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“Educate.” With Charlie Katz & Cristina DiGiacomo

Educate. Plato said one of the most important roles a leader should embody is that of an educator. Leaders who are open, transparent and communicative at all times, who take the role of the teacher, gain a closer connection with their employees, as opposed to one who is at the top of the mast. Chip Paucek, […]

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Educate. Plato said one of the most important roles a leader should embody is that of an educator. Leaders who are open, transparent and communicative at all times, who take the role of the teacher, gain a closer connection with their employees, as opposed to one who is at the top of the mast. Chip Paucek, from 2U, does a great job of this as he connects with employees in his company’s daily broadcasts.


As part of my series about the “Five Things You Need To Be A Highly Effective Leader During Turbulent Times”, I had the pleasure of interviewing Cristina DiGiacomo.

Cristina DiGiacomo, author of Wise Up! At Work, is the founder of MorAlchemy, a philosophical consulting firm. She also is the inventor of industrial philosophy and is the driving force behind the idea of applying philosophy in the workplace for the benefit of the leadership of organizations. DiGiacomo has 20 years of corporate executive experience at companies such as The New York Times, Citigroup, AMC Networks, and R/GA. She holds a master’s degree in Organizational Change Management from The New School. She also dedicated nine years to the study and practice of philosophy.


Thank you so much for your time! I know that you are a very busy person. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

About 10 years ago I was on my way to a regular status meeting at my job and I experienced a panic attack. Afterward, I realized that it was absolutely due to stress and anxiety at my job and things needed to change. At the time I had started taking adult education courses in philosophy. I realized some of the things I was learning applied to problems I was having at work, such as feeling overwhelmed, feeling pressured, feeling like I wasn’t doing the work that I wanted to be doing, and even simple issues with the grumpy coworker in the next cubicle. So I began to experiment and started practicing philosophy in how I approached feeling better at work. In essence, Socrates saved me, because philosophy helped me a lot. It taught me how to examine my thoughts, manage my behaviors and gave me ideas on how to make good decisions and how to act on them. Over the years I got deeper and deeper into my study and practice in philosophy and I saw how it directly changed for the better how I viewed myself, other people, and the world. Eventually, I realized I wanted to help people who experienced the challenges I faced because there were things I felt that I wouldn’t wish on anyone. The working domain can be a big presence in people’s lives in so many ways. For me the thing to do is put my energy and knowledge towards incorporating my love of philosophy into creating great workplaces. So, I decided to start my advising firm MorAlchemy.

I call what I do “Industrial Philosophy.”

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘takeaways’ you learned from that?

This should validate any IT person out there. I needed to migrate to a new email address and a new domain. I had just sent out an announcement about a new program to my mailing list and I thought, “Well, I’ve got to get this technical thing done, so I’ll just start migrating my email to get this off my To-Do list.” What I did not know was that my old email address, the one I sent the announcement from, was going to go down before my new email address and migration was complete. I thought my old email address would still be available. Soon, I was getting emails from people who knew my personal email address letting me know that when they responded to opt into my program, they were getting bounce-backs. It’s funny because it just shows that this stuff probably belongs to IT people, and I had a good laugh at myself because I had to let go of the idea that I had flubbed this whole announcement thing. So the lesson here is:

Don’t fix what isn’t broken during business hours.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

A 2,500-year-old assassinated dead guy was the one who helped me along the way. I was studying philosophy for a while before this happened, but I can tell you the moment I was “all in” on philosophy. This was about five years ago. I was reading The Apology with my class. And I immediately fell in love with Socrates. Fell hard. The Apology is the account of Socrates defending himself to the Athenian Senate who wanted to execute him for teaching “radical” philosophical ideas to the youth in Athens. We would read sections of The Apology out loud and when it was my turn I always got Socrates’ feistiest passages, the ones where he was thumbing his nose in the Senate’s faces. So here I am laughing while reading these words and looking around at my classmates and I’m like, “Are you guys not getting this? He’s hilarious!” I had a blast with The Apology and I felt I met a friend, albeit a 2,500-year-old one. I realized the power of philosophy, that a 2,500-year-old assassinated dead guy could give me so much joy just by reading his ideas about how to stand up for myself, the truth, and live a good life. I’m forever grateful to him and many others.

