How to Coach your Boss

Most people who attend my workshops know that I believe coaching is not only reserved for managers who coach their direct reports. Coaching shouldn’t be a hierarchical privilege; not at all. Coaching is a communication style that everyone can adopt, it’s an attitude, it’s a way of conversing with others so that they can develop or clarify their ideas, motivations and actions. 

Coach with open-ended questions

So, given this premise, you can absolutely coach your boss in a variety of situations. A foundation coaching skill is the ability to ask open-ended questions. These can help you have very fruitful coaching conversations with your boss. 

For example, imagine you have been given an assignment and it’s not very clear. Often, we receive rush assignments in the workplace like... get this done, do this, solve that, and we don’t get many details around the issue. Sometimes we might waste a lot of time going in the wrong direction. So, you’re better off having a short conversation with your boss, coaching him,using open-ended questions, to understand what they want, what is really at stake, and how it may affect other projects you have going. 

Clarify outcomes

You can start by asking your boss a very simple but powerful question: “I have this project, but what is the outcome that you really want?” You might be surprised to receive many more details then you were previously given. This simple question will give your boss the opportunity to be more specific about the ideal outcome for themselves and for the organization.

Key players

The next question you might ask is, “Who else is involved?” You want to get an idea of what other departments, clients, and stakeholders may be affected by this project. You also need to understand the wider context. Sometimes you’re cooped up in your corner doing the task but you don’t have the complete picture, so, don’t forget to ask “What is the larger context of this task?” 

Resources

Then you might ask for support. For instance, “Are you able to help me with resources from other departments?” Or, “How will we find the support I need to get some funding for this?” Make sure that you involve your boss in providing you the resources you need in order to complete the project in a timely and satisfactory manner. 

Deadlines

You will also need to clarify the deadlines. If they are very short, and you have many projects lined up, it may not be possible. Don’t be shy to ask questions to make sure the priorities are clear, such as “When is this project due?” “How flexible are you in this deadline?” “How shall I prioritize when there are other ‘urgent’ projects?” 

These are valid and legitimate questions whatever your role is, whether you are a project manager, an IT developer, an executive assistant, or a sales-person. Don’t assume that things are clear. The only way to avoid misunderstandings is to have a clear and open dialogue. So make sure to you ask open-ended questions to clarify everything that your boss wants in terms of output and execution on any project.