TL;DR: "I'm bad at breakups, particularly when it comes to employees or investors. When those moments arise, what's the smartest approach to those tough conversations? Should I just go "full honesty" or is there a better way to think about it?"

The one thing everyone remembers about a relationship is how it ended.

As Founders, if we're around long enough, we're going to see the end of a boatload of relationships, and as such if we're not keenly aware of how important it is that we end those relationships gracefully, we're going to end up with a whole lotta angry exes.

There's really no way around this. Unlike our lives as an employee, where it was just us and our boss, when we are the boss, we're at the center of so many important relationships. Whether it's investors, staff, customers, partners, even the media — all of those relationships have a cost, and when they end, those costs actually multiply.

Later on in life, we learn how important it is to have "good breakups" because we have enough "crazy exes" come back to us later in life to haunt us. What we'd like to learn now, before our metaphorical ex is showing up at our doorstep at 3 a.m. pounding on our door demanding our head, is how to manage those breakups.

Today’s Advice Sponsored by Fundable

The Cost of a Bad Breakup

Every relationship has value, good or bad, which means every breakup intrinsically has a cost to it. If someone leaves our organization on good terms, there's a chance they may say nice things about us someday. But if someone leaves the organization on bad terms, well, there's a 100% chance they are going to run our name through the mud.

No one calls attorneys, competitors, and trolls job board reviews to tell everyone what a great breakup they had. The cost and damage of a bad breakup are exponential, and yet, as Founders (or people in general), we completely overlook the damage done because we're so focused on the moment at hand.

If we don't truly consider the cost of breaking up, then the importance of mitigating that cost is going to completely fly over our heads.

The Last Words Matter Most

Think about every breakup we've ever had — we always, always, always remember how it ended. There were likely a million interactions, good and bad, leading up to that breakup that we probably forgot. But in most cases, we can remember the time, place, and details of that specific conversation.

Breakups are a forever brand in the minds of both parties. They form an entire construct not just for the end of the relationship, but for the go-forward framework of how that relationship will always be viewed. And let's face it — it's usually super shitty.

Imagine we've had to part company with our investors, for any number of reasons. They will remember that we had a rough time with our startup, but they will project our last words forever. If they walk away thinking we were incredibly smug and indignant about how it ended — that's the forever brand of us in the investor community. But if we show some genuine contrition and take ownership, that's also how we're remembered. Which would we prefer?

A Moment That Matters

What's interesting about all of this is our "breakups" are typically fairly short engagements. Sometimes it’s no more than a single conversation. But that moment shapes years to come, so why wouldn't we go out of our way to absolutely make sure that moment shapes the best possible future?

If we're breaking up with an employee, why wouldn't we make sure we provide as much support and empathy as possible? If we're winding down our startup, why wouldn't we show investors that we completely own the outcome and have learned from it? That approach will form the basis for not only our relationships in the future but our reputation as a good Founder and human overall.

Collectively we're talking about our reputations which are built on many interactions, but if we had to isolate one consistent interaction that absolutely forms our reputation — it's our breakups. No matter how badly we may want to spew venom in that moment of truth, it's never worth it. We have to recognize those final moments as potentially the most important ones, and we have to do whatever it takes to shape them toward a future and reputation that we hold dear.
 

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