Content, Structure, Structure, Delivery

In the age of 6 page memos and product press releases (thanks Amazon), writing has become a core skill at work. Great professional writing brings together insightful content, a logical structure, and good delivery.

Insightful content is what gets us through the door when we write. This is different from public speaking as you can get away without saying much and still give a good speech. Insert a few jokes, say things your audience want to hear, and you could give a good speech. But, writing well is much harder than speaking – your content shines through (or not).

Assuming you have insightful content, the element that most gets in the way of good writing is a logical structure. While many labor under the assumption that they’d be better if their grammar, vocabulary, and language was better, “delivery” generally helps move very good writing to great writing. Structure is what moves you from passable to very good.

The challenge with structuring documents is that our first draft is often our first attempt at thinking through the idea or question at hand. And, once we put our ideas down, the initial structure becomes art that mustn’t be tampered with – in our minds. That, then, gets to the challenge of good structure – we need to find ways to either separate the thinking process from the writing process by structuring our narratives upfront. Or, we must write our first draft and then do a complete rewrite by putting yourself in the shoes of your audience.

I expect to write more about structure as I spend more time learning how to do so. However, the first step is improvement is awareness. Today’s takeaway is simple – when you write next, obsess about structure.

3 steps to making that big career transition

When we make career transitions, we typically change one or more of the following – (1) Company, (2) Role, (3) Industry, and (4) Location. These are ordered in ascending order of difficulty with changes in location – for the majority of the folks on the planet who do not possess rich country passports – being the hardest by a distance. Most importantly, combining these factors does not simply mean adding up the difficulty – the change gets exponentially harder.

Thus, career transitions can be very hard to make. While there is something be said about experimenting in the early stages of our careers, there are benefits to being in the right (for you) location, industry, and role early. Career transitions are also hard because they require dealing with all the feelings of insecurity and inadequacy that accompanies job hunting. This is heightened if you are an immigrant as you are doing it with the weight of uncertainty about how your change will work given your immigration status.

The result, for many folks, is multiple cold inMails and connection requests to folks they find on LinkedIn searches to ask for referrals or mentorship. This is understandable. Attempting to make a career transition is stressful and any help is appreciated. Sadly, cold inMails to strangers turns out to be the least effective approach.

Over the past five years, I’ve been fortunate to make a transition that involved changing all 4 factors. As with most things, it took a combination of intention, work, dumb luck, and accumulated privilege. We’re still working through visa challenges – so the location change is far from final. Nevertheless, I thought I’d share a 3 step approach toward making big career transitions. To ensure broad relevance, I’ve focused on the key principles while also adding color based on my experiences.

(1) Construct plans A-F: The first and most important assumption I’ll make is that you know exactly what you want to do (if you don’t, please see the resources section below). Once you do so, construct plans A-F. This means having at least 6 routes to the destination. I think the word “destination” is particularly applicable if you are trying to make a cross-country switch as it is worth tackling that head on.

I say plans A-F because it is highly unlikely your plan A will work. And, as you cycle through them, it’ll become easier to move past F to other alphabets. :-) For example, I learnt about the Bay Area and tech while working on a student job portal start-up (that eventually failed) through university. That’s when the idea of working in tech in the Bay Area took hold. But, as I mentioned above, location switches are the hardest kind to make if you don’t have the right passport. In the next 4 years, I cycled through plans A-F before finally finding a graduate school in the US that took a chance on me. (Graduate school is a staple in the immigrant playbook to switch locations)

The next step was to make an company + industry switch – i.e. find a tech company that would take a chance on me – and then a role switch – I’d learned about product management and believed I’d found my functional home. But, how do you get a start when everyone wanted folks with relevant experience?

Below is an image with the 6 questions I’d suggest asking.

Next, my suggestion would be to build your plans by attacking as many of these options. For example, here’s how I approached it  –
A: Was connected to a role thanks to a past colleague.

B: Was connected to a few folks by the same past colleague (he’s a good samaritan) – one of these folks worked at LinkedIn. Also got a referral into someone from my graduate school alumni network. She helped with an interview call.

C: Didn’t attempt connections with strangers on LinkedIn as I wasn’t sure how I’d do so in a thoughtful manner.

D: I signed up for interviews with most companies that took a shot on MBA students without visa sponsorship for Product Management positions.

E – I thought highly of LinkedIn’s product and the vision and felt I’d fit in well. But, LinkedIn was also very mainstream. So, I was also focused on a company like VMWare that was focused on solving solutions with a high level of technical complexity. I figured thorough prep on server virtualization would be a competitive advantage – since few folks would actually do it.

F – I ended up betting on an internal transfer to move into Product Management at LinkedIn. These sorts of transfers are painful in most places. So, this wouldn’t have been my dominant strategy had it not been for an intersection with an opportunity to work with someone I liked and respected, a company whose mission resonated deeply and because of immigration considerations.

All in all, once I’d managed the location move, I attempted all options except emailing a random stranger because the chances of that working are minimal at best. If you are keeping count, I was well into plans M and N by this point.

(2) Understand base rates, preferred demographics and stereotypes: This step is designed to accomplish two objectives – i) Add a dose of realism to your search, and ii) Aide your preparation for an interview which you hopefully will land.

Step (1) was all about mapping your path to what you believe is a dream role. However, it helps to get a sense of the odds. Here, there are 3 questions that might help –
A. Base rates: Are there folks “like you” (similar education, work experiences) who are in those roles in companies you want to be?
B. Preferred demographics: Are you in the demographic that companies are hiring for right now?
C. Stereotype: Do you fit the stereotype that recruiters/hiring managers love?

