【LEAP 职场说 Recap】Ace Difficult Conversations With Your Boss

The first installment, Ace Difficult Conversations With Your Boss, was held in June and featured three long-time dedicated LEAP mentors, Prof. Veronica Guo, Assistant Professor of Clinical Business Communication at USC Marshall School of Business; Doug Schafer, Director of Software Engineering at Dell/EMC; and Lisa Yuan, Principal at Tyton Partner. Through role play skits, panel discussions, breakout room mentoring sessions, the workshop was well received running overtime. Three distinguished speakers shared their insightful advice with the audience on the following specific topics:

Listen and analyze your audience first to collect information. A good understanding of your listeners and what they care about would be helpful to tailor your answer during the conversation. Speak in a pyramid structure by prioritizing the central idea. If the conversation is about a work challenge, solutions and next steps are more important than explanations. 

You don’t have to say yes to everything even if you are at the bottom of hierarchy but when you say No, you should have some leverage on hand such as a better offer at another company and always offer an alternative to your team. 

Structure your conversation and know your boss’s ‘walk-away’ point. Your bargaining zone is the range in which an agreement is satisfactory to you and your boss. Having leverage on hand and predicting your boss’ walk-away would help you to be one step closer to the ideal situation for you. 

Managers need to be knowledgeable but can’t possibly know everything the team knows. They need key facts and the ability to drill down later. As young professionals, we could utilize that information to structure emails/slide decks/word documents with a short, few-bullet summary on top and details/context beneath as needed. A good rule of thumb is to assume the manager would use the summary and go to the rest if needed.

Managers fear being surprised and need bad news before one of his/her peers tells. Never come to your boss with problems only but come with solutions and next steps. Give early warning of risks to projects and know what you don’t know by examining the assumptions and be honest about them. 

Managers don’t like managing. Employees that know what the team needs and act accordingly are a source of comfort to managers. Take the steps that your manager would take and think like in a video game where your challenge is to get things done and the company’s job is to step you.