Effective Corporate Leadership

Leadership is a quality that society values. It can be seen early on in a person’s life. It benefits those that excel at it, in school, in sports, with friends, and in careers. Many believe that people are born leaders, that it comes naturally.

I believe that leadership is a quality that a minority of people are born with. I also believe that one’s environment will hone this quality for some, and not for others. I believe that if you aren’t born with it, you can learn much of it, but many of the best leaders start with a natural talent.

What I don’t believe is that leadership qualities alone will make you successful as a business leader. Leadership personality traits are not the same as being an effective leader of a company. Being a successful leader in a business means taking your personality traits and using them in specific ways to drive results. Results don’t just happen because someone is a natural leader. Results happen when leaders take action.

Leaders come in all shapes and sizes, so-to-speak. You don’t need a title to be a leader, but some titles require you to be a leader. You can be a great Business Analyst, a great Designer, a great Sales Executive, without being a leader, but you probably won’t be a great Chief Marketing Officer, or a great Vice President of Product, if you aren’t a great leader. It’s a choice, until it isn’t. If you weren’t born with it, you better start figuring it out.

I’ve been thinking a lot lately about what a great business leader is, and what a great business leader does. I say it that way intentionally, is and does. A definition and actions with outcomes. Below is what I’ve come up with. I am sure this is a far from a dictionary definition, probably because my take is less a reflection of business leadership itself, and more about what I personally strive to be as a business leader.

What a great business leader is:

  • Someone that inspires others, to act, to be great, and to grow

  • Someone that coaches and mentors their direct reports, bringing out the best in them

  • Someone that takes responsibility, seeking it out and rising up to it

  • Someone that puts the organization on their shoulders, not as a burden, but to carry others and raise them above the fray

  • Someone with vision for the organization and a course charted to reach it

The above is great, and impressive, but how do great leaders turn those qualities into action and results?

They see the bigger picture

Great, effective business leaders share a similarity with chess players: they see two, three, four moves ahead. They don’t stop at the obvious, they see what others don’t and can identify what really matters. With this vision, they can speak and act in a way that inspires others.

They have a positive outlook

Great, effective business leaders put energy into positives, rather than negatives. They don’t ignore challenges or concerns, but seek balance in their focus and how they communicate with others. They smile, show joy, recognize success, and lift-up the spirits of others. With this quality, they attract others to them and go into every opportunity or challenge leading people that believe in success is not only possible, but likely.

They say the right thing, at the right time

Great, effective business leaders know that listening is more powerful than speaking, and how to use their words for the greatest impact. They often don’t speak first, collecting the information they need to speak with authority later. What they do speak, their message is well thought out and organized. They have a way of knowing exactly what others need to hear, at any given time.

They are calm under pressure

Great, effective business leaders are the rock of an organization when pressure builds. They still worry, but they know that others will observe and mirror their behavior, so they remain clam in all they do, whether that be day-to-day work or a crisis. They don’t overreact or act too quickly, but instead they take a measured approach to challenges that is seen by others as well planned, organized, and thoughtful. They’ll never appear to be overworked or exhausted by the pressures of work.

They act and speak with confidence

Great, effective business leaders believe in themselves, their experience, and their ability to get the job done. When they speak, they believe it. When they act, they know it’s the right thing to do. They are confident, but not cocky. They may have doubts, but those doubts don’t hold them back, and instead drive them towards continuously growing and learning. This confidence inspires others to do the same.

They know the details that matter

Great, effective business leaders stay abreast of the details they need to know. They understand that they can’t lead while in the dark, and they seek to consume knowledge. They are properly informed on what their teams are doing, what their successes are, and what their challenges may be. They don’t micromanage and aren’t know-it-alls, but they recognize that information is the most important input they need to deliver the outputs their organization needs. Most importantly, they use this information to properly coach, mentor, and manage their team.

They show gratitude

A great, effective business leader recognizes the work of others and shows appreciation. They understand organization dynamics and that often teams accomplish greatness, rarely do individuals. They recognize the human side of work and understand the power of gratitude. They deliver that gratitude with heartfelt meaning and genuine appreciation. They deliver gratitude in big and small ways, not requiring a stage to deliver it on.


