I’ve never met anyone who enjoys being blindsided. With people working remotely in the silo of their own home while experiencing limited visibility, this may be happening even more frequently. It’s always tough to deliver bad news, whether it’s poor sales performance, a lost account, or losing a key team player. Additionally, you’re not passing by the boss’s office during your typical workday to just pop in and let them know what’s happening. But delaying or holding the news back from your leader is never a good idea.

So how would you prepare for such a dreaded conversation?

Here’s an outline of how I coach my clients through this issue?

First, it’s important to get yourself in the right frame of mind.

Many times, you may be anxious about this conversation and you’re worried that blame will be assigned somewhere. That’s not where your focus should be. Instead, ask yourself the following three questions to get grounded:

Frame of Mind

  1. What do I want for the organization in this situation?

Thinking about the bigger picture allows you to approach the situation from a different perspective. Instead of thinking about people and fault, focus on how this impacts the organization and how it could become an opportunity. The loss of a customer, while impacting the short term, could be an opportunity for a new marketing strategy, or new product developments. The loss of a high performing team member could be a chance for someone else to step up, or a development opportunity for a rising star.

  1. What do I want for my boss in this situation?

Putting yourself in the shoes of your boss allows yet another point of view. If you were the boss, what would you want in the current situation? What would your expectations be of someone in your position? What would you NOT want? Use your answers to provide a framework for your conversations.

  1. What do I want for myself in this situation?

Lastly, think about what you want for yourself? How do you want to feel after the conversation has occurred? What do you want to walk away with? Are you asking for confirmation of a path forward? Are you providing potential solutions to a problem for consideration? What do you need from your boss in this situation, if anything?

After considering these questions, you can now focus on how to deliver the message and your demeanor. I call this the “Who do I need to be?” step. In order to achieve everything that you want for the organization, your boss, and yourself, envision what kind of delivery, tone, confidence, and professional presence is required. This is who you need to be.

Now that you’re mentally prepared, you can address the nuts and bolts.

Make the time

Since you’re working virtually, you’ll need to set up a time to talk unless you already have a meeting on the calendar. Give the boss a heads up that you’d like to give an update and how long it will take. If the issue is of an urgent nature, then reach out appropriately. Either send them a text or instant message to ask for some time, or contact their administrative assistant to get on their calendar as soon as possible.  Leaders are busy people with full calendars, so you’ll need to utilize their time wisely.

Be concise

bad newsBecause leaders are so busy, they appreciate messages that are to the point without a lot of story or meandering. What is the issue, and what are you going to do about it? Deliver the evidence with laser-like focus so your boss understands immediately what they are faced with.

Don’t address the issue with a long background story, or even the root cause analysis. Be prepared with this information if your boss asks for it, but certainly don’t lead with it. Leaders want to know that you’ve got control of the situation and that they can count on you.

Be prepared with proposed solutions

As a rule, never deliver problems to your boss without proposed solutions. This allows your boss to have whatever input they’d like and co-create the path forward with you. In some cases, they may give you free rein to decide the path forward on your own. In any case, your job is to make their job easier and to keep them as informed as possible.

Confirm the resolutions and determine what your boss wants for future communications regarding the issue at hand. Be clear about how they want to be informed, the cadence of updates, and any other communication plan that needs to occur.

If you are known as the leader who keeps their boss informed, never blindsides them, and always comes with solutions, you’ll make your star shine a little brighter.

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