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Michael Seibel on Leadership Attributes in Successful Startup Leaders (torch.io)
149 points by camerony 65 days ago | hide | past | web | favorite | 38 comments



“Level Two thinking is about creating an environment and empowering people such that they do produce great outcomes without you having to tell them. If they can get into a mental model of what’s good for the company, and if they can be motivated and feel empowered, then they start doing great things. You don’t have to direct them. ”

“If you want to build a ship, don't drum up people to collect wood and don't assign them tasks and work, but rather teach them to long for the endless immensity of the sea.“ - Antoine de Saint-Exupery


but what happens if number #1 doesn't like the ship they built?


Then they iterate? Nowhere does this say that the CEO stays out of the way. CEO can act as the editor, co-designer, arbiter, curator and whatever. Like you hear how Steve Jobs operated.

Mode two thinking does not mean you can't be critical. In fact, critique is critical for the best end result. It means you must understand how to skillfully switch between type 1 goal oriented and type 2 creative mode. That's the trick - you need BOTH. And utilizing mode 1 so that it does not kill mode 2 is really hard. You have to be compassionate, emphatic and work from the common understanding that everyone is striving towards the same goal.

It's "Build this my grandest design to me now!" vs. "Ok, hotshot, show me what you can build and we can tweak that into the ultimate ship".


Thanks, there must be several styles of switching between the modes/management styles that determine how one is interacting with his colleagues. What are your thoughts here?


Mm, I'm really not an expert and don't have anything constructive to add except to simplify what I said:

IMO the key thing is that the work is done in open mode, and the results are observed critically.

This means that the constraints, implicit or explicit, should be as unlimiting as possible, because all constraints will limit the space of solutions that people can think of. This includes such limits as performance metrics and various financial incentives. Which means if you want creative output, you should generally fund peoples and projects, and not milestones. And then when they deliver something, gauge that critically, and if the thing they make sells well, give them a bonus so they will feel fairly treated. But don't incentivize the innovation process itself and don't hold the bonus up as a promised gift they will wait for.

This is of course completely different way than you would incentivize sales people or people doing linear repetitive tasks where performance based incentives are shown to work pretty well.

Dan Pink's TED lecture is pretty good.

https://www.ted.com/talks/dan_pink_on_motivation?language=en...


Out of the big five personality traits agreeableness is the the one most corollated with being a CEO. Negatively correlated, that is.

There is a reason for this. Most people have really low standards. Most people are lazy. Inspiring them to build the ship fixes the second problem. Telling them that the ship's sails are junk and they should design better ones fixes the first.


I find it funny that the others here assume the problem is with the builders and not with #1.

Good leadership requires that you come to terms with shortcomings, both your own and those of other people.


More generally, most people always think it's someone else's fault. It's hard for people to look critically at themselves, but only once you learn that skill can really start to improve.


This is incredibly true. At Torch we are constantly building feedback loops into leadership process. It works because even hard feedback comes with genuine respect and care for the other person. Without care, it's like two Vulcan's giving each other feedback, and that starts to look more like criticism...which in fact is one of the most toxic qualities in a company culture.


The CEO still manages and communicates the vision on a regular basis. Autonomy is a sliding scale.


Then they hired the wrong people.


Or there might have been a failure to negotiate requirements and priorities, or that different parties were pushing in different directions. Many choices exist. The endless sea may not appear to be the same to everyone.


For the first part of your comment to make sense you have to assume there is a right answer and a correct solution both which don't make sense in the real world as you eluded to.


A good Casting is as important as a good script. Sometimes it is more important


The topic of leadership seems to come up frequently in these circles and I think it's great and important.

It does strike me as odd though that there is almost no recognition or reference to the vast world of case study and literature about leadership, and technical leadership to boot.

For example, Siebel talks about "Level 2" thinking as well as self awareness as important attributes to being a good leader. These attributes can be found discussed in great detail with well worn concepts like "Servant Leadership"[1] and "Referent Power"[2].

Further, actively seeking high consequence/stress situations like Siebel discusses is a well understood way of learning leadership.

So my question is, if it is important for tech CEOs or other tech people to understand and embody these leadership principles, why not seek out the huge amounts of training and learning on this - and to that end seeking out people who have gone through a lot of it, rather than trying to start from first principles?

Let me be clear too, I'm not suggesting you can learn this stuff from a book. Far from it. What I am saying is that there are a lot of great people out there with tested leadership experience, that are overlooked by the tech world because it does not specifically select for it.

[1] https://en.wikipedia.org/wiki/Servant_leadership

[2]http://www.communicationcache.com/uploads/1/0/8/8/10887248/t...


