My Journey Towards Authentic Leadership

I’ve been reading and listening to Jerry Colonna for five years now. I was fascinated by the first post he ever wrote, disappearing into the fire. It captivated me. Like many bloggers, Jerry was able to talk with authenticity about the experience of entrepreneurship. But unlike anyone else I’ve read to date, his perspective somehow managed to combine eastern philosophy with the harsh realities of capitalism in a way that spoke to me. There are others. Brad Feld thinks this way, although he hasn’t made it his life’s work to teach others going through this journey. Parker Palmer thinks this way, although he doesn’t live in the entrepreneurial world to the same extent. Jerry is, in my experience, unique.

While I was fascinated by the concept of “authentic leadership”, I didn’t really know what to do with that thought process. In the ensuing years, I’ve been on a continual journey to re-shape my ego and shift the way that I build relationships. I think I will be involved in that process forever, because I know just how far I still have to go, and yet I have begun to see the fruits of my labor. I’m fascinated, and humbled, as I start to see this happen.

I’m writing this because I want to share what I’ve learned so far from my attempts at practicing authentic leadership. My hope is that these practices will become more widespread.

Admitting that you are human—limited, fallible, imperfect—is a superpower.

It absolutely changes the way you relate to everyone you work with. The people that work with you are empowered, because they’re not counting on you for answers all the time. They’re also able to admit their own failures and imperfections and have honest conversations about them, because you have created a safe space to do so. These egoless conversations give everyone the opportunity to get better, and improvement becomes a collaborative process where both sides bring something to the table.

Human fallibility is an absolute, incontrovertible fact. You are not perfect. If you truly embrace that, openly and publicly, it is amazing how dramatically it will change both individual relationships and the dynamics of an entire team. My team today is the most honest, non-defensive, straightforward, hardworking group of people I have ever had the pleasure to be a part of. We’ve found that the people who join this team and get exposed to this culture blossom in really dramatic ways. Comparing this to teams that I have led in the past prior to my exposure to Jerry is like night and day.

The practice of mindfulness is an absolute requirement of a leader.

I’ve heard Jerry describe mindfulness as the practice of creating a space between a stimulus and a response that you can use to make a decision. I thought that was absolutely brilliant, although if you’re not familiar with mindfulness it might not sound like much. Here’s what this means. Going through your day as a leader, you’re bombarded with stimuli: people asking for things, data on performance, to-do lists, disagreement/conflict… As this is happening, you’re often in a flow state, just handling one thing after another after another. You’re very much relying on system 1 to do a lot of this processing, and as such most of what you’re doing feels very instinctual.

Mindfulness is the ability to recognize, in the moment, when a situation requires you to pause, come out of that flow state, and process it with system 2. Stop, pause, destress, think, pause, pause. Then react. Say something or do something, but only after that period of mindfulness. This can still happen all in the space of a few seconds, but it requires extreme mental effort, because you’re exerting a very high degree of self-control in pulling yourself out of flow and exercising a much more effortful mode of thought. But it’s the difference between acting annoyed and acting calm, between shooting from the hip in an important decision and stopping to gather more data. It’s the process that allows you to question a long-held belief.

Stop, pause, destress, think. I’ve specifically trained myself to recognize certain situations that require mindfulness. When I feel combative, or particularly stressed, or annoyed. When someone feels particularly strongly about a viewpoint that runs contrary to something I believe. I’m not perfect by any means, but I’ve made massive strides using this tool over the past year.

You only have one self, and you have to share it all.

To truly be authentic, you can’t just share your “work self” with your team, you have to share your whole self. People trust, and identify with, people. Your authenticity will resonate with them, but it requires you to share your entire self, not just some edited version of yourself that you’ve decided is safe-for-work. Eventually, most people will get comfortable sharing their complete selves in return when they realize that it is safe for them to do so.

Once you have developed two-way true-self relationships, communication, productivity, and happiness begin to climb for everyone on the team.

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That’s all for now. Authentic leadership is absolutely the most important and impactful competency I’ve developed over the past six years working in startups, and I have a lot more to learn.

Thanks Jerry.

Are we still explorers?

I saw Interstellar last night. Like many movies that deal with topics I’m interested in, I was simultaneously engaged by the subject matter but disappointed by the way in which it was handled. I would have been significantly happier had there not been any voyage to the inside of a black hole. That, and essentially everything that followed, took my entire movie experience from :D to :-|.

But there were seeds in that experience that have been bouncing around in my head ever since, and I’m grateful for that.

Here’s what I’ve been thinking about. I think that our progress in science and technology over the preceding 100+- years has led our collective consciousness to a certain ego-centrism. I think that we have moved from our toddler phase where we don’t know anything at all (and we wouldn’t even know what questions to ask) to our teenager phase where we think we know, if not everything, than a considerable percentage of everything.

