The 4-Step Playbook on Adopting New Systems

 💡 Step 1: Choose thoughtful systems to implement.

Before rolling out any new process, take a step back and identify the real challenges your company is facing. What's actually broken? What needs fixing?

In my experience working with fast-growing startups, there are usually two main pain points that emerge:

1. First, information becomes siloed between departments and leadership. The CEO, who used to have a perfect pulse on everything, now feels anxious about missing critical updates. This is completely normal as you scale, but you have to solve it before it gets really messy and spins out of control.

2. Second, decision-making becomes cumbersome and takes too long. Too many people get involved in decisions that should be straightforward.

   In this case, the key is to reduce the number of stakeholders involved in decision-making, and focus instead on communicating the "why" behind a decision. Don’t fall into the trap of Design by Committee, too many cooks in the kitchen, or Crowdsourced Leadership.

   This requires deep trust in your team! So ask yourself again: Where is my team today? Can my CEO trust the people on the team? Can he/she let go of control enough to implement new systems?

Successful System Implementation: AngelList

When I was working as a Chief of Staff, I got the chance to produce this episode interviewing AngelList’s former CEO, Naval Ravikant.

In the interview, we focused the discussion on Naval not really wanting to be CEO because it was de-energizing for him. That was the problem at hand.

The solution, then, behind AngelList’s success, was hiring capable people (ex-founders) and giving them a lot of autonomy. If we’re discussing systems, AngelList’s solution to the problem was hiring capable people Naval trusted and keeping teams small - about 1-2 people.

After we did that interview, I remember reaching out and having a conversation with AngelList’s CTO Xinran Xiao to corroborate what Naval said. Was it true that small teams allowed them to continue executing at a high velocity, despite being a larger, more establish company?

Xinran confirmed this - he shared with me that AngelList relies on 1-2 person teams to maintain a high velocity. I also had a few other colleagues who worked at AngelList as ICs, and they all agreed it was their favorite part of working at the company (and why so few of them wanted to leave quickly.)

Naval started by identifying what problem they were trying to solve for, before choosing a solution. For them, fewer people making decisions = faster execution = more autonomy.

When choosing which systems to implement, start with the problem. Then, choose a system that actually addresses that problem head-on. Don’t just choose a system or solution because an article told you it’s the de facto way to run your company. Think critically about your company and the problem at hand.

Consider your company’s cultural values

When choosing systems and solutions, you also need to consider your company's cultural values.

For example, if you're an async-first workplace, your processes should reflect that - everyone needs to be comfortable with written and video updates. In fact, screen for this in your interviewing process: can you make the interview process as asynchronous as possible? Can you check for response times and writing clarity?

If async communication isn't sufficient, then implement structured meetings with clear agendas. I highly recommend checking out this write-up, Run efficient meetings that don't suck | Coaching Founder.

Finally, add teeth to your process - for example, if someone doesn't prepare materials ahead of time, they don't get speaking time during the meeting. (See more below on Step 4: Carrots and sticks.)

💡 Step 2: Create a memorable "Rule of One".

One of the most effective ways to drive behavioral change is to create a single, memorable rule that's so striking, your team can't help but think about it constantly. This approach comes straight from Ben Horowitz's playbook (as outlined in his book https://amzn.to/3E78Yse).

One of my favorite examples from Ben’s book is a16z’s famous "$10 per minute late" rule for founder meetings. The value they wanted to instill was simple: "We value founders' time." By making the rule almost outrageous, they ensured everyone thought about it (and more importantly, lived it.)

Of course, as you might have caught on by now - I love corroborating things I read and hear, to make sure it actually works. I remember talking with a friend and asking if partners really paid the $10 per minute late fee. The answer was an unequivocal “yes.”

Successful System Implementation: Startup, growth-stage, 70 people

(Keeping this company anonymous to protect them, but this is a real story!)

I once worked with a CTO at a Series D company who wanted his team to ship simpler solutions instead of over-engineering everything. The engineers who worked for him were utterly brilliant, but often would get in their own way by trying to find the perfect, elegant solution. This led to slower shipping speeds and code that was complex for the sake of complexity. From what I gather, this is actually quite a common problem for startups where the product is extremely complex, and requires brilliant engineers with extensive research backgrounds.

This CTO’s goal was to get his team to ship faster and try more things. He told me, “I wish they would ask themselves, ’How can I simplify this solution even more to ship faster and try more things?’”

I asked him, “Well, why don’t you turn yourself into a meme?”

If we’re following the Rule of One, one of the best ways to be memorable is by turning yourself into a joke. I told him, if he could use broken record strategy by making one of his default responses to his team, “How can you make this simpler?”, they would begin asking it themselves.

I encouraged him to turn himself into a meme, and told him if he was bold enough, he could print it out and put it all around the office. Here's what we created:

By the way - it worked. After launching the broken record strategy in every meeting, 1-1, and memo, in just two weeks, the team was shipping the way this CTO wanted them to ship. Behavioral change really can happen that quickly.

Make a memorable rule - even if it means making fun of yourself. :)

💡 Step 3: Lead by example with top-down implementation.

