Breaking The Bottleneck - Episode 5b: Cure For Established Companies with Low Tech - Documentation, Cross-Training, and the Broken Culture
This article is Part 5B of “Breaking the Bottleneck”, an 8-episode series on key person dependency risk and organizational resilience.
If you’re an established company (roughly 50–500 people) with low technology adoption, you already know your key people by name. Work routes through them. Decisions bottleneck around them. When they’re away, execution slows. And you’ve probably tried the standard fixes (“document more,” “cross-train,” “hire an extra person”) only to watch the organization snap back to old habits.
That’s because this isn’t primarily a tooling problem. It’s a behavioral and cultural one: job-security fears, low psychological safety, and incentives that reward heroics over system-building.
This episode is a cure strategy built for low-tech realities: how to stabilize risk without heavy platforms, how to communicate the change without triggering defensiveness, and how to make documentation/cross-training actually stick.
Previous episodes in this series:
Next episode: “Cure: For Established Companies with High Tech: Finding the Hidden Bottlenecks in Your Systems” is coming soon.
You have a problem and you know exactly who it is. There's a person (or a handful of people) without whom nothing gets done. Customers call them directly. When they're on vacation, the work stops. When they leave a meeting, people come to them asking "so what did that really mean?"
You've tried documentation but it didn't work. You've tried cross-training and it didn't stick. You've tried hiring more people, yet they still end up going to the key person.
Here's why: you were treating it as a technical problem when it's actually a cultural and psychological problem.
It's Not About Systems. It's About Trust and Safety.
Let's be honest: in an organization with entrenched key person dependency, several things are true:
People are afraid of job security. If they share their knowledge, they're replaceable. So they hoard information, even unconsciously.
There's low psychological safety. People don't feel safe admitting they don't know something, or asking for help, or making a mistake while learning.
The culture rewards individual execution, not system-building. Heroes are celebrated. People who build systems are invisible.
There's no incentive to share knowledge. Your performance reviews don't measure knowledge sharing. Your bonuses don't depend on it. Your promotions don't require it.
Leadership hasn't created the conditions for cross-training to work. There's no time, no resources, no follow-up.
Until you address these psychological and cultural issues, any technical solution will fail.
A documentation tool won't work if people don't trust it will be read, or if they fear being exposed in the documentation.
A cross-training program won't work if people fear losing their job, or if they're too busy, or if the person being trained isn't empowered to actually use what they learned.
You need to fix the culture first.
The Change Management Reality
Here's the thing about established companies: change is hard. People have worked a certain way for years and asking them to change creates resistance.
This is normal. Expect it.
The research is clear: 70% of change initiatives fail due to employee resistance. Organizations that successfully navigate change do it by:
Creating psychological safety so people don't fear the change
Communicating the "why" consistently so people understand what's changing and why
Engaging leadership visibly so people see leaders modeling the new behavior
Providing support and resources so people can actually succeed in the new way
Celebrating progress so people know they're on the right track
Maintaining patience because cultural change takes time
This is a 6-12 month process, minimum. If you expect to fix key person dependency in 90 days, you're going to fail.
Cure Strategy #1: Create Psychological Safety as the Foundation
Everything starts with psychological safety. Research is crystal clear: people are more likely to hoard knowledge when they have low psychological safety. They're more likely to share knowledge when they feel safe.
Psychological safety means:
I won't be punished or humiliated for speaking up
I won't lose my job if I admit I don't know something
I won't be blamed if I make a mistake while learning
My contributions are valued
Here's how leaders create psychological safety:
Model vulnerability. The leader admits what they don't know. "I don't have the answer to that. Let's figure it out together." This signals that it's okay to not know things.
Reward learning, not just performance. "I made a mistake, I learned from it, here's what I'm changing" gets the same recognition as "I nailed the delivery."
Create a blameless approach to failure. When something goes wrong, the question isn't "who's to blame?" but "what can we learn?" This removes the fear that honest communication will be used against people.
Ask for input and act on it. When you ask people "what do you think?" and then ignore their input, you kill psychological safety. Listen. Incorporate feedback. Show that you changed something because of what people said.
Be visible and accessible. Leaders who hide in their offices kill psychological safety. Leaders who are visible, accessible, and listening create it.
Ensure equitable treatment. If some people are treated as "special" and others aren't, you kill psychological safety. Fair treatment is non-negotiable.
This takes time. You can't create psychological safety in one meeting. But once you commit to it, people feel it.
Cure Strategy #2: Address the Psychological Barriers Head-On
People are resisting knowledge-sharing for a reason. Not because they're mean, but because they're trying to protect their security. Address this directly.
