Foundational Values Vulnerability

Hey, What’s Your Angle?

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For the very first blog post here, I want to address my motivation.

A good friend of mine recently shared:

“I have always feared executives. They always have an agenda and they have the power to hurt me. I have trusted very few executives in my career.”

Can you relate to that?

If you are an executive or a manager of any kind, there is authority baked into your role, and that very authority all-too-easily gets in the way of our human relationships. People are conditioned to follow people in positions of labeled authority, whether it is in their best interest or not. While it is one thing to be followed, it is an entirely different thing to be trusted. Early on in our journey on The Progressive CIO, it bears noting that this dynamic will be at the very heart of our discussions.

The notion of vulnerability is something that springs to mind, and there is a reason that I list it first on the values that you see on this site.

We are born vulnerable, and if we are lucky enough to grow past childhood into adulthood, it is our very vulnerability that encourages others to protect us, to guide us, and to groom us.

As adults, when we see a young adult, our minds seem to appreciate the independence of the creature who stands before us. We do not attempt to steer or offer guidance to that person in the same way we would an infant. You must recall the feelings you sometimes have when you speak with young adults who think they “know it all” — you know that nothing you could offer will give them what time and experience will.

As we grow, others around us are much less likely to guide us in the way we were when we were young…when we were vulnerable.

But if we can show vulnerability to others as adults — as leaders — something remarkable happens. If I say to someone:

I am afraid of something.
I am lacking something.
I need help with something.
I am sad about something.
I am confused about something.

…what happens? Others are more likely to step in to help me and to guide me, and I stand a much better chance of learning something as a result. Why is that? Because humans are so well-conditioned to help others who are willing to show vulnerability and ask for help. It is immediately relatable, because inside, we are all filled with doubts. We too often hide those doubts in the interest of looking confident. But that gets us absolutely nowhere good and is, in fact, the ultimate manifestation of the lack of true self-confidence.

Truly self-confident people know who they are inside. They can admit when they do not know something because they are not ashamed of it. Most importantly, they know that if they expose those vulnerabilities, they are much more likely to learn and grow through the help of others.

The fear of executives — of anybody in a position of authority — has a clear mitigation strategy for those who are feared: Develop the ability to show vulnerability at the times you are feeling vulnerable. You will help others to do the same, it will be easier for others to come to trust you, and you will see remarkable results in your teams, from those who elicit software requirements to those who provide help desk support. You will spark a chain reaction that will bring joy to those who you serve. We’ll talk in great depth about this in posts to come.

My angle for The Progressive CIO is to provide thoughtful discussions in print form that can be shared, digested, and considered by teams of technology leaders as they face their own challenges. The goal is to build a central repository of information that is easily available to help foster what I believe is a more rewarding approach to technology leadership.

Any questions?

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Foundational Values Humility

It’s a Trick! Don’t Fall for It!

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What do your teammates call the audience for the software you create or deploy for your organization?

  1. Employees
  2. End users
  3. Humans
  4. Associates
  5. Users
  6. Customers

If I were a betting man — or a cheap psychic — I might bet that your answer is 2 or 5. Despite my wary ways, however, I wouldn’t hesitate to bet that you didn’t answer with 3.

Over my decades in this business, I confess that employed answer 5 many times. With each passing year, though, when I say “users,” I feel more and more ashamed of myself. I’m going to be lazy here and quote myself from an interview I did in 2019 with Phil Weinzimer:

I encourage my teams to avoid the terms “users” and “end users” whenever possible. These terms imply a class divide. Arguably, our industry has adopted these terms to help us empathize with people who we are not. But I find that to be an incomplete thought. It’s a very condescending concept when you think about it. We are all people, and we share similar limitations. If we are solving problems, and we create an “us” versus “them” scenario, we are really not putting ourselves in the same bucket as our customers. Some people will say to this, well, if I create something that works for me as an engineer, it will not work well for a non-engineer. I say: don’t create something that works for you as an engineer. Create something that works for you as a non-engineer. If you cannot get in touch with your inner non-engineer, then I believe you have further personal development to do!

