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9 Mar 2025 — Jan's Rules for Building Extraordinary Companies:

Bending Without Breaking: When Can You Relax the Rules?

Discover the art of balancing flexibility and discipline in your business. Learn when to bend the rules without breaking your company's foundation.

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The Tightrope Walk: When Does Discipline Bend, Not Break?

Running a business is a bit like walking a tightrope. You need unwavering focus, a steady hand, and a clear sense of direction. But even the most seasoned tightrope walkers stumble. The question isn’t whether you’ll wobble, but how you recover. At Skipa, we’ve seen countless companies navigate this balancing act, some gracefully, others… not so much.

I remember working with a media company once that was expanding rapidly. Their sales team was smashing targets, but their CRM system was a mess. Data was duplicated, leads were lost, and the whole thing was held together with digital sticky tape. The CEO, understandably focused on revenue, turned a blind eye. “If it ain’t broke, don’t fix it,” he’d say. Of course, it was broken. And when a competitor launched a more targeted campaign using better data, the cracks started to show.

The truth is, absolute, unwavering discipline is a myth. It’s unsustainable and, frankly, inhuman. The real challenge lies in defining acceptable lapses – those moments where flexibility trumps rigid adherence to the rules. It’s about understanding where you can afford to bend without breaking.

So, where do you draw the line? It’s a question every business leader needs to grapple with.

Let’s consider a software development team. They’re under pressure to deliver a new feature by the end of the quarter. To meet the deadline, they cut corners on testing. Is that an acceptable lapse? Maybe, if the feature is non-critical and the potential impact of a bug is minimal. But if it’s a core component of the system, the risk far outweighs the reward.

Or take a marketing team running a social media campaign. They accidentally post an outdated statistic. A quick correction and apology might be enough to smooth things over. But if they consistently fail to fact-check their content, it erodes trust and damages the brand.

The key is understanding the potential consequences of each lapse. What’s the worst that could happen? How likely is it? And what’s the cost of preventing it?

This is where a strong operational foundation becomes crucial. Clear processes, well-defined roles, and robust monitoring systems can help you identify and manage potential lapses before they escalate into full-blown crises.

Now, let’s think about this from a few different angles.

For those of you building rapidly growing companies, the temptation to prioritise speed over process is strong. You’re under pressure to deliver results, and every minute spent on documentation or training feels like a wasted opportunity. But remember, shortcuts often come back to haunt you. A little investment in infrastructure early on can save you a lot of pain later. Think of it as building a safety net for those inevitable wobbles on the tightrope.

And for those of you looking to acquire businesses, this is where due diligence becomes critical. Don’t just focus on the headline numbers. Dig deeper. Look for the hidden cracks in the operational foundation. Are processes well-documented? Are roles clearly defined? Are there any signs of corner-cutting or complacency? These are the red flags that can signal potential problems down the road. A thorough operational review can uncover hidden risks and help you negotiate a fairer price.

If you’re contemplating selling your business, now’s the time to address those areas where discipline might be lacking. Clean up your data, document your processes, and invest in training. Not only will this make your business more attractive to potential buyers, but it’ll also protect your legacy. You want to be remembered for building a solid, sustainable business, not one that was held together with sticky tape.

The rise of automation and AI is changing the game, too. These technologies can help you enforce discipline in areas where humans are prone to error. Automated testing, for example, can catch bugs that might otherwise slip through the cracks. AI-powered monitoring systems can detect anomalies and alert you to potential problems before they become critical. But remember, technology is just a tool. It’s still up to you to define the rules and set the standards.

Ultimately, finding the right balance between flexibility and structure is an ongoing process. It requires constant vigilance, open communication, and a willingness to learn from your mistakes.

So, what are the key takeaways?

  • Define your non-negotiables: Identify the areas where discipline is absolutely essential.
  • Assess the risks: Understand the potential consequences of each lapse.
  • Build a strong foundation: Invest in processes, systems, and training.
  • Embrace technology: Use automation and AI to enforce discipline and detect anomalies.
  • Learn from your mistakes: Treat lapses as opportunities for improvement.

Building extraordinary companies isn’t about achieving perfection. It’s about building resilience. It’s about creating a culture where people are empowered to take risks, learn from their mistakes, and continuously improve.

We’d love to hear your thoughts on this. What are your non-negotiables? Where do you draw the line? If you’re looking for help building a more resilient and disciplined organisation, get in touch. We’re here to help you build extraordinary companies that can withstand the inevitable wobbles along the way.