In group communications:
"We're changing how we work. We need knowledge to be documented and shared. Here's why: because no one should be irreplaceable. If you get hit by a bus, the company should keep running. That means we need to know what's in your head. This isn't about replacing you, it's about making you more valuable. Once your knowledge is distributed, you can work on bigger, more strategic problems. You become a leader instead of an executor. We need both, but we need you to scale."
This reframe is important: sharing knowledge makes you more valuable, not less valuable.
In one-on-ones, listen to fears directly. What are people worried about? Job security? Looking stupid? Losing status? Address each fear.
"If I train someone else to do my job, won't I become irreplaceable?"
"No. When you train someone else, you become more valuable. You become a leader who develops people. That's a higher-value role. Your job isn't to be the only person who can do the work. Your job is to be the leader who makes sure the work gets done, whether you're doing it or not."
Provide concrete reassurance:
Document what the role actually is (and it's not "be the only person who knows the thing")
Show clear career paths for people who develop and scale
Make "developing other people" an explicit part of job descriptions and success criteria
Reward people who share knowledge and develop teammates
Cure Strategy #3: Get Leadership Visibly Committed
This is critical. If the CEO says "we're going to fix key person dependency" and then the CEO doesn't change their own behavior, nobody will believe it.
What does leadership commitment look like?
The CEO/Founder stops being the bottleneck. They delegate. They trust people to make decisions. They don't override decisions just because they would have made a different choice.
Leadership openly admits their own knowledge gaps. The CEO admits, "I don't understand the technical architecture. I'm going to spend time with our tech lead to learn." This models learning and knowledge-seeking.
Leadership visibly uses the new processes. If you're asking people to document their work, the leadership team documents their strategic decisions. If you're asking for cross-training, leadership participates in it.
Leadership allocates resources for the change. Time for documentation. Time for cross-training. Training budget. People see this and know it's real.
Leadership celebrates knowledge-sharing. When someone shares knowledge publicly, when someone develops a teammate, when someone documents a critical process—leadership notices. Recognizes it. Celebrates it.
When people see leadership changing, the resistance starts to crack.
Cure Strategy #4: Implement Documentation That Actually Works
By the way, your old documentation effort probably failed for a reason. It felt like busywork. Nobody read it. It got outdated immediately. Do it differently this time.
Start small. Don't try to document everything. Pick the top 5 critical processes. Document those. Do them really well. Then expand.
Make documentation part of daily work. The engineer solving a problem documents how they solved it. The salesperson who closes a deal documents the approach. The operations person who figures out a shortcut documents it. It's not "special documentation time." It's just how work gets done.
Use a template so it's easy. Not a blank page. Here's the template: Problem, Approach, Solution, Next Time. Fill it out in 5 minutes.
Make it dead easy to find. One place. One system. Not scattered across email and Slack.
Assign someone to maintain it. Someone reviews documentation monthly. Is it accurate? Is it being used? What needs updating? This prevents it from becoming a graveyard.
Make it a criterion for job performance. "Did you document your critical work?" is part of the evaluation.
Once people see that documentation is being read and used, they become more motivated to create it.
Cure Strategy #5: Implement Cross-Training the Right Way
Your old cross-training probably failed because:
People were too busy to train anyone
The trained person didn't actually use what they learned
There was no follow-up
The original person felt threatened
Do it differently.
Make cross-training a dedicated, time-boxed effort. Not "in addition to your normal work." Actual time allocated. 4 hours/week for 12 weeks, for example.
The person being trained is 100% focused on learning. Not doing their normal job while trying to learn. Actually focused.
The person teaching is rewarded for teaching. Their performance is measured partly on whether they successfully transferred knowledge.
Create accountability. "By the end of 12 weeks, you will be able to handle X, Y, Z independently." Not vague. Specific. Measurable.
Provide ongoing support. After the training ends, the original person is still available for questions. The trained person has regular check-ins. It's not "train once and you're done."
Create a feedback loop. "What was confusing? What did I explain poorly? How can I improve the documentation?" Learning goes both ways.
Do this for at least 2 people in critical roles. Don't cross-train just one person. That doesn't eliminate the dependency; it just creates two bottlenecks.
This takes real time and resources. But it actually works.
Cure Strategy #6: Address the Workload Reality
Here's a hard truth: many key people are key because they're working 60 hours a week and everyone else is working 40. You can't fix key person dependency without addressing workload.
The questions to ask:
Is this person overloaded? (Probably yes.)
