I’ve supported several companies – and the people leading them – through that sometimes horrifying yet exhilarating phase between startup and scale-up.

What I’ve seen again and again is this: when you simply add more people without evolving how people work together, you end up magnifying chaos in parallel with the growth.

That’s why I like the phrase upscaling chaos. Nobody wants that, yet many companies do it unintentionally – because what once worked so well suddenly stops working, and they don’t know why.

In this article, I’ll share what I’ve witnessed firsthand across multiple Czech and European startups – including Runecast, Avast, and others – and offer practical steps to help leaders avoid scaling their problems along with their organizations.

The scary but necessary shift

When your startup has 10 to 30 people, everything feels fast, flat, and informal. You don’t need many processes, as everyone wears a lot of hats and just jumps in to get things done.

That works beautifully for a while, almost like magic. But once you start hiring beyond your immediate circle, more specialists and fewer generalists, the informal approach quickly breaks.

Growth inevitably brings new hires, new layers of complexity, and new expectations and requirements. Suddenly, you’re not all in the same meetings and Slack channels. Decisions start happening in ad-hoc chats that nobody documents (and often in team members’ native languages, rather than in English). 

Roles overlap, ownership blurs, and generalists become too busy to jump in and help wherever needed.

Meanwhile, specialists are unable to jump in and help wherever needed (more on this later), and ‘hot potato’ tasks end up bouncing from person to person, sprint to sprint, quarter to quarter… until they are neglected entirely.

Founders often resist the formalization that this stage demands – calling it ‘bureaucracy’, for example, and saying things like “We need to keep a flat hierarchy,” or “We don’t need processes; we should stay agile.” But without deliberate structure, chaos scales faster than clarity.

How we scaled without the chaos at Runecast and Avast

I’ve seen this pattern repeatedly, including during my time supporting Runecast’s growth journey. When I joined in 2019, the company had just over 20 people – still naturally operating with that ‘everyone wears multiple hats’ mindset. 

As we grew (during a global pandemic!), and both our software and our GTM strategies matured greatly, and our hiring approach became fully remote, we had to rethink how we made decisions, how we communicated, and how we aligned new job functions around shared goals (read more in On Helping to Build Runecast (Acquired by Dynatrace)).

What keeps a startup grounded when transitioning to the scale-up phase is a unifying purpose. For Runecast, it was to be a leading CNAPP security vendor by 2025 (which we had also further defined).

For Avast, it was to beat AVG (in number of global active users). These were clear directions to qualify every decision we made or process we introduced. 

At Avast, we would regularly ask each other, “Is this helping us beat AVG?” That clarity of purpose is what allows you to scale sustainably without losing your original spark. It enables you to think two or three years ahead and consider what challenges your larger team might have with the many workarounds that you think are ‘smart’ today.

Two common reactions – both dangerous

In supporting startups, I often see two opposite but equally risky approaches that impede scaling:

  1. Keep doing everything informally, trusting that the early magic will somehow scale. It doesn’t (at least not in the way anyone expects).
  2. Overcorrect into rigid, top-down bureaucracy, killing creativity and agility.

As in most aspects of life, the ideal is somewhere in the middle. Scaling well means adding structural stability and ensuring clarity – while simultaneously protecting flexibility, autonomy (via trust), and a culture of human connection.

Nine essential steps for scaling effectively

As companies move from startup to scale-up, it's crucial to focus not just on growth, but on creating systems that support sustainable success. 

In this section, I’ll share nine practical strategies that can help you build a strong foundation for scaling – avoiding the pitfalls of chaos and ensuring your organization remains focused, efficient, and agile as it grows.

1. Document everything (before you think you need to)

One of the biggest myths in young companies is “We all know how we do things.” That’s true – until a new hire doesn’t know.

Documentation isn’t just for compliance or audits; it’s the backbone of organizational memory. Write down decisions, meeting notes, role definitions, and even mundane operational details.

It doesn’t need to be formal. A shared drive or internal wiki with logical folder names and simple version control can save hundreds of future hours annually. 

