Leah's Leadership Guide - Part 5: Experimentation Culture
Making your team fail forward successfully
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I wrote an article on the topic of why Alignment is at the heart of every great leader; it was one of my most-read articles to date:
Leadership, to me, is about leading people in a given direction, not necessarily managing them. At the heart of it is the art of creating alignment and inspiring people to move.
While I think that every manager is, to some degree, a leader, not every leader has direct reports, and IC Leadership (leading without managing people) has been a huge unlock in my career to understand that you lead more people than you manage.
In this 5 part series, I’ll dive into each one of these critical components:
Experimentation culture (this article)
Part 5: Experimentation Culture
If you’ve stuck with me through storytelling, market knowledge, frequent communication, and personal growth, you’ve already got the foundation for strong leadership. But now it’s time to take it to the next level: a good experimentation culture.
This is where things get tricky. Most leaders know they should experiment, but few build a culture where failure is not just tolerated but embraced. After all, we are all hired to make changes, not to simply maintain the status quo.
Success is never the direct goal of an experiment or change. Learning is, in order to maximize our chance of success over time.
Does your team see it that way, too? They’re probably not convinced. It’s your job to show them (and not just say it) that failure in the name of learning is the real win.
So let’s get into it - how to define success, why it’s crucial to set expectations early, and how to balance moonshots with more achievable wins. This is how you turn an experimentation mindset into a superpower for your team.
Experimentation ≠ Guesswork
Fostering a culture of learning over winning
I’ve saved this for last because it’s the hardest to pull off and the one that most people struggle with – creating a culture of experimentation where failure is okay and encouraged when done in the service of learning.
In short, success is not the goal. Failure is how we learn, and learning is the goal. By learning, we succeed in the long run.
And even though you might know that, your employees almost definitely don’t or see it as a glossy marketing phrase.
As with so much else in this guide, the root issue that we’re solving for here is that we, as leaders, grossly underestimate how clear we’re being with our team.
You may think that, of course, running an experiment to improve your onboarding flows is not just about success or failure and mostly about what you learn through the process, but your team members/employees, whom you are responsible for, probably don’t.
So, being the rational upstarts they are, they’re going to assume that the only way to succeed is for an experiment or change to work. If it shows a positive ROI, they’re doing great. If not, everyone will look down on them.
Which is a perfectly logical thing to think! It’s also the safe thing to think, and the thing that we’ve all been taught is true in the workplace our entire lives - results matter, so if you mess up, you’re screwed.
Define success clearly, explicitly, and early
This is why it’s essential to define the goals and the success state of our experiments before they happen. I make sure to communicate this to my team along three main criteria:
Explicit - Is the success state clear and explicit?
Early - Is it shared before the experiments themselves?
Expectations - Are the expectations well-defined?
Explicit
Are you being clear and explicit about what success looks like for this particular project or initiative? Or do you think you’re being clear but your direct reports have no idea what you’re talking about?
A quick way to make sure here is to ask them back. “What does success look like for us in your words?” You’ll be surprised at how often people are not yet aligned with your vision or simple goals for changes you want to drive.
“We are testing X. Success means we learn Y, even if the outcome is Z”
Early
Have you shared your expectations ahead of time, or are you telling people after the fact that it’s actually no big deal that the thing you tried didn’t work? By then, it’s too late.
They’ve already got a story in their heads about failing and will see your statements as trying to make them feel better. This’ll make them lose trust in you and themselves.
A good practice is to celebrate well-prepared initiatives and experiments when they are launched (especially if you feel the preparation and execution were exceptional), and don’t necessarily wait till the results are in.
Expectations
In a classic B2B SaaS organization, the majority (>60%) of all experiments are going to fail. That’s okay. It’s the nature of things, and in bigger companies it’s even lower.
So why do we try things? Because of the outsized impact the successes will have. Those things compound. But your team has to understand this. How? By telling good stories that inspire them and make them feel safe and part of the team. We take risks when we feel safe to do so.
It is your job as the leader to create a sense of safety for the team, so that it’s not about the flat number of times we win and the individual changes, but the big picture.
If you want a deeper dive into the overall maths behind it, consider reading my deep dive:
Balance - Managing Risk without Killing Ambition
It’s easy to overindex on moonshots that are destined to fail. Some leaders are exceptionally visionary and always dream big. Others are too scared to try out big stuff.
Balance here is key – as a leader, you want to give your team the right challenges. It’s tempting to push for those lofty goals, but if you constantly hand out five tasks that are all long shots, you risk burning your team out when they fail over and over again.
Yes, we want to celebrate the learnings from failure, but it’s essential to strike a balance. Your team also needs smaller optimizations or easier wins to stay motivated. Successes, even smaller ones, build momentum. Without that, it’s just frustration on repeat.
As a leader, it’s your responsibility to watch for this frustration and step in before someone feels like they’re going to give up entirely. If your team is always failing - no matter how many times you tell them it's okay - they’re going to start losing their drive. They’ll stop going to the gym, so to speak.
Instead, give them a healthy mix of challenges. Celebrate the big things that land on slides for management, but also make sure to provide enough attainable goals to keep morale high. Success compounds, but so does failure, and it's up to you to find that balance.
