The pragmatic approach

I was in the midst of an engaging and perspective shifting conversation with someone who’d given thoughtful consideration to big ideas like the effects of climate change on our species, the effect of the evolution of modern medicine on the notion of  “death” (will it be a choice soon?), among others.

It was a fascinating conversation – one of those that gets you thinking about ideas well beyond your current host of minor problems.

As we approached the end of it, I asked this person how he balanced the perspective from thinking about problems like climate change with having to, for example, close a deal next week. He responded half jokingly – “Because this is the life I’ve been given and I want to make sure it doesn’t suck.”

I’ve reflected on that note a bunch since our conversation. It struck me as the definition of pragmatic. Through his career (a very successful one), he’s done a great job “making sure it doesn’t suck.” And, in doing so, he’s acquired the resources required over time to effect meaningful change to the causes he cares about.

There’s a lot of attention given to romantic pursuits of problems that disregard practical considerations. But, at least in my experience, the pragmatic approach – especially when combined with thoughtfulness and long term planning – is often very effective.

Shopping for clothing – mixing outcome and process

We went to a Target outlet recently to purchase a piece of winter clothing. We’d looked it up online and it was supposed to be in stock at this particular outlet. After combing through the relevant aisles, we finally learnt from the customer service desk that the “in stock” status on their app isn’t the most reliable.

The natural response here might be to say this was a bad outcome. We drove a bit longer to get to this particular outlet and failed to get what we wanted.

But, that would completely negate the process. We did our research, found the one spot where we’d find what we were looking for, and then learnt that their stock status isn’t the most reliable. There’s not much we’d do differently.

It is one thing to know that it is important to separate outcomes and processes. But, it is quite another thing to actually do it when we encounter small outcome setbacks everyday. I’ve learnt to view incidents like this one as practice sessions. As we build our muscle memory to evaluate processes instead of evaluating outcomes, we invest in more learning focused, thoughtful, and happier versions of ourselves.

PS: We ended up finding another version of what we wanted online. It easy to take it for granted – but, online shopping is such a game changer.

Knowing thyself – the foundation of long term career progress (feat. user manuals)

We kicked this series off with a look at the 4 core skills of an individual contributor Product Manager – problem finding, problem solving, selling, and building effective teams. Then, we defined what a product manager doesa product manager brings a team of cross functional stakeholders together to build a product that is valuable, usable, feasible. Today, we’ll dive into that small matter of career progression and explore the foundation of long term career progress – knowing thyself.

Khe Hy, a blogger at “RadReads,” had a useful illustration on a general career arc.

As Khe’s illustration demonstrates, there’s a lot to be gained from exploration early in the career as it helps us figure out what we’d like to be good at. Then, we invest in becoming specialists. And, finally, if we’re interested and able, we get to zoom out again as executives who oversee multiple specialist areas.

While these ideas translate well for product manager careers, my version of the the career arc for product managers would look something like this.

Individual contributor/IC PMs start with a focus on narrow features and small products. Over time, they take on larger products and product areas. Larger product areas are typically led by people managers (“Group”) or senior ICs (“Principal,” “Staff”). And, product executive teams typically oversee entire marketplaces and ecosystems.

Now, if we were to visualize this career trajectory as a building, the foundation would be self awareness. The deeper the foundation, the sturdier the building.

While this holds for careers across industries and roles, it is very pertinent to any role building technology products. Building a technology product takes a village – with team members across functions coming together to ship a finished product. Given the critical nature of teams and people in this process, emotional intelligence is a key asset. And, self-awareness/knowing ourselves is the cornerstone of emotional intelligence.

(Note: There is the alternative approach to building product teams which we can call the Steve Jobs v1.0 approach. This involves “my way is the highway” + some reality distortion + hopefully backed by once-in-a-generation product intuition. This post is for the rest of us.)

What is self-awareness and how can I get more of it?

There are two kinds of self-awareness –

i) Internal: This represents how clearly we see our own motives, values, passions, aspirations, fit with our environment, reactions, and impact on others.

ii) External: This represents our understanding of how others view us.

My observation is that external self awareness is crucial for career progression while internal self awareness is correlated with career fulfillment and happiness.

The challenge with both kinds of self-awareness is figuring out how to get more of it. Approaching this topic can feel very daunting. Ergo, my favorite tool to make this process easier – a “user manual.”

How do I creating my own User Manual?