I see this pattern a lot: leadership advice in the form of general principles/first principles, but not a lot of advice on the nuts and bolts of how you accomplish those things. Human emotions, motivation, and communication are far fickler things than software, and it takes a lot of skill and work to create consistency and resilience from that mess.

For example: how do you tell someone that they're underperforming while still motivating them? There's a lot of partial advice out there like "frame it as a growth opportunity." But how? What words do you use? Half of the new managers will flinch before they give the feedback, and the other half will flub the delivery. It's a hard-earned, fundamental leadership skill.

MBA programs actually encode a lot of time-tested wisdom on leadership and management for the students who go looking for it. Huge emphasis on the caveat because not all MBA students are looking for that. They even do simulations to give you practice in a low-stakes setting. As a risky generalization based on my own observations, I think Silicon Valley has thrown the baby out with the bathwater with its historical hostility towards MBA's.

Speaking of which, I think executive coaching is worth its weight in gold for younger startup leadership.


> how do you tell someone that they're underperforming... MBA programs

When you ask someone, "Describe the person you'd like to work for," I seriously doubt talented people say, "An MBA."

So surely you'd see why so many mediocre people wind up working for them.


Talented people aren't going to decide on the basis of whether their manager-to-be has an MBA. Talented engineers will gravitate towards teams with likewise talented engineers and good leadership.

I'm suggesting that, as a reliable way to raise the bar on leadership, engineers who want to manage might benefit a lot from going through MBA training.


Engineers who want to manage would definitely benefit a lot from learning about psychology and leadership. MBA training however does produces great leaders that attract skilled people. There is a reason MBAs are complained about so often - the reason is that their management style tend to be demotivating and offputting.


would definitely benefit a lot from learning about psychology and leadership

That's a significant chunk of the MBA curriculum. Of course you don't have to get it from there, but if you look at who teaches in business schools, quite a few of the professors specifically research those subjects.

the reason is that their management style tend to be demotivating and offputting

What about it is demotivating and offputting? The typical complaint I hear isn't about their leadership skills, it's about a lack of technical expertise or lack of appreciation for subject matter expertise. As an example, I've seen some of Harvard Business School's materials, and their curriculum definitely teaches to seek technical expertise.


> That's a significant chunk of the MBA curriculum. Of course you don't have to get it from there, but if you look at who teaches in business schools, quite a few of the professors specifically research those subjects.

I am mostly judging it from results of MBA managers. It seems that highly motivated happy teams are rather exception then rule. This kind of psychological knowledge seems to lead to manipulative behavior that most eventually figure out in the span of months and consequently leads to lack of trust, demotivation.

> The typical complaint I hear isn't about their leadership skills, it's about a lack of technical expertise or lack of appreciation for subject matter expertise. As an example, I've seen some of Harvard Business School's materials, and their curriculum definitely teaches to seek technical expertise.

As general as both complains are, they are closely related to leadership skill, they are not independent of it. The "no appreciation for subject matter expertise" is euphemism for "experts under their leadership are unable to use their skill and knowledge and are treated without respect and without regard". It means that project is running into the same problems again and the leader does not care, because problems are not affecting him right now and experts are effectively talking to a wall that smiles back.

Lack of technical expertise means that experts are forced to implement decisions they know will lead to problems and then get resentfulness when those problems happen and they are blamed for it. It means you work around the manager and not with manager. It means that you have to keep secrets and manage manager, because manager cant be trusted.

I don't know what exactly those schools teach, so I can not say what exactly is wrong with it. But I had managers that I respect to this day, not all of them were technical and they seemed to be able to work around lack of technical knowledge better then mba I have seen. Mba are good at creating illusion of well run project for upper management. That absolutely has value, especially in corporation, but is not really leadership skill and is not same as actually run the project well.


A concrete example of motivation: when someone on my crew identifies and issue and dispalys just beyond a moderate amount of interest - boom - just just volunteered to drive that issue, direct resources and own the outcome. People grow fast with responsibleity and accountability. Sometimes it's a little messy. Play a long game.


While I agree with your general desire to teach/learn leadership, I don't think true Leadership can be codified as easily as other skills/qualities can. As Siebel says at the end of the interview, the single biggest trait he looks for in a good leader is communication. How do you teach good communication? Is the combination of empathy, wit, general+specific knowledge, active listening, etc etc something you can really teach someone so they communicate better? I'd argue these traits, if teachable at all, are developed at a young age. I've frankly never seen an adult evolve from a bad communicator to a good one. And that's just one quality of a good leader. Now try to codify, much less teach, something like charisma. Or likeability. These things, while nebulous, are definitely part of the leadership equation.

