HAVING SUCCESSFUL HIGH-STAKES DISCUSSIONS

Curated insights to help you lead and perform at your best.

I told a friend of mine what this week’s title and topic was, and he said
“Oh man! C’Mon, hard conversations? We want the happy stuff!”

What if this is the unlock to the happy stuff that you’re hoping to get to by managing the really hard and stressful stuff.

You don’t have to have the “Sunday Scaries” if you know you have strategies for the really hard discussions that keep you up at night.

This is the moment of your day where you have to decide:

Do I close this and go back to my Egg White, Cheddar, and Avocado Breakfast Wrap (maybe with a little bit of hot sauce) and pretend that I’m being healthy?

- OR -

Should I stay in here for 3 ½ more mins, let that wrap hang out and hear about how Jon’s fear of heights might help me next week?

Good Choice. Let’s Dive In

You’re About To Have A Hard, High-Stakes Conversation

It has to happen. It’s weighing on you, it’s holding you back, it’s holding your team back, and you can’t get to where you need to get to without this conversation.

It feels like there are two possible outcomes.
They are either leaving this:
WITH YOU
OR
AGAINST YOU

And it will probably suck.

You only have One Shot! One Opportunity! And you have to get it right.

The risks of screwing this up feel high. You could lose a valuable member of your team; lose the trust of a friend; impact motivation to continue to contribute to your mission; or impact the performance you need out of them.

In the work I do with leaders trying to lead teams of all kinds, this comes up more than anything else. And the strategy we take has proven to be undefeated in delivering an outcome of exceeding their expectations.

They are about to - OR - know that they need to:

• Share a difficult message

• Let someone go that they respect and know the value of maintaining
  a relationship of respect.

• Have a high-stakes conversation

• Communicate a need of their own to their big and powerful boss

• Tell someone they need to be in a different role

• Discuss playing time

But they’re about to approach it in a way that WILL

• Lead to an argument or debate

• Get the discussion stuck going back and forth on minutia

• Burn bridges

• Be good for the leader but not the other side

• Land poorly

• Miss the mark

Here’s the strategy I guide people to use to have better high-stakes/difficult conversations and the mistakes people usually make that they think will work but don’t.

Raise The Sights

Reframe Your Approach So The Eyesight Is On The Destination. On The High-Level Goal, The Reason For The Message, Or The Decision Being Made

I’m afraid of heights.

If I were to attempt to go zip-lining over the jungle on a family vacation, and you put me on a 3ft x 3ft ledge, 75ft up in the air, strapped into a fool-proof harness with 3 steel cables that has successfully supported 7,892 previous zip-liners, my legs would be weak, my heart would be racing, my palms sweaty and there would be only one thing going through my head at that time

I Can’t. 
Because If I do, I’ll be THE ONE. I’ll be the one that you’ll be reading about who tragically fell 75 ft to their death at the World-Renowned Jungle Canopy Adventure Park

Standing up there, needing to launch, you can lob all of the logical safety data you want at me at that moment.

“But the cables are Galvanized Steel Aircraft Cables with 7X19 construction,
7 groups of wires, 19 wires per group, 1/4” in diameter. They can hold up to 2,500 lbs!!”

“But Jon, this park has been open for 7 years. 7,892 adventurers have gone through the course. We’ve never had an accident”

THAT SOUNDS WONDERFUL. NOW WHY THE HELL IS YOUR STAND ONLY 3FT X 3FT!!!??? CAN’T YOU MAKE THIS THING BIGGER?

“Jon, an 8 yr old girl Jennifer just did this!”

SHE SOUNDS COOL, I'M NOT HER. MAYBE I’LL MEET HER… ON THE GROUND!! WHERE I’D LIKE TO BE! SO I DON’T DIE!!!

“Jon, I’ve been in your shoes, I’m afraid of flying, and we flew here - you can do it”

THANK YOU FOR FLYING THE FRIENDLY SKIES, I’M SURE THAT SUCKED. LIKE THIS SUCKS. BUT THAT DOESN’T HELP ME FROM DYING RIGHT NOW

You’re in control of how high-stakes moments can go, but you have to remember, that you cannot beat the brain.

The brain has one boss. It is made to serve its boss and its boss alone - and it is chemically and biologically equipped to do so.

When someone is sitting across from you; receiving high-stakes news that impacts them directly, their brain’s very first instinct is to do what it knows to do - protect themselves.

Instinctively they defend where they are, feeling stuck in a corner, defending their position, and their eyesight will only be on what is immediately in front of them. Every tiny little data point will be looked at as an attack on their safety.

It doesn’t always make them irrational or a bad teammate, it usually just means they are human.

Hard, High-Stakes Conversations Are No Different Than Me Standing On That Ledge 75ft In The Air

There are a lot of mistakes people make, but the most common one is they think leading with “data” will do enough to logically convince the other person that the news they are delivering should (or will) make sense to them and get them to move in the direction they want them to.

Here are things people who are receiving tough news do not care about at that precise moment.

• They do not care about your feelings about the situation

• They do not care about your supportive data

• They do not care about what Jennifer did

• They do not care that you think they’ll be alright

• They do not care about Green Eggs and Ham

• They do not care about Sam I Am

You’ve probably been in one of these, and It goes like this:

You: “Greg, you haven’t done what we’ve asked you to do”
Greg: “What do you mean I haven’t done what you’ve asked me to do?”