I want to finish what they started.

Extensive research suggests that “purpose driven businesses” are more successful in many areas. When your company started, what was its vision, what was its purpose?

My vision is simple and two-fold. First, to debunk the notion that philosophy is inaccessible and only for the privileged few. That’s simply not true. It’s meant for all of us. The second is that I want to make the world a better place by transforming the workplace. And I believe that philosophy offers true transformation, which is why I use it as a method for achievement.

Wisdom at work.

Thank you for all that. Let’s now turn to the main focus of our discussion. Can you share with our readers a story from your own experience about how you lead your team during uncertain or difficult times?

I look at my clients as a team. Here’s how I’m leading them during this difficult time. It’s not enough to listen and plan and come up with advice about how to deal with the uncertainty. That’s dime-a-dozen stuff. The way you help people through something like this is to be open about how you’re going through it and leading yourself through something like this openly and transparently. Plato talks about a leader who is an example, so I do this with my clients. I set the example in terms of always being sure I’m calm, demonstrating keen insight, and living a disciplined life. And they benefit from seeing someone who is taking this situation and making something good out of it. I’ve never been more productive and more creative than I am right now, and my clients see that and are in turn motivated by it.

Be the example.

Did you ever consider giving up? Where did you get the motivation to continue through your challenges? What sustains your drive?

Considering I’m doing something extremely niche, most people have never heard of the notion of combining philosophy with the business world, it sometimes feels you are forging the path on your own. There are few role models. So yes, there was a time early on where I wanted to give up. My ego was flipping out on me, telling me things like, “No one is going to understand this or you. You don’t know how to run a business. It’s going to be hard.”

Then I remembered a practice I learned in philosophy school: “My thoughts about the work aren’t as important as the work itself.” I needed to be committed if I was going to make this work. I get motivation from leading a philosophical life — from being someone who is very thoughtful about my thoughts, who questions, and is always looking for the right way to do something. Even if it means working on myself. What sustains my drive is the fact that knowledge, especially of the Self, is infinite. There are always things to discover, and I’m never bored. There is never a dull moment where I don’t have something to work on or be creative about or study. When you begin with yourself and understand the depths that you can go, it can be very motivating, especially when you begin to see the positive outcomes in doing that kind of work.

Be your own motivation.

What would you say is the most critical role of a leader during challenging times?

Be the Still Point in the Room. We tend to think a leader needs to be saying a lot of stuff, making a lot of noise, being super visible, and being a mythic presence around others. But in actuality what people are looking for right now is constancy. The constancy of thought, constancy of action, constancy of speech, and for a leader the more they embrace being still and steady with their people, the more they will be seen as a source of strength. It’s really interesting because it’s a bit of a paradox — when everything is chaotic and you are still of mind and presence, you realize you don’t have to do much except be there for people, be there to make a decision, just be. Be the still point in the room and the answers and the way forward appear more clearly for yourself and everyone.

When the future seems so uncertain, what is the best way to boost morale? What can a leader do to inspire, motivate, and engage their team?

Xenophon was a military leader and philosopher who had to lead an army of defeated soldiers who had just gotten their butts kicked by the Persians, and he had to lead them through hostile territory to get home to Greece. Peter Drucker, the godfather of management, said Xenophon’s work The Art of Leadership is one of the best leadership books ever written. The interesting thing about Xenophon is he created the ideas and tactics of retreat, and was so beloved by his army. They voted him to be the one to lead them in the difficult journey home. He believed in something very simple: leading from behind. He believed that a leader should always be in the same space as their people. This is one of my favorite quotes of his: “Leaders must always set the highest standard. In a summer campaign, leaders must always endure their share of the sun and the heat and, in winter, the cold and the frost. In all labors, leaders must prove tireless if they want to enjoy the trust of their followers.”

