9 out of 10 Tech Problems are Actually People Problems

Ninety percent of the chronic “technology problems” I see in organizations are actually people problems. That might sound glib, but it’s a pattern that’s emerged over decades of building, scaling, fixing, and now coaching technology organizations. Sure, code can be broken, architecture can be faulty, and tooling can be bad, but all of that is acute and fixable. Even tech debt can be maintained and eliminated with the right program. 

But when I walk into a company that’s “plagued by tech issues,” it is almost never the technical nuts and bolts that are the true challenge. Companies rarely work on something so complex or cutting edge that the actual technology is the crux of their efforts. The real problem is almost always leadership, culture, and how people work together.

The State of Most Companies

More than 80% of technology work is built on repeatable practices. It’s like law: most of law  is grounded in case law. Sure, there are new rulings and edge cases, but you’re standing on decades of established precedent. Engineering is similar. Most software development is a blend of tried-and-true engineering practices and some greenfield innovation layered on top.

The companies that are revolutionizing AI or building net-new technologies may need to confront new technical frontiers, but most other companies just need to adapt what is known and established to their own use cases. If a company consistently struggles with this, it is usually not a crisis of functional technology. Instead, it is a crisis of functional leadership.  .

The symptoms of this type of crisis show up in familiar ways:

• Willy-nilly promotions. People get elevated into leadership roles because they were there early, or because they’re great individual contributors, not because they can actually lead.

• Managing through fear and insecurity. Leaders with sharp elbows, who micromanage, interrupt, and dominate every conversation. They lead through fear. There’s no quicker way to drive out good people.

• Learned helplessness. Teams that say, “Yeah, that’s broken. Too bad. Not my problem.” Challenges turn into permanent roadblocks instead of problems to be solved.

• Chronic issues that never get fixed. The same outages, the same performance problems, the same bugs, again and again.

I’m not saying good companies don’t run into these symptoms. Of course they do. But they fix them, measure them, learn, and adjust. When the same symptoms keep resurfacing for months or years, that’s when you know you have crossed into the world of leadership problems rather than tech problems. 

Questions I ask about a struggling tech leader

When I work with a struggling company, I start with some simple questions about the technical leadership:

1. Are they self-aware? Do they know what they don’t know? Are they coachable? A good tech leader needs the humility to recognize gaps in their knowledge and also needs the curiosity to close them.

   
   

2. Do they have deep intellectual curiosity? One of my favorite quotes is from Tiger Woods: "No matter how good you get, you can always get better, and that's the exciting part. I believe any great leader should embrace that mindset. If a technology leader is stuck in “expert mode,” that’s a likely sign that chronic problems are present.

   
   

3. Are they toxic? That might sound harsh, but you know it when you see it. Leaders who interrupt constantly, who don’t listen, who take over the conversation halfway through your sentence. Leaders who use fear to control. Those behaviors are deeply ingrained. In my experience, those people rarely change in a meaningful way.

The first thing to know about addressing “people problems” in an organization is this: there are some people whose behaviors are so deeply rooted that they aren’t worth investing time in. These people should be let go, and sooner as opposed to later. This may sound harsh, but understanding this opens up much more bandwidth to work with the vast majority of people who can and will change. 

Most people are salvageable (if they want to be)

Despite the harsh truth above, my rule of thumb is that most people are salvageable.

From both a human and business perspective, I like to assume most people are inherently good. Maybe that’s naïve, but I’ve had enough success turning problematic people around as a leader and a coach that I still believe it. These people just need a firm but kind hand. 

One example of this was a brilliant, architect-level engineer I worked with. Technically, he was as good as they come. And yet no one wanted to work with him, because he generally didn’t listen to other people’s ideas and was insistent on his way

As a result, other teams would not bring their issues to him and the organization as a whole faced regular architectural issues that could have easily been prevented if other people felt comfortable working with him. 

Once I realized this, I sat him down and said, essentially:

“Look. No one wants to work with you. You’re great at your job, but strong companies are made up of strong teams composed of strong individuals. Lone wolves lead to weak teams. If people won’t work with you, I’m not going to keep you. No matter how good you are.”

