I went to get donuts for my family yesterday morning, and while driving back, I ended up in a little situation.
I'm a sucker for a maple bar. I've also learned that maple bars are not a normal thing around the world, which was depressing to hear. Apparently, they are a "very West Coast, North American" thing, which I had to learn the hard way when we moved abroad. ("What do you mean you don't have a maple bar?!?!" Me, in a bakery in Dubai.)
Even in Canada, where maple is a thing, they're not universal, and in the Midwest and other parts of the United States, they are called Long Johns. Who knew?
Thankfully, I live in Seattle, and maple bars are a thing because in the donut rankings of the world, it's maple bar number one, and everything else is underneath it. If I had to rank two through five, then I'd go:
- Maple Bar
- Cronut (if you're at a bakery and they know what they're doing)
- Pershing
- Old-fashioned glazed
- Cinnamon sugar ring
Don't talk to me about things like apple fritters, anything jelly-filled, or anything with powder on the outside of it.
But enough about my opinions on donuts. While I was driving back home, I reached into the box and grabbed a maple bar and started eating it like a man who hadn't eaten in an hour.
I was listening to some music, enjoying a slow morning, and making my way through the streets when all of a sudden I came to a three-way stop that sort of has a side street cut off that you can go down. Now, keep in mind, I'm three-quarters of the way through a maple bar and not really ready for what was about to happen.
I sort of pulled a few feet out into the path, and the car to my left needed to maneuver around me to take the side street. This driver apparently felt like I was too far out there, didn't appreciate where my car was sitting, and decided to tell me about it.
The driver gave me one of those hands-in-the-air, go-fuck-yourself sort of looks. Well, I think he actually said those words out loud as he pulled around me.
In this moment, I had two options. I could either place my hand in the air and mouth back the universal traffic dialogue of "no, you go fuck yourself," or I could just let it be and move on.
I chose to let it be and move on. Why, you ask? Because I had maple glaze on my lips and half a donut in my right hand, and nobody has ever won an argument while starting from this negotiation position. I mean, who would take a guy seriously who is shouting out of his car window while holding a donut? I would have looked like a damn fool.
Understanding your negotiation position is key if you're going to win an argument, and it's even more crucial if you're trying to ask for more money or get a better position at work. I've seen lots of people try to ask for more money during an offer letter, push for a pay raise during a busy work year, or try to leverage another offer from another company to get more at their current one. Negotiating isn't ever a bad idea, but the timing and your leverage will make all the difference in the world.
When I was being recruited to work in Dubai, I had eleven meetings with the C-suite over the course of about sixty days before they finally invited me to meet everyone in person. I knew that the calls were all going well, and they even gave me a preliminary offer before I flew out there. So, barring me from completely messing things up during the visit, the job was mine.
On top of it, they flew my family and me business class, put us up in one of the nicest hotels in town, and rolled out the red carpet in many ways. I knew that if I was going to accept the offer, I had room to negotiate because they clearly signaled they wanted me. You don't spend that kind of money and time on a candidate and then pinch pennies in the negotiation.
And they didn't. I got everything I asked for. In fact, I look back and wish I had asked for more because I probably would have gotten it.
But it was all because I knew the position I was in.
As a leader, I've turned people down for more money or perks in their negotiation because I knew they didn't have any leverage.
In fact, it happened to me when I went to Zillow. I was negotiating for more money, and then I casually asked for free parking. Turns out, nobody got free parking, and I just didn't have any room or power to negotiate for it. I applied to the job, I was one of several candidates, and if things fell apart with me, they could have taken the next person. Trying to bend over backward for another perk wasn't going to make or break the company.
One time I had someone ask me for an 18% pay raise just because they wanted more money. They had no real business justification other than that they were doing a good job for the time being. It was a bold ask, but there was nothing more to back it up. We weren't in a review cycle, and 18% wasn't even in the ballpark for their situation. Most promotions at the company came with a 10-12% pay raise pending the role, so to ask me for 18% showed this individual didn't do their homework and was fishing for whatever they could get. I said no.
There was another time when I was running short-staffed, needed someone to take over a book of business, and they knew they were a top performer. When they asked for more money, I said yes to whatever they asked. Leverage and timing matter, but more importantly, this person knew their value.
It's not about whether you should ask. You absolutely should. It's about whether the moment you're choosing actually gives you a shot to win. Walking into a negotiation without leverage is like arguing at a stoplight with maple glaze on your face and half a donut in your hand. You might feel justified. You might even be right. But nobody is taking you seriously, and deep down, you know it.
The people who consistently get more aren't louder, they aren't more aggressive, and they aren't more deserving. They just understand when the deck is tilted in their favor, and they choose that moment to push.
So before your next ask, pause for a second and take inventory. What signals have been given? How badly are you needed right now? What alternatives exist if you walk away? Because when you align timing, value, and leverage, the conversation changes entirely. You're no longer hoping for a yes — you're expecting one. And if you can get yourself into that position more often, you won't need to force outcomes. They'll start showing up because you finally learned when to speak, and just as importantly, when to keep your mouth shut and finish your donut.
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