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  • Writer's pictureDaywey Chen

The tactic of asking questions under different types of conversation

Some professionals such as journalist, doctors, attorneys are taught to ask questions as part of their training. But not all people including the company executives are trained in asking questions. As result leading to a lot of missed opportunities.

Questioning is a powerful tool when done right. It can unlock the true value of companies during the Business M&A. Asking the right questions spurs learning and the exchange of ideas. It ignites innovation, leverage performance and build trust among team members... Asking questions is important!

Today I would like to share about how to ask questions under a competitive conversation and how to ask questions under a cooperative conversation.

Competitive conversation means that the person sitting at the opposite end of the table has a contradictory view from you. The other party does not share the same interest as you. For example during a trade negotiation, during a leverage buyout, a HR investigation, a sales negotiation, a meeting between different department within a company.

Cooperative conversation means that both party shares mutual interest and are in a amiable collaborative situation. For instance two friends having a conversation. A conversation between co-workers during a brain storming session. During a feedback session for the person sitting next to you at work.

Competitive Conversation

When you are asking


Your conversational partner is reluctant to share information and my even lie


  • Ask direct or "yes or no" questions to avoid evasive answers

  • Ask detailed follow-up questions (even if they're redundant) to pry out more information

  • Frame tough questions using pessimistic assumption (ex. We have experienced some headwinds in the sales, right?) to reduce the likelihood that respondent will lie

  • Ask the most sensitive question first. Subsequent questions will feel less intrusive, making your partner more forthcoming

When you are answering


Answering questions could put you at a strategic disadvantage


  • Prepare: Think in advance about the information you want to keep private to avoid answering impulsively

  • Dodge the issue by answering a similar question you'd prefer to have been asked

  • Deflect and gain control of the conversation by posing a question in return

  • Consider when to share negative information - rather than refusing to answer to build trust

Cooperative Conversation

When you are asking


Friendly colleagues may shy away from conflict or hesitate to share bad news


  • Ask open-ended questions (ex. if you were to do it over again what would you do differently?) to draw out negative feedback

  • Begin with the least-sensitive questions to build rapport and escalate slowly

  • As in competitive contexts, frame tough questions using negative assumptions

When you are answering


We forget to focus on making conversations productive and delightful, or we speak too freely


  • Avoid droning on and on. Use energy, humor and storytelling to engage your partners

  • Avoid talking too much about yourself, and remember to ask questions of others

  • Deflect tough questions by answering with another question or a joke

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