The Right Thing vs The Hard Thing
”Compounding Hardness” - It’s a Courage Thing
One of the best and most referenced Silicon Valley books ever written is Ben Horowitz’s “The Hard Thing About Hard Things”.
I’ve had my own version of this long before Ben wrote his book… but Ben wrote it down and it’s my turn to contribute. I offer a critical framework with specific actions to take to ensure you try to always do the Right Thing in the Right Way and try to avoid delaying the Hard Thing.
This post was inspired by a deep conversation I had with one of my clients recently and is worthy of another week’s Substack Newsletter + I’ve been given permission.
I’ve rarely met a leader who doesn’t know what the right thing to do is.
But I’ve met many leaders who don’t trust their instinct(s) and doubt/second guess themselves.
Only to later say, “I knew it” and “I should have done it way earlier.”
This is not a data problem. It’s not a focus or clarity problem.
It’s a Courage Problem.
The right thing to do is almost always obvious… especially in hindsight. The hard thing to do is to act on it today or this week.
When you delay the right thing, hard things only get harder. Every day you postpone a decision, the cost compounds… financially, emotionally, and/or culturally.
I’ve made all these “hard thing” mistakes as a leader and operator. Now that I’m coaching operators, I’m seeing the familiar pattern play out again and again.
Almost always ending in this familiar quote:
“I should’ve done this so much sooner.”
The Spreadsheet of Regret
One of my clients (I have permission from him to post this - let’s call him JJ) built his most recent, powerful, almost painful lesson into a spreadsheet of regret!
(Yes, Peter H, Zach, or Rich… that JJ… in case you are wondering why this story is going to sound familiar.)
I didn’t ask JJ to do this. It was his own creation after a deep conversation on doing the “Right Thing”. We walked through a few timelines of the recurring issue and worked on frameworks and playbooks for doing the right thing in the right way.
JJ is an amazing CEO (former CFO!) trying to “cross the chasm” in his emerging company category. An incredibly instinctive founder, grinding operator, deeply loyal to his people and his concept of “team”. Deeply competitive with a very high EQ.
Over the years, he had personally hired many early employees who helped him get to his first $5M in revenue. But as the company grew, the business began to outgrow some of those same people.
Eventually, after a few tough quarters and knowing he’d delayed some very hard decisions, JJ did something very few leaders do… he went back and audited his own decisions after we did a walk-through review of a 1/2 dozen of these “hard decisions”. Note: I didn’t ask him to build what he called his “spreadsheet of regret”. He did this all on his own… taking some of my frameworks and insights and creating something even better for himself.
He listed the last dozen people he had to let go many of whom he had personally hired and coached. For each one, he wrote down two dates:
When he first knew, in his gut, that the person wasn’t going to make it to the next stage.
When he finally acted on that realization.
On average, the gap was 10 months… his calculation to which I emphasized “average” with him!
Ten months of indecision. Ten months of extra salary, meetings, management cycles, team drag and delayed progress. 10 months of personal angst on JJ himself. He estimated the total cost to the company was over $1 million - real runway for a startup still finding product-market fit.
When he showed me the spreadsheet, he shook his head and said quietly:
“That $1M+ is a lot of runway for us… it’s nearly a whole year… this one’s on me!”
It was one of the most honest reflections I’ve ever heard from a founder.
Compounding Hardness
When you delay a hard decision, the costs aren’t just financial. The costs compound in mostly invisible ways creating team dysfunction and executional complexity.
Time and Money Cost: JJ proved it with his spreadsheet of regret. More months of salary, opportunity cost, wasted cycles. Time is maybe the most valuable thing in a startup. Every week or month in delay is time you can’t get back.
Compounding Cultural Damage: the longer a bad apple stays, they more they misalign with strategy, the more negative impact they inflict. Team morale drops. Most everyone already knows the person isn’t performing. They start questioning your judgment, or worse, the culture of this company. People learn that poor performance is tolerated more than excellence is celebrated. Toxic energy emerges. Finger pointing, gossip and silos grow. Beware the team that anchors on mediocrity or worse, under-performance.
Execution becomes harder and slows down: meetings multiply, re-work piles up, and energy leaks into managing the issue instead of solving it.
Emotional Tax: the weight of delaying the decision builds. Stress, sleep, and second guessing provide regular distractions to focus.
Compounding Negotiation Risk: more often than not, once a person knows they are being considered for termination (due to the delay), they shore up potential defenses, they push harder, sometimes threaten, and everything just got harder… due to your delay. Shields up!
The Time cost is likely the most important one. I’ve stored “Time” quotes in my best of library over the years. They help me personally focus when I need my own kick in the pants.
“Time is free, but it’s priceless. You can’t own it, but you can use it. You can’t keep it, but you can spend it. Once you’ve lost it you can never get it back.”
- Harvey McKay
“Time is your most precious gift because you only have a set amount of it. You can make more money, but you can’t make more time. When you give someone your time, you are giving them a portion of your life that you’ll never get back.”
- Rick Warren
The irony? I believe we all instinctively know the longer we wait the harder it becomes for us to act.
