Keep somebody on their toes Definition 1 of 1Pro Tip 1/3Situational Alertness Used when someone needs to react quickly to changing situations. An emergency room nurse must always be kept on their toes. Pro Tip 2/3Active Engagement Suggests someone is being encouraged to stay actively involved or interested. This challenging puzzle will keep you on your toes. Pro Tip 3/3Positive Pressure Implies a sort of beneficial stress that promotes personal growth or improvement. I like working on tricky projects; they keep me on my toes.