To his credit, he didn’t get defensive. He said, “Okay, give me some examples. What can I work on?”

So we got to work on:

• Being a good listener.

• Thinking before responding instead of shooting from the hip. 

• Having constructive conversations.

• Aiming for consensus when possible.

• Embracing the team concept rather than being the smartest person in the room.

Six months later, his team’s feedback had shifted. A year later, everyone wanted to work with him. He had the technical chops from day one, but now he had the behavioral capability to match. He went from being a net negative to being a major asset to the company.

Coaching his behavior change was absolutely a lot of work, but it was far less costly than replacing him. However, if we hadn’t been successful, we would have had to face the cost of replacing him even after we had invested in coaching. 

That’s why, when a leader shows even a glimmer of willingness to change, I advocate for a trial period—typically a three-month coaching or mentoring engagement focused on specific behaviors. If you see positive changes, keep investing.If they don’t, say goodbye. But, if there is no willingness to change from the start, it is best to just end things. 

Very few people are truly unsalvageable from the outset, but you need a hypothesis on whether or not they will change, a time-bound experiment, and clear expectations. 

The true cost of “just firing them”

Though I am an advocate of firing fast when there is no other way, you can’t just fire everyone that struggles a little bit. From a human perspective, it is unfair, and from a business perspective, it is overly costly. 

When you terminate someone, you’re usually taking on:

• Severance cost

• COBRA or equivalent benefits costs

• Human cost (both to the individual, as well as to the rest of the team)

• Replacement cost, including:

  • Writing a new job description

  • Engaging a sourcer or recruiter

  • Multiple rounds of interviews and resume review

  • Your time and your team’s time spent interviewing instead of executing

The more senior the role, the more all of these factors end up costing.

In a best-case scenario, filling a senior role takes three months. In reality, it’s often six to nine months. That’s six to nine months without a fully contributing leader in a critical role, which translates to a loss in productivity and value creation, which is another cost. 

As a result, even a difficult person is usually worth making an investment in for change if there is any hope at all.

There are exceptions, of course. I’ve absolutely seen situations where removing a truly toxic person immediately improves team performance so much that you don’t even need to backfill. However, there is almost always some cost to removing someone, especially in leadership roles. 

Why objective analysis of people is so hard

The hardest part of deciding whether to invest in a person or to terminate them is being truly objective about it. Doing the cost/benefit analysis of coaching is murky, and involves abstract questions like: 

• How bad is it, really?

• Is this person worth investing in?

• How receptive will they be to coaching?

Those are subjective calls, inherently, but there are tools that can be used to improve decision-making quality. 

Tools like:

• 360 reviews – feedback from above, below, and peers.

• Style surveys – tools that reveal different leadership styles.

• Personality tests – Myers-Briggs and others.

These tools can be useful, but they all have the same limitation: they don’t tell you whether someone is a good leader or a bad one. They tell you how someone thinks and behaves, not whether that set of traits creates good outcomes.

I’ve seen great leaders and terrible leaders who share the same personality profile.

The real questions are:

• Are they succeeding in their role according to their manager?

• How well do they manage their team?

• How well do they manage sideways across the organization?

• How well do they manage up?

Again, abstract questions with unquantifiable answers. This leads to the critical point: no tool replaces a candid conversation. You can’t “tool away” communication. Communication is the essential avenue for fixing people problems in an organization. 

There’s (almost) no such thing as chronic tech problems—only leadership problems

Tech problems become “chronic” because of deeper process and communication problems, and those process and communication problems persist because of leadership problems.

Good technical leaders do three things consistently:

1. They measure.They instrument what they build. They know their uptime. They know their latency. They know their error rates. They have clear targets, like “We want 99.99% uptime” or “We want a query response under 15 milliseconds”, and they regularly measure progress against those targets.

2. They communicate.They listen first. They make space for people to finish a thought before responding. They are candid without being cruel. They make sure everyone knows what “good” looks like and why it matters.