That’s a broad statement, and while writing it I was challenging myself to be more specific, so let me do that. I don’t mean to say that we think we know everything about, say, human aging and how to eliminate age-related death. We clearly don’t, and I think that we all know that. What I suppose I mean to say is that we feel like we understand the fundamental forces that shape our universe and how they act.

For the past several hundred years, we have consistently made massive fundamental discoveries about the universe. Gravity. Electromagnetism. Nuclear. Relativity. Quantum mechanics. These discoveries took us from a place where we literally couldn’t explain the world around us to a place where we could. The universe became comprehensible, and deterministic.

I think the public perceives science, now, to be a matter of application. How can we apply our knowledge of how the universe works to solving problems related to health, communications, standard-of-living, etc. But, I don’t think most people ever imagine that maybe there are more fundamental discoveries to be made.

I think our general mindset is one of mastery: we “get it”. Even if we don’t know exactly know a particular answer today, all we need to do to get from here to there is allocate the right amount of grant funding and some researchers will certainly figure it out.

I remember when I was young my dad was reading a book about Einstein’s search for the GUT--the grand unified theory--that would, essentially, create a framework for understanding all of the four fundamental forces. He was never able to get there because gravity never really fit in, but the picture that my dad got from reading the book (and relayed to a ten-year-old me) was that if Einstein had only figured out that last piece of the puzzle, then we’d basically understand everything, all of it. We’re so close to understanding everything.

“We are explorers.” Matthew McConaughey’s line stuck with me. But there is nothing innately exploration-seeking in humans. It is a trait that we have cultivated over the past 400 years because it has been a successful strategy. The Enlightenment made scientific inquiry incredibly productive. The discovery of the new world made physical exploration a worthwhile pursuit.

I think that the explorer mindset also leads humanity to be its best self. It gives us a sense of hope, a sense of shared purpose, and something to productively engage our minds (and our lives) in. And ultimately, it’s the only real chance we have of avoiding extinction.

But I don’t think we should take that mindset as a given. If we really believe we understand everything, we’ll stop searching.

Have we really discovered everything we can about how the universe works? I don’t think physicists believe that we have. I think that this misconception is one that is only harbored by lay people. We just don’t come face-to-face with questions that we don’t know the answer to any more, which makes us feel very sure of ourselves. To bump up against the questions that really boggle our understanding of reality, we need to be looking at a black hole, or a subatomic particle, or...

This isn’t a knock on normal people (like me). I’m not impugning our lack of imagination. I just think we need to find ways to stay engaged with the bleeding edge of physics to recapture our sense of awe, of humbleness, and of excitement about the future (and desire to get there). The world around us doesn’t just hit us on the head with these questions today in the same way it did in Newton’s.

Why and How to Scout your Enemy

Scouting is one of the most important aspects of Starcraft. Deciding when to scout, what to look for, and clever execution are critical skills for any tournament player. 

Why

If you don't play, I can explain why this is rather easily. Starcraft is a game about managing your economy, your technology and your army. Because of this, you essentially have four main strategic choices.

• You may want to build up a very strong economy and crush your opponent in the long run with more resources.
• You may want to built an elite group of units very quickly and do critical damage to your opponent before he has the technology to defend himself.
• Or, you may want to get a lot of very cheap units very quickly and overrun your opponent.
• Pursue a balanced strategy, mixing aspects of all of these. 

All four of these approaches are very reasonable choices—there isn't a right or wrong approach. Great players have their own styles, but almost all of them mix in all four of these strategies.

The interesting question is actually not "Which of these strategies should I choose?" since all are great options. Rather, players need to answer "Which of these strategies should I choose based on what my opponent has chosen?"

If your opponent has chosen to invest heavily in technology in hopes of crippling you early, you had better not invest all of your resources in building your economy or you will lose. If your opponent is pursuing a balanced strategy, you likely won't be able to kill him/her outright so it might be better to get ahead economically. 

And so on. This is referred to as "the strategic wheel"—if you do x, I should do y. What makes Starcraft such a fascinating game is that it's infinitely recursive: since I'm now doing y, you should switch to doing z. The art of professional Starcraft is one of navigating this strategic wheel, and figuring out clever ways to outfox your opponent.

This entire interplay depends on scouting what your opponent is doing. If you don't scout, you're quite literally playing with your eyes closed. Your opponent will scout you, figure out an appropriate response to your strategy, execute it, and you will lose.

This applies for overall game strategy, as discussed above, as well as tactical scouting ("There is a dropship with some marines about to land in the back of my base!"). In the early parts of the game, strategic scouting is very important because the range of options available are unbounded. As the game begins to develop, tactical scouting becomes more important.

Novices often like to sit in their base, build a lot of stuff, and then move out and attack, all without having any idea what their opponent is up to. When they start playing experienced players they begin to wonder why this approach doesn't work.

The critical insight here that newcomers to the game often don't understand is that you're not playing single player. Your goal is to beat another human opponent, and in order to do that you're going to have to formulate your strategy in response to theirs.

