And A Tree Fell Across the Path: Responding to Startup Adversity

Unforeseen problems. Disrupted plans. Surprising changes. Startups are all about ups and downs and responding to adversity. When the unexpected occurs, it is time to swing into action.

“Hey, we have a problem! There is a tree down across the driveway and we can’t get out!” The intense windstorm overnight had created unanticipated hurdles to following through on our plans for the day. As I gazed down the driveway at the tree trunk blocking our path, my first thought was “Now what do we do?” and my startup-honed problem-solving skills started to kick into high gear.

The essence of startup life is continuous problem-solving. Some problems are straightforward to anticipate and plan for solving. For example, how will you manufacture your product once it is developed? Where will you find that critical next hire to expand your team’s capabilities? How will you get that regulatory approval that you need? These problems require focus and execution, the bread and butter of startup building, but they are not surprises.

Sometimes, for a few moments, I wish that building a startup was as simple as developing an organized project plan and then seamlessly executing on that plan. However, where would the fun and creativity be in that? Those of us who are drawn to the startup world had better be drawn to the chaos and excitement of the never-ending variety of new and interesting problems that unexpectedly present themselves. Startups might best be described as the continuing experience of disrupted plans. Those disruptions can be terrifying, overwhelming, and start-up survival threatening. At the very least, they are often massively inconvenient and stressful.

Oftentimes, the problems we encounter as we lead our startups are complex and multidimensional. For example, the tree across the path analogy extends for me because that morning our chainsaw was unwilling to start and there was actually more than one broken tree across the driveway caused by that powerful windstorm. The second broken tree was large and split down the center with half of its canopy now suspended twenty feet in the air above the driveway. Plus, the divided trunk had exposed the top of a 6-foot honeybee hive which a local bee expert later estimated had at least 80,000 bees in it. Now this was a real multidimensional problem: we had the risk of the suspended tree falling unexpectedly, a hive of 80,000 pollinators whose home was now destroyed because it was exposed to rain (apparently bad for hives), and the other half of the 90-foot tree was unstable and unsafe. Cascading were the dual problems of the beekeepers who could not remove the hive unless we could get the tree trunk down so they could find and capture the queen bee, and the arborists who refused to tackle bringing down a massive tree trunk while it was filled with thousands of agitated bees. Cap it off with the complications of no one wanting to share protective beekeeping suits in the season of COVID-19. The problems of the trees across the path just seemed to keep multiplying as we tried to disentangle and solve each aspect – and that felt exactly like a startup!

Switching to a startup context, some of the more vivid memories I have of startup trees across the path, also known as unexpected, multidimensional, emergent problems, include:

Approaching our first venture-led round with a signed term sheet in hand, one of our beta tests surfaced a missed set of requirements that demonstrated our product was not ready for primetime. The first problem layer was convincing the lead VC to complete the investment at half the previously agreed upon valuation (ouch!). The next layer was using that investment for another nine months of engineering work to complete product development to the level of the discovered set of requirements so we could go primetime.
Seven years into product development, our renewable energy startup with a novel turbine-free design that was projected to cut half the cost out of an offshore windfarm faced a competitive environment change that wiped out its entire projected cost advantage. We tried unsuccessfully to find a technical path forward to restore the competitive advantage. In the end, however, that dramatic market move led directly to the decision to shut down the company.
A software development team’s work product just kept getting more brittle by the day until we started to get software releases with more new “features” (bugs) than were being fixed. That required recognizing that the existing team could not do the required work, emotionally accepting the abandonment of a massive sunk cost, finding a new team with the right competencies to meet our use case, and redeveloping the software architecture and implementation.

These are “big tree” examples, however, the same patterns apply on the smaller day-to-day and week-to-week problems of a startup. Despite the variety and complexity of the problems that crop up, the approach to tackling them follows a common pattern:

Recognize that an unexpected problem has emerged. I often am tipped off by the feeling of “now what?!”
Take a deep breath, step back, and think. What are the dimensions of the problem? How significant is the problem? What are the potential implications and impacts – primary, secondary, and tertiary?
- I find it helpful to write down my thoughts in a mindmap, note-taking app, or document. Just the act of sorting out the relationships between the different pieces helps me regain a sense of control and identify what aspects of the problem we can work on.
- Remember to focus first on understanding the problem before you start solving it. Make sure to tease apart any complex and multidimensional aspects. Be aware that there is often “fresh, hot data” involved as I described in a recent post.
- Ask for help from your team and potentially from others who could help improve your problem-solving process.
Once you and your team have taken the first steps towards understanding the problem, begin to work the problem.
- Identify what additional information you need to obtain and get someone working on gathering that information.
- Identify options to address the different elements of the problem. Pay attention to what you can control and what you cannot control.
- Evaluate your options, figure out what the most important action points are, and prioritize what is likely to lead to a resolution.
Do not forget the other things you were working on before the problem emerged as sometimes the urgency of an immediate problem will suck all the oxygen away from other important priorities. You do not want to create more problems by losing sight of the big picture.
Communicate with important stakeholders like your Board of Directors once you have had a chance to assess the situation. Engage them when you can characterize the problem and let them know what you will do about it. Do not forget to ask for their help and support.

Problem-solving is the essence of a startup. You will have trees that fall across your path. A key to startup success is developing the resilience to face and tackle each set of problems that emerges even as you continue to solve the planned path.