School of Thought: Management / Leadership Principles

I wrote this as a google doc in 2020, and have shared it with many colleagues as an answer to their question “I’ve just been put in a leadership position. How do I do this?”

So I’m sharing more publicly here.

Every good leader of people has learned the lessons I’m going to share with you.  If you hope to become a leader, or are a new leader of people, this program will help solidify concepts that prove to you and your team that you will be successful in a leadership position.  If you are an experienced leader, this program will put words to ideas you already know, and I can be your partner in executing these ideas.  In any case, I’m confident this program will help you 10x your growth, increase the value you deliver to your company, and increase your capture of that value (usually in the form of compensation).  

Why is being a leader hard?

As a Leader, you have two jobs:

1. Determine the most important thing to do
2. Make sure that thing gets done

That’s it.  Only those two things.  As you increase your responsibility within an organization, both of these tasks get harder.  When you are a business analyst at McKinsey, your Engagement Manager tells you what the most important thing for you to do is.  All you have to do is: do it.  When you are a partner at McKinsey, you have to be much more thoughtful and influential.  As a partner, you need an opinion on what valuable work you can provide your clients, convince them that it’s valuable, and then convince a team of people to execute against that work.  Not only that, but you have many ongoing projects at the same time, so you can’t just do all the work yourself.  

Can you break it down a bit further?

Sure.  Determining the most important thing to do and making sure it gets done can be broken down into 6 component parts:

1. Create a vision for the future
2. Develop a strategy to make that vision a reality
3. Design a machine (people, process, technology) to make progress towards that strategy 
4. Define objectives and key results to create a way of measuring the outcomes generated by the machine
5. Operate that machine to execute towards those objectives
6. Improve your vision, strategy, objectives, and machine on a regular cadence

1. Create a Vision for the Future

If you don’t know where you’re going, you’re going to have a hard time getting there.  This is the most important task for the leader who is “determining what the right thing to do is”.  This shouldn’t be the same as goal-setting.  Your “vision” is how the future will be different from the past, and cast your team as the protagonist in the story of its fulfillment.  This vision is important because it is required to get the most out of your team.  In the parable of the bricklayer and the cathedral builder, you want your team to know they’re building a cathedral, even while they spend most of their time laying bricks.  

Vision at a Startup

If you work at a startup focused on bringing price transparency to the healthcare industry, your vision for the future might be one in which patients can actually shop for their healthcare – you can envision a future in which patients are able to evaluate the cost and value of the healthcare they will receive before they receive it, which is the opposite of how this works in the US today.  That’s much more motivating than telling the team that the goal for the quarter is to “build APIs for the two largest insurance companies”.  

Vision in a Large Multinational Corporation

If you work at Procter & Gamble which produces consumer packaged goods and famously has 9 levels of management, creating a vision for the future as a band 2 manager is both more straightforward and more difficult.  It can be more straightforward because you have 7 levels of management setting strategic vision before you get to set yours — that’s how corporate hierarchy works.  But that also makes it more difficult, because you have less freedom in defining the vision for yourself.  Let’s imagine you’ve been handed a mandate from your level 3 manager that you’re responsible for upgrading the communications protocol across your business area’s manufacturing lines.  You’re going to be leading a team of 6 employees and 15 contractors to get the job done.  That’s pretty well-defined, and so the opportunity to create a vision for the future is more limited.  But if your goal is advancement to level 3 and beyond, you need to find ways to demonstrate that you have the skills of a level 3 manager, while also crushing the job your boss actually asked you to do.  Thankfully, the principles of strong leadership will help with both.  

Remind Your Team of the Cathedral Regularly

In the P&G scenario, the vision for the future that I would repeat to the team on a weekly basis might sound something like: “Great work this week, team.  We are one step closer to making Procter & Gamble the best manufacturer of packaged goods in the world – this communications upgrade will enable us to increase our speed of production while decreasing the number of quality incidents.  When we do this well, we will: (1) set the standard across all of P&G; (2) be noted across the organization, which will be good for all of your promotions; (3) increase the value of P&G stock, which will increase the value of your retirement accounts”.  This might seem laboured, but I promise it’s worth it.  You might object that weekly is too often, but I disagree.  If people spend 40 to 80 hours a week laying bricks, you can afford to spend 0.03 hours reminding them they’re building a cathedral.  

Don’t take your eye off the ball; constantly remind your team what cathedral you’re building.  But first, you need to know what cathedral you’re building.  That’s step 1: envision the future you want to create.