When someone asks, “Why did we decide on this?”, you should be able to point them to a document or page rather than them asking around until they learn who might have been involved and then having to rely on that person’s memory.

Documentation is for the future. In the same way good parents imagine their children as adults when considering how to raise them, a good business leader will imagine how future colleagues might be impacted by goals and decisions made (and hopefully documented) today. This applies to any internal knowledge. 

Maybe your whole three-person Marketing team knows how to publish a new webpage, but everyone will still benefit from a simple “Web publishing QA checklist” page added to Confluence.

It’s much more efficient to share a page or document link with someone than to schedule yet another meeting and have to explain the same things again and again. Write it down, share it, keep it current – and make sure it’s all in English. Future-you (and future hires) will thank you. 

2. Make meetings matter or cancel them

Few things impede scale-ups more than meetings that suck away our expensive time and don’t produce outcomes. We all know a person who can turn every small obstacle into a huge problem, which must then be ‘solved’ with a series of 27 meetings, 12 Confluence pages, and five new processes...

These simple habits can help to mitigate this risk:

  • Always do the math: Inviting 15 people x 45 min = 11.25 work hours (now calculate the salary cost of this!).
  • No agenda? No meeting: It’s about efficiency and professional respect for everyone’s time.
  • Rotate facilitators to encourage leadership and more engagement.
  • Aim for efficiency: With a little focus, you can make 25 minutes the default meeting length, not 60.
  • Capture and share outcomes immediately (see “Document everything” section).
  • Audit recurring meetings quarterly: If they’re not adding value, stop them ASAP with a brief explanation (e.g., “For better efficiency, we’re making this series a weekly status update in Slack”).

During a workshop, I once asked participants: “If you canceled 30% of your meetings, what would break?” The laughter that followed was telling – because everyone knew the answer was nothing.

Meetings should have one of three purposes: alignment, decision-making, or unblocking. If your meeting doesn’t clearly serve one of those, it’s likely just a habit or worse… political (company politics limiting teams from within is a far bigger threat than external competition).

Here are some simple topics to add to your meeting agendas, to help keep them creative, productive, and apolitical:

  • Updates: Share key progress, wins, or challenges from the past week.
  • Strategic goals: Review where we are, next priorities, and upcoming tasks.
  • Feedback: Discuss observations, give and receive feedback.
  • Support: Discuss any blockers or areas where additional help is needed.
  • Action items: Clearly define next actions required to keep things moving forward.
  • Professional development: Check in on growth or learning goals.

I’ll close this section with some favorite quotes that I’ve accumulated from meetings over the years:

“This isn't a company; it's an arrogance contest.”
“It sounded like nonsense.”
“The survey results show that we have the highest problems in 'problem solving', so I think we should focus on problem solving insights in the survey.”
“Actually, there is no point three – the less we explain about this, the better.”
“It may not be fully accurate, but if it's at least consistently inaccurate, that's probably good enough right now.”
“To tell you the whole story, the people who made the deal with you have all left the company.”
“Oh goodie, we're about to learn that our customers are... a) human, b) have electronic devices, c) live somewhere on planet Earth.”
CEO (in a Q4 meeting): “You promised this back in July.” 
Head of R&D: “Don't dwell on details, this is a high-level meeting.”
Me to a CEO after 14 feedback rounds: “How many more times are we going to do this?”
CEO: “How many more times are you going to bring it back to me?”

3. Build a real feedback culture

As companies scale, distance grows between teams, levels, and perspectives. Regular feedback is the bridge that keeps trust intact. And trust is the grease that lubricates every company mechanism – not only with customers and channel partners, but also (and especially) internally.

I’ve facilitated feedback sessions where we followed a simple format such as “I saw, I felt, we need...” The power of that phrasing lies in how it centers behavior and impact (not blame) and transitions personal observation/impact into the needs of the whole team.

