There’s an old Yiddish proverb, “Man plans and God laughs,” which summarizes the fact that life doesn’t always go as planned. Entrepreneurs and startup pioneers know this truth especially well. In fact, having led several startups myself, I’ve come to expect that the path to success will almost never be what I had originally planned. That introduces a quandary into my planning process - since I know that the plan won’t ultimately work out, why should I even try to make a detailed plan? Granted, that sounds silly, but for someone who isn’t a natural planner to begin with, it’s caused me a good amount of angst. But somewhere along the way, I discovered a metaphor that really helped me make sense of things: effective planning requires both a Treasure Map and a Road Map approach.

Treasure Map

Think of the treasure maps you’ve seen in fictional stories. They’re sketchy, not drawn to scale, show a circuitous route from landmark to landmark, and sometimes have hidden clues along the way. When you follow a treasure map, you’re in for an adventure, and it’s not for the faint of heart or those who get hung up on details. And when the going gets tough, it’s the allure of discovering the treasure that helps the explorers persevere. I can’t think of a more fitting metaphor for the journey of growing an early-stage company. Even though there are general success principles to follow, the path doesn’t come with clear instructions - it’s a journey with only vague milestones for guidance, and plenty of learning opportunities and plot twists along the way. The treasure map approach has some real limitations when it comes to planning. When it comes to execution, your team needs a solid plan with action steps, timelines, and measurable goals. A treasure map provides none of those.

Road Map

A road map approach reflects a very different mentality. Think of the maps app on your smartphone. It calculates the fastest, most direct route possible with step by step, turn by turn, directions. It tells you exactly what to do, and when to do it. Your expectation is efficiency, accuracy, and no surprises. And when things get confusing, it serves as a reference guide for the team to keep executing on the plan. When it comes to operational planning and execution, a road map mentality works well. Seeing the end from the beginning helps the workers plot incremental steps for success. Budgets, timelines, and resource planning all contribute to ensuring the plan runs as smoothly as possible. However, over-reliance on the road map approach isn’t wise for early-stage companies. Your team can get lost in the details and lose sight of the big picture. And when a major disruption comes (and one will – count on it), the plan will need to be modified and the previous efforts that went into planning the details get wasted.

True Story

Take the example of one of my startups to see how these dynamics play out. We were the first commercial anti-spyware company back in the early 2000s, and we built the company from zero to $16 million in revenue in just three short years. Sounds great, but we had to make some major pivots along the way. Our team knew the anti-virus industry players very well, so we thought that working with them would be the obvious path to success, but that wasn’t the case. Neither the vendors nor their end users wanted to admit that their existing AV products didn’t catch spyware trojans, so our positioning strategy quickly hit a brick wall. Ultimately we found a different pathway to success (contact me if you want the details), and we wound up getting acquired for a healthy multiple by an industry giant. Now, if our team had only used a road map approach, we would have given up when we hit those dead ends, because they looked like an apparent failure. The treasure map mentality allowed us to pick up some fresh clues along the way and follow a non- obvious path. If we only had a visionary treasure map mentality, we wouldn’t have executed well enough to drive up the revenue so quickly. Our chances of getting acquired would have been greatly decreased.

Getting Practical

The reality is that you need a high-level vision and you need tight execution. It’s not an either/or scenario; it’s both/and. So here’s my recommendation the next time your team has a planning session. First, lay out your treasure map the way you think it will work out over the long haul (multiple years). Identify your big landmarks along the way, and define what the treasure is at the end of the journey. (Tip: this exercise is great if you use non-traditional, visual methods to build that map – dream big and have fun!).

Second, identify the next landmark/milestone on the treasure map. That might be the next product ship date, when you acquire a certain # of customers, or simply the next calendar quarter. Whatever it is, don’t let it extend beyond three to six months.

Third, map out a detailed execution plan (your road map) between the planning session and that milestone. Consider expenses, realistic revenue projections, resources needed, timelines, and use best practices project planning. Don’t plan beyond the stated Milestone.

Now, go execute according to the road map. And stick to the plan. New opportunities will arise. Disruptions will come. You might get bored. It doesn’t matter - stick with the plan. Unless there’s a real situation that threatens the very viability of your entire company (very rare), everyone sticks with the plan.

When you reach the milestone (or even if you missed it), pause and do your planning again. Debrief with your key stakeholders. What part of the road map worked? What didn’t? What did we learn? What do we need to change? What do we need to keep on doing?

Now go back to the treasure map. View the answers to the debriefing questions in the previous step as if they are the clues that you needed to gather along the way in order to discover your next landmark. Get agreement on what the next landmark should be, and repeat the cycle all over again.

Next Steps / Challenge to Action

In the end, the maps are more than just guidance tools - they reflect different mentalities. Knowing which mentality to adopt for which purposes will go a long way in charting your path and leading your team to success. I hope you found this helpful. Let me know what’s worked for you – I’d love to hear your thoughts and experiences.

Want to hear more of my thoughts about these two maps? Watch my video below.