Managing and leading teams

Dustin Moskovitz shares his lessons on leadership

The New York Times recently asked readers, “can you learn to lead?”

The article sourced a number of prominent educators about the recent trend of teaching leadership skills (as opposed to management skills) at top business schools.

As it turns out, the topic of leadership is a complicated one — some skills, it seems, can be taught, while others are a bit more nebulous. The article sparked a discussion amongst Asanas including Co-Founder Dustin Moskovitz. So we sat down with him to chat about what makes a great leader, what resources leaders have to become better at their jobs, and what skills can be worked on.

Let’s start off with the most obvious question: what is the difference between a manager and a leader?

Management is operational; it’s about setting priorities, evaluating priorities, hiring and firing decisions, compensation decisions, things like that. A leader is more of a coach, or even a spiritual guide. She is responsible for maintaining energy, keeping everyone on the team inspired and helping them grow, and for ensuring everyone is aligned in the same direction. A leader must be a point of strength and stability across changes.

Can someone be a leader but not a manager?

Definitely. At Asana, Areas of Responsibility (AoRs) correspond to leadership roles — most are not connected to managing people. There are also many formalized leadership roles without people management responsibilities at other companies (for example, tech leads and product managers).

What characteristics help determine if someone will be a great leader?

That’s a subjective question, but I believe someone who is empathetic, passionate, and has good social skills is more likely to be a great leader. Beyond that, someone who is clear-headed, intentional (as opposed to brash), and who isn’t easily shaken. I don’t necessarily believe that all these characteristics can be taught if they’re not innate, but some of them can be coached. For example, the Conscious Leadership Group training can help a leader or would-be leader learn how to be more intentional, both in their decisions and their communication, and therefore better equipped to lead.

Let’s talk more about the skills that a leader or would-be leader could learn.

Sure. A good leader can be taught:

  • Speaking skills
  • Writing skills
  • The ability to turn vision into strategy

A good leader should also possess good interpersonal skills, some of which can be taught through executive coaching.

What can a leader not be taught?

If a leader isn’t trusted, none of these things [skills] matter. You can teach people ethics, but not integrity. Additionally, even with the very best teaching, you are likely to make mistakes until you learn how to apply judgment and customize what you’ve learned to the specific context in front of you. Unfortunately, wisdom can’t be taught.

What do you think makes someone a great leader?

In a nutshell: people want to follow a great leader because they are headed in a direction that people want to go. You can have well educated managers coming out of training, but if no one wants to follow them, then they’re (tautologically) not leaders. A great leader must possess a great vision for a project AND have the kind of personality that makes people want to work with them to manifest it. These things matter at every level of an organization: the strength of an individual department is dependent on the strength of its leader.

What factors make people good partners in leadership?

Complementary traits are valuable. A big reason the partnership between Justin (Asana’s co-founder) and me works is that we complement each other’s strengths. Some of our individual strengths even contradict those of the other. Justin is aggressive and idealistic, a constant fountain of new and exciting ideas. I am more conservative and grounded, choosing to focus my energy on the execution of our existing plans. A company founded by Justin alone would have an expansive and differentiated vision, but may never bring a product to market at all. A company founded by me alone would deliver on time, every time, but create a product that was more like everything else out there. Neither of those would be a good company. The one we are creating together contains the best of both perspectives.

How should leaders handle disagreements?

In my experience, all disagreements come down to a difference in base assumptions. We use a coach here at Asana (she’s available to speak to any Asana as part of our mentorship program) and she emphasizes that the first step to reaching an agreement is to start by listing all the things you agree about. You’ll likely come up with a long list and will be left with a small set of assumptions that you happen to have different intuitions about. From this point, you’ll often be able to collect the data needed to determine which assumption is right. Even when you can’t, it’s a lot harder to feel like you’re “fighting” when you get down to that level of detail.

I’m also a big believer in maintaining clarity of responsibility: leaving room for ambiguity can cause a lot of conflict. We use the AoRs system to ensure that each leader knows what they’re leading and what they’re not — someone else’s AoR is an area where they ultimately must defer on any important decisions.

Of course, there are occasions when disagreements simply can’t be resolved. In those instances, it might be necessary to involve a third party to mediate or one person may even need to leave the company.

How and where can you practice leadership skills?

There are resources for anyone looking to practice leadership skills. At our company, we offer a number of opportunities like giving internal and external talks, mentorship programs, and the ability to take on important AoRs that require coordination among multiple people. We’re also big fans of the Conscious Leadership Group, which recently came out with a great book that I think is worth reading for anyone interested in being a more level-headed and mindful leader.

What are some of the most important leadership lessons you’ve learned / been taught?

I’ve learned a lot over the years, but here are a few key learnings that I employ regularly, in no specific order:

  1. Not delegating enough is bad for me and bad for people who could be getting more autonomy and learning more skills.
  2. Acknowledging that everyone else is a partner in what you’re trying to do and not an enemy.
  3. Recognizing that you agree with people more than you think you do. Where you disagree is probably a difference of input assumptions and not a real conflict.
  4. Avoiding paradox of choice and making decisions even if you’re unsure of what’s strictly the best one at that very moment. Letting a decision linger for too long is energy-draining; don’t let perfect be enemy of the good.
  5. Making sure there are regular checkpoints for reflection and there’s time to think at a high level and not just being tactical all the time is extremely important.

At Asana, a lot of leadership is actually baked into our values; we tend to attract the sorts of people who want to be led in this way. It’s not an objectively right way to do things but it works for us, and the people who work here. At the end of the day, we want to operate in integrity of those values.

What do you think? Can leadership be taught? What are some great leadership lessons you’ve learned over the years?

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