For any new system or process to truly take hold, it needs to start from the top.

Your CEO should be the first adopter, followed by the leadership team, before rolling it out to the rest of the company. This creates a powerful cascade effect where adoption becomes natural and expected.

In other words: your CEO has to be so insistent on whatever you want to implement, everyone else agrees that it’s the best modus operandi for the company.

It’s hard getting a CEO to give a shit about processes, especially if they’re allergic to processes. Many CEOs become CEOs because they hate bureaucracy. It’s not uncommon, therefore, for CEOs to think that you’re stifling the org or adding red tape by introducing processes.

Win them over by pointing out the issues you see, and what you intend to do about it. Then, make it ridiculously easy for them to adopt it. Do this by making as little work for them as possible.

You can do this by drafting clear, compelling messages for your CEO to send out - this makes it ridiculously easy for them to communicate the change, and importantly, it positions them as the driving force behind the initiative. Instead of you being a nagger, it now looks like the CEO is the one that cares about this, and you’re backing them up - rather than the other way around.

Successful System Implementation: CompanyOS

At my previous company, CompanyOS, we were selling complex enterprise software to companies that had as many as 5,000 employees in it. How could we get their teams to adopt our software en masse?

Easy. We made sure the leadership team of each of these companies used it first, starting with the CEO. We would then bring in other leaders one by one, where we created a natural tipping point where the tool became indispensable due to the sheer volume of important information being shared in the app.

Here's another powerful tactic: offer dedicated office hours for any new tool or process you're implementing. I witnessed this firsthand when Notion was still relatively new - we had a team member who held regular office hours to help people learn the platform. The company even offered a small stipend for employees who wanted to take additional courses to master the tool.

Free Office hours for Tool Adoption

At one of my earliest jobs, On Deck, Notion as a tool was new and most people didn’t know how to use it. As a result, I remember there was someone who held office hours teaching teammates how to use it effectively and powerfully. He was incentivized to get everyone onboard so we could have a single source of truth that was neat and organized. And on top of internal office hours, I recall several teammates purchasing courses to learn how to use Notion effectively.

So if the top-down implementation is tricky because it involves new tooling, dedicate resourcing to it in the form of office hours.

Pro tip: Many software companies offer free office hours or training sessions because they want to ensure successful adoption of their products. Don't hesitate to reach out and ask if they'd host a session for your team - they'll likely say yes if they're business-savvy! Some great examples include Superhuman, Coda, Notion, Vimcal, and many, many other tools. In fact, I’d encourage you to reach out to tools you love and asking if they’d come do a free office hour for your entire team. It would be a huge win for them, as it would mean more users and feedback for their product.

One important warning: avoid the temptation to hire a Chief of Staff or Ops person for every department just to drive adoption. At CompanyOS, this was something the CEO tried getting teams to do, and it was disastrous. This created unnecessary organizational bloat and too many people - and we all know that translates to inefficiencies and eventual layoffs.

💡 Step 4: Create rewards and consequences.

When implementing new processes, you need both positive reinforcement and accountability measures in place. I’ve written pretty extensively about Carrots and Sticks in this edition of Force Multipliers - check it out here.

I don’t want to re-write what has already been said, but I’ll highlight the most important takeaways:

• Use carrots to celebrate and encourage the behaviors you want to see more of. Two effective approaches I've seen work well:

  • Create dedicated Slack channels for shoutouts and recognition. When someone follows the new process exceptionally well, publicly acknowledge their effort. This not only makes them feel good but also shows others what success looks like.

  • Factor system adoption into performance reviews and promotion discussions. When someone consistently demonstrates they can adapt to and champion new ways of working, that should be celebrated and rewarded.

• Use sticks to discourage behaviors you don’t want to see and enforce consequences. While it might feel uncomfortable, having clear consequences is essential for driving real change:

  • Make process adoption a key component of performance reviews. If someone consistently fails to adapt to new processes, it should be treated as a significant area for improvement.

  • Tie career advancement to demonstrated ability to follow and champion processes. This includes things like proper goal setting, results-driven evaluation, and other key behaviors you want to see.

  Of course, you don’t want to force bureaucracy for the sake of bureaucracy. That’s why Step 1 above is so important - be thoughtful about the systems you choose! But if you choose them wisely, it should be a no-brainer for anyone to see that adopting it is, in fact, the best way to drive results forward for the entire company.

Want more operational content?

Check out Coaching Founder for over a dozen free, downloadable Notion templates to use at your company, and tons of write-ups on how to level up your execs, your teams, and yourself.

About Regina Gerbeaux

Shortly after her role as Chief of Staff, then COO, she opened her own coaching practice, Coaching Founder, and has worked with outrageously talented operators on teams like Delphi AI, dYdX, Astronomer, Fanatics Live, and many more companies backed by funds like Sequoia and Andreessen Horowitz.

Her open-sourced write-ups on Operational Excellence and how to run a scaling company can be found here and her templates can be found here.

She lives in the Pacific Northwest with her partner Lucas and dog Leia, and can be found frequenting 6:00AM Orangetheory classes or hiking trails nearby.