Effective feedback is:

  • Real-time, not quarterly
  • Specific and kind, not vague or personal
  • Two-way – leaders ask for and model how to receive feedback, not just give it

Organizations that normalize open, constructive feedback tend to scale more smoothly because small issues don’t have a chance to develop into big ones. 

The SCARF model (Status, Certainty, Autonomy, Relatedness, Fairness) is an example of a framework that can help teams explore and understand why feedback often feels scary or threatening.

Once teams see the psychology behind their emotions, feedback becomes less about individual ego and more about continuous improvement of the collective whole.

In my experience, conflicts that stem from mismatched expectations usually have their roots in poor communication, especially when the value of each person’s knowledge, experience, and skills isn’t fully appreciated.

Conflict resolution experts will tell you that this is also a primary factor behind the vast majority of geopolitical conflicts. My recommended approach to rectify this:

  • Be open about the pressures you face – with more ownership and admission of honest feelings about a given situation.
  • Approach discussions as dialogues, not debates.
  • Try to always state a clear agenda and the ideal expected outcome of any formal conversational exchange.

4. Leadership must evolve (or get out of its own way)

One of the most challenging transitions that I’ve witnessed for founders and early executives is learning how and when to let go.

In a startup, the products are like the founder’s babies. New hires are like babysitters, who must first earn trust before being left alone with the children. It might sound cute, but that mentality is a major bottleneck for any scale-up.

Leadership must shift from doing or being involved in everything to enabling everyone:

  • Delegate with purpose and trust your people.
  • Evolve middle leadership – the unsung heroes of scaling.
  • Be completely transparent about decision-making and priorities.
  • Model the behavior you want others to adopt – e.g., accountability, feedback, documentation.

If employees trust you to lead the company, you have to trust them to do their work. If you don’t trust them to do what you hired them to do, then they naturally won’t trust your leadership.

Budgets are a great example of this. I once wrote in my weekly report: “We're wasting so much time looking at small investments in so many different ways, that it will likely cost 3x as much as initially proposed, simply due to the salaries involved in the time it takes to make a decision and actually do something.”

Set and agree on a budget, then trust the people you’ve hired to leverage that budget the best way possible.

At Avast and Runecast, for example, the founders stayed accessible and engaged – but they also learned to empower functional leads to own the expected outcomes. That balance of autonomy and support made a huge difference in morale and internal efficiency.

I remember the moment that one leader at another company realized this on his own and said to me, “That’s a classical ‘I stand in my own way’ problem.”

And when you find yourself playing ‘hot potato’ with responsibility, it’s probably a signal that priorities, ownership, communication, or even roles or teams need realignment. Yes, we all see warnings written about how companies sometimes reorganize because they don’t know what else to do, but in the startup-to-scale-up transition, occasional reorganization is a must. 

When whole new teams and job functions get added (e.g., HR, QA, BI), it changes operational dynamics in a major way – and that evolution should be reflected in how teams and roles are defined.

5. Hiring for a scale-up, not a startup

Scaling isn’t just about adding people; it’s about adding the right mix of people.

Early on, startups often thrive with generalists – flexible, self-motivated entrepreneur types who cover any gaps, thrive in ambiguity, and get things done. These are ‘MacGyvers’, the multi-purpose tools you would want with you in a post-apocalyptic hellscape. 

As the company matures, you need to find specialists who can deepen expertise, build systems, and train others – and somehow achieve a new balance between them and the generalists.

It also helps to openly discuss and define two clear career tracks for teams: manager (for those who lead people and/or drive projects) and expert (for those who lead through greater depth and innovation) – both are essential. Generalists often make better managers, and specialists better experts, though there can definitely be exceptions.

Sometimes, founders need to “get out of their own way” by hiring (and listening to) experienced scale-up leaders who’ve been through this phase before.

Your company is a growing business that must compete in a market that will not wait for you to catch up – so even though leadership should improve over time, you cannot afford to be a ‘school’ for anyone learning leadership from scratch. Hire the best people, then do anything you can to empower them.

6. Think global (and modular) before you think you need to

Many companies wait too long to ‘go global’. They build everything for their home market, often in a local language, and then try to retrofit later.