[You’ve already lost the conversation]

You: “Look, Greg, I don’t want this to get into specifics, this is hard enough as it is for me, but you’re the 7th ranked salesperson out of 15, and our expectation for you is to be in the top 3”
Greg: “Well I’m sorry this is hard for YOU, you’ll still be in your position after this conversation. But top 3? With that account package? Who’s expectation is this? How am I supposed to know what you expect, all you ever ask me is how many meetings I’ve had with the clients and what my expenses are”

[Now it’s spiraling]

You: “Well, for instance, Jennifer has less accounts and is outperforming you”
Greg: “Why are we talking about Jennifer? Maybe one of Jennifer’s accounts had some huge change and placed a big order? Who knows? Why does Jennifer matter to me and my accounts?”

You are now officially “In the Weeds,”, Arguing back and forth.
Whatever the outcome is it is already going to be worse than feared.

Why? Because all they are hearing is you think they suck.

All they are hearing is that they might not have a job.
That their role is no longer their role.
That there have been a few specific things you brought up that have led to this.

(Which may all be the case, and they probably even know it!)

And they WILL - In all cases, instinctively go into protection mode.
They need to defend themselves from the fall.
They have limited ability to see the bigger picture.
They are playing back in their mind all of the little things they have done WELL to try and preserve their dignity and defend their performance.
They need to explain to you why some of those metrics are what they are.

You’re now arguing over things that both sides might even be true, but will only leave both of you disappointed.

They are focused only on one thing.
Why is the ledge I’m standing on only 3ft x 3ft and how do I keep myself from falling?

Where The Game Changes

The game changes, when the framework is set with what the ultimate larger destination is - and how the direction, decision or change is a function of those needs.

If data eventually needs to support why the change is needed to get to that destination, with a framework of where we’re trying to get to, the data is received with reason or understanding.

You Can Get The Other Person To Step Off Of The 3ft×3ft Safety Ledge, And Continue On The Path With You Together.

As I’m walking 75 ft up the stairs to the ledge, If I know that when I get there I will have to step off in order for my whole family to get home, I can start owning that responsibility and working backwards with all of the data that supports why I’m going to be okay 300 yds down the other side of the jungle.

Now my line of sight is on the destination. And as scary as it might be for me, my brain that is there to protect me is instead allowing me to focus on working backwards from the fact that 7,892 people have done this before me, that the cable holds up to 2,500lbs, and that little 8 yr old Jennifer just did it.

It might suck right this second, but I know it has to happen.

And I know I’ll be okay.

A Real Life Example:
I worked with a senior member of a team (we’ll call him Jim) in a leadership coaching capacity. But within the timeline, he was growing uncertain about where he ultimately stood in the eyes of Senior Leadership.

To Jim, the message he felt he was receiving from leadership, as he picked apart every message he saw as signals, telling his own story to himself, was that if he couldn’t deliver, he might be out.

He didn’t feel confident that he was trusted to deliver, and he knew that the only way he could perform to his full potential was to feel that trust.

The fact was, leadership trusted him - immensely. But probably hadn’t communicated this with purpose, in a way that allowed him to swing away.

He scheduled a 1:1 with his boss and his own strategy was to “find out where he stood in the organization”. Jim was going to ask specifically - “I’d like to know where you see me in 2 years?”

I warned him, that if he asked that question, he was going to get…. AN ANSWER to that question. The conversation was 100% going to shift to:
“Well tell me, where do you see yourself in two years?” 
[Here is where you can replace company role & visibility with playing time and role on a sports team. It is THE SAME]

And with that, his boss would go through a series of specific data points and metrics that he would need to get to where he wanted to be in 2 years.

He would leave with metrics, but he would leave WITHOUT what he
came for - TRUST. 

His boss would move on, feeling like they had a clear game plan, and feeling like that was productive, and yet Jim would leave feeling no clearer in where he stood if he missed on any of those metrics.

He would be right back where he started.

So What Did We Do?

I instead guided him to go in and frame the conversation with a broader scope, raising the eyesight to how he knows he succeeds as the line of sight for the conversation.

This wasn’t about measurements or data or 2 years. It was about trust.
I guided him to share at the very beginning of the conversation that he was struggling a little bit. And that it was important for him to share what he knows about himself. That when he has succeeded the most in his life, it’s when he has had the trust of his coaches or bosses that he could execute his strategy and do his best, and that if for some reason he struck out or something went wrong, that he would still be able to keep trying.

He needed to share that what he knows about himself is that he has always succeeded when he knew he could swing away freely. And that right now, he just didn’t know what would happen if he missed.

He did that. He shared that.

Notice he didn’t accuse his boss of not giving him what he needed. He didn’t lay out specifics about a certain circumstance right up front. Jim just shared with him what he knew about himself. He shared that he was struggling, and that he simply wasn’t sure what would happen.

The response of his leader was everything he (and we) wanted it to be. I actually give his boss a lot of credit, but I also know that Jim allowed for that response to occur through his strategy.

The boss’s response:
“I probably haven’t been doing a good enough job of communicating my level of trust that I have in you. And I need you to know that we’re all a team here. We want to succeed of course, but if we miss on something or don’t hit our target here and there, then we ALL have to do a better job, it doesn’t just lie on your shoulders”

He added: “Let’s you and I start having more 1:1’s. I think it’s important for us to keep talking”

BOOM

With that in hand, and only with that in hand, they went through the specific metrics of where they’d like for him to try and get to, and how they’d approach it. Together - in full collaboration.


These conversations can feel binary. They usually are, but they don’t have to be.

In most cases, when you’re on a team, leading people or being led, everyone around you wants you to succeed. They need you to succeed. They have your best interest in mind.

They don’t want you falling 75ft of a ledge, but they also have to know that getting you to step off will feel like life or death.

As always, trying to approach these with the mindset of emerging from the conversation feeling TOGETHER, vs a mindset of delivering information for the person to process on their own up front, will lead you to more successful high-stakes conversations.

Because.

TOGETHER UP!

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