Author: Benjamin Trent

One of my most important principles is to strive to never make the same mistake twice. We all make mistakes, and though it’s important to be accepting and understanding of these failures in ourselves and our team members, it’s equally important to extract as much educational value as possible from mistakes in order to improve. A goal and commitment of never making the same mistake twice is guide that can help us to extra maximum value from these learning experiences.

“Never make the same mistake twice” is a mantra that resonates with most people, because most people recognize that making the same mistake repeatedly is detrimental to personal growth and development. Every mistake we make is an opportunity for growth and self-improvement, as long as we take the time to reflect on what went wrong and how we can avoid making the same mistake in the future. By consistently learning from our mistakes, we can make steady progress towards our goals and become more efficient and effective in everything we do.

Another benefit of avoiding the repetition of mistakes is that it helps to build our credibility and trust with others. When we make the same mistake over and over again, it can cause others to question our ability and judgment. On the other hand, when we take the time to learn from our mistakes and make an effort to avoid repeating them, we demonstrate to others that we are reliable and trustworthy. This can be especially important in professional settings, where our reputation and credibility can significantly impact our success.

For these reasons, the principle of never repeating the same mistake has broad implications on a larger journey toward success and improvement, and can be a guiding light that leads to patience, a better work ethic, increase objectivity, humility, and open mindedness.

Making important decisions when afraid, in any context, can have negative consequences. This is as true for a business or technology team as it is in nature. When an organization is dealing with negative market trends and poor performance, fear can take hold among its employees and leadership. This fear can cause decision-making to be clouded by emotion, leading to rash and potentially harmful choices.

When this happens, it’s critically important for leaders to remain calm and focused. They must avoid making decisions based on fear and instead maintain focus on facts and logical thinking. Seeking out advice from trusted people in your network and outside sources can also be helpful in making well-informed decisions.

It’s crucial for businesses to recognize the potential negative effects of fear on decision-making and take steps to mitigate them. For example, finding ways to reduce stress within the group will promote clearer thinking and lead to better decisions. This can be a difficult challenge when there is mounting internal and external pressure and an atmosphere of increasing uncertainty, but by doing so, businesses can avoid making decisions that may exacerbate negative market trends and further harm their performance.

Before you ask a question that may have a damaging answer, mentally double check to make sure you are prepared and ready to accept the worst possible answer. If you’re not, don’t ask the question.

Often people will ask me a sensitive question without fully realizing the ramifications of an unexpected answer. This could be an opinion of a person, or an evaluation of a project that the asker has championed. A positive, emotionally supportive answer is expected. If instead the answer is negative, the questioner will usually get defensive and the conversation will become strained.

That is an outcome that no one wants and that produces no value for either participant or for the organization. Before getting into that situation it’s far better to either frame your question in a way that leads to the type of answer you’re looking for, or to let unspoken criticisms remain unspoken.

Repeatedly throughout my life, when I’ve met someone who had a particularly pronounced intolerance, for example against hypocrites or procrastinators or conceited personalities, it would turn out that one of that person’s own greatest character flaws would be that exact thing.

I don’t know why there is a connection but I’m certain that there is a connection, and being aware of it can help in navigating relationships. If someone I do not know well expresses a personality or cultural annoyance, I recognize that they are likely to exhibit this same behavior at a later time and can prepare for it.

Similarly, if I find myself becoming frustrated or annoyed by someone else’s character flaw, I first ask myself if it’s my own weakness in that area that is frustrating me, or something close to it. In those cases, sometimes by determining how to improve myself I can improve life for the other person as well.

In some ways this job is like a maze: where we wind up is rarely where we think we’re headed from the start. We also have limited information with which to navigate and, though there are methods and skills we develop to help us make the best decisions possible, sometimes the lack of information leaves us with nothing better than a gamble.

