Looking at the people that I enjoyed working with the most so far, I come to realize that they have a very diverse collection of backgrounds, skills and characters. However, there is one thing that they all have in common: I call it the obstacle-embracing personality.
Let me try to describe to you what this trait is. Consider you are sitting down with your tech lead to discuss the implementation of your next product or feature. Consider that this product/feature is already well specified from a functional point of view. I claim that in most cases 95% of the actual implementation is pretty straight-forward and you will develop a pretty good idea of what needs to be done right away. Those 95% of the job are a mere routine for a good tech-guy. I am not saying that everyone can do that part of the job. It requires strong skills and hard work as well. What I am saying though is: what sets good people apart is how they communicate about the remaining 5%, the tricky bits of the job, already in an early phase. And this holds true not only for tech people but for practically anyone involved in your ventures advancement.
I find it extremely rewarding to work with people that embrace the obstacles that they see on the way. Great people try to get a feel for the tricky bits awaiting them right away. They put the concept upside down and turn the knife in the wound. They try to make worst case assumptions and try to find the points of the concept that begin to fall apart under pressure. They try to identify critical co-dependencies and point to likely sources of failure. They push others and themselves out out of their comfort zone when they feel that critical questions are left unanswered. Sometimes people mistake this for being pessimistic and overly critical. I argue: It is the only way that leads to building something sound that has an edge to it. I also believe that the best people always welcome the challenges that are imposed on them by this approach. And I am sure that in the end it creates a more honest and more satisfying team spirit for everyone involved.
Sometimes though you will find that in the concept phase individuals or whole teams will just communicate on the ‘easy’ 95%. They only know answers, no questions. They will feel confident and enjoy the soothing effects of not having to see the obstacles on the way. Everyone can remain in his or her comfort-zone. No one plays the devils advocate and asks uneasy questions.
This behavior may have different causes. Some people just don’t see the obstacles they are going to face. That is often caused by a lack of experience and not a problem as such. You can make up for that by offering a more experienced sparring partner who points to the obstacles that are likely to occur. What is more critical is the kind of person who does not want to see the obstacles. The kind of person who denies the obstacles. These people come with a solve-that-problem-when-I-run-into-it mentality that is both extremely frustrating and dangerous.
In the best case ignoring future obstacles in an early project phase will lead to false predictions about costs or required resources. In the worst case this denial will affect the assessment of the overall feasibility. Good people know that the tricky 5% are what makes or breaks a great product.
The willingness to identify all critical obstacles as early on as possible, to be brutally honest about them to yourself and to your team mates, and to have an intrinsic drive to find viable solutions to them is a must-have quality. It is a question of personality. Company culture and management can support or suppress it. But in the end it is a personal trait
I am not saying that plans must always be implemented according to all the obstacles anticipated. What I am saying though is that if someone deems an obstacle to be unimportant (for the time being) that should be a deliberate and informed decision and not one that is reached purely because of a lack of willingness to admit to the obstacles existence. To give you an example: if you are launching a product as a mere proto type for market testing it does not matter, if that prototype is scalable. But you have to have a sensibility for the obstacles that await you when having to scale it. If you do not have an honest answer on how to do that early on you either have the wrong team or an undoable product. Both is bad.
My point is: Try to surround yourself with people that embrace the tricky bits. People that ask and answer the questions that hurt. People that seek fulfilment in solving the hard bits. Beware of the people that see no bumps in the road coming and have a ready answer to everything.
In the end that is what entrepreneurship is all about: Solving the problems that others can’t.