This becomes even more complicated in a tech setting, where the 0s and 1s of computers clash fundamentally with the nuanced requisites of a good leader. They're not mutually exclusive, of course, but what we're talking about now is a true left brain/right brain individual with a healthy dose of X factor that makes him/her someone that developers, sales folk, and office managers alike trust and get behind.

I wish I were wrong. I wish you could teach these things, but I really don't think you can. Otherwise we'd be living in a much different world.


How do you teach good communication? Is the combination of empathy, wit, general+specific knowledge, active listening, etc etc something you can really teach someone so they communicate better? I'd argue these traits, if teachable at all, are developed at a young age.

They are definitely teachable. I had to learn them. I won't say I'm great at it, but there was a drastic difference between my effectiveness as a leader early on vs. later on.

Just like technical acumen, you have to start with building low level muscles, and then you build on top of that to develop increasingly complex, integrated skills.

Here's an example breakdown of how to build communication skills from a set of low level skills. I've seen adults (including engineers) improve dramatically with direction and practice:

1. Learning to tell when you are getting angry and building the habit of stepping away instead of escalating

2. Learning to tell when you are reacting in the moment vs. analyzing, and practicing the habit of moving to analysis during tense conversations

3. Learning to stop automatically attributing bad motives to things other people say that you dislike

4. Learning the formula for conflict handling: (1) acknowledging their point, (2) repeating it back with a charitable interpretation, then (3) responding with your point

5. Learning to make exploratory statements and ask questions to establish common understanding

6. Learning to identify and not make overconfident/dismissive/glib statements


One is so critical for people. Stepping back, even something as simple as just pushing away from the table, can help you see the situation in a clearer light. Many of the rest can be summed as check your ego, and be humble.

Check out Jocko Willinks podcast sometime if you're into leadership. He talks about all of these things using examples from his life when he led Navy Seal teams.


I think I've reached acceptable level in all 6 categories however I definitely feel my communication skills could improve drastically.


Oh for sure there's much more after that, but I wanted to show that you can actually break down soft skills into teachable pieces.


Ah gotcha. I think the one skill that makes the difference is being able to communicate more with less words. Essentially mastering the elevator pitch technique.


I really enjoy your comments. Would you be open to me reaching out to you? My email is also in my profile, if that’s easier.


Sure, I'll send you an email.


In the spirit of the comment with the quote which includes this part: "teach them to long for the endless immensity of the sea", I think a lot of what you suggest can be learnt if one adopts a different mindset while communicating. I learnt a lot just by consciously practicing "what set of assumptions or circumstances would make this person's statements correct/valid" instead of "let me see how I can explain to this person that s/he is wrong". Even if the other person is holding on to a position which is objectively incorrect, it makes it much easier to see how s/he came to that position. Anyway, the gist of what I'm trying to say is that without a change in mindset, there is no motivation to function in a different manner. So, it might appear that some people will always work in a certain way but I think if they are motivated to change, then it's not really an extraordinary thing for them to undergo a notable transformation.


I think the book How to Win Friends and Influence People can go a very long way to teaching people communication skills.


Interesting point. My impression is that YC/SV is a lot “sexier”, and that’s why people are drawn to Seibel rather than Greenleaf or French/Raven.

The PDF you linked looks incredibly dry; On the other hand the link in this post is very easy to digest and understand.


In the military, this is also called “Commander’s Intent”.

https://en.wikipedia.org/wiki/Intent_(military)

I have never been in the military, nor do I know much about it. And, tech companies are very different from militaries. But, I sometimes come across military leadership readings that help give me ideas, and “Intent” is something that has stuck with me.


The problem with CEOs talking about inspiring people to get stuff done is... they write their articles in an inspiring way, leaving out the inevitably uninspiring parts of reality.

Visionary envisaging can easily become meaningless corporate speak, and L2, with its tendency to abstract ways of talking about things.... it opens more door for this... for example.


This is an ad


Looks like leadership characteristics are mostly "manufactured" kind. For example, you manipulate (motivate) people into doing stuff you will benefit the most in the long run. This might go against the values of some people.


> manipulate (motivate)

> go against the values of some people

This reads like you have experience with bad leaders.

When I try to motivate colleagues or team members, it's not at all manipulation. It's helping them through issues that they're dealing with and getting them happy about what they're doing. I'd rather do that than let them be unhappy and unmotivated. When you manipulate, people will see through it, when you motivate, people will appreciate it and work harder because they want to. I'm not sure why that would be a bad thing.




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