Get in the trenches with your people.

What is the best way to communicate difficult news to one’s team and customers?

The first thing is to acknowledge it’s difficult news. It’s also really important the person delivering the news is as close to the hardship as possible. In other words, never have someone deliver news who isn’t directly feeling the impact of the situation themselves. This fosters a connectedness to the impact no other person can. Sure, I could say something standard like “always be truthful,” be authentic, or use the compliment sandwich — all great tools. But what’s most important, what the person on the receiving end needs to know is that the person delivering the news understands how hard it is. So, start with “this is hard to say.” At least there’s some acknowledgment of the difficulty in actually delivering the news and shows respect for that other person. I’ve always appreciated people who acknowledge the moment in that way.

Acknowledge the difficulty.

How can a leader make plans when the future is so unpredictable?

Frameworks, plans, models, processes, matrices, and measures have all been rendered obsolete. The one thing that’s never obsolete is the mind, the ability to think, the ability to see what’s in front of you. So, my advice is to see the need and meet the need that’s in front of you. That’s it. To think it has to be more complicated than that is to introduce more complexity than is necessary. It’s become clear that you can plan and then there’s another plan that gets in the way. Also, always be on the side of doing what’s good. What’s good for the group, what’s good for the customer, what’s good for another person. Unpredictability is always there at any time, so there’s no need to focus on unpredictability. There’s only a need to focus on what’s there and desire the work that you can control.

See the need, meet the need.

Is there a “number one principle” that can help guide a company through the ups and downs of turbulent times?

Accept the ups and downs — know that’s reality. And tell your people you’re ok with their ups and downs. Go with the flow. Do not put more meaning on the “ups” than is necessary and do not put more meaning on the “downs” than is necessary. It’s all part of a bigger picture. Allow a situation to unfold. Do your best to adapt to it, respond with a good manner, and do not be in resistance to it. New solutions arrive because of a situation if you think about it in the right way. The ups and downs are what inspire growth and strength in a company.

Expect it so you can accept it.

Can you share 3 or 4 of the most common mistakes you have seen other businesses make during difficult times? What should one keep in mind to avoid that?

The first mistake is to think that there is a problem. Wittgenstein says: “The solution of the problem in life is seen in the vanishing of the problem.” I think he means that if you have the attitude that what’s in front of you is not a problem in itself, therein lies your solution. To catastrophize starts from the mind, so the attitude that all is lost or nothing can be done is a big mistake.

So get your mind straight.

The second mistake is to ignore your people and their needs. Focusing on function and process over the needs of your people is where I see leaders get tripped up. After you, it’s your people that will see the company through this.

Take care of your people.

The third mistake is obsessing over what’s going to happen. Voltaire said: “While doubt is an unpleasant condition, certainty is absurd.” If you focus too much on outcomes you’re limiting the potential for new ideas and new avenues to explore. Respond to what you can, in the best way possible, and let the outcome follow. You can’t be certain of outcomes, especially now, but you can control the means along the way.

Focus on what you know..

The fourth mistake is relying on the past. If a situation arises that requires an extra level of effort or an extra level of creativity, do not shy away from it and revert to historical ideas and processes. A lot of companies go into efficiency measures or cutting measures thinking that to reduce and shrink is where the survival is. Survival is not the mentality or the model for situations like this. The model for situations like this is creativity and innovation. Do what you want that’s been on your bucket list. There’s nothing left to lose.

It’s not time to shrink, it’s time to advance.

Generating new business, increasing your profits, or at least maintaining your financial stability can be challenging during good times, even more so during turbulent times. Can you share some of the strategies you use to keep forging ahead and not lose growth traction during a difficult economy?