If they're overloaded, why? (Insufficient staffing? Inefficient processes? Wrong priorities?)
What could be automated? What could be delegated? What could be eliminated?
Sometimes fixing key person dependency means hiring. If one person is doing the work of 2 people, hire another person. Not so they both do the same work, but so the work is distributed.
Sometimes it means streamlining. The sales process is too complex. The approval process has too many steps. The customer onboarding takes too long. Simplify.
Sometimes it means saying no. Not everything is a priority. What are the few things that matter most? Focus on those. Let other things go.
If the key person is overloaded and nothing changes, they will leave or burn out. You have to address this.
Cure Strategy #7: Communicate the Change Story Consistently
Change fails when the communication is inconsistent or unclear. Tell the story.
"Here's where we are: we have people who are indispensable. That's great because they're valuable. It's scary because if they leave or burn out, we're vulnerable. Here's where we want to be: a company where knowledge is distributed, where people are cross-trained, where anyone can take a vacation without the company falling apart. Here's what we're changing: we're implementing documentation, cross-training, and redundancy in critical roles. Here's why: because we need to be resilient. Here's what I need from you: participate in documentation, help cross-train teammates, be open to learning new things."
Tell this story in multiple ways:
All-hands meeting
One-on-ones
Written communication
Regular updates
Tell it over and over and over. You'll get tired of saying it. Then people will start to believe it.
Be honest about the timeline. "This is a 6-month journey, not a 30-day project. Here's what we're doing month by month. Here's how we're measuring progress."
Celebrate progress. When someone documents something critical, celebrate it. When someone successfully transfers knowledge to a teammate, celebrate it. When the team solves a problem without the key person, celebrate it.
Cure Strategy #8: Set Up Middle Management as Change Agents
Middle managers are critical. They're the ones closest to the work. If they buy in, the change works. If they resist, it dies.
Empower middle managers:
Give them training on how to coach people through change
Give them talking points for their teams
Give them authority to hold their teams accountable
Give them support when they're struggling
Make them responsible for change in their teams:
Are people documenting their work?
Is cross-training happening?
Is knowledge being shared?
Are we reducing dependency on key people?
Support them visibly.
If a middle manager is struggling with change resistance on their team, the senior leader helps them. Sits in on a meeting. Reiterates the message. Shows support.
The Timeline for Cure
This isn't quick.
Months 1-2: Build psychological safety, communicate the vision, establish team buy-in
Months 2-4: Begin documentation, start cross-training pilots
Months 4-6: Expand documentation and cross-training, address resistance as it emerges
Months 6-9: Consolidate gains, handle the people who are still resistant
Months 9-12: Sustain and deepen the changes, prepare for the next phase
By month 12, you should see:
Documentation that's actually being used
Cross-trained people who can handle critical work independently
A culture where knowledge-sharing is normal
Reduced dependency on key people
This is still an ongoing process. But after 12 months, you're no longer in crisis mode.
Expect this pattern:
Months 1-2: Initial enthusiasm. "This is a good idea. Let's do this."
Months 2-3: Active resistance. "This is taking too much time. We're not getting anything done."
Months 3-5: Frustration. People are tired of the new way. Old habits are tempting.
Months 5-7: Breakthrough. People start seeing results. The documentation is actually being used. The cross-trained person successfully handled something. People start believing.
Months 7-12: Integration. The new way becomes normal. New hires are onboarded into this way of working.
This is normal. Don't panic when the resistance phase hits. It means it's working.
Key Takeaways
✓ Start with psychological safety, not systems
✓ Get leadership visibly committed to changing their own behavior
✓ Address the psychological barriers directly: people fear job loss, not documentation
✓ Implement documentation that's part of daily work, not special projects
✓ Cross-train properly with dedicated time, accountability, and follow-up
✓ Address workload reality: you can't fix bottlenecks if people are overloaded
✓ Communicate the change story consistently, over and over
✓ Empower middle managers as change agents
✓ Expect a 6-12 month timeline for real cultural change
You can fix this. It takes commitment and time, but you can fix it.
Ready to assess your company’s organizational health?
If you want help evaluating how well your company is currently dealing with key person dependency, I offer a free assessment for founders and leadership teams:
About Francesco Malmusi
I’m Francesco Malmusi, founder and C-level operator. I help CEOs, founders, and COOs reduce key person risk and rebuild execution capacity, especially in established organizations where the problem is already entrenched.
My work focuses on the intersection of operating model, culture, and incentives: making knowledge sharing safe, sustainable, and measurable without requiring heavy technology programs that the organization won’t adopt.
