This talk describes how an engineering lead can identify prospective team members, enable them to gain experience in the proposed role, and ultimately make the switch. Done well, this represents a win-win: the engineer enjoys a role they are excited to take on while the lead gets a motivated employee whom their experienced engineers can mentor. This talk is based on my experience at Square, first switching from a machine learning engineer role to a backend software engineering role and then into engineering management. In both instances, I was able to try out the new role, gaining confidence that it was the right choice for me all while proving my ability to succeed at it. More specifically, this talk will discuss how to:

• Ensure sufficient motivation
• Align on goals
• Avoid impossible guarantees
• Create a support system to maximize chance of success
• Gain confidence the candidate will be effective in role