Entrepreneurs have a tendency to dream either too big or too small.

It usually goes something like this: either "What's my plan for the next six months?" with no concept of five years out, or "Five years out, land on Mars!!!!!" with no clear plan of what tomorrow's work is.

Let me lay out my very practical strategy for getting it just right.

I once saw a graph that broke down how the board, the CEO, and the management team spend their time:

  • The board should be thinking five years out.
  • The CEO should be strategizing three to five years out but executing one year in.
  • Your management team should live in the current calendar year.

So, as a CEO, every three months, I went out of the office and had a recurring strategy date by myself with a single spreadsheet on which I answered some very critical questions.

In no particular order, these are the questions on that spreadsheet:

  1. What's our product? How does it evolve?
  2. Who's our demographic? How does that evolve?
  3. Who's our competition? How does that evolve?
  4. Who are the advisers I have, and who are the advisers I need? How does that evolve?
  5. Who are my most critical staff who drive our revenue and client growth? How does that evolve and scale?
  6. How is the broader landscape changing? How are our funding needs changing? How much money is in the bank today, a year from now, three years from now?
  7. What milestones would I, ideally, accomplish every three months from now to five years, if things were going quite well?
  8. And, finally, a vague one: What scares me?

I call this my strategic-planning offsite. For the most part, it was just me, but sometimes it involved other people whom I loved hearing opinions from. I looked ahead three months, six months, nine months, a year, two years, three years, and then three to five. For fun, you can have a 10-year category, which just generally for me is to take over my industry.

Every three months, in a methodical manner, I charted this out. By starting backwards.

That's the key to dreaming big: Start backwards

Rather than starting with today, I like to dream big first. Where do I want to be in five years? Maybe it's engaging a million paying customers. Being the category killer with a C-level management team that I'm in awe of. Having the best investors in the industry.

When you do it, be as clear as possible. Use numbers. When numbers don't make sense, describe it in as many words as you can. Write it all down. What this exercise forces you to do is be clear on where you're trying to go.

And then from there, say OK: If that's five years away, then where do I need to be in four years, in three years, in two years, one year, six months, three months, and today? All at once, you'll begin to realize if you want to accomplish that thing in one year, your goals for the next three months need to be bigger. You need to go faster. Maybe you need to make a big new hire, like a chief revenue officer or a CMO, because your client numbers aren't moving fast enough. Or funding has to happen, because you're going to run out of money.

Whatever your challenge, this skeleton plan gives you a clear strategy and, more important, a framework that you can use to communicate to your board and your management team.

For me, this was a fundamental way of operating. So get out of the office, pull up your spreadsheet, and start dreaming. And don't forget to make it big.