Step 1 – Create a first draft user manual: Block out 60 minutes of your calendar next week and take a crack at a 1 pager that has some or all of the following –

1) Getting responses and work done: E.g. share your preferred work hours, preferred communication channels, and best times to schedule meetings.

2) My style: 3-4 must know characteristics about your working style

3) What I don’t have patience for: Focus on specific behaviors that drive you nuts.

4) How to best communicate with me: Share how you prefer to consume information – e.g. some prefer written memos or sketching on a whiteboard while others prefer verbal pow wows.

5) What people misunderstand about me: These typically involve flip sides of your signature strengths.

6) Things I’m trying to get better at: 2-3 improvement areas you are focused on.

7) Random Quirks: Something fun. :)

Step 2 Share with close teammates for feedback: Share with a few folks (/work friends) who know you well and see if this one pager accurately represents you.

Writing the first draft involved drawing on both your internal and external self-awareness. While very few can help you better articulate what you care about, feedback from close colleagues can help give you a measure of your external self-awareness.

Step 3 – Set up 30 mins to review with yourself every month: The power of the first draft of the user manual is that it marks the beginning of the journey. We never “achieve” self-awareness. We just get on the train with our first draft user manual.

As you spend more time with it, you will find yourself tweaking the user manual after every review and crystallizing your random thoughts (at least at first) into themes. For example, I ended up synthesizing the 3 aspects of my personal culture (hungry, thoughtful, learning focused) as I iterated on sharing “my style” as part of this process.

As a bonus step, you might even want to consider reviewing your user manuals jointly as a team. We did this on one of our cross functional teams recently and it turned out to be a very powerful team building exercise.

Conclusion: While short term career progress tends to be a function of good on-the-job skills, long term career (think: decades) progress tends to be correlated to our self awareness. The beauty about self awareness is that it is a skill that is foundational to better relationships – which has implications well beyond our time at the office. And, I’m a fan of using user manuals to aide the development of the skill.

If you find yourself stuck with creating that user manual and would like to see an example, please feel free to check out the Quartz article below for further reading. I’ll also be happy to share mine if that might help – please feel free to send me a note on rohan at rohanrajiv dot com.

Further reading:

i) Tasha Eurich, an organizational psychologist and executive coach, assembled a team to share her findings on both kinds of self-awareness. If you haven’t seen it, I’d recommend reading it here (you can also see my 5 point synthesis here).

ii) This Quartz article on user manuals is a helpful starting point.

iii) If you are curious about more resources to figure out your motives and values – here are a couple of posts (motives, values and mission statement) that might help.

How many followers? How much money?

If someone asked you how many followers you have on your favorite social media site, would you know? How close would your guess be to reality?

What about if you were asked how much money you make after tax in a year?

Now, what if the question involved sharing how many hours you spent engaged (no phones, just paying attention) with the people you care about in the past week?

How accurate would the answer to that be relative to some of the other questions?

We monitor and optimize metrics we measure.

Perhaps the most important thing we can get done this weekend is to figure out what those metrics should be.

Stan Lee

NPR had a lovely article celebrating the life of Stan Lee – the person who created characters like the amazing Spiderman and the X-Men.

Stan was known for creating superheroes who struggled with being human. He explored insecurities, unhappiness, and themes like racism through his stories. He put being human before superhuman and did it all while ensuring he made us smile.

In his words – “Before Marvel started, any superhero might be walking down the street and see a 12-foot-tall monster coming toward him with purple skin and eight arms breathing fire, and the character would have said something like, ‘Oh! There’s a monster from another world; I better catch him before he destroys the city.’ Now, if one of our Marvel characters saw the same monster, I’d like to think Spider-Man would say, ‘Who’s the nut in the Halloween get-up? I wonder what he’s advertising?‘ ”

When reflecting on his career, he once said – “I used to be embarrassed because I was just a comic book writer while other people were building bridges or going on to medical careers. And then I began to realize: Entertainment is one of the most important things in people’s lives. Without it, they might go off the deep end.”

Thank you, Stan. You will be missed.


“According to its teachings, as social beings, the path to happiness for humans is found in accepting the moment as it presents itself, by not allowing oneself to be controlled by the desire for pleasure or fear of pain, by using one’s mind to understand the world and to do one’s part in nature’s plan, and by working together and treating others fairly and justly.” | Wikipedia on Stoicism

Someone recently asked me about the kinds of changes writing here for a decade had inspired. I always share a few example themes when asked this question – learning to focus on process vs. outcomes, to reflect and synthesize, to be intentional, etc. It is hard to tell the full story as the change daily public writing has inspired is both vast and deep.

