Deciding how long to give the entrepreneur or new employee to make it work takes a wide variety of factors, depending on circumstances. Most important for an entrepreneur is to keep in mind industry timelines, highlight key milestones and be realistic, financially sound, flexible and have a keen eye for mentorship. Research industry timelines, define key milestones and provide a clear roadmap. Monitor the ability to adapt quickly and how payment and cash management is handled. Mentorship can greatly help the progression. Spell out role expectations, provide training, conduct performance reviews, making sure they possess the right culture fit, offer the resources necessary to succeed. Hire on a probationary period of 6-12 months, where there is enough time to learn the ropes and be shown the right way to deliver. However, continually evaluate, send signals by providing feedback, and recalibrating support as warranted by performance. Ensure that communication remains open-ended so that you know what their pain points are, as well as their aspirations. Make a decision based on performance metrics, ambition level, and alignment with your long-term goals