As I look back on what I just wrote, I see a common theme: Communication. Leaders and effective executives are great communicators. They communicate genuinely, thoughtfully, intentionally, and non-verbally.

I’m going to keep studying leadership and honing my abilities. I recently read a great book on leadership, What You Do Is Who You Are, and I may revisit my favorite book on communication, Crucial Conversations.

My 2019 year in travel

We’ll, I guess this post could be more late than it is! Every year I write two year in review blog posts, usually in January. One about what I read, and one about where I traveled. Finally, in April, I am getting around to my 2019 year in travel!

Two thousand nineteen was a big year of travel for me! I did a decent amount of domestic travel, but international was the big story of the past year. I am lucky that my work provides me the opportunity to see both the country, and the world. From there, I never miss a chance to travel for personal desires, with my wife and I choosing to spend much of our disposable income on travel.

Speaking of my wife, in 2019 we got married in Puerto Vallarta, Mexico! Our wedding didn’t just account for 1 international trip, but two as we went once for planning and once for the wedding. We also took a pre-honeymoon honeymoon a few weeks later to Cabo, which was a first (and probably last) for both of us.

In June I was asked by my employer to travel to London, and I jumped at the chance! Better yet, my wife (who I worked with at the time) was also asked to go so we spent a few extra days on our own dime to get a little vacation out of it, too.

You’ll see in the data below that June was by far my. most active month for travel. After London, I flew right to Atlanta to speak at a conference, then home to San Francisco. A week later I was in New York to speak at another conference. I ended the month with a short hop up to Portland from San Francisco to spend the 4th of July weekend with my parents and friends.

My work brought me to Atlanta a total of 3 times in 2019, and Toronto twice. I changed jobs in October, which will mean fewer trips to Toronto but likely the same or more trips to Atlanta in 2020. I’ll miss my trips to Toronto, it is a fantastic city, but I’ll enjoy even more time in Atlanta, another wonderful place.

The highlight of my year in travel was our honeymoon to Argentina! Neither my wife or I had ever been to South America, and as both wine and steak lovers, Argentina was an easy choice. We flew to Buenos Aires from San Francisco, via Houston, and spent 10 days in the country. At the midpoint of our trip, we flew to Mendoza for a few days of wine tasting, and loved it! We even faced a little hiccup with our travel when the airline union went on one short strike and threatened another while we were holding tickets to return to Buenos Aires. I even took the step of buying backup flights on a budget airline from another South American country, but at the last minute, literally, the country and union came to an agreement that would avoid the strike that was to start the morning of our return flight. It was worth a couple hundred bucks to have a backup plan!

Without further to do, here are the numbers:

  • 86,814 miles* flown (a 27% increase from the prior year)

  • 53 flights (a 2% increase over the prior year)

  • 6 airlines used (I prefer United, as you’ll see below)

  • 6 trips home to Portland (1 more than the prior year, mom)

  • Shortest flight: 325 miles from Washington Dulles to Hartford Bradley

  • Longest flight: 5,368 miles from San Francisco to London (although I earned more from Frankfurt to Atlanta)

  • First flight of the year: Jan 20th from San Francisco to Puerto Vallarta

  • Last flight of the year: Dec 28th from Portland to San Francisco

My 2019 year in books

In 2018, I read 8.5 books (I just couldn’t finish one and stopped halfway through). For 2019, I didn’t set a firm goal for myself, but I surely hoped I’d read more than I did in 2018. For 2019, it looks like I read 7.5 books, a dip from the year before and a negative trend considering I read more in 2017 than in 2018, which was more than 2019.

I’m not going to worry about the amount I read. Sure, I’d like to read more, but I have no lack of new information and entertainment in my life. If I can read more in 2020 than 2019, that would be fantastic. If not, it’s okay.

Without further to do, here is my reading list from last year, with titles linking to each book on Amazon.

