Approach Your Boss With Confidence

Updated: Mar 4


How many times have you put off something because you didn't know how to approach your boss or upper management? Like a new idea. Or a raise for an employee or yourself. Or justifying the need for more resources.

Here are some proven strategies straight out Emerging Leader Workshop:

1. Prepare the Appropriate Amount of Detail: Prepare in advance and think about the amount of detail your boss prefers. Does she want summary information and bullets, or does he like pages of detail? Then, consider the medium she prefers. Should it be a PowerPoint presentation with diagrams and photos, or a Google doc with “just the facts.”

2. Make Sure the Timing is Right: Did she just come off a tough week of back-to-back meetings? Then pitching a new long-term idea should wait a day or two. On the other hand, if it’s bad news that needs addressing immediately, don’t put it off.

3. Anticipate Questions: Be proactive and think about the questions she may have and prepare options for her to consider. For instance, if you’re proposing a new system or procedure, do some research on what’s been done in the past and have two or three innovative alternatives.

4. Align With Core Values: Make sure your idea, your ask, and your approach supports your organization’s core values. As an example, if a high level customer experience is expected, then emphasize how this new approach, or an added person would benefit the customer.

5. Follow Through and Take Charge: During your meeting take good notes and follow through on any extra research you need to check into and schedule time right then to meet again to continue the conversation.

Remember that approaching your boss or anyone in upper management is not just a one-way presentation. It’s an opportunity to build trust, build a relationship and exhibit your leadership qualities authentically.

Trust is built on telling the truth, not telling people what they want to hear. Simon Sinek

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