Fixed and broken puzzle pieces

Things Are Always Broken

In Leadership, Entrepreneurship, Execution, Managing Risk, Strategy Insights by Steve Sliwa

When people enter into a senior role, it often comes as a shock that things are broken. It may not happen every day or week, but without fail, people complain to leaders about broken issues in the organization, which can be a surprise. Up until that point, the view of that new executive was that things were working, smoothly and calmly. It amazes me how much time one spends on fixing problems, so leaders must have a strategy for addressing it. Interestingly, this applies to startups as well as well-established firms. 

Large Organizations

In more mature and successful companies, leaders understand that things break and actively encourage problem identification. Although, I have seen managers in a few large businesses who try to eliminate anything that could break. The best way to accomplish that is to take few risks, avoid trying new things, and in essence do very little, which is not a viable long-term strategy. 

To grow and keep the company moving forward, one must create the freedom to maneuver. For example, agile companies have more iterations of experiments to find out what works and what fails. Invest more in the successful ones and eliminate the ones that do not work out. It is vital to create initiatives on a variety of fronts to advance the corporation.

The challenge is that established businesses hate broken items. I talked to a leader who described how companies are usually comprised of two types of people – creators of value and protectors of assets. Creators of value are the ones disrupting the status quo to find new directions to pursue. By the nature of doing that, they are breaking things. The protectors of assets try to keep problems from happening and are in prevention mode. 

Once things are broken, the question is, “Who fixes them?” In large organizations, the creators of value are typically not good fixers. For that matter, the protectors of assets may not be either because their directive is to prevent errors, not come up with processes and new methods to minimize risk. Sometimes, leaders form a special operations group to support and solve broken issues and fix them or identify specific people to go to when a problem is found. Another strategy is to select a fixer and pull them out and assign them special duties.

Several options exist to solve the problem, but if left to its own device, then a power battle between the creators of values and protectors of assets is likely to happen. This struggle resembles a pendulum, swinging too far in one direction before going the other way. First, the creators of value get out in front and break more things than the organization can handle. The reaction is that the protectors of assets jump in, put processes in place, and create systems that prevent things from breaking in the future. Leaders must determine the correct balance.


In more established organizations, problems happen often, but with a startup, my mantra is that everything is always broken. When starting, what is built can only work for a certain size. As a company continues to grow, ultimately it is going to outgrow the original designs. It is challenging to create something that will last from 25 employees to 50 to 200 to 1,000. The plans put into place for 25 people cannot possibly work well when the organization reaches larger numbers. 

In a sense, as the company’s headcount and sales grow, everything is broken. That iteration has to be built into the culture. The Lean Startup movement is less about planning for all eventualities and more about creating agile experiments centered around client experiences and the feedback from the market and customers.

I think the fun of a startup is the fact that things are always broken. It is exciting trying to develop an evolving set of strategies and tactics for choosing which problems to solve in what order. Rather than running a big ship where things come up occasionally, this process involves continually designing and redesigning – creating experiments and cutting off the ones that don’t work and replacing them with ones that do. Leaders must continuously adjust and pivot. This is the norm for a startup.

Scaling is about fixing things, but how much? When building the back-office, compliance, and support systems, a leader must decide if the designs will be good enough for when the business doubles, triples, or quadruples. They also must determine the amount to invest and make the tradeoffs for how long a design should last. It is a balancing act as the organization grows.


For any company, realize that when something is broken, it is not time to panic. Whether issues pop up daily or occasionally, do not panic!

If you shoot the messenger, soon they will no longer speak up about broken items. Instead, send the message, “We welcome risk-taking and want to identify the issues and problems.” Encourage team members to take risks, identify mistakes, and fix them. Without a healthy environment for people to report these incidents and add them to the list, things remain hidden. This drags the organization down because leaders must then actively look for problems. 

Rewarding issue identification and creating a process for fixing them provides a chance to shape the future, so view it as the best opportunity for leadership. Use this occasion to make cultural, technological, and organizational changes. In fact, the best time to make these course corrections is when a problem exists because people are focused on resolving issues, meaning it is easier to introduce new concepts.

Leaders must figure out the order of problems to fix and what investment level they should make, given that there are so many things to address. When employees bring up issues, they think theirs is the most critical. Work with the team to prioritize the items, realizing that some will not be addressed. Groups do not uniformly agree on the importance, so the leader must develop a process, such as the consensus decision process (CDP), to bring everything together – what gets fixed, level of investment, and priorities. The final step is developing a communication and execution plan. But keep in mind that another problem is just around the corner!

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