Hey, it's Rachel Cook, your modern mentor. And today's episode is for anyone who's ever had to have a hard conversation at work, which is everyone. Because those conversations, the ones that make your head sweat and your stomach clench, they need to happen in order for us to get a better outcome. So how can we do it in a way that's empathetic and strategic and sure to maintain your relationship?

Here are some of my thoughts.

Last week, I was catching up with my friend Sam.

When I told him I had to go, he gave me the sad eyes and the giant sigh of a guy not looking forward to something.

I asked him what was up, and he told me

one of his colleagues had been dropping balls lately, like a lot of them. A missed client deliverable,

a messy meeting that wasn't well prepared for, an unpaid invoice that resulted in late fees,

the list kind of went on. I'm not his boss, Sam told me, so it doesn't feel like

my place to give him feedback, but something's really got to give here. Whether a friend has

disappointed you one too many times, or your boss just won't give you a straight answer about that

promotion, or your doctor's advice leaves you feeling like she hasn't heard a word you've said,

you've been left. You've been left feeling sad or scared or hurt or mad at some point.

We've all been in situations requiring us to have that icky conversation. They're hard and

they're awkward and we postpone them until we can't anymore. So if you are or have ever been where

Sam is, let's talk about how to have one of these difficult conversations well. First, choose your

battles. Before you dive into the difficult, be clear about what you want. Because if all you want

right now is to vent, then phone a friend,

friend, and do not engage with the object of your angst. A great question to ask yourself is,

is this annoying or is this a problem? Your teammate who checks his phone one too many times

during your presentation may be annoying, but your teammate who continuously cuts you off while

you're speaking? That's a problem. We're focused here on the problematic situations,

the actions or behaviors that are infringing on your ability to be successful. In Sam's case,

...