When you drop the issue, who does it land on?
Show up to problems with potential solutions.
When you run into a problem or a roadblock, don’t drop the issue on your manager’s desk and ask, “What should I do”?” Instead, take ten minutes to think of two possible ways to fix the problem before you reach out. Even if your ideas aren’t perfect, showing up with “I noticed this issue, and I think we could try X or Y” immediately show you’re a proactive thinker, not just a task-follower.
The ability to analyze a situation and suggest a path forward builds your decision-making skills. As you move up, your job will shift form following instructions to making tough calls under pressure.
This strategy is powerful because it builds trust and save your team time. And you’re providing options. Do the mental heavy lifting for your manager to make it easier for them to give you a quick answer and move forward. Over time, this habit creates a reputation for being a reliable problem-solver who can handle challenges independently. You’re not just reporting problems; you’re helping the business stay in motion, which is exactly what leaders look for when deciding who to promote or give more responsibility to.
Put these approaches into practice.
Let’s look at practical ways to do the "mental heavy lifting" before seeking guidance.
“I used to pride myself on my speed, which meant I would message my boss the second a software error popped up. One day, she told me, ‘I hired you to help me, not to give me more work.’ Now, I take ten minutes to troubleshoot first. Half the time, I find the solution myself; the other half, I go to her with two options already vetted.”
DON’T immediately ping or email your manager the second you hit a roadblock to offload the stress of the problem.
DO take ten minutes to analyze the situation and brainstorm at least two possible ways to fix the problem before reaching out.
“A vendor missed a deadline, and I was panicked. Instead of asking my manager how to handle it, I said, ‘The vendor is late. We can either pay the rush fee for a new supplier (X) or push our internal launch by two days (Y).’ My manager picked Y in seconds. He later told me he appreciated that I didn't just give him a problem—I gave him a choice.”
DON’T use open-ended questions like "What should I do?" which forces your manager to start their thinking from scratch.
DO frame your outreach as: “I noticed [Issue], and I think we could try [Option X] or [Option Y]. Which do you prefer?”
“I was stuck on a data discrepancy. Instead of just showing my boss the error, I pulled the logs for both possible sources of the mistake. I showed her the heavy lifting I'd already done. She didn't have to go digging through files to help me; she just had to look at my summary and point the way.”
DON’T assume that your job is only to report problems; realize that your value lies in your ability to suggest a path forward.
DO complete a preliminary research and analysis for your manager to make it as easy as possible for them to give you a quick answer.
“I suggested a fix for a client's complaint that my manager ultimately rejected for a different idea. I felt embarrassed until he said, ‘I like that you’re thinking about the "how." Keep bringing me those ideas.’ It wasn't about being right; it was about showing I was capable of making a tough call under pressure.”
DON’T fear making a suggestion that isn’t accepted; understand that the act of suggesting a solution is more important than the solution being perfect.
DO use every roadblock as a low-stakes training ground to build the decision-making skills you’ll need as you advance.
“I noticed a recurring bottleneck in our onboarding process. Instead of just complaining about it in a meeting, I drafted a new workflow and brought it to my lead. I told her, ‘This would save us three hours a week.’ My lead saw I wasn't just filling a seat—I was actively looking for ways to make the company faster.”
DON’T view obstacles as a reason to stop work or wait for further instructions.
DO position yourself as a partner who helps the business stay in motion by resolving challenges independently whenever possible.
The next time you hit a snag, can you think of two potential solutions before you tell your boss about the problem?
Integrate these professional strategies into your workflow—whether you’re refining your own work or mentoring your team or clients.