Waiting “Compounds Hardness.” (I just made up that term. I really like it!)
Why We Delay
Let’s be honest. We delay because we care. Because it’s going to be a hard conversation.
We delay because we believe in people. Or we can “save them”. Or we delay because we want to be fair. Because we think another quarter, another role change, or another project might turn things around. We delay because they hit that rare double and get on base but are still batting under .200 (ode to recent World Series).
The irony? Most of the people on JJ’s hot seat knew they weren’t performing fully but sprinted in fits and starts and created false hopes, only to collapse again during the next crunch. Sound familiar?
Ultimately, when it came time for JJ to make the hard decision, the person was relieved they didn’t have to keep spinning their own plates anymore and accepted the decision. The person let go also wished either they would have quit or JJ would have let them go earlier. Also sound familiar? I thought so.
We delay because conflict is uncomfortable. We tell ourselves that loyalty and giving people more chances and empathy are leadership virtues (they are).
We delay because the hardest conversations to have are with the people we’ve personally hired or mentored.
We delay when we HOPE we think we can help fix it. More coaching, more time, new incentives. We believe a talented, nice person will adapt.
And sometimes they do… and that’s a great save. But most times, once you get to this stage, we continue to hope for one more quarter, and then one more quarter… until the data and effort becomes overwhelming… and they are now batting .150.
Delaying the hard conversation isn’t doing anyone any favors. Especially not them, certainly not you. The people impacted are the rest of your team, your company, and your personal leadership credibility.
Many times we forget as leaders that clarity and accountability are also core values. 2 values that people and teams need most from their leaders.
Ron Carucci once wrote in Harvard Business Review:
“The delay often does more damage than whatever fallout the leader was trying to avoid.”
Every time I see a leadership team in gridlock, if it’s not a strategy problem, it’s usually a courage problem around poor performing people wrapped in a narrative of delay or waiting for more information.
When Great Leaders Choose Courage
Some of the best leaders in history have had to learn this lesson the hard way.
Andy Grove built Intel around the mantra, “Only the paranoid survive.” He institutionalized “constructive confrontation” - the practice of calling out problems early, not late.
Scott McNealy and Jeff Bezos were big believers of “disagree and commit” into both Sun Microsystems and Amazon’s operating DNA. Hammering home that indecision and consensus paralysis were the real risks to innovation.
Ben Horowitz wrote the book on “The Hard Thing About Hard Things.”
Every one of these leaders knew that speed and clarity were clear leadership and cultural choices.
New leadership framework: “Sending Signals”
Delay = Compounding Damage
Courage = Compounding Trust
When you do the right thing, you send a signal.
You show your team that clear action matters more than comfort.
You show your investors that capital will be protected by discipline.
You show yourself that your leadership muscle - courage - grows through reps.
These reps build trust. By definition not everyone will agree with your decisions. Agreement/Consensus is rare in leadership. Leadership is hard because it’s you who has to make the clear and decisive action. Trust compounds when your team and investors know what you stand for and why.
The Playbook: How to Act Sooner
Here’s a playbook you can embed into your leadership DNA
Define non-negotiable thresholds: (performance, culture, values). Define what “next-stage ready” looks like for every key role. Oh yeah… IMPORTANT… WRITE IT DOWN… and publish it publicly inside the company.
Name it early: when you see a gap, mind the gap. Communicate your expectations. Put it in writing. Ambiguity is delay’s best friend.
Set a decision date: 90 days? PIP (Performance Improvement Plan; yes, requires that “writing it down” thing again! Create a date-driven decision-function.
Audit your own delays: Be like JJ. Track when you first knew, and when you acted. It’s humbling and clarifying.
Close gaps faster: Focus on closing gaps you see widening. Clear communication followed by decisive action is the ultimate leadership signal.
Communicate 1st principles: Tell your team that “doing the right thing early” is part of your culture and you are doing your best to do it “the right way”. Share as transparently as you can how hard the decision was and why it was hard. But be clear and just as transparent that not everyone makes it through every company stage. State the fact that less than 25% will make it through all the stages of company growth Seed to IPO. (3 out of 4). Look to your left. Look to your right… and maybe look in the mirror.
Offboard cleanly and respectfully: offer structured transition plans and offer any help in finding the person the right role for their right stage strength. (assuming they are respectful in return). Off-boarding with respect and recognition of past accomplishments should also be part of a great team culture.
The earlier you “make the call”, the earlier you learn. Almost every time it’s less painful, less expensive, and more respected.
Don’t ever forget, as a leader you are always modeling. People are watching closely. You are modeling clear communications, “the why”, “our purpose”, “our principles”.
Leadership actions nearly always speak louder than words.
The Final Paradox
The right thing and the hard thing are often the same thing.
But the longer you wait, the less “right” it feels and the harder it becomes to do.
Leadership is a series of moments where clarity and courage intersect.
The best leaders act early, act authentically, and transparently, and over-communicate.
“Because doing the right thing late is often worse than doing the wrong thing early.”
