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A difficult conversation awaited Roberta Chinsky Matuson when her boss asked, “Can we talk?” Before she could say anything, her boss added: “Come see me in my office.”

After trying to pull herself together, Ms. Matuson took a seat in her superior’s office. What followed was a crisp declaration that she was not meeting the boss’ expectations, although the boss added that perhaps she had not indicated that previously to Ms. Matuson.

Often what follows is an opportunity squandered. Too often, the subordinate merely responds “okay” to anything the boss says. It should be a dialogue, not a monologue.

“This has to change if we are ever going to a place where we can achieve better outcomes and a more humane workplace,” Ms. Matuson writes in her book Can we Talk?: Seven Principles for Managing Difficult Conversations at Work.

Clarity is obviously critical in a tough conversation – and often missing. She notes you may not control or have any say in when the conversation takes place. Even if you are well-prepared, having thought through the issues you may want to raise, too often your main objective is to end the interaction as quickly as possible. When initiating such a conversation, she urges you to “keep in mind that you may have had plenty of time to think about what you want to say. However, the person you’re speaking to is often hearing this for the first time.”

In establishing the right objective for the conversation, consider what you want for the relationship. Is this a chance to clear the air and move on, re-establishing a strong rapport with your boss? Or is it a step toward leaving? Ask yourself: What specifically do I want the other person to do after this conversation?

With that clarity, consider time and location if you are seeking a meeting. Don’t pick 2 p.m., when a series of back-to-back meetings for your boss is ending. Find a less frantic time. Similarly, Ms. Matuson advises that if your boss or a co-worker comes to you at a bad time for a conversation, don’t immediately acquiesce. Try: “My sense is you have something very important that you want to discuss with me. I want to devote my full attention to you, which I can’t do at this moment. Can we reconvene later today or first thing in the morning?”

An unexpected tool she suggests is silence. If the conversation becomes heated, silence can tone it down. Silence can convey you are listening. And it can nudge the other person into speaking first, which can give you a negotiating advantage.

Silence can give you a chance to slide out of the conversation. You might say “it looks like we are going to have to agree to disagree” – probably not something you would declare to your boss, but it might work with a colleague – or, “I’ll let you get back to what you were doing.” But Ms. Matuson stresses that if a conversation is important to you, you are best off not ending with silence. Instead, try, “I know this has been a difficult conversation for you. Let’s reconvene in a day or two to discuss where we go from here.”

How can you tell if such a conversation is imminent, in the first place? Ms. Matuson notes it may be in the offing if you have gone from being your boss’ “right-hand man to no man’s land.” Perhaps conversations with your boss used to extend for hours, but now resemble a Twitter missive. Or your boss is avoiding you and you can’t do anything right.

Your confidence has sunk to zilch, yet assurance is a key ingredient to successfully reversing the situation. So jettison the one-sided conversations in your head as your internal critic browbeats you. Start trusting yourself. Others probably do, coming to you for advice. Start keeping a journal of your successes. Test yourself in difficult conversations by picking a few you have a good chance of handling reasonably well.

Difficult conversations are, indeed, difficult. Ms. Matuson’s tips might help.

Quick hits

  • People behave more sadistically when bored, a series of psychology studies suggest.
  • In advertising, unconventional thinking works, according to advertising consultant Roy H. Williams. If you steadfastly believe in doing what is correct and expected, he would love for you to be in charge of his competitor’s marketing because you won’t be all that effective. Great ad writing is counterintuitive.
  • In presentations, the instinct is to be focused on your content – the slides, charts and case studies you are projecting on a screen or reading from your text. Instead, public speaking coach Gary Genard says you should be looking directly at the people you’re talking to when sharing the key things they need to know, making a strong connection.
  • Ottawa-based sales consultant Colleen Francis’ research found that 75 per cent of orders come to the supplier who responds first after a prospective customer does initial research. “Hot leads stay hot for minutes, not days,” she warns.
  • Good advice at the wrong time is bad advice, stresses Atomic Habits author James Clear. Life is full of seasons, and each season has different requirements. Know which season you are in to better define what ideas to utilize.

Harvey Schachter is a Kingston, Ont.-based writer specializing in management issues. He, along with Sheelagh Whittaker, former CEO of both EDS Canada and Cancom, are the authors of When Harvey Didn’t Meet Sheelagh: Emails on Leadership.

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