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Microsoft exec: My 2-step rule for having hard conversations at work

Chris Capossela
Photo: Chris Capossela

All of us have had to — or will — deal with a frustrating work situation at some point in our careers, whether it's a loud deskmate, an unproductive meeting or a project that went off the rails. 

As tempting as it is to storm into your boss's office or fire off a passive aggressive email to an insufferable coworker, rash, emotional responses don't solve problems. 

There's a better approach to handling difficult conversations at work, Chris Capossela, Microsoft's chief marketing officer, argues — and it starts with clear, confident communication. 

"Communication can be an especially difficult skill that takes a long time to hone, but it's one of the most important skills you need to succeed in the workplace," Capossela, 53, tells CNBC Make It, adding that when it comes to stressful topics, "communication can often go badly."

Capossela has spent his 31-year career at Microsoft mastering the art of communication, even serving as a speechwriter for then-CEO Bill Gates between 1997 and 1999. 

Here, he shares his best advice for navigating a difficult work conversation: 

Write your thoughts in an email — but don't press send 

Think of the "draft" section in your inbox as your new work best friend: a place to share your unfiltered thoughts and feelings without judgment that you can revisit and revise at a later date. 

Before Capossela initiates or participates in a difficult work conversation, he starts with an email. 

"I write all my thoughts about the situation down in an email draft that I can work on and get to be as tight, well-written and emotionless as I can," he says. "When people can take the time to hone what they want to say, it always goes better than if they're just doing it verbally off the cuff."

Once he gets the writing to be as "clear, crisp and calm" as he wants it to be, he uses it as a script to initiate a conversation with the person, or people, involved in the situation, or as a precursor to find time to meet. 

For example: If you're asking for an overdue promotion, Capossela says, the final version of your script might say, "Hey boss, I'd really like to talk to you about my career progression, I would love to know what it would take for me to get to the next level. I'd love to meet with you and hear your thoughts on what those steps might look like. Please let me know when you are available." 

Ask questions and listen 

The most successful people in the workplace are life-long learners, Capossela says, willing to ask a lot of questions and listen to other people's opinions and experiences — especially when confronted with a heated discussion or uncomfortable situation. 

Being curious and asking questions can help defuse negative emotion and keep tensions from rising, he explains. Pausing before responding and listening to what the other person has to say also shows the other person that you want to work together toward a solution and can move the conversation forward. 

For example: Instead of ambushing your boss and saying, 'I deserve a promotion, why haven't you given it to me?' Capossela suggests a script along the lines of: 'I'd love it if you could educate me on how promotions work within the company, and I could explain to you the things that I believe I've done to grow.'

"The better you can start and sustain a dialogue, the more you can normalize difficult conversations as just part of what we do at work," he says. 

Check out:

2 time-management tricks Microsoft's CMO learned from working with Bill Gates—and how they can help you be more successful

The No. 1 mistake people make when applying for jobs, according to Microsoft's head of recruiting

28% of people quit because of bad managers: The best way to confront your boss before it's too late

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