Make Time

This is the follow up book from 2 of the authors of Sprint, one of my favorites that I’ve read twice in the past. While Sprint talks about generating and validating product ideas in 1 week, Make Time is focused on how to manage both personal and work time in order to align with your priorities in life. The book has some interesting ideas and was a great reminder that time management matters in life, the book wasn’t exactly a page turner and didn’t blow my mind.

Talking to Strangers

Talking to Strangers is the latest book from my all-time favorite author Malcolm Gladwell. This book is all about communication and how two people can have very different experiences around the same event. It is clearly inspired by the current political and social divide in America today. It’s not Gladwell’s best book, but an interesting read none-the-less. If you really want to dive deeper into this topic, I recommend Crucial Conversations, which was a life changing read for me many years ago.

Overcoming the Five Dysfunctions of a Team

The Five Dysfunctions of a Team is one of the most well known business books of all time, one I read many years ago. In 2018, I was lucky enough to hear the books author, Patrick Lencioni, speak on the topic at a conference. In 2019, I was navigating a team dysfunction at work, and my leadership counterpart in Engineering and I decided to both read this book as a way to arm ourselves with tools for how to help our team get back on track. It was helpful and I am really glad I read through this supplemental to the best seller!

The Subtle Are of Not Giving a F*ck

I kept seeing this book in airport bookstores, and the title really stands out at a glance! The title is brilliant marketing and I had to pick up a digital copy to read! I expected an irreverent, sarcastic view on the world, but what I got was a solid, fantastic read on how to manage the stress of life. This book isn’t about not caring, it’s about how to care about the right things. I highly, highly recommend anyone read it, unless you’ve already reached a state of zen and have no worries in life.

I Used to Be a Miserable F*ck

I actually came across this book when I was searching for The Subtle Art of Not Giving a F*ck. Not only did the title catch my attention, just like the other book I was looking for, the content sounded interesting, so I bought it. This book is made up of very short chapters that each focus on a quality that the author advises men to embrace. You might consider this book an operating manual on how to be a good and masculine human being that others want to be around. The author shares stories from his past, and I related to many of them…which isn’t great considering how miserable this guy, and I were, but also a sign that I’ve moved past those pathetic behaviors that used to define me.

The Lean Startup

This was a re-read for me in 2019 as part of the fledgling book club I was running at work. I like this book because it demonstrates how to quickly, and efficiently, develop products and test ideas. It uses stories from startups, but the concepts can be used by any product development team. I recommended it to my colleagues, and read it along with about 8 others. After reading, we discussed our favorite stories and concepts from the book, imagining how we could do similar in our work at PagerDuty.

The Score Takes Care of Itself

My new boss and CEO of Zenput recommended and gifted this book to me after a discussion we were having about leading teams. This book is the career autobiography of legendary football coach Bill Walsh. Coach Walsh transformed a number of football teams, most notably the San Francisco 49ers, who won 3 Super Bowls under his leadership. Walsh took a completely different approach to leading his organization, and shares his playbook here. I absolutely LOVED this book and have already changed my approach at work. Similar to The Subtle Art of Not Giving a F*ck, Walsh offers some great insight on how to care about the right things, and manage them. Love, love, LOVE this book!

Flow

This is the half book mentioned at the top of this blog post. I saw two friends talking about books with each other on Twitter, and this book was recommended to one by the other. It sounded great, advice on how to get into a flow of life and work such that its effortless. Unfortunately, it reads just too much like a textbook, and I couldn’t get more than 20% through the dry content. Oh well, better to just move on and find something else I would enjoy!


So what’s on my list for 2020? I’ve already started reading Survival of the Prettiest, a gift I received from a coworker. I also plan to read Patrick Lencioni’s new book The Motive, Ben Horowtiz’s latest What You Do Is Who You Are, Monetizing Innovation, and many more!

Americans have become weak

We’ve had it too good, for too long. Even with the 2008 financial crisis, we are in the midst of an incredible stretch of prosperity. Even with mass shootings, never in history have we been as safe from harm as we are today.

Life is really fucking good for many Americans.