3. They target.They decide what truly matters and focus ruthlessly on it. They don’t let teams drown in competing priorities or shifting whims.

4. They iterate.  As Voltaire alluded to, “Perfect is the enemy of Good”. Release something that improves the state of things previously.  Then learn from it and continue to improve upon it incrementally.

   
   

When those four things aren’t happening, you get “chronic tech problems”: systems that are never quite stable, teams that are always “almost there,” and organizations that live permanently in firefighting mode.

What this looks like in real companies

Let me ground this in two real (but anonymized) examples from advisory work I have done with Techquity.

Company A: Learned helplessness everywhere

With one company, we spent about three months doing a deep assessment of their engineering and product organizations. I personally interviewed close to thirty people, read existing documentation, and looked for patterns. 

One pattern was so prevalent it became the theme of our engagement: learned helplessness.

It showed up as:

“We’ve had  problems, but they were introduced by previous management, so it is what it is.”

Instead of addressing the elephants in the room, leaders and teams just stepped around them. That attitude spread, until it was endemic across the entire engineering and product organization.  Changes were made, but no one took ownership to correct the issues.

Our recommendations were straightforward but not easy:

• Reorganize the team structures.

• Hire new people with a mindset of ownership and accountability.

• Exit some people who were unwilling or unable to change.

• Help others find roles that are a better fit for their strengths.

• Make it clear who owned what outcomes.

After a few quarters of dedicated work on this, the learned helplessness had largely been replaced with real accountability.

Company B: From bad to great through accountability and hiring

With another large industrial company, we ran a similar play.

First, we identified the leaders who were salvageable (people who had the right core capabilities and values but needed development). Then we identified those who needed to go (those without necessary skills or whose values were not aligned with the company’s direction). In parallel, we helped hire into the key gaps.

Over time, we:

• Provided actionable recommendations and then helped leadership implement them.

• Helped hire several new leaders.

• Screened and interviewed candidates, acting as the first line of defense to ensure they were truly accountable leaders, not just strong résumés.

• Reinforced accountability as a non-negotiable in every conversation.

From the initial assessment to now has been about two years. In that time, their culture has undergone a full turnaround. Ownership and accountability have turned 180 degrees. 

The technology itself is better, but that’s an outcome, not the starting point. The fix that allowed for this outcome was in the leadership of the company. 

How Techquity helps

When brought in to work with a company, we don’t arrive with a squad of junior consultants and a deck of frameworks. That model doesn’t work when the stakes are high and the problems are people problems.

Instead, we:

• Assess. Interview people across levels and functions. Read what exists. Observe how decisions get made. Look for patterns in both what’s said and what’s left unsaid.

• Diagnose. Identify the root causes (systems, leadership, culture) that are really driving the visible “tech issues.”

• Co-pilot. Work alongside the senior leaders to implement changes. This could be coaching individuals, reshaping teams, helping hire, and helping decide who needs to leave.

• Exit. The whole point is to leave the organization stronger and more self-sufficient, not to create permanent dependency.

Our work often takes the shape of leadership development, hiring help, and organizational coaching wrapped together. The problems may show up as “tech problems,” but the work is almost always fundamentally about the people.

If your org has chronic tech problems, start here

If you’re a CEO, investor, or board member and your organization is plagued by chronic technology issues, ask yourself:

• Is my technology leader self-aware, curious, and coachable, or stuck in “expert” mode?

• Are we promoting people into leadership roles because they’re great at their current job, or because they can actually lead?

• Are there toxic personalities we’ve tolerated for too long because they are talented people?

• Do we measure what matters, or are decisions made by gut feel?

• Are we having the candid conversations we need to have, or hiding behind tools and surveys?

• Have we built a culture of accountability or a culture of learned helplessness?

Remember: there are no chronic tech problems, only leadership problems that haven’t been addressed. The first step to addressing them is admitting that the problem isn’t “the stack” or “the market” or “the team.”

Most of the time, the problem is us. That’s good news, because we have full power over our capacity to grow and improve.