I’ve had several big successes in my career and honestly I’m less responsible for those successes than people would like to believe. Likewise, I’ve had some failures, and honestly I’m less responsible for those failures than it would seem to a casual observer. Certainly there are ways to measure CTO abilities and outcomes, but usually you have to dig in deeper than the resume bullet points or anecdotes that are often the only things communicated.

You can go through your maze and make all the best decisions and still hit a wall, or you can go through and make all the wrong decisions or act chaotically and get through in record time. Over a large enough sample size outcomes will normalize, but few of us do this long enough to get there, and usually early outcomes lead us into the mazes of our future.

A lot has been written on the subject of management vs leadership when it comes to guiding teams. I’ve heard it argued that great executives lead whereas poor executives manage. I think this fails to recognize that management and leadership are equally important and that success is not likely unless both are done well.

Peter Drucker has said that “management is doing things right; leadership is doing the right things.” The idea of managing people should not always imply micromanagement. Like nearly every other executive skill there are both strategic and tactical aspects of people management, and different levels of involvement ranging from deeply immersing yourself in a team member’s day-to-day to only framing success conditions for a project or role.

When I think of what management means as opposed to leadership, I think of setting constraints. There is a perception that setting constraints on mature, professional people is a waste of their abilities or even insulting, but I believe quite the opposite: failing to set constraints, or to put it another way, expectations, reduces the likelihood that people will find their way to success and makes it harder for them to succeed.

People know how to do their jobs better than you do (hopefully) but they don’t necessarily know what the broader group, or the rest of the organization, or the CEO, or the board, or your users, or the market really needs from them. It’s up to you to manage these expectations by setting very clear success criteria whenever possible, and to manage their paths to meeting those expectations by course correcting early and often if they begin to drift off course, because though everyone on the team should have the ability  to succeed on their own, almost no one will have the perspective to know how they’re doing at all times.

There are four kinds of investors:

Those that know your business and know that they know your business. They are sources of wisdom. Use them.

Those that know your business but act as if they do not know your business by being hands-off. They are sleeping partnerships. Awaken them and extract value.

Those that do not know your business and know that they do not know your business so are hands-off. They are helpful in other ways and can be great support.

Those that do not know your business and do not know that they do not know your business. They will impose their will upon the business and destroy value. Shun them.

– Somewhat taken from Bruce Lee

We are often faced with a dilemma when considering how to use software to solve a problem: whether to build the solution to that problem, or whether to buy a product or service that we believe can solve it. Many people and groups struggle with this choice, and also struggle to find a reliable method for making well thought out decisions. 

Every situation is different but as a rough guide I’ve found it useful to ask 5 directional questions:

1. Is there an adequate solution that you can buy?
   • You can integrate it
   • It fits timing needs
   • It has features you need now
   • It has features you’ll need later or can be modified
   • It is reliable
   • There is support available
2. Is this a key differentiator for your business?
3. Is there an industry standard solution that you can buy?
4. Can you build it adequately for less than the cost of buying it?
5. Do you have other projects that would be a better use of your time?

Often, this is how those questions guide the way to an answer:

I’ve heard CTOs described as Product-focused versus Tech-focused, and I’ve heard people described as strategic versus operational, but I wonder if these are false dichotomies. I wonder if a better scale may be Product vs Operational — or to put it another way — CTOs that excel more at considering what to build versus CTOs that excel more at considering how to help many different people build it.  

Executives at either end of that spectrum can be strategic or tactical at different times. It’s a common misconception that operational CTOs are weak strategically, when in fact it seems impossible to implement long-term vision of operational excellence without having a strategy to guide decision-making. Likewise it’s a common misconception that Product-focused CTOs are weak technically. Some of the most gifted Product people I’ve known were also very strong implementers. 

However, I’ve known hundreds of CTOs and I don’t think I’ve ever found a strong Product-focused CTO who also excelled operationally at scale, and likewise I don’t think I’ve ever known a strong operational executive who excelled in Product creation. I’ve known many people who have done both, but in all cases they were either excellent at only one of them or neither.