The philosophical response to this question led me to some different perspectives. In focusing on people and meeting the need, keeping your current customers happy and increasing customer engagement is most important. Then making sure that your basic needs and your employees’ needs are met is most important, not increasing your profits or trying to take more than what’s needed or given. I’ve also found now that there’s strength in numbers, and fostering collaboration with other businesses for new ideas and programs, and opening yourself and your company up to partnerships is something that has also been a supportive aspect of my business.

Focus on all relationships in your work.

Here is the primary question of our discussion. Based on your experience and success, what are the five most important things a business leader should do to lead effectively during uncertain and turbulent times? Please share a story or an example for each.

A lot is being asked of leaders right now, and there are no easy answers, and they have to make tough choices that impact people’s lives. They need to truly understand exactly what is changing and what will change. But there are a few things they can do to strengthen their resolve and demonstrate leadership.

  1. Educate. Plato said one of the most important roles a leader should embody is that of an educator. Leaders who are open, transparent and communicative at all times, who take the role of the teacher, gain a closer connection with their employees, as opposed to one who is at the top of the mast. Chip Paucek, from 2U, does a great job of this as he connects with employees in his company’s daily broadcasts.
  2. Know the Depths of Your Own Mind. Emerson said: “When you know the depths of your own mind, you know the depths of all men’s minds.” Emerson was big on listening to your “inward leader” and being fiercely independent from influence of any kind. In this day and age, it’s hard for leaders to know which way to turn. What’s being offered here by Emerson is if you understand who you truly are first, then perhaps you gain insight into the hearts and minds of your people. I see this in Elon Musk, who has an undeniable commitment to his vision and self-awareness.
  3. Preoccupy Yourself With the Truth. Francis Bacon said: “There is no pleasure comparable to standing on the vantage ground of truth.” Socrates was obsessed with questioning until the truth reveals itself. There’s so much information, and misinformation out there now that it’s imperative for a leader to get as close to the truth as possible. The quality of decisions is determined by the quality of the truth they are based on. I think that Bill Gates is doing an incredible job of being of service to the truth in these troubled times.
  4. Show Reverence. This is not the time to be cavalier or in denial of the current situation. Plato talks about showing reverence for people, situations, and society in his Laws. What this means is to respect everything going on around you as a leader and everyone involved and the role you play in it. I see this in Brian Niccol’s quote to The New York Times that the current situation is “a grind to the organizational psyche.” That’s real talk right there.
  5. Have No Fixed Position. One of my favorite philosophers is Lao Tzu. He espoused spontaneity and flow in action according to the situation at hand. He also said one of my favorite things: “Let reality be reality.” The old ways of doing things and approaching things are quickly being put out to pasture right now. There is no playbook for what we are going through. Leaders who are agile and adaptable are much better suited to dealing with the uncertainty we have today. An example is Jane Park, Tokki CEO, and the former Julep CEO, who pivoted her packaging company to create masks for the consumer space.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“The sage acts without pressure from within or without.” — Sri Shantananda Saraswati.

Far be it from me to call myself a sage, but I love this idea of acting without pressure from within or without. This is so relevant to me in my life because a lot of my frustrations and experiences that were difficult were really a reaction to the perceived pressure I was experiencing. Yes, there were challenging times, but I made them even more challenging by having all kinds of thoughts about them (hat tip to the Stoics). But what I love about this quote is that it is a reminder about the moment you need to act. Because we all do at some point have to leave our thoughts behind and do something. And this is a reminder to always act without pressure. This is no easy feat, which is why I find it so aspirational.

How can our readers further follow your work?

I’d love for people to connect with me on LinkedIn: https://www.linkedin.com/in/cristinadigiacomo/

I also have a book Wise Up! At Work: https://bit.ly/wiseupatworkbook

If you go to my website you can sign up to get a free excerpt of my book and access to my monthly newsletter “Wise Up! Monthly”: www.cristinadigiacomo.com

Tune into my podcast Wise Up! — where I have thoughtful elevated conversations with leaders on the issues facing business and society today. https://podcasts.apple.com/us/podcast/wise-up-with-cristina/id1510125819

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