Tactful Timing

Many assistants I know have a regularly scheduled meeting with their supervisor, but that is not feasible for my boss and me. I am the only one to blame for not setting our time together since I help to block out his appointments. This is mostly because I tend to sacrifice this meeting time for when people  just need "15 minutes". So instead, I have an ongoing list of questions that I can quickly access whenever my boss is able to meet with me.

However, one thing I am not very good at is gauging the best timing for more difficult questions or serious topics.

For example: Wednesdays are set aside for my pastor to prepare the Sunday sermon. When he came in to the office, he asked me to connect about a few receipts and items to follow up on before he got to studying. I pulled out my list and used this opportunity to ask some quick questions. But while I was on a roll, I dropped a thoughtfully heavy topic regarding our structure/procedures. This was not an easy topic and it was absolutely the wrong time to ask. He was just about to study for a message and I left him with a topic that could easily linger in the forefront of his mind, and keep him from focusing on what is more urgent and important. 

So this blog post is less about advice on "how to" and instead a question of "how do you".  All I have to offer are these proverbs: 

Proverbs 10:14 NLT- Wise people treasure knowledge, but the babbling of a fool invites disaster.

Proverbs 17:28 NLT- Even fools are thought wise when they keep silent; with their mouths shut, they seem intelligent.

Proverbs 21:23 NLT- Watch your tongue and keep your mouth shut, and you will stay out of trouble.

Your Turn: What are your tactics of tactful timing for addressing difficult topics with your boss?