Fail like an executive

A leadership role is a series of experiments, and most won’t work out

👋 Hi, it's Greg and Taylor. Welcome to our newsletter on everything you wish your CEO told you about how to get ahead.

I love giving “battlefield promotions” – bumping up rising executives who've earned increased responsibility and are almost ready for the next step up in scope and risk. Key word: “almost”.

What no one tells you is that your success means you will likely taste failure – more of it and sooner than you'd like.

It just comes with the territory:

• You have more scope, so more chances for things to go wrong

• You’re expected to take more risk to try new things

• You’re doing some things for the first time, so you will make mistakes

The key isn't to avoid failure. The key is to fail early, fail often, and get used to it. Trying to avoid failure entirely means you'll play it way too safe. It might have worked as an IC (where quality of work matters most); it won’t work as a leader.

So I want my rising executives to fail, learn, build resilience, and maintain the right attitude about it.

Here's how.

– Greg

Why VPs fail more than ICs

VP is the worst job in corporate America. It’s the first job where you’ve “made it,” but it’s brutal. You’re not “safe” like the C-suite, but you’re the one doing the real work – not them. When shit goes wrong, you’re the one working all weekend to fix it.

As you progress, three things change that make failure inevitable:

1. The stakes get higher. Messing up a client deliverable as an IC is a footnote. Losing a multi-million dollar client account as a VP can define your year.

2. The inputs get more complex. More stakeholders, more variables you can't control, more decisions outside your comfort zone.

3. You're expected to take bigger swings. Playing it safe isn't an option anymore. Innovation and growth require experimentation, and most experiments fail.

That's why your anxiety goes up, understandably. So to get good at it (and do it without losing your mind), you need a perspective shift.

Here’s the shift: you don't need it all to go right. Most stuff in business doesn't work out. You're not looking for a 1.0 batting average – you’re trying to get “good enough” across a portfolio of bets.

The portfolio approach to executive initiatives

The key to managing the anxiety of failure is to think of your job like a giant experiment. Each experiment (whether successful or failed) gives you more data about what actually works. At the end of every quarter, you want to be able to point to many different experiments you made and what they taught you.

Here’s what you should expect from your portfolio:

• 70% of experiments underperform (yes, you want to be taking enough risk that this many will fail)

• 20% meet expectations

• 10% are home runs

Don’t try to optimize for successful experiments – you’ll end up playing it too safe if you do that. Instead, optimize for making good, defensible decisions about your experiments.

How to experiment and fail productively

1. Change your mindset. Your job is to find out what works, not to make everything work. Thinking this way is very liberating.

2. Know the context. Not every number is essential to hit, or to hit exactly. In some companies, you can miss the plan by 10% and it doesn’t matter – in others, if you miss a target, you’re dinged. The key is to understand the context, and the consequences of hitting or missing a target or date. That helps you prioritize, and cascade down to your team what’s missable vs. unmissable.

3. Diversity your portfolio of experiments. You want a combination of small, medium, and large experiments running at all times. Don’t overweight large experiments – that puts your outcomes at risk, and people get fired for that. But don’t run too many small experiments either – some things won’t work if you don’t invest in them.

4. Communicate failures fast and clean. Own it, communicate it quickly and honestly with data and lessons learned. Never shade or bury bad results, and don't exaggerate good results either. The faster you communicate failure (or success), the faster you can move to the next experiment.

5. Short-circuit your ego. Your brain will be quick to turn a failure into a story about your identity. Short-circuit that tendency by asking someone for feedback and turning it into a moment of growth. “What did I miss?” “How could I have handled that better?” “Is there something I'm not seeing?” Speed matters here – the faster you ask, the more likely you'll be able to shift your perspective on what happened – and keep your inner critic in check.

6. Apply lessons prescriptively. Don't just say “we learned a lot.” Be specific about how those lessons will be applied in what comes next.

Good failures vs. bad failures

There’s a difference.

Good failures are:

• Fast and cheap (most of them – some take longer and cost more)

• Based on clear upside with a feasible chance of success (not delusional)

• Generating articulated lessons learned

Bad failures are:

• Single big bets that can break the quarter (I had a good friend who got fired from SAP – not for missing the number, but for putting the company in a position where one deal was make-or-break)

• Repeated mistakes that show a failure habit or pattern

• Failures where you didn't really do the work upfront

My advice

Your ego wants to turn every failure into a referendum on your competence. It wants to make you defensive, secretive, or blame external factors. But your ego is working against you.

Change your relationship with failure to lower your anxiety about it. Treat failure as data collection, not competency score.

When something doesn't work, your first thought should be “what does this tell us?”, not “what does this say about me?”

The faster you can make this mental shift, the faster you'll advance. Leaders who can fail without getting their ego bruised every time are the ones who take the right risks and learn quickly enough to stay ahead.

If you're experiencing major failures every other week, either your industry is fucked, your company is shit, or you need to adjust your approach. But if it's happening half a dozen times a year, you're probably taking the right amount of risk.

Have a great week,

Greg