My former mentor, Stephanie Schoss, summarized this brilliantly:
“Do good things, and talk about them.”
You’re not just their leader - you’re their coach and trainer. You’re there to help them to grow stronger and more capable over time. But just like any good trainer, you can’t throw them under a 200kg squat rack and expect them to do anything but break their back.
They need the right mix of big goals and achievable wins to stay motivated. It’s your job to guide them through both, to push them when necessary, but also to provide the realistic support they need to keep moving forward.
Only then will they hit their stride and start gaining real momentum.
A good mental model to balance is: 70% safe bets, 20% incremental, 10% moonshots.
“How do I know if it’s working?”
You will feel an energy of trust and a willingness to make mistakes that is shared by everyone on the team.
So what do you do when it’s not there?
Ask.
Just as you would with ICP customers or prospects, you need to have honest conversations with your team and understand what’s gotten in the way.
Nine times out of ten, it will be because of something discussed in this guide - expectations aren’t clear, they don’t think you have credibility, miscommunication, or simply past experiences that make them suspicious about “why should it be different now?” etc.
This is where learning in public and being okay with your own failures are so important. By modeling to everyone that you are okay with not being right, you show (not tell) them the same.
Without this show and living it out yourself, it’s hard to demand the same from your team.
Why you shouldn’t focus on success directly
I know there’s a Gary the Sales Guy inside you (he lives in all of us) that’s asking, “uhhhh, why not just focus on success? Isn’t that a faster way to, ya know, succeed?”
In our current market dynamics, the simple, high-reward, predictable tasks are already taken. The system rewards those who crack the code, leaving fewer low-risk, high-return options for the rest of us.
We must take big risks, and with big risks comes a higher likelihood of failure.
But the question is: have you accounted for this in your organization? If you treat big, ambitious bets the same as smaller, safer ones, you’re setting yourself up for disappointment.
Do you expect the same success rate from moonshot ideas as from incremental optimizations? If you do, you’re not giving your team room to breathe. You need to allow—and even encourage—your team to take bigger swings, with the understanding that they’re going to miss more often.
At Smallpdf, we made a point of being transparent about this. We attached success rates to our big initiatives when we presented them, often as low as 10-20%. It sparked the obvious question: "Why bother if we're likely to fail?" The answer is simple - the potential payoff makes it worth the risk.
But not everyone sees it that way. Conversations about risk and reward need to happen regularly. You can’t expect your team to suddenly embrace big swings if they’ve spent the entire year focused on precise, validated optimization.
You need to teach them how to think about risk, about failing often, and about how that’s okay, especially when the stakes are high.
Including failure scenarios to manage risk:
Have a mental decision flowchart on when to:
Pivot
Persist
Or kill a project
Formulate those when you work out a plan with your team for every bigger initiative by adding threshhold metrics: “If we can’t validate this initiative after 3 sprints, we will kill it.”
Best practice processes
“Failure is okay” is, at this point, probably an overused phrase; we need to back it up by showing how to fail in our processes (for instance, your post-mortems), keep those always:
Blameless
Data-Focussed
Action oriented
A playful way is also to have recurring fail nights where your team can share their most spectacular failed experiments.
Learning repositories
Sooner or later, you want to organize the learnings for your teams so they can have them accessible in the future.
At Microsoft, we followed this simple structure for documenting our experiments when they failed:
Hypothesis tested
Why it mattered
Failure root cause
One actionable insight
Try following these core principles when organizing them in a repository:
Single source of truth: Consolidate all knowledge (docs, videos, presentations) into one searchable hub. Bonus if you can put an LLM on top that has access to it. While it’s easy to discuss experiments in your internal chat tool like Slack, make sure that there is a recurring process that these insights don’t just rot away there.
Taxonomy: Manual or good AI - autotagging helps others to browse through learnings, even if they might not specifically know what they are looking for. We used a simple notion table at Smallpdf to organize our hundreds of experiments, and it did us good service.
Sunset ancient history: Everything around us changes with time. I try to occasionally just do spring cleaning by deleting or archiving stuff that has become irrelevant.
By time: Older than 12 months
Usage: Unused assets (never viewed in months)
Keeping a repository like this simple honors the limited bandwidth of your team and, in my mind, is a key responsibility for leaders because it usually falls through the cracks otherwise.
Summary
Empower your team to take calculated risks as long as they align on the upside
Impact is more important than win rate
Simple and accessible repositories make learning from failures easier
Celebrate insights from failures in recurring processes
If there’s one thing to remember from this part, it’s that failure isn’t the enemy. It’s part of the process. And as a leader, you have to foster an environment where your team feels safe enough to fail—and smart enough to learn from it.
What’s next?
Check out the other parts of this guide if you haven’t:
Experimentation culture (this article)
Sponsored by Attio, the CRM for the AI era.
Sync your email and watch Attio build a powerful CRM - with every interaction you’ve ever had, totally enriched and organized.
👉 Start your free trial today.
I’m going to add this as required reading in my LEAD program… fits right into Look & Leap… as a leader you have to take risks to show others it’s ok to fail.