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Be confident in what you are saying and why you feel that way. Try to take away the emotion from the reasoning and make it based on facts and understand it will be uncomfortable.
For business related decisions/conversations:
-Set up some time on their calendar. Always come prepared to these conversations. Do your due diligence and bring data to the table. But, most importantly, you're battling against the problem and not each other. You should approach the conversation with an open mind and be willing to understand their side of the logic (sometimes we aren't always given the big picture and it causes us confusion on the why behind decisions). Know what support you need from them in order to succeed. Generate recommendations. That way they know exactly what actions they need to take to alleviate the problem and support your success.
If it's a personal issue that requires a conversation then it will require a different approach. Delivering feedback to your boss or bosses' boss can be difficult. Again, set time aside on their calendar. Make sure the feedback is sincere and doesn't attack the person. Help them understand the issue and how it impacts you/your team's productivity. And validate the feedback is actionable by the person you're speaking with. If it's not actionable then it's probably not worth bringing to the table. Also bring recommendations to the table: mechanisms to shore up gaps in communication, productivity, or other related topics. This will help them understand what the expected endstate is from you. I've found that misaligned expectations cause a multitude of issues and should be addressed as soon as possible. 99% of the time, leaders want to support and see you succeed. And we aren't perfect, so bottoms up feedback is generally welcomed when approached correctly.
Either way, it's all about delivery. It's both of you vs the problem and not each other.
Be prepared for the conversation. Set up a meeting with them. Make sure to document everything in writing. Try to get feedback and accept criticism, provide recommendations. Mostly stay calm. You've got this!
This has always bothered me and made me feel intimidated. However, make an effort to approach the situation with assurance and professionalism. One tactic I use consistently is preparation. I always go over what I want to say in my head before I speak, and I keep my attention on the particular problem or undesirable behavior I want to address.