Listen to your teams over several hours or days. You will likely hear the term “users” pop up from time to time, and it might just start to feel like weeds or crabgrass in your lawn or garden in mid-summer. I suggest that this as useful an indicator of an opportunity for elevated humility that you can find in our teams.

It’s wise to remember that we are all simple bags of blood and bones. No one of us is more special than another. We may be asked to perform duties because of certain willingness or abilities, but the people who we serve deserve every bit of us being just like them that we can give them. You will never — never — deliver a brilliant solution to the people you serve when you come to the table as the person who you are, but who they are not. This gets to the root not just of humility, but of empathy as well.

Will you admit that you are a small, meek animal in a universe that is infinitely larger than you are? Will you admit that you really understand very little, and that you will never truly understand everything about your life?

If not, why not? What have you got to lose?

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Empathy Foundational Values

Oh No, Not Again!

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As a leader, there is no doubt you’ve been saturated with writing and lessons in empathy. Since empathy was at the center of my life studies, there was a time when I was going to write a book about it. As some folks might say: “But Amazon.

Given all that, what could I offer you in regard to empathy that you might not have already read?

You and I likely agree that, in order for you to do a world-class job at eliciting requirements in any discipline, your ability to hone your empathy skills is of utmost importance.

But one thing that I will share with you that many other writers might not is: no matter what your experience with empathy, if you are to get somewhere great, the work is very, very difficult. After all, if it were that easy, why would there be so many books to try to teach you how to make it easy? Empathy is a lot like running, biking, swimming, or weightlifting. It takes regular exercise and practice to keep you at the top of your game.

When I teach software engineers about empathy, nothing I have found illustrates how hard it is to empathize well better than the following exercise:

The next time PowerBall or MegaMillions begins to ramp up to an insane value, have everyone in your team buy a ticket. Not in the shared office sense, mind you…no, have every single person buy his or her own ticket.

(In order to really do this exercise well, it’s important for each person to have actually bought a ticket. Disclaimer: please don’t do this if you have a gambling addiction. I do care for you.)

Knowing that each person has an actual chance at winning (while simultaneously acknowledging the old adage that the lottery is a tax on people who failed math), have each person ponder:

“What will life be like if I won?”

You will find your teammates saying all sorts of interesting things. But here’s the rub: If you don’t get at least a little scared of a few things, you’re not thinking hard enough.

I’m not going to try to explain why in this post — I can follow up on that at a later time. But the point is: if you cannot empathize with a future version of yourself, how can you empathize with somebody else?

The answer: because empathizing is hard.

Almost all work is a requirements elicitation exercise. From coal mining to neuroscience, from taking orders for tacos to sending people to Mars, we all spend much of our time at work understanding other people’s problems so that we can formulate solutions.

The key to successful requirements elicitation is in understanding the people we are serving, and empathy is the key.

But it is hard. Work on it. Every. Single. Day.

More to come.

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Foundational Values Patience

Planetary Patience

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How would you feel if someone asked you to slow down?

(Would you welcome it? Would it give you anxiety?)

What lasting things have you achieved by rushing?

(Would you list those things as your proudest accomplishments?)

In my mid career, I had the pleasure of working alongside one of the most driven people I have ever known in my life — a man named Raman Padmanabhan. Raman moved from Mumbai to the United States in 1997; received his Master’s degree in 1999; worked as a software development contractor through 2005, and by 2012 became a divisional CIO for Xerox Corporation. He started working for Highmark Health in 2014, and by 2016 he had moved back to India as founding CEO of Thryve Digital Health (a division of Highmark), which hit 1,000 employees in 2018.

I’m out of breath just thinking about it. From a graduate student to a CEO of 1,000 employees — in thirteen years!

I say that Raman was driven. At times, I would say that it seemed he was impatient.

But one thing that distinguishes good leaders is that, somewhere on their journey, they realize that patience is what really wins the day. I recently reached out to Raman, presuming that he — like I — had discovered the value of patience. Because of what he had achieved, I was fairly sure he had come to discover what I had discovered.