If you run a startup, scouting is equally as important. Your customers have choices. They can buy your product or your competitors'. They can use your app or ten other apps just like it. At the start, all products are undifferentiated because we all start out with the same thing: a credit card, a Macbook, and Internet access. It's up to you where you choose to go from there, and the only way to win is by making those choices within the context of your competitive environment.

How

In Starcraft, scouting is done by sending small, fast, and cheap units running around the map to gather intelligence. Often times you'll have to send units into your opponents base knowing that you'll lose them. (This speaks to the importance of the information you receive, because you're giving up a tangible asset—a unit—in order to receive intangible benefit—information.)

When it comes to your startup, its useful to think of scouting in the same way. You're a single individual, and a single individual only has a very small line of sight. You can only read so much, only acquire so much information on your own. In order to really know what's going on in that wide world of the competitive landscape you play in, you need to amplify your information-gathering tools.

Here's how I approach that problem. 

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1. Network

By far the single best way for you to improve your scouting is to employ others to do it for you. That does not mean hiring them and giving them paychecks, it means having large networks of really smart people who respect you and care about your success. If you have such a network, it will effectively turn into your own personal information-gathering service.

• "Did you see this article?"
• "I heard that Competitor A comps their sales reps better than you do."
• "Company B is preparing to go down-market with lower price points."

You can't possibly see everything. Make sure you know a bunch of smart people who know something you'll be interested in when they see it.

2. Look at competitors' job postings

Hiring is a leading indicator. Companies hiring heavily in sales are clearly building their company in one direction, while those hiring heavily in engineering are pursing another. Job descriptions themselves can provide key information. At Argyle we foresaw a strategic threat because of an infrastructure engineer job posting on a competitor's website.

3. Understand your competitors' products

If you're not using your competitors' products, you have your head firmly planted in the sand. This is an incredibly rich dataset. What's most important here is not that you understand competitors' current capabilities, but that you infer future direction.

Too many startup folks refuse to look at competitors' products because they don't want to get caught up in a feature-by-feature comparison. I agree with this. The point is not to do a competitive checklist, it's to understand the technological investment underlying the product and to anticipate where that investment could allow the product to go next.

While many of RJMetrics' prospective customers wonder about the difference between us, Mixpanel, and Kissmetrics, the underlying technology of these tools is extremely different. KissMetrics and Mixpanel are sophisticated tag & API-based web analytics tools, whereas RJMetrics is an ETL & data warehouse platform with a visualization layer. This difference says a lot about our respective forward-looking product roadmaps. 

4. Invest in scouting technology

In Starcraft, there are technologies that allow you scout better. A protoss observer with the speed upgrade is significantly better at collecting intel than a slow observer. Researching these upgrades costs resources, which reduces the amount of resources you have to build an actual army.

In the same way, you can invest in technology for competitive intel. This will take engineering time away from building your actual product, but if you're able to make better decisions with the information you gather, then it's more than worth it.  

An example: build a dashboard on a public TV that charts adoption of your product alongside the adoption of competitors' products. Layer on a feed of customer commentary, either from Twitter, app review sites, or support message boards. How can you figure out adoption? Scrape the web, look at app store leaderboards, look at information in press releases and infer growth rates, look for incrementing customer IDs in their product... There's definitely a way to at the very least get a proxy.

5. Turn your customers into your eyes and ears

Your customers not only understand their buying choice—why they went with you over your competition—they also are the consistent recipients of all of the marketing communications from your competition. If a competitor is trying a new sales tactic or marketing campaign, your customers are likely to know about it first.

Perception management is obviously tricky here. You can't email your customer list and say "Hey I'd love it if you could just let me know if one of our competitors ever tries to win you away." You'd sound like an overly jealous boyfriend. 

But if you cultivate real relationships with your customers, this type of information will flow freely. If you stop being a corporation and start being a person who's trying to build something great you can enlist them on your team over the long run.

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This is how I scout. It is a constant, active process. It's fun, it sparks my competitive drive, and it keeps me sharp. Actually, the reason most novices don't scout in Starcraft is that they're scared—it is psychologically easier to not know what you're up against and rather than to know for a fact that you're losing. Don't succumb to that fear. You can't win if you have your eyes closed, and knowing you're losing should just spur you to want to win more

PS: Basic solutions like "follow your competitors on Twitter", "read industry blogs" and "set up Google Alerts" are table stakes. If you're not already doing them I would recommend you pursuing a different line of work that is more in keeping with your lack of curiosity and drive.

PPS: If, upon reading this post, you find yourself objecting to the fact that Starcraft is a zero-sum game (one winner, one loser) and that technology startups are non-zero-sum, then kudos. This is a reasonable, and sophisticated, counter-argument. However, I do not believe that it negates the advice, only adds a layer of depth. If you find yourself in a truly pie-expanding competitive situation, then scouting is admittedly less important.

Hate the world enough to never be satisfied with how shitty things are, love the world enough to stay engaged with it anyway.

Cathy O'Neil

We live in a house made of each other.

​Watsky, via Jerry Colonna