February 7, 2026 | Read online
I think life is a lot about expectation setting.
Think about the last time you were pissed off about something. I almost guarantee your expectations were mis-set.
For instance, say you go to a restaurant on a busy Friday night and you can tell the waiter or waitress is overwhelmed with too many tables and it’s probably going to take them a while to take your order.
They have two options on how to handle the situation.
- The first option is they come over to your table to greet you and let you know it’s going to be about 15 minutes before they can take your order.
- The second option is they don’t say anything and wait 15 minutes until they come over and take your order.
In both scenarios, you get your order taken in 15 minutes, but which one are you happier with?
If the first scenario happens, you’re probably not thrilled it’s going to take 15 minutes, but they set your expectations so you adjust.
What happens in the second scenario? Within about 5-10 minutes you’re starting to poke your head up over the dividers or into the aisle to look around to see which one is your waiter, and eventually start asking any waiter who walks by if they’re going to take your order.
Let’s bring it to the world of Sales.
Here are some tactical ways to set expectations that make a big difference.
COLD CALLING:
When it comes to cold calling, expectation setting is key. Almost everyone we call wants to get off the phone as quickly as possible with us. That’s why how we introduce ourselves matters. Here are a few I’ve used over the years to set their expectations and buy myself some time:
- “I know you weren’t expecting my call, so I’ll be brief”
- “Can I get 30 seconds to tell you why I’m calling before you hang up on me?”
DISCOVERY:
The majority of discovery calls don’t have an agenda and start with the rep doing some fake rapport-building crap before they dive into a bunch of interrogation questions and then making a hard shift to their “pitch.”
This is why most executives tend to interrupt sales reps and say stuff like “could you just show me the demo” or they jump right to “so how much does this cost.”
I wrote a post a long time ago about how executives are like children, they need structure. If you’re not using agendas to structure your calls, they’re in control, you’re not. A simple ‘shared agenda’ sets expectations for when certain things will be discussed and gives you something to fall back on if the conversation gets off track.
SENDING INFORMATION/PROPOSALS:
I can’t even count the amount of times I’ve set unnecessary expectations with a client and told them I would send them information or a proposal by the end of the day without even asking them when they needed it.
Not only does this put unnecessary pressure and stress on me based on all the other things I have going on, but it sets me up for failure if, for some reason, I can't get it to them by the end of the day.
Now I simply ask, “When do you need this by?” and “Why?” which leads to potentially more insights into their decision process.
GHOSTING
Ghosting is one of the more frustrating parts of being in sales. We try to do everything the client asks for and then poof, they disappear on us and don’t even have the common courtesy to let us know they either went in a different direction or aren’t interested anymore.
That’s why I try to proactively address it these days, and set the client’s expectations that I’m totally ok with them telling me no, and sometimes even asking them to not ghost me.
It usually sounds like this: “As we go through the process together, if it’s evident to you that I’m not a good fit for whatever reason, are you ok with telling me no?”
It sounds like a stupid question but the reason I do it is because I want them to know that I am totally ok with them telling me no. "Yes" is obviously the best answer in Sales. "No" is the second-best answer. "Maybe" or no response is the worst, and turns me into the stalker that neither of us want.
I’ve also straight-up asked the client in some cases not to ghost me. It usually comes at the end of the initial discovery call where there are some obvious next steps. Right before I get off the phone I say: “Can I ask a quick favor? If for some reason it’s evident at some point throughout this process that I'm not a good fit, could you just let me know and not ghost me?”
They usually laugh and agree. Then, if they still do ghost, I can have some fun with it and send them an email with the ghost emoji or whatever.
LEADERSHIP
Leadership is all about expectation setting, in my opinion. For instance, if you’re doing performance reviews with your team and they’re surprised with any type of negative feedback or criticism you have for them, then you’re an asshole and a bad leader. Real leaders set clear expectations with their teams and hold them accountable.
With the Super Bowl coming up this weekend my entire Instagram feed is filled with Patriots content and this video of Mike Vrabel (the coach of the Pats) to me is a perfect example of how to lead and set expectations from day one. I think what he’s done with the Patriots is a masterclass in what real leadership looks like.
On that note, I’m writing this email on my flight to Phoenix where I rented a house for the weekend to hang out with some friends for my belated 50th birthday. We’re golfing on Friday, heading to the Waste Management Open on Saturday and then back to the house on Sunday to watch the Pats play in the Superbowl. My expectation is pure mayhem and debauchery 🙂
LETS GOOOOOO PATS!!!!!!
By the way, the picture below is of me and my wife at the last Pats/Seattle SuperBowl where we sat 30 rows back on the goal line where Butler intercepted the ball to win the game. Still one of the top days/experiences of my life :)