“Drew, I laughed when you reached out to me,” Raman shared. “When we met, I was 27 years old. You and I were so much younger. We were in a culture where we couldn’t get anywhere unless we were aggressive. But just last year, I participated in a 360° review, and the feedback from the people I work with revealed that they could not understand why I was so extremely patient. They expected me to be impatient — that I should just ‘make a decision’ quickly about so many things.

“When I moved to the United States, my father told me: ‘Impatience is driven by fear and ambition.’ That fear and ambition is what made me impatient. You don’t want to become a poster child of failure. You want to feel like you ‘made it.’ But I lacked the experience to know any differently. Every time I look back, I know it was those two things (fear and ambition) that led to my impatience.”

In our conversation, Raman shared that there is a special Hindi word that is used to describe patience that has no direct English translation: Saburi, which is strongly associated with the teachings of an Indian spiritual master known as Sai Baba of Shirdi. In this context, Saburi finds itself strongly associated with the concept of Shraddha, which is essentially what we might call faith. In order to have patience, one has to have belief that there is a possibility for change.

Yes, Raman had discovered the value of patience.

The most vital manifestation of patience in any organization, I believe, is a culture that values coaching of employees. If you are lucky enough to witness a culture that values coaching, you will be in awe. Why? Because you will quickly see how difficult it is to copy. It requires an immense amount of patience.

If we coarsely break down three types of issues we encounter in life into the following categories, we can illustrate a point:

  1. Issues whose lifecycle is measured in hours or days (problems and small conflicts)
  2. Issues whose lifecycle is measured in weeks, months or years (projects, which have a start and an end)
  3. Issues whose lifecycle is measured in years or decades (personal growth and development)

We can envision these as concentric planetary orbits around the Sun, from Mercury to Venus to Earth:

[Three orbits]
Planetary patience.
  1. Mercury’s orbit, which is the innermost, is the most eccentric (let’s just call it “spastic”). One orbit around the Sun: three Earth months.
  2. Venus’ orbit, which is predictable and nearly perfectly circular. One orbit around the Sun: seven Earth months.
  3. Earth’s orbit, where we live.

There are three different sorts of tools we use to accommodate those three orbits of our life and work:

  1. Problems: Advice or ideas
  2. Projects: Collaboration and discussion
  3. People: Coaching

Advice, which is offered quickly, frequently, and easily, is the cheapest of the three, and is nearly disposable in nature. It’s the inner, most spastic orbit. It’s as hot and fast as Mercury itself. That is not to say that it is useless. It just doesn’t find purchase for lasting impact. It gets you through the now. By its very nature, it comes from without, and not from within, so it requires others to be there. You would be very hard pressed to provide your own new advice to yourself on a regular basis.

Collaboration and discussion get you through an initiative. It is people working together over a long haul on things that need to have a definitive end. It works like the clockwork that is Venus’ picture-perfect orbit. This is where the self and the other come together to accomplish a greater goal.

Coaching, however, is something that takes time. Coaching is all about asking questions and changing the ways that people think. It is as deep and complex as the Earth itself. No coincidence!

People don’t move at the speed of advice; people move at the speed of coaching, and making the decision to invest in this sort of work takes…well…Saburi and Shraddha. Organizations that embrace a coaching culture at all levels — where every employee is encouraged to help others think, and not just to dole out answers, from the bottom to the top — are the ones whose orbits are the most difficult to disrupt.

So why don’t we do that so easily, or so often?

What did Raman’s father tell him?

What exactly are we afraid of?

Of not knowing what might happen. Of not being able to develop the skills. These are valid things. But the willingness to overcome these things…to devote the time and afford the patience to invest in the humans you collaborate with…will reap rewards that will be difficult for those you call your competitors to replicate unless they choose the same path.

It is within your reach, and within your control. Will you be satisfied merely giving advice and collaborating? Or will you have the patience to coach, and ask others to follow?

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