Instead, build modularity from the start – in processes, communication, and culture. That doesn’t mean being more ‘corporate’, it means creating frameworks that can scale across borders, languages, and time zones.

As someone who’s spent over 15 years helping European companies expand globally, I’ve seen how early cultural awareness and documentation of decisions can either enable or slow expansion efforts.

Thinking globally means more than translating your website, brochures, and employment contracts – it’s about risk mitigation, designing your organization’s operations in a way that ensures cultural differences and geographical distance don’t hinder your progress.

7. Evolve marketing into a strategic partner

Scaling also requires marketing to mature beyond mere intuition and the HiPPO (highest-paid person’s opinion). For scale-up growth to be more intentional than reactive, marketing should be included as a strategic partner rather than being thought of only as an in-house agency or support function.

  • Involve marketing early in product R&D – not just as an afterthought a couple weeks before a launch.
  • Involve marketing in customer success efforts – it will help prevent churn and aid revenue generation (renewals, upsell, and cross-sell).
  • Define your ideal customer profile (ICP) early – not just demographics, but motivations, challenges, and buying dynamics.
  • Clarify your 5Ws/1H – Who you’re talking to, What value you provide, Why it matters, When and Where it’s relevant, and How they take the next step (your CTA).
  • Maintain messaging consistency across regions – local nuance is good (e.g., transcreation beats localization for conversions), but brand coherence remains essential.

Marketers should schedule regular feedback sessions with account executives and really listen to whatever speedbumps they encounter throughout the funnel.

At Whalebone, after I heard the same challenges repeated a few times, to proactively counter those challenges, I developed a DNS4GOV Onboarding Guide – which demystified the process and accelerated time to proof of concept. Salespeople are a marketer’s goldmine.

As marketing functions notoriously either get blamed or don’t get credit, you can help to preemptively counter such stereotypical patterns by sharing regular updates about successes, observations, changes, or challenges in marketing trends with other teams.

8. Align people, metrics, and incentives 

I’ve seen OKRs used brilliantly or merely turned into complicated spreadsheets that nobody looks at again – until they need to create them again for the next quarter. The difference is intent and maintenance. Organizations that approach OKRs as ‘set it and forget’ OKRs are doomed.

Keep your OKRs…

  • Simple: Start with three meaningful objectives for the company – and for each team, three that support those company objectives.
  • Aligned: Every job function should be able to explain how their goals support the company’s goals.
  • Dynamic: Review regularly; it’s okay and encouraged to make adjustments based on a changing reality.

In my article A Simple but Effective Approach for Planning OKRs & Making Them Stick, I emphasized that OKRs must be owned by teams, not imposed by leadership. They should tell a story of where you’re going together, not just serve as quarterly bureaucracy.

9. Beware the ‘best practices’ trap

One of the biggest forms of company self-sabotage that I’ve observed hides behind best practices. When leaders say “we follow best practices,” they often mean “we’re afraid to think or do things differently.” But ‘best’ depends entirely on context: your stage, your culture, your market, your moment in time.

So whenever someone suggests following best practices, ask:

  • Why is this ‘best’ for us right now?
  • What assumptions is this based on?
  • Which aspects should we adapt or discard?

Scaling successfully requires open and discerning minds, not dogma. There's a now-famous declassified 1944 CIA sabotage manual that includes a list of methods that the CIA recommended for sabotaging organizations. In my article How Companies Self-Sabotage with ‘Best Practices’, I listed my top picks of the list that reflect ways that I have seen companies sabotage their own operations over the years.

Scaling is a human process

At the end of the day, scaling isn’t just about funding rounds, strategy decks, or headcount. It’s about people – how we connect, communicate, work together, and trust each other as the company evolves.

I’ve supported enough organizations through this stage to know that chaos doesn’t simply disappear with growth but rather compounds – unless you build the structures and habits to contain it. 

So, before you hire your next 20 people or open that next office, stop and ask, are we building with clarity… or are we upscaling our chaos?