Coach your boss for better results!

A foundation coaching skill is the ability to ask open-ended questions. These can help you have very fruitful conversations with your boss. They enable you to gain clarity, get additional information and in general dispel any hidden and maybe contradictory assumptions that you or your boss may have about how a job should be done.

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 enough details around the issue. We might make assumptions and refrain from asking clarifying questions.  We may end up wasting a lot of time going in the wrong direction. So, you’re better off having a short conversation with your boss, coaching them to understand what they want, what is really at stake, and how it may affect other projects you have going.

You can start by asking your boss a very simple but powerful question: “I have this project to work on now, 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 much more specific about the ideal outcome for themselves and for the organization.  

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, for example who the external stakeholders are, or the strategic importance of the project. 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?”

Then you might ask for support. For instance, “What help can you get me from other departments?” Or, “How will we find the funding I need for this?” Make sure that you involve your boss in providing you the resources you need to complete the project successfully.  They are likely to have access to key people in their network to your support project or solve specific problems that are beyond your direct influence.  It's  the role of your boss to find solutions to organizational or funding hurdles, so don't deprive them of the opportunity to support you, just ask!

You will also need to clarify the deadlines. If the timeline is very short and you have many other projects lined up, it may not be possible for you to take on a new task without putting something else on hold.  This is an area where bosses are often reluctant to engage in.  They would just like you to deliver everything on time, however many new projects get piled up because they might be under pressure from clients or their board.

Don’t be shy to ask questions to make sure the priorities are clear and be ready to negotiate deadlines. You can start with a simple query such as “When is this project due?” and follow-up with “How flexible are you in this deadline?” or  “How shall we prioritize with the other ‘urgent’ projects?”     Since you are on the implementing side, you probably have a better idea than your boss on what is actually feasible, so make their life easy by proposing shifts in deadlines, or ideas on sharing of resources.   

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.

Open-ended questions are non-threatening and they help create an atmosphere of curious inquiry. They are ideal for brain-storming, inviting people to express their views and engaging in dialogue, rather than  arguing or convincing at all costs.

So go ahead and coach your boss for better results for everyone!