[note: could potentially include something here about vision for Skywise]

2. Develop a Strategy to Make that Vision a Reality

The strategy is all about pathing, and it’s incredibly important.  The vision is the “why” and the strategy is the “how”.  To do this, you need to map out all the relevant stakeholders for the project or startup, and figure out what needs to happen to make this vision come true.  In a startup, your time constraints might come from investors, competitors, or from your own financial situation.  In a large company, your time constraints likely come from the myriad other projects or goals that depend on your project’s completion.  In a large company, the most important stakeholder is your boss – make sure you’re in lock-step with what will make them successful.  [note: could elaborate why this is important, but might be obvious].

During the strategy formation stage, you need to answer key questions like:

1. What am I trying to achieve?
2. On what timeline do I need to achieve that?
3. Who are the key stakeholders I need to make sure are aligned with my outcomes?  What about the pathing? (strategic stakeholders versus tactical/operational stakeholders)
4. What are the problems that I’m likely to encounter on the way?
5. What skills do I need to solve those problems?
6. Who can I recruit to the team that has those skills?
7. How do I get access to the resources I’ll need to successfully complete this project?

3. Design a Machine to Make Progress Towards that Strategy

This means building a team, processes, and technology that will enable you to execute against that strategy.  Note that this is an iterative process.  You set goals through strategy, design your machine to enable the achievement of those goals, set OKRs to measure the outcomes the machine generates, and operate the machine to create a kick-ass culture and get the most out of the people on the team.

[design from Ray Dalio’s book Principles; commentary my own]

4. Define Objectives and Key Results to Measure Outcomes Generated by that Machine

OKRs are one of many frameworks for tracking progress towards a goal with accountability built-in.  The important thing to note is this is the stage at which you begin to transition from being the designer of the system to operating the system.  The system is made up of the people, processes, and technology that are being used to execute against the vision.  In the early stage, you are designing the system.  Now that you’re defining measurable outcomes, you need to operate within the system as a leader of people.  That means getting buy-in from the people on the team regarding what the OKRs should be.  Getting buy-in does not mean convincing everyone your ideas are great.  It means genuinely enabling the people on your team to become owners of ideas.  If they come up with the ideas, they’re going to execute against them 5x better than if they’re just executing on your idea.  This skill of managing people to come up with ideas that advance your vision without handing them your solution is one of the skills you’ll develop in this program.

5. Operate that machine to execute towards those objectives

You need to build a team with a strong culture.  This is the most important task of a leader in the operational capacity (making sure the thing gets done).  

The most important concept for a leader is servant leadership.  Remember that you are not the protagonist: each member of your team is the protagonist in their own story.  You need to figure out what narrative will motivate them, and then bring that narrative to life in a broader context.  This means having a growth thesis for every single member of your team.  You must hold yourself accountable for providing them the opportunity to grow in ways that are aligned with the business needs and their desires.  You must hold them accountable for creating time and space to grow in those ways.  You must create a culture of healthy feedback, combined with accountability, to fuel this growth (read: Radical Candor).  You must create a culture where everyone feels like an owner of the outcomes of the project (read: Extreme Ownership).

There are lots of processes that can help solidify these intentions: daily standups, weekly 1-1s, etc. but they will all be 10x more effective if you have a world-class team culture.  Your team’s culture will only be as strong as they trust that you have their back, and the consistent focus on their individual success in addition to the project’s success is the best way to achieve that.

[note: this is also good to build a following within your organization that will help you become recognized as a leader].  

6. Improve your Vision, Strategy, Objectives, and Machine on a regular cadence

You need to frequently revisit all of the above.  You need to answer questions like:

1. Is my vision for the future still relevant?  Is it still possible?  How can I make it either more attainable or more grand?
2. Is my strategy missing something?  Are they unaccounted for stakeholders?  Have stakeholders changed?  Have priorities in my organization changed?
3. Are my objectives reasonable?  Are they actually advancing us closer to achieving our vision?  How would I achieve my strategy if I had half the time?  What about half the people?  What could I achieve if I had twice the people?
4. How can my Machine be improved to more effectively (time, money, quality) create our vision for the future?  What skills are missing on the team?  Who on the team is performing well, and how can I increase their output?  Who on the team is performing poorly, and how can I either mitigate their weaknesses, provide them more resources, or level them up?  Is there anyone on the team whose skills don’t match the needs of the project?

With this feedback loop, you continuously refine your vision, strategy, organization, and operation.

To any who read this: I hope this was helpful. I spend a lot of time thinking about this, so would love for you to reach out to discuss directly!