You’ve seen that meme that says, “Lack of planning on your part doesn’t constitute an emergency on my part.” That’s the story of my life at the office – my boss’ poor planning results in rush projects and late days for me. How can I address this to achieve a change?

Cagily, gingerly, persuasively and realistically.

Cagily. I once reported to a high-level executive who made a very clumsy public comment. He wasn’t aware that it bombed. Embarrassed for him, I pondered what to do, and made a calculated risk based on two considerations. First, I gauged him to be humble. And two, he was passionate about being an effective leader. So I decided to roll the dice.

Gingerly. I figured the best approach for both of us was a delicately stated note that included the wording for a suggested apology. I submitted it with perspiration. It worked! He later apologized to the same group. They broke into applause as I wiped my brow. It was a rare win, win, win – for him, his audience, and me.

Persuasively. Appeal to your boss’ self interest. How would better planning benefit him and the output of your office? Cite an example of when he planned well, and its effect. How could your own performance and product improve (and better reflect on him) with improved planning?

Realistically. Bosses usually don't like corrective input from their subordinates. If they did, they would invite it. Plus, it can backfire. The boss can conclude that you’re the problem; that you’re not nimble and flexible. And even if he does receive it, making the change will probably not be easy.

If that’s the case, gird your loins, grit your teeth and build your resilience. David’s boss, King Saul, chased him all over Israel to kill him. If you can’t take it, seek a better option.