But, in the spirit of synthesis, it occurred to me recently that a lot of these coalesce to form some of the tenets of stoicism. To accept things as they are, to prioritize discipline and commitment over desires and fears, to be thoughtful, to seek to be aware of the environment, and to view the world from a lens of abundance and collaboration.

Interestingly, and perhaps most significantly, the stoics believed that the truest measure of what people believed lay in their behavior. The idea that we shouldn’t listen to what people say and, instead, watch what they do has been among the more hard earned lessons I’ve taken away in the past decade.

So, a better description of the impact writing here has had on me is that it has helped me understand some of the fundamental principles of stoicism without seeking to understand it.

If I had to boil it down to four words whose meaning I’m slowly beginning to understand, I would choose “awareness,” “thoughtfulness,” “commitment,” and “perspective.” I think the act of writing about what we learn everyday inspires this journey toward understanding.

I am grateful for that and for your role in that journey.

Don’t optimize sub-systems

If you are manufacturing cars, there is no point doubling down on manufacturing doors or steering wheels if the rest of the car isn’t being produced at the same pace. “Understand the goal” and “don’t optimize sub-systems” are thus key principles in operational effectiveness.

These principles have powerful life lesson equivalents. First, they ask the question – what is the car equivalent we’re building in our lives / what are we optimizing for? And, what is the right amount of production for each of the aspects (work, home, social or however we define them) in our lives to build it well?

Second, they speak to the futility of comparing certain aspects of our lives with that of others. Unless we’re optimizing for the exact objectives someone else is optimizing for, there is no point comparing the sub-systems.

The FIRE movement – tactics versus principles

In case you missed it, there’s been a lot of recent press about the “Financially Independent, Retire Early” or FIRE movement. The news is a mixed bag with many strong criticisms about the idea. Amidst all this varying sentiment is a lesson for all of us on taking the time to separate tactics from principles as we communicate ideas.

While the “retire early” part of the name is provocative (and seems to be drawing most ire), the central principle behind the FIRE movement is to become financially independent by being conscious about our financial well being.

Financial independence doesn’t mean not working – it just means being able to build a career and life without worrying about money. This is done with a strategy based on 3 simple tenets – i) Save more by living simply and cutting costs, ii) Invest aggressively in low cost index funds, and iii) Increase your income.

Would anybody argue against these principles? I’d posit that we should all be part of this movement.

The deeper learning here is that it is human nature to lose sight of the principles as we get caught up in the details. So, as we work to communicate our ideas every day, it is on us to obsess about sharing principles versus tactics.

Is right vs. looks right

Shane Parrish, author of the generally excellent Farnam Street blog, had a great post this morning about defensive decision making – the type of decision making that focuses on what “looks right” vs. what “is right.”

Defensive decision making is the “IBM” option. Since “no one got fired for buying an IBM,” it is intended to protect the decision maker. Organizations can often create a massive decision-consequence asymmetry in that they become so risk averse that most decisions come with small upside if they go well and large downside if something goes wrong (e.g. get fired).

So, the natural incentive is to just make the “default” decision. There is no risk to one’s reputation and it is always defensible.

This points to why so many cultures talk about “thinking out of the box” but never actually do so. It also speaks to why cultural change is very hard.

And, finally, it is a great reminder that approaching building products and services for customers with first principles thinking and hypothesis isn’t just about hiring the right people.

It involves building a culture that incentivizes attempting decisions that are right instead of rewarding those that look right.

Cleaning and insecurities

Does cleaning ever get done?

It doesn’t matter how beautifully we vacuum our home this week. We will still need to vacuum next week.

Of course, it helps that we don’t expect to ever be “done” with cleaning or washing vessels or exercising. We understand that our commitment to being clean will be tested every day of every week. It is on us to recommit, take action, reflect, and keep improving how we take action.

It turns out that dealing with our insecurities works the same way. Our trysts with imposter syndrome, our deepest insecurities, and most powerful demons never go away. They are ever present and part of who we are.

And, we must deal with them like we deal with dirt or unwashed vessels every day. Re-commit to acting from wholeness instead of our wounds, take action, reflect, and iterate.