Learn to Master Managing Up with One Simple Question

WHERE TO: You effectively engaging with your manager and gaining their support through thoughtful questions and clear communication.

WHERE FROM: Feeling unsure about how to ask for help.

WHERE NEXT: Mastering how to present problems and solutions, seeking valuable advice, and refining your approach based on feedback to enhance your work.

Over my years of coaching and mentoring people at all levels, there are a few things I have repeated countless times. The advice below is one of them, first said to my younger sister 15 years ago when she started her first job. It still rings true today, and will tomorrow, and the day after that.

Whether you are early in your career or at the executive level, you will often need to turn to your boss for advice. Many people are afraid to ask their managers for guidance, thinking they will be perceived as not skilled enough. Approaching the situation with the right mindset and preparation will help you earn your manager’s trust and confidence, even though you are relying on them for help.

The common advice is to only come to your boss once you have a solution. But if a problem is already solved, why are you bringing your manager’s attention to it? Bringing an issue to your manager’s attention in the wrong way, will negatively impact their perspective on your ability to do your job…There is a smarter way to go about this, let’s make sure you get it right!

Let’s imagine there is a problem that needs solving. You’ve evaluated the issues and generated what appears to be a solid solution, but you’re not 100% sure it’s the right path forward. It’s time to get advice from your manager about it.

First, make sure to discuss the topic with your manager at the best time. Bringing something up in the last 5 minutes of your one-on-one will not get you what you need and will make it seem like it’s not a high priority to find a resolution. Timing also applies to empathizing with what might be going on in their world and making sure they have the headspace to properly consult with you. Give them a heads up that you want 15 min to chat about something and ASK them when would be best.

Once you’ve got their dedicated attention, start by presenting the problem to be solved and the proposed resolution you have ideated. This way, your manager knows you have done your homework and are not trying to have them do your job. Be ready to answer questions which dive deeper into the problem and your thought process on generating the current solution.

Generally, the What?, So What?, Now What? format is a great way to present anything, but you can take this approach a step forward. Share the situation AND admit your answer might be lacking. It’s an effective way to gain your manager’s respect AND get good input from them at the same time. I often refer to this as balancing Hubris with Humility.

You invested time deep diving into the problems and generating the best ideas to solve them. By definition, you are more intimate with the details than your supervisor, BUT there is still something for you to learn from them. This is why you should engage your manager in a productive discussion where they can provide insights into how to improve your well-reasoned plans.

I suggest you ask questions like:

• What would you add to the current plans to make them more successful?

• What adjustments can we make to have a greater impact on the problem?

• What relevant context do you have that I should consider?

Posing these questions shows that you are confident enough in your ideas to know they will probably work, but humble enough to realize you don’t always have a full picture of everything at play. They also show that you operate with a kaizen mindset, always looking for opportunities for improvement. The goal is to have your manager share insider information you were not privy to or to recommend some alterations which will improve its chances of success.

Next up is actually taking their insights and applying them to your plans. Only implement their suggestions after careful thought and validation. The bottom line is that, they aren’t aware of all the nuances of what’s going on, but now, you are.

Once you have a new solution, share with your manager how you have adapted your approach based on their advice. This demonstrates your ability to be flexible and that you care more about having impact than the idea being 100% yours. It also gives your manager confidence that the items you are working on will yield the desired outcomes. It is a win-win situation that you should try to create as often as possible.

The earlier you learn to master asking these sorts of questions, the faster your career trajectory will accelerate. What’s great is that it’s equally effective in your first job and if you are an executive turning to the CEO for help. You always want to show your boss that you grasp the situation, have a solid plan, AND are aware that you do not have all the information. You know that and your ideas will generally be better if you seek advice.

Still afraid of asking the question? I get it. My executive clients often turn to me to refine their talking points before approaching the CEO. It is helpful to have someone to bounce ideas with before sharing them with the people above you. This is also the safest way to identify the context you should provide, especially when you are trying to convince someone.

If you've tried this, please share how it worked out for you in the comments.

Not sure how to apply this to your reality? I’m here to help. Check my programs to find the right fit for you or schedule a FREE 30 min chat to talk about your current situation. You can also always send me an email at [email protected] to share your story or a question.