's a competitor or organization in a different field that inspires you?

What's the biggest opportunity we're currently leaving on the table?

If we had to double our impact with half the resources, what's the first thing we'd cut?

What's a question about our future that keeps you up at night?

What's something we assume is true about our customers or market that we should probably verify?

If we could wave a magic wand and solve one problem overnight, what would it be?

What's the best idea someone on this team has had in the last six months?

What's a 'sacred cow' in our organization that needs to be retired?

Where are we being too cautious, and where are we not being cautious enough?

What's a strength we have that we're not fully leveraging?

If we were to write a headline about our organization five years from now, what do we want it to say?

What's a blind spot you think leadership might have about our current reality?

What's the difference between what we say we value and what our actions actually reward?

What's a trend in the world that we're either ignoring or underestimating?

If we could steal one practice from a completely different industry, what would it be?

What's a decision we made in the past year that we should revisit or reverse?

What does 'winning' actually look like for us in measurable terms?

What's the gap between our stated mission and our actual daily operations?

If we truly believed we could change our industry, what would we do differently tomorrow?

What's a fear about the future that, if addressed, would unlock our next level of growth?

Who are we becoming as an organization, and is that who we want to be?

What's a truth about our organization that we're avoiding as a leadership team?

What would our harshest critic say about us that might actually have some truth to it?

What's the most important question about our strategy that we haven't answered yet?

If we knew we couldn't fail, what bold move would we make in the next year?

What's the legacy we want to leave in our industry or community, and are we on track for it?

What's one thing we need to stop doing to make room for what matters most?