Tim Ferriss has a famous quote that I’ll paraphrase here:
“Your success is proportional to the number of uncomfortable conversations you’re willing to have.”
Fundamentally true, but our work in executive search has revealed a huge caveat:
It’s not enough to HAVE the conversations.
It’s about HOW you have them.
I can tell everything I need to know about a person based on HOW they navigate uncomfortable conversations.
As an example, let’s use the hiring process:
Any high performer can interview well, demonstrate skills, show beautiful portfolios, smile, be likable, fit in with the team, get the offer. Those are the easy parts.
The difficult conversations come next:
The offer comes in slightly lower than you’d hoped. You’ve got a kid with special needs which will affect your relocation requirement. You have a non-compete that you forgot to mention. Another company made you an offer the same day.
These things can be stressful, and most people approach stress sideways. Let the offer sit, email over a few vague negotiation points, come back the next day with a few more, buy some time, be hard to reach, and ultimately fail miserably… and genuinely not realize they’re doing anything wrong.
When the offer letter hits your inbox, a countdown begins. Your quality of character is now on full display. Here’s how to demonstrate your exceptionality and get what you want:
GET SERIOUS
Unless you’re not serious. If you’re not, gracefully decline.
If you are serious, recognize that the offer stage is a very specific stage.
It is not the time to casually mention that you've been secretly shopping multiple offers against each other, question the company’s 5 year growth plan, or say anything else that you should have said weeks ago.
Your behavior at this stage is a preview of how you’ll behave after joining the company.
ORGANIZE YOURSELF
You might scan the offer and see 6-7 things that you’re not 100% excited about.
Your mission is to identify the top 2-3 and prioritize them, because a compensation gap is not on the same level of importance as a typo on your middle name.
KEEP IT UPBEAT
“I’m excited about this, and I think we’re close. If we can get that number to X, I’m ready to sign today.”
“I noticed the PTOs policy is a bit tight. Is that an enforced rule, or just a formality? If you say it's flexible, I’m ready to sign today.”
“Can we push the start date 30 days? I need to establish residency so my kid can change schools. If that works for you, I'll sign today.”
The offer originated from a template. The template originated from policies. Take nothing personally.
DO IT VERBALLY
Attempting to have tough conversations in writing is pure amateur activity.
KEEP IT SHORT
The shorter your sentences, the more believable you are.
The more clearly you state your wish, the easier it is for them to grant it.
ALL AT ONCE
Your mission is to get what you want, with no more than 1-2 back-and-forth ping pongs.
Any more than that, things get laborious. Excitement, on both sides, turns to irritation.
Before the conversation, prepare ALL of your asks.
FOLLOW THROUGH
The most toxic emotion that can seep into an offer process is DOUBT.
Speed and clarity are the antidotes to doubt.
Reassure the company of your intentions.
Tell them you’ll sign the amended offer the moment it arrives.
Then do what you promised.
And that’s it.
You conveyed that you need more.
You said it with professionalism and respect.
You made it easy for them to give you what you want.
You did it in the right tone: “we’re on the same team here, let’s get this done.”
You gave them a taste of how truthful and transparent you’re going to be on the job.
It’s difficult to nail all of these, but you must. These are actions that establish character quality, and character quality is king, even if it's not listed on the job description.
It doesn’t matter how sick your apparel designs are. If you can’t organize your thoughts, look someone in the eye, and convey the spirit of partnership… you’re playing at a disadvantage.
As you might have gathered, these principles go way beyond job offers. The skill of communication will elevate every aspect of your life.
Become the type of person who can have difficult conversations with elegance.
