Here is a mistake I have made continuously throughout my entrepreneurial career. The planning fallacy...
The simple tip is this... do not let the charismatic founder or charismatic leader set the timelines. The reason is because as the visionary leader, often times when we see new strategic directions, we see the path as a straight shot to success. The reality is the straight path is more like a rollercoaster. Along the way we're going to encounter learning and challenges that we were not anticipating.
This is one of the ways that we feel scarcity of time, as founders, and as team members. Often times the founder will say, "Hey, we're going to be cash positive in six months," and the founder is not actually considering all that it's going to take to become cash positive. As soon as challenges set in, and the founder realizes they are not going to hit their timelines, then all of a sudden everybody becomes stressed. You begin working long hours trying to make up for the fact that at the beginning, the founder was simply off in their planning.
The way to correct the planning fallacy is to bring in an experienced advisor or coach. Somebody who can objectively look at the timelines you're setting as the founder and leader and provide you a realistic assessment of what it will actually take to get there. Accounting for all the learning, the growth, and all the ups and downs that you're going to experience along the way. This will ultimately help you expand your time.
Here is an example of a real-life and recent example of the planning fallacy going horribly, horribly wrong. This company is now in the middle of a $100MM lawsuit and FBI investigation because they failed to see the obstacles... https://www.fyrefestival.com/
Cheers - The Good Startups Team