Four Questions to Ask BEFORE Starting a Difficult Conversation

Guest Post by Nathan Magnuson

Republished from

Join Nathan’s 30 minute webinar “Mastering REALLY Difficult Conversations” on Oct 28 at 12pm CST.

Something happened at work that set off your alarm bells. Maybe you’re a nurse and the physician ordered a drug you believe may trigger an allergic reaction from the patient. Maybe your employee showed up late for the third time this month – and this time it caused you to miss an important deadline. Or maybe another department set up a new process that inadvertently doubled the reporting requirements from your team – which you’re not staffed to accommodate.

What happened wasn’t your decision – otherwise you’d just fix it. You’re not the person in charge. Someone ought to say something, right? And if so, that someone is probably you.

We’re all confronted with nuanced situations in the workplace from time to time that require maturity, discernment and emotional intelligence. So why does the tension catch us off guard when these opportunities present themselves?

In our Leadership-in-a-Box program “Engaging in Difficult Conversations,” one technique we share to navigate difficult conversations effectively is to pause and ask ourselves a few questions before we speak up.

What makes this conversation difficult?

Difficult conversations have their own criteria: high stakes, high emotions, multiple points-of-view or a requirement for change. They aren’t the same as asking how the weekend went. Until we define the source of our discomfort, it’ll remain an invisible enemy.

What is the reporting dynamic?

In the three brief scenarios above, the reporting dynamics ranged from superior to subordinate to peer. Reporting dynamics don’t let us off the hook for initiating a necessary conversation, but they do inform our approach.

What is the cost of not having the difficult conversation?

This is probably the ultimate question to consider. If a situation calls for an intervention, there is always a cost for not speaking up – to us, to the other person or party, to the organization or to the customer or stakeholder – and maybe to everyone involved. All those costs add up.

Should I initiate the conversation?

This is the moment of truth. If the cost of a potential negative outcome is high, it’s our responsibility to speak up – despite our own discomfort.

“A person’s success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have.” – Tim Ferriss

Once we’ve reached the point of responsibility, the steps required for engaging in a difficult conversation effectively aren’t actually that complicated, as we’ll share in our “Mastering REALLY Difficult Conversations” webinar. It’s the decision that is the toughest part.

When the going gets tough, will you speak up?

Nathan Magnuson


Nathan Magnuson is a corporate leadership consultant , facilitator and founder of Leadership-in-a-Box, an innovative training company that provides 60 minute interactive leadership workshops. Nathan is also the author of Stand Out! and Ignite Your Leadership Expertise. Contact Nathan at



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