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Overpreparing undermines outcomes in crucial conversations

Written by Hubspot Author | Aug 4, 2025 3:30:00 AM

Source: HR Daily (30.07.2025) - subscription service

It's important to prepare for difficult conversations, but when managers do so with the wrong mindset it undermines their results, a behavioural specialist says.Approaching conversations with a "fight" mindset means so much time is spent gathering information and evidence that the team member becomes an "opponent", and the leader's emotional brain takes over, EI and human behaviour specialist Amy Jacobson says in her new book, The Emotional Intelligence Advantage: Mastering change and difficult conversations.

"Chances are there will be very little listening and more just waiting to talk... We don't even think about the outcome we are looking to achieve or that there could possibly be a reasonable explanation. That is all pushed aside as the need to be right and 'win' takes over."

This overpreparing "kills us!", Jacobson says. Managers "become robotlike on a mission", and it's not a mission that will yield the best results.

There should be preparation, she says, but not with a view to defending and defeating. Instead, leaders should prepare with a view to understanding:

  • What happened, and when?
  • Who was involved and who was impacted?
  • Why did it happen? Why is it an issue?
  • How will it be fixed and what is the outcome that we desire?

"Until we hear the other person's answers to these questions, we tend to make some pretty big assumptions," Jacobson notes.

"Once we know the answers there will be more time to gather the information that is genuinely required to achieve the solution."

Afterwards, the leader can reflect via five questions:

  • What went well?
  • What didn't go so well?
  • What will I do better next time?
  • What actions will I take to rectify the situation based on the role I played in what didn't go well?
  • What do other people need from me now to achieve a good outcome?

Reflection is "our number one opportunity for growth and development", Jacobson says, but it's "frequently overlooked".

"Change involves developing new neural pathways in our mind, and this requires creating new habits and beliefs – but, more importantly, knowing how to let go of the old ones first."

The "ultimate" question to ask

In any difficult conversation, "how do we fix this?" is the "ultimate" question to ask an employee, Jacobson says.

And "we" is the most important word in the sentence, she adds. It shows the manager and employee are "in this together".

"There is no us and them; we are united and we are there with them to fix this."

The question helps move towards a solution in ways that gives the employee some ownership over how to achieve it. "It can also force them to face and own the fact that [the issue] can't be fixed and therefore there is no option other than to accept it, learn from it and move on."

Whatever the case, Jacobson warns that the transition might not happen easily.

"The first time we ask the question, they might not hear it and keep talking about the problem or looping in their emotional state, so we ask the question again: 'How do we fix this?'," she says.

"Continue to ask this question until they are ready to move into solution mode."

It's possible the employee will offer an unrealistic solution, in which case it's important to be honest about that, and then, "try to provide them with a few possible options", she says.

As for ending the conversation, Jacobson says all difficult conversations should conclude with 'next steps' that include an offer of support. Asking, "How can I further support you?" creates "ownership of and commitment for what we have agreed upon and the actions required".

Those expectations should be clear for everyone involved, Jacobson says. "Anything that is mentioned or committed to at this stage of the conversation should be documented and everyone involved should be held accountable.

"Accountability is one of the biggest parts of EI and helps us to avoid ending up in another difficult conversation."