How to fail as a leader?

Notes on starting a leadership journey

One of the best articles I’ve read on choosing the EM vs IC track was by Daniel Na recently that did the rounds on various social channels/HN. The author does a terrific job of breaking down what you achieve, what you give up, and shares his own personal motivations for taking this path.

This reminds me of a conversation recently with somebody about the expectations from a leadership role. The pros and cons of a leadership role are well documented like in the article above. The good news is that there's a ton of material on how to be a great leader — books to read, rituals to follow, expectations to set, and so on. The best practices of modern leadership theory along with personal examples of good managers easily many of us a playbook: 1-1s for building trust, servant leadership, setting vision and goals, building a high performing team, psychological safety and empathy, reward and recognition, mentorship and coaching, and so on. However, how do we know if we are tracking in the right direction? All of these factors are so subjective.

This brings up an important point about modern careers: Nikhyl Singhal covered this really well in his guide to the best interview question you can ask: if I have failed in this role in twelve months, what did I do wrong? Very often we focus on what will make us succeed and that generates a laundry list of good behaviors but how do we prioritize them? How do we figure bring focus to the conversation around expectation and goal setting?

Let's think about the success path for people: 1. Be right a lot, succeed a lot more often than fail, and incrementally achieve greatness throughout their careers. 2. Swing wildly between magnificent success and terrible failure but truly hit it out of the park in one of their successes. #2 probably creates more billionaires (and those stories are heavily amplified), but most people fall under #1 and have a more classic linear career trajectory. It’s equally important for us to understand what we need to do to NOT fail and how to identify both the symptoms and the root causes and course correct if one is on the wrong path.

Here are some of my notes from my recent discussion. I have also broken down the elements that give us second chances vs not. Leaders are not perfect on day one - in most cases, they will be forgiven for their mistakes as long as they are not egregious: which ones are the most critical, and what can we learn and grow in.

  • Attrition and Pulse Surveys: Any leadership role is as good as the team and the ability to bring it together. A lot of challenges within the team ultimately manifest themselves in attrition (of the regrettable kind) and pulse surveys may give early warning signs. If as a leader, your regrettable attrition rate is higher than the company baseline (or an industry equivalent), you really need to think about what is going wrong, and perhaps it is something in one of the core tenets of leadership mentioned earlier. Not doing some of them will ultimately result in clear metrics around this, so this is something managers have to watch like a hawk. As it’s often said, people leave managers and not companies: if the leader is failing at one of their core tasks, people will ultimately vote with their feet, and that really puts the leadership role at risk.

    Corollary 1: Awareness of the team's problems: If there are clear problems in the team, it starts doing the rounds pretty quickly, and if the leader either fails to recognize it or fails to act on it, it’s a clear recipe for disaster. This could be any kind of problems - perhaps technical, external dependencies, personality issues, team thrashing that you just can not wish away - they will bubble up in conversations both within and outside the team, and the best leaders actively work on unblocking and solving problems and supporting their teams in the best possible way. Once the cat is out of the bag, sometimes it’s too late for the leader to fix those problems.

    Corollary 2: Not Delegating or Empowering / Micromanaging: This is probably not in the same category as the above, since many leaders can get away with these in the short term. Some will also get a second chance to get better at it over time. Optically, the overall output of the team may still continue to look good. However, this creates two problems: (a) Good people in their team will leave over time if they don't get growth opportunities, (b) If they are doing somebody else's work, who is going to do their work? Or how will they get the additional bandwidth to grow and take on bigger and better things?

  • Failure on a key goal: In any organization, there are thousands of projects being executed at any time. However, for any leader, there are 2-3 key projects or goals that they are most critical. For an engineering leader, it could be the delivery of a major feature, but for a sales leader, it could be a revenue target for a critical district. A leader’s role is to always be clear on the can not fail category — a lot of the rest can be delegated and, in fact, empowering your teams to take on more will help them grow. For these projects, leaders have to be focused on identifying risks, removing bottlenecks, maybe even closely project managing, and should things start to go south, managing expectations actively instead of just letting the project fail. Sometimes, projects may start looking really risky and the immediate supervisor has to jump in to save things — always a bad warning sign.

    Corollary 1: Inability to manage expectations: Stakeholder expectation management is one of the key roles of any leader - whether the stakeholder is your division head, your customers, peers, investors, and the like. At any given point in time, leaders have to be masters at the fine art of aligning expectations and bringing clarity to what is required. If expectations are managed well, the project wouldn't fail - the expectations and goals will have been reset. These two go hand in hand.

  • Inability to Hire: This is another key requirement of a leader. Ultimately, leaders are only defined by their ability to build and grow teams and increase their impact on the organization. A lot of skills that go into hiring are intrinsic to what strong leadership demands - the ability to sell a vision, inspire people, build trust with strangers, and so on. An inability to hire when you have the need will set you back but just like micromanaging above, you can perhaps survive without thriving for a short while. Esp. in competitive markets, leaders’ main role is to find and hire the right talent.

  • Poor Relationship with the First Team: Leaders have to understand that while they support their own teams and organizations, they are also equally accountable to their First Team - the collection of peers they are most accountable to. Having a strong relationship with other leaders in the organization is as critical to success as the relationships within their teams, if not more. Between two managers - one who has strong relationships and can unblock easily and create more opportunities for their team, another who is very inward-focused and ritualistic, we can probably guess who most high performers will pick. It's also important to remember that during performance reviews, peers form a very critical aspect of the feedback process.

What other things would you recommend watching out for esp. if somebody is stepping into a leadership role?

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On a similar note, loved this article from Pat Kua - leadership is not based on the title. Anybody should be able to take initiative, inspire people, and set examples. Nobody needs permission to lead. Each of us needs to be a better leader irrespective of their formal role, and thereby a better professional. In many companies, this is done through a "DRI" model (Directly Responsible Individual).


  • This profile of Paradigm was really interesting. As a crypto-focused fund, they took the call to double-dip in crypto - invest in crypto companies but also chose to hold their fund in crypto - a huge risk that paid off big for them (esp with the crypto asset class). Still haven't heard of any of their companies yet though.

  • Alex Danco's 6 lessons after 6 months in Shopify are a must-read. Learning #1 is really powerful— that you need to understand how your leadership makes decisions and figure out how to get them to say YES to things. In order to succeed in any role, you need to figure out how to get the top leaders, esp the ones with the lowest attention span, to say Yes.


Engineering and Products

  • Aside from the fact that they are probably peddling the tool, some of the key takeaways in this article about ML not following the typical software development processes make so much sense. It's all about incremental improvement once you have a baseline. The statistical proxy as a spec/PRD and 1-day sprint makes a lot of sense.

  • Everybody talks about Tech Debt, but agree that we need a broader conversation about product debt. Product decisions made with a speghetti vision of having multiple ways to achieve the same thing confuse users and carry the debt forward - kind of like Google's messaging efforts. However, it’s useful to note that in many enterprise settings - this is also a great way to lock the customer in. If one sells to a big financial institution that pays 8 figures per year, a few of these can be invaluable. Not so great in most other settings.

  • We have all read the book, now we have to meet the man: Don Knuth's profile in NYT