After assigning him a future project, immediately meet to discuss the best ways to carry it out. Then, clearly define a successful outcome for that endeavor. For example, after talking about how to execute the project, you might state that the goal is to generate at least 200 new leads or no fewer than 5,000 social-media impressions, thus forming a definitive bottom line measuring what is and is not a success.

At that point, ask your assistant questions about your directions for both the methodology and the results you want. That will allow you to see how much he understands and clear up any misconceptions that could very well cause him to stumble before he even begins. Following that, reiterate the discussion in writing, which gives you a chance to both reinforce the approach and outcome you hope to see. By using these techniques to make him a part of the planning process, you'll be setting him up to hit a home run and ensuring you don't have to worry about him striking out when the bases are loaded. E