So why rock the boat? Why risk what we have individually for the greater good? Why go out on a limb to uphold everything that this country stands for? We can let Washington D.C. fight on our behalf, we don’t want to miss brunch with our friends, followed by shopping for all the gifts we’ll give this holiday season.

In the meantime, our democracy is falling apart. We are at grave risk of losing the system that gave us the prosperity we have. If trust and sanctity are lost, we are screwed. We may never come back from it, but even if we do, it will take a generation or more.

Recently, the President of the United States of America admitted to breaking the law through the way he used a charity bearing his name for his own financial gain and personal benefit. He admitted it! And was fined $2mm by a court of law.

That would have been enough for any past president, Democrat or Republican, to be impeached AND removed from office. Not this president though. As a country, we’ve had things too good for too long, why rock the boat and worry about his actions? They didn’t harm us.

Now, we sit through a toothless impeachment process because the same President used his office, and American taxpayer dollars, to bribe a foreign government to advance his own political goals. While I am happy that Congress is seeking, and will likely approve impeachment, the process is toothless. The Senate will get the case next, and the leadership has vowed to quickly clear the President’s name, allowing him to continue doing what he has done for his entire life.

Democracy as we know it will be gone. A joke of a concept, really. If charity fraud isn’t enough, what is? If bribery with taxpayer funds isn’t enough, what is? If asking for a foreign government to hurt your political opponent isn’t enough, what is?

Democracy will be over.

So what are we doing about it? Nothing, really. We go to our holiday parties and talk about how awful things are, but our conversations are soft.. We get angry on Twitter, then turn our attention to a football game, too afraid to get angry IRL.

We are weak. We are soft. This isn’t about political parties. This is about freedom. This is about losing the democracy that changed the world, for the better.

The same country that was founded on protests, the same country that went to war to enforce our constitution, the same country that took to the streets for Civli Rights and to end the Vietnam War, that same country is doing nothing. We are writing toothless blog posts.

The people of Hong Kong are are risk of losing freedoms, and they are doing something about it. They are protesting, making noise, telling the world they won’t stand for it.

Protesters in Hong Kong. Image credit Studio Incendo.

Protesters in Hong Kong. Image credit Studio Incendo.

Iranians are facing economic hardship and potential collapse, because of the poor geopolitical decisions their government is making. So what do they do? They are protesting, making noise, telling the world they won’t stand for it without a fight.

In Egypt, Tunisia, Jordan, Lebanon, and many other Middle East & North African countries, the people stood up, said they were feed up with corrupt and oppressive governments, and they did something about it. They protested. They risked what little they had and took to the streets. Day and night. Until change happened.

Thailand, Chile, France….they fight when their government does wrong by them.

What are we doing about our corrupt government? What are we doing about our eroding democracy? How are we bypassing our polarized political parties to hold our government accountable?

When the United States Senate takes up Impeachment and decides if President Donald Trump should be removed from office, what will we do? Complain to a fellow pinot loving friend during meaningless conversation at a holiday party? Get mad on Twitter?

Or, protest? Make noise. Tell the world we have standards we are willing to fight for? At least try to save our democracy?

Is Product Management really all about the customer?

The last time I updated my resume, I wrote a headline that said “customer obsessed product leader.” it’s true, I LOVE engaging with customers and serving their needs, those are my favorite things about product management. I’m not alone, putting the customer first is what many product managers agree on. Customer focused Product Managers are what employers want to hire. Who wouldn’t agree that being customer obsessed is great?! There’s a problem though. This very true and appropriate focus may cause some other things to be overshadowed.

They other day, I had coffee with a colleague who said they had just read one of my blog posts on Product Management. That got us talking about stakeholders, one of the 9 things I said that great product managers have mastery of. Spoiler alert, the customer isn’t the only stakeholder product managers need to care about, and they may not even be the the stakeholder with the most weight, or part of the equation at all.

I believe that product management requires explicit consideration of 3 different groups of stakeholders: the current customer, your future customer, and finally the company vision & strategy. It is not good enough to simply focus on your current customer and their needs. That may be good, but optimizing for all three is great.

