• Where do you want your business to be in three years (in specific terms)?
  • What outcome do you seek (continued growth, sale, succession)? Does your three-year goal position you on that path?
  • What’s the gap between where you’re headed by default and where you actually want to end up?
  • What should your role be in the business?  What will you need to build or change to achieve this?
  • What would you have to be true about your business in three years for you to feel like this was worth it?
  • Is your competitive advantage structural, or does it depend on continued effort?
  • Are you becoming more differentiated as you grow?
  • Which of the things you’ve built in your business would matter most if it disappeared?
  • What’s something you’re doing today that would make the business easier to run, or harder to derail, three years from now?
  • Are you building flexibility into the business, or locking yourself into today’s decisions?
  • What percentage of revenue comes from your largest customer or customers? What would change about the business and your path forward if you lost them?
  • Are you intentionally reliant on a single customer, channel, supplier or other aspect?  Is that choice worth the risk?
  • How will you ensure that you have sufficient capital to continue to grow?
  • Where do you face gaps, bottlenecks or other potential significant risks or impediments?
  • What’s the single most important thing that has to happen in the next 12 months to ensure you’re on track?  What do you need to see in 90 days to be confident you can achieve it?
  • Is this objective an important step toward your longer-term goals, or simply an achievable outcome from where you stand today? 
  • What are you accountable for? Who will hold you accountable for the next 12 months, and how will you check progress? 
  • What will it cost (cash, time, energy) to reach your goal, and can the business fund it?  What are you spending time, money, or attention on that isn’t moving you toward that destination?
  • How will you decide whether to adjust goals, pivot or simply push harder?

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