The best practices and approaches of modern digital product development—from technical methods like Lean, Agile, and Human-centered Design, to support for psychological safety and growth mindset for employees, and even the leveraging of more authenticity, diversity, and sustainability in strategy, branding, and marketing—are all increasingly embraced by bold and progressive companies that are not only more successful in the market relative to their competitors, but also lauded as great places to work. Our diagnostic helps you build your company into one of them.

The humanities are more important for senior leadership than technical skill or domain knowledge. The best CTOs have a strong command of language and a good sense of people, in addition to their technical background. And you get that from studying the humanities, whether formally or informally. The humanities exposes one to the nuances of the human experience. Technical skill only focuses on machines, abstract or concrete, not how they affect the people who build them or the people who use them. A tech leader with letters under their belt is more likely to succeed at the top than one with only numbers in their toolbox.

Over the past few years, I’ve heard some version of the above from countless leaders. There always seems to be an urgency to turn things around and move the organization forward. But the fact they are talking to me is likely because they haven’t been able to effectively make the transition from an urgent mindset to a strategic mindset.

No matter what challenges your organization is experiencing, 9 times out of 10, there is a lack of strategic vision guiding the organization.

Finance has a tendency to exacerbate bubbles, as we’ve seen, which can cause significant challenges for technology CEOs who are trying to make decisions based on values and purpose. While the integration of technology and finance has undoubtedly brought about many benefits, it is important for industry leaders to remain vigilant against the risks that arise from this relationship. CEOs of private firms who strive to make a positive impact on the world will encounter significant pressure from venture capital or private equity, while those steering public companies face the same pressure from Wall St.

It is important to realize that you can only ever influence people to change. You cannot force them, no matter how much authority you may technically have over them. Changing an organization is much more about changing the mindsets and attitudes of the people in it than changing rules or procedures. You can change the rules or procedures, but that will not necessarily guarantee compliance. If you haven’t secured the buy-in and enthusiasm of those you hope to change, no amount of coercion will do.

As a new senior leader, your job can be confusing and frustrating. It's a huge relief when you finally figure out how to work with your CEO and the rest of the leadership team. Managing up to the CEO requires seeing them as a real person with feelings and needs rather than a power broker before whom you must always grovel. People think CEOs want to control them, but it’s actually the opposite. They want you to take initiative. Controlling people sucks!

The foundational technical practices of Agile software development, like Continuous Integration/Delivery (CI/CD), Pair Programming, and Test-Driven Development (TDD), are sadly missing from most so-called Agile transformation programs. There is a strong correlation between organizations that struggle to adapt the people and process elements of Agile and those where the technical practices are not embraced either. I do not believe there is one-way causation in this situation, but rather a dialectical relationship where the presence (or absence) of one set of conditions tends to encourage the presence (or absence) of the other.

Modern high-growth businesses have realized that a critical aspect of their performance is that their people have autonomy over their work, not just in terms of how they do it (the process), but also in terms of what they do (making decisions about opportunities and risks).

When organizations lack a clear and coherent purpose and strategy, people in the organization are more likely to trigger games with each other, play politics, and participate in other dysfunctional behaviors as a way of structuring time, fighting for social position, and exchanging negative strokes that feed recognition hunger.

There are scenarios when a private conversation with someone about a difficult issue provokes that person to be even more difficult. But those scenarios occur only a tiny fraction of the time. Most of the time, hard conversations that may seem insurmountable at first go more smoothly than we ever expected. Our fear is far greater than the actual impact of the conversation.

There is a delicate balance between expressing confidence and displaying arrogance. There is also one between taking feedback seriously and taking it too personally. Striking both balances simultaneously is key to wielding power successfully as a senior leader.

People are not all the same. It seems so obvious, we tend to just look past each other. But it is surprisingly difficult to keep in mind that someone you work with might have a very different perspective on the problem you are solving together. Those differences can be easily overlooked or brushed aside.

Decision making is a key facet of leadership. But leadership doesn’t mean making all of the decisions yourself. It means knowing which decisions to make, and which to delegate to others. It also means knowing how hidden cognitive bias can affect any individuals’ decision making, and setting up systems to take advantage of a diversity of perspectives in order to arrive at the best possible decisions.

Meeting requests, emails asking for a reply, invitations to networking events, and so on, are all arriving in our inboxes each day. Do you have time for all of them? Of course not. You will have to choose. But how do you decide what is important and what is not?

We all have internal barriers, deeply ingrained behaviors that operate from our subconscious, seemly on auto-pilot. These behaviors make it difficult for us to perform the new skills required of leadership. Once we understand the nature of internal barriers, we can clear the space to learn new leadership skills.

Truly successful leaders are not motivated purely by financial gain. They are driven by a deeper sense of purpose. That purpose may be something technical, like the joy of mastery of a craft or skill. Or it may be something social, like the support of a particular social group. Or it may be a set of values such as justice, freedom, or compassion. But whatever it is, the pursuit of purpose has been a driving force behind the development of humanity since the dawn of civilization.

Words hold extraordinary power over the human psyche, and always have. The great Joseph Campbell, prolific scholar and progenitor of a concept from literature you’d probably recognize as The Hero’s Journey, considered all mythology from every culture on earth to be telling us basically the same universal story.

Feeling stuck is very common these days. A friend, a product manager in a high-growth tech company in San Francisco, confessed she feels stuck in a dead-end job.

“From the executive point of view, the decisions are bigger, and information from the front lines is less available and more coarse grained. It has been filtered up through various management layers before it gets to them. At their scale of responsibility, your ask is one of a hundred others just like it.”

The type of leadership we see in these endeavors, not just at the top, but throughout the organization as a whole, makes or breaks the long-term success of the organization.