The actual hard thing about hard things
How to be a leader without losing yourself
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The actual hard thing about hard things
When I was early in my career as a head of marketing, I read Ben Horowitz’s book The Hard Thing About Hard Things. This book lives in the canon of startup literature because of its unflinching look at the harsh realities of decision-making and the incredible results that come from being courageous in times of turmoil. Horowitz co-founded a company called Loudcloud (lol they really name startups anything, don’t they) during the dot-com boom, struggled to keep it alive through the crash, pivoted it into the software company Opsware, and eventually sold it to Hewlett-Packard for $1.6 billion. Happy ending! (Except for the people he fired, and the carnge he left in his wake.
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To be a good leader, one could surmise from the book, you must make hard decisions. In fact, you might be signing up for a career’s worth of hard decisions. And heartbreak. And high blood pressure.
Why would anyone sign up for that?
That book shaped my early career in startup leadership, and it probably shaped hundreds more careers, too. For better or worse.
As part of our agency work at Bonfire, we do a fair bit of coaching with marketing leaders, and this concept of hard decisions seems to come up often. What we keep hearing is this: The hard thing about hard things is that hard things are hard. (Ben Horowitz, you can steal that title for your book sequel … for $1 billion.) When you’re in charge, you have nowhere to hide from responsibility. But if you don’t act, then nothing happens. There’s no way out, which can very understandably feel hard when you are stuck between painful action or painful inaction.
As time has gone on, I’ve realized that there are many good lessons to take away from Horowitz’s book, but that balancing the hard-things ethos with other leadership perspectives leads to healthier outcomes for everyone. We coach leaders to do the same. Let me unpack how we think through a more balanced approach to navigating hard times and tough calls.
Takeaways from The Hard Thing About Hard Things
If you haven’t read the book, let me summarize a few of the most salient lessons from Horowitz’s tales of startup leadership life:
There is no formula for the hardest decisions.
Management advice is useful until you have a situation where every option is bad.
A leader’s job changes whether you’re in “peace time” or “war time.”
Tell people the truth, and never hide bad news.
Take care of people, products, and profits, in that order.
Hire for strength, not for the absence of weakness.
A leader must be able to make painful personnel decisions.
Culture is what leaders reward and tolerate.
Do not carry the burden entirely alone.
The struggle is part of the job.
Do you find these to be true in your experience as a leader? (Or as someone being led?)
What makes sense to me
Looking back, a lot of Horowitz’s experience maps to what I felt while being in marketing leadership roles and what I feel today co-running a business.
There is no formula for the hardest decisions. Accurate!
Throw management advice out the window when everything is bad. Gladly!
Take care of people before profits. Amen!
Those are not easy things to do, of course. None of that list of 10 takeaways is easy. There will always be temptation to hide behind playbooks or to over-index on profits. In a lot of cases, the alternative to doing the hard thing is to willfully do the safer thing or the easier thing: to fall back on a playbook or let a spreadsheet dictate your next move. But what I find particularly interesting about the list of hard things above is the items from the list with dire consequences when you do nothing at all.
A leader must be able to make painful personnel decisions
Culture is what leaders reward and tolerate
Sometimes, those painful personnel decisions never get made. Sometimes, culture evolves because unintentional behavior gets tolerated until it becomes canon.
I have made mistakes before by not making painful personnel decisions soon enough and by letting aspects of team behavior linger for too long. The results are noticeable, and unfortunately for the leader, they make all subsequent decisions to remedy the situation all the tougher.
What doesn’t make sense to me
While I agree with several aspects of the book, more and more I find myself disagreeing with the overall implication that being good at leadership requires you to cultivate a hard edge. Maybe this is because I have built my personality on butterknives and people pleasing. But no, I do believe that one can navigate the hard moments of leadership without losing themselves to the grind.
In particular, I struggle with Horowitz’s take on peace time vs. war time and on the notion that the struggle is part of the job. To think that effective leaders must flip a behavioral switch between good times and hard times at a company suggests that leaders should become someone other than themselves. Yikes! Authenticity seems especially important during times of stress, rather than experiencing the Jekyll-and-Hyde of Peace Boss and War Boss, I think most people would prefer the reassurance that Boss-Boss will always be the same no matter what.
Will you have to do hard things as a leader? Yes. Do you have to be a different version of yourself in order to do them? I would hope not.
And as for the notion that the struggle is part of the job? Well, that may be true in a lot of cases—famously, statistically, starting your own business is a struggle, so too is pretty much every marketing leadership role as of 2020—but the implication that you better just resign yourself to struggling, Buster, is where it falls apart for me. You can always … leave the job. There are struggles for which you might be way more capable (see: success currency).
Balanced leadership takes: Collective Genius
If we accept that a big portion of leadership is doing hard things, I’d like to believe that there are a lot of ways to approach these hard things and to build a personal repertoire of sorts for how you deal with the drama. One of the ideas that I’ve found to be a good balance to the advice in The Hard Thing About Hard Things is the framework called Collective Genius. Harvard Business School professor Linda Hill came up with the concept, and what I love about it is that it counterbalances Horowitz’s fortress of solitude with a vision for a collaborative approach to tricky issues.
In Collective Genius, there are three parts to creating a community of workplace peers, C-suite teammates, co-founders, etc. who can help you innovate through troubled times:
Creative abrasion: Generating ideas through debate, disagreement, and diverse perspectives.
Creative agility: Testing ideas, learning through experimentation, and adjusting quickly.
Creative resolution: Combining competing ideas into better solutions instead of allowing one side to simply win.
So rather than go it alone with your hard decisions, sometimes you can rely on a team of others to help you through.
But wait, there’s more! Waaaaay more. The business book section is full of additional leadership perspectives. Some of the ones that I’m familiar with include:
The Trust Triangle by Francis Frei and Anne Morris
Jim Collins: Humility plus will
Psychological Safety by Amy Edmondson
Anything that Allison Stadd 🥁 writes on Substack
All make for excellent reading if you’re up for more books and articles.
In conclusion: The actual hard thing about hard things
Is leadership hard? Absolutely.
Is it hard for all of the reasons that Ben Horowitz and Linda Hill and everyone else list exhaustively? For sure.
But what I have found to be the hardest part of all is that sometimes, after you’ve worked your frameworks and enlisted your crew and pulled out all your inclusive and innovative leadership tools, a hard decision has to be made. And you’re the only one to make it.
And in times like these, rather than lose yourself to war time or inure yourself to emotion, you simply do your best, with the information you have and as the person that you are. And you’ll be okay.
But wait! There’s more…
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