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Stop mind reading and start asking questions!

Updated: Sep 15, 2023


Fear of asking direct questions can stem from a variety of factors, including social norms, personal insecurities, concerns about how others will perceive us, a fear of rejection, a fear of confrontation, a lack of confidence, uncertainty about the answer and a possible power dynamic. This is especially true of early careerists, where approaching the boss can be a bit scary! We go through life in perpetual and unconscious states of mind-reading, so we don't even bother asking the question? Learning to ask good questions (and listening to the answer) is a super power for effective communication, building stronger relationships, career development and most importantly, in my opinion, peace of mind. Here are some guideline tips to help you to get started

1. Identify your ideal outcome Before you dive into asking your boss or colleagues tricky questions, take some time to write out possible answers to the following questions;

a. Why do I need to ask this question?

b. How is not knowing the answer currently affecting me? c. What would be the best outcome? d. What would be an okay outcome? e. What is the worst thing that could happen? f. I am okay with not getting the answer there and then? g. If I don’t get the response I am hoping for, what will be my next move?

2. Get permission to ask a question


A smart approach to asking an important question is the seek permission first. This shows respect for the person's boundaries, it also gives them the opportunity to decline if they are not comfortable or prepared at that time. It also helps to focus their attention to the fact that a question is coming their way! Example: “May I ask you a question? / “Is it a good time to ask you a question?

3. Ensure time & place are appropriate and give context! Never ambush your boss (or anyone for that matter) in a public place. Make sure they not hassled, running out the door or dealing with a crisis. For that important question, set up a meeting. Timing is king and context is queen. Example: “Are you free for 10 minutes later today, I have a question I would like to ask you about my salary or about a special project or about my role here at the company”. Bosses freak out too! They might fear you are handing in your notice or there is something wrong if you don't give that all important context.


4. Set the tone You have given context, now set the right tone. It is good to use “I feel” or "I believe". Example: "The reason I am asking this question is out of concern for my career prospects OR I believe I am little overwhelmed and would appreciate your support.

5. Don’t beat around the bush Once you have permission to ask the question, the time is right and you have set the tone, don’t beat around the bush. Be a grown -up and use your words. Example: "The purpose of this conversation is to chat about the possibility of me being brought onto the next project."

6. Choose your words carefully When asking tricky questions, it's important to choose your words carefully. Avoid using language that is confrontational or accusatory. Instead, use neutral language that is respectful and professional.

7. Practice active listening Once you've asked your burning question, stop talking. Listen, listen, then listen some more. Listen actively to your bosses response. Give them time to answer fully and try to understand their perspective. This will help you to respond appropriately and keep the conversation constructive and open.

8. BUT OUT - POWERLESS leading sentences not to use

  • You probably won’t want to do this, but

  • You are probably too busy, but..

  • I could be wrong, but

  • I know I am not ready yet, but…

  • I know you are going to say no, but…

9. Powerful leading sentences


  • Would you consider the possibility?

  • Do you think it would be possible?

  • How do you think I could go about?

  • What would you consider to be?

  • What flexibility do you believe maybe around?

10. Send a follow up note thanking them for their time and outlining the outcomes or agreements If you have had that great conversation and an agreement was reached (even if the agreement is to revisit the topic at another time), send an email thanking your boss for their time and outline what you believe was agreed. Asking your boss or senior colleagues powerful questions will significantly help you to build strong relationships.

Always prepare and identify the ideal outcome, get permission, choose words carefully, practice active listening and confirm any agreement in writing. If you would like career guidance or coaching on how to approach a career critical conversation, change a specific behaviour, ask for a promotion or you have an important interview coming up, send me a message on linkedIn. Go live your Onelife! Susan


Published by Susan Keating Career Development Coach for Businesses I One-to-One Coach for Career Progression | Lunch & Learn Talks for Business and Community Groups Stop mind reading and ask questions. A real super power, especially for early careerists! #careerdevelopment #careeradvice #coachingtips

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