Two Questions Your Boss Needs to Hear
Everyone asks, “How can I get the boss on my side?” It’s the wrong question. The right question is, “How can I get on the boss’s side?”
Don’t explain what you want the boss to do for you. Explain what you can do for the boss. What kind of person do you aspire to be? A taker or a giver?
Two Questions Your Boss Needs to Hear
#1. What’s your vision?
Help your bosses get where they want to go. You might be asking me, “What if I disagree?”
It does no good to resist the boss. It’s self-sabotage to disengage because you don’t like something your manager is doing. It’s also childish.
If you have a great manager, good for you. And make the best of it if you have a lousy boss.
When your leaders are doing something illegal or unethical, disobey. Other than that, help them succeed until you find another job.
#2. How can I best help you achieve your vision?
Let higher ups know you show up to contribute, not complain. Stop being a drain and start being a driver.
When your leaders lack clarity, they still have pressures, goals, and hopes. Find a way to “pull with” instead of being dead weight.
Earn influence by supporting someone else’s success. It takes more than talent and hard work to get ahead. Be helpful.
You don’t have to agree with everything. Bring your best anyway.
More Questions Your Boss Needs to Hear
- What are your priorities? How can I best focus my efforts?
- How will you measure success?
- What challenges are you facing?
- What kind of progress would most energize you?
“You can have everything in life you want, if you will just help other people get what they want.” Zig Ziglar
What questions would you like to ask your boss?
What questions help people understand another person’s perspective?
From Great Place to Work: https://www.greatplacetowork.ca/en/articles/5-ways-to-develop-a-better-relationship-with-your-boss





Similar to #2, I find, “What can I take off your plate right now?” is an easy way to relieve some pressure, especially if you’ve already established that they can place confidence in you.
Thanks, Brent. You bring up an important point. What’s the nature of your relationship with the boss? Are you new? Is there mutual trust? Do you have a track record of adding value?
Question #1 is one my boss tires of me asking, as it relates to seeking direction brought from her boss/our division leader. It is as institution-wide struggle with the division leader where many lack understanding the vision. However, I see the opportunity with question #2 (alongside the ‘more questions’) to reframe the question as I seek clarity from my boss, and hopefully she to her boss. These last several years have been a transition from the servant leader we previously had at the division level, to the hierarchical leader now in place. How I can adapt and adjust is where I continue to reflect and focus energy in order to to be the servant leader I work to be for those within my teams. Thanks for helping guide me on this journey!
Thank you for your reflection and insight. Some bosses don’t know what their vision is. It’s sad, but true. Lack of vision makes decisions difficult and progress unlikely. People who don’t have a vision are good at maintaining the status quo.
Some bosses don’t have the authority to set vision. Or they don’t want responsibility to answer the questions. Less-than-ideal situations present opportunities.
I suspect many people experience the same thing you do. One challenge we all face is accepting reality as it is and finding a way to work within it. I get frustrated that things aren’t as they should be. When that happens, I focus on things outside my control. It’s frustrating.
I’m rambling a bit. Your comment got me thinking. Cheers
I always appreciate your rambles! You hit on the mindset and I will say to myself (out loud) when I begin spinning on the frustrations of reality being different than my control-freak self would like: “Focus on what you control, and kick a** at it.” This comes from a respected leader years ago who shared her journey of accepting an interim position and instead of just doing what was needed for the temporary moment, decided “I’m going to kick a** at this” – and she eventually earned the promotion. My intent is not to be crass; rather, pump myself up to do what I do really, really well despite all obstacles.
Your approach inspires me.