Product-Stakeholders.png

The Current Customer

Make no mistake, I am not minimizing the importance of your current customer at all! This is the stakeholder that allows your company to pay the bills, the stakeholder that advocates for you to potential customers, the stakeholder that trusted you over others and gives you more than just their money, they give you, the product manager, their time.

As product managers, we must meet this customer’s needs. Often that means solving the problem they came to you for, delivering on the table-stakes in your space, and providing a delightful user experience that allows them to easily accomplish what they pay you to accomplish. Sometimes they’ll come to you with feature requests and ideas that are related to your core. Listen to these. Work them into the product roadmap when they make sense. Keep this customer happy! They represent 1 of the 3 key stakeholders you must optimize for as a product manager, you’ll always do good work if you serve them well.

The Future Customer

If you are ready to do great work, this is where you begin to evolve as a product manager, when you look outside the current customer as your core stakeholder, and seek to serve more through your work. The future customer can be many things. It can be a customer in your target market, but one you haven’t won over yet. I might be the customer you have today but with needs well beyond what you do now. It could be the future of the industry, the way it works in the future and new problems it doesn’t have today. It may be a new industry you could enter, expanding the reach of your products and technology.

Regardless of how you define the future customer for the project or decision in question, considering this stakeholder will take you and your product to the next level. Serving the future customer allows you to grow with your market and customer base, rather than just selling it a little bit more. Serving this customer is how you become or protect your position as the leader in your space. Meeting this customer’s needs isn’t about paying the bills today, it’s about paying the bills tomorrow.

Keep in mind that serving this stakeholder doesn’t mean you are acting against your current customer. Instead, this is your opportunity to align the current customer with the future, to understand where they are going and get there before them. It could also be an opportunity to ask yourself how you might build for the current customer and show the the way to the future, at the same time. Solve a problem they don’t know they have….yet. Be the hero that solves it before the realize it.

The Company Vision & Strategy

There is one more stakeholder that you must consider, and in some ways it is the most obvious, but in other ways it is the most elusive. I believe that great companies have a vision and purpose that transcend the product, and transcend the market. They serve a higher purpose. Sometimes these visions and mission statements seem corny, but they are the hallmark of enduring companies. For example, at PagerDuty, they don’t serve oncall engineers, they serve anyone in a digital business doing real-time work. They don’t send alerts to the right responders, they empower people in moments of truth so they can elevate their work to outcomes that matter.

To be a great Product Manager, you must ask yourself what the company needs from you and your product. Most company mission and vision statements require inventive, focused, and considerate product managers to make them a reality. They leave enough room for the product manager to make decisions that not only align with the company’s vision, they also serve the current customer and position the product for success with the future customer.

This stakeholder can be elusive in a couple ways. If you work for a company with no higher purpose, with no vision beyond the current customer and their existing needs, you’ll feel as if there are not 3 stakeholders to consider, just two, since the company vision and mission are the same as the current customer’s needs. My advice here is to either help your company desire to be and do more, or get a new job. The latter is probably easier. The other way you may find this stakeholder elusive is all about you. If you can’t separate your current customer’s needs from the company vision and mission. Frankly this is easy to do. You see what you current do for customers, and you equate that to the company vision and mission. You take a bottom’s up approach, so to speak. To be great, spend some time thinking top down. In the example of PagerDuty, what could real-time work encompass? When do moments of truth happen? What are the possible outcomes that matter? If you give yourself space to take a top down approach, you’ll often find that there is so much more there than what your customer is ask you to do today.


This stuff doesn’t come naturally. It is so easy to consider just the current customer, and not the other stakeholders. It is hard to know how much weight to give to each. Do you have to consider all three, or can you serve just two? If you serve just two, is one required in a way others are not? These are all great questions, and you know what? I don’t know the answer! I don’t know because it depends on what you are building. I also don’t know because I’m not perfect, and I am still working on being a great, not just good Product Manager.

As I reflect on myself, I think I am pretty good at considering all three stakeholders as I guide, create, and decide. What I am currently struggling with is selling my vision to others, as one that considers all three stakeholders appropriately, for the maximum benefit of our vision and mission. If you have advice on how to do that, I am all ears!