I understand these may sound like controversial sounding questions. But, just because no one likes talking about them doesn’t mean they aren’t a key part of the hiring process.

In my case, the base rates were encouraging. There were folks with similar education, experiences in roles in tech. However, I wasn’t doing good on B. No one was jumping out of bed excited to add another Indian guy who needed visa sponsorship – which was getting more and more problematic – to their team. And, my stereotype was a mixed bag. The consultant + MBA combination was appreciated by some and despised by some. Now, you might say – “Hey, but what I did in the past doesn’t/shouldn’t define me.” Yes, it shouldn’t. But, given our human need to make quick decisions and label people, it does. So, we might as well learn to overcome it.

While you can’t do much about base rates and preferred demographics, it is important to note that you can do something about stereotypes – especially if you don’t believe you are the typical specimen. – by working on your story in your interviews. I didn’t think I was. I also had spent 3 years in a start-up and worked on plenty of side projects. I hoped to weave that into my story.

I had 2 key takeaways from my own inventory check –
1) This change was possible but was not going to be easy as the field was very competitive.
2) I’d have to find a way to make any interview calls I receive really count. I didn’t have experiences at a big name brand pre-graduate school. This generally means fewer interview shots since fewer folks are willing to take a chance on you. That, in turn, meant I needed to over index on interview readiness as I’d need to have a higher conversion rate.

(3) Take a really long term view. Do you care enough about your career switch to work on it for 5 years? If you do, that is good news. Here are 3 reasons why a long time horizon helps –

1) You will learn and grow through the process of attempting to make a switch. All these experiences will make you a better candidate – if you are willing to persist.

2) It is easier to change fewer variables at a time. For example, a change of location and role or location and industry are easier switches than attempting to change company, industry, role and location. This is particularly the case if you are immigrant – getting your location via visa sponsorship will likely be your dominant strategy.

3) You will have the time to convert random strangers and acquaintances to friends and well wishers. This is really really important. A big part of making transitions is building a network of relationships who will support you through it. And, it is very hard to build this network if you want immediate results. You can’t plant trees the day you want fruits.

I have a couple of stories to make my point. In my case, one of my failed early plans to move involved a final round interview that didn’t go well. However, I stayed in touch with the friend of a friend I’d mentioned above. We ended up meeting in person a couple of times and, thanks in no small part to the help I received, I ended up working on their team a full two years after we connected. Second time lucky.

Another related story – I was connected to someone by an acquaintance. This person stayed in touch via my blog with email exchanges over three years. That led to an in person meeting, then another one, and then a few calls. A full four years later, I was thrilled to help this person find a role where I work.

I could share a few more such stories to continue hammering this point home. But, I’ll stop. The key takeaway – our career journeys are long and full of surprising and random twists and turns. You never really know who will open a door for you some day in the future and you definitely don’t know if a good/bad day is so. It is futile to connect dots forward. So, a better approach is to make commitments on directional plans in the long term, be kind and thoughtful, and keep plugging away.

If this post is reaching you in the midst of a tough time, I’m sorry to hear that. It is surprisingly common on such journeys as the odds are always stacked against you. But, I’ve come to believe that the arc of success and opportunity bends toward merit in the long run. It helps to approach the whole journey as a mixture of scientist and student. Start with hypotheses, run experiments, test, learn, and iterate.

As the wonderful saying goes – “Things work out fine in the end. If it’s not fine, it is not the end.”

I hope this is helpful. Wishing you all the best on your journey.


Additional resources: Here are 5 resources that might help.

(1) The 3 phases of a job search process: This is a companion long read that dives into the details of the job search – figuring out where to apply, getting interviews, and doing well:

(2) 3 principles of asking for favors

(3) How to ask for help from people you don’t know and related – Ask advice better by replacing the generic question with a hypothesis

(4) How to ask for a cold call

(5) The 3 laws of privilege: Slightly off topic – but important. :-)

Bad workplaces, poor work experiences and incompetent managers

It is natural to work hard to avoid one or more among bad workplaces, poor work experiences and incompetent managers. And we should. But, it is also hard to overstate their value in the long run when we do find ways to overcome them when they happen.

Spend a bit of time reflecting on your painful experience and you walk away with perspective that will stay with you for the rest of your life. It is very hard to appreciate what is really bad if your experience of work only involves fancy office spaces, free food, projects that involve smart colleagues and hyper growth, and thoughtful managers.

However, if you’ve worked in a mind numbing data entry job, dealt with a manager who never failed to make you feel insecure or cleaned toilets at a restaurant for three months, it makes it a lot easier to appreciate what you have.

I don’t think the takeaway is to go seeking bad career experiences. But, I do think there is value in seeking varied experiences in our careers – especially in the early days. One of the biggest benefits of doing so is that some of those varied experiences will turn out to be bad.

And, while great workplaces typically help build great careers, bad experiences can give us the sort of perspective that can help us build happier lives.

PS: If all you have experienced is a great work environment, this is just a reminder to work extra hard to be conscious of all the privilege and be grateful.

Interpersonal skills vs. Intrapersonal skills

Job descriptions frequently cite interpersonal skills – or variants like the ability to influence cross-functional stakeholders – as a required or preferred qualification. While intrapersonal skills get the occasional mention (“self starter” or some equivalent), they don’t seem to ever make it up to the list of top 3 skills required.

What are intrapersonal skills and how do they differ from interpersonal skills? While interpersonal skills deal with the communication between two people, intrapersonal skills are about the communication we have with ourselves. They deal with our mindset, our approach to analysis and learning, and our response to situations.

We’ve likely had plenty of training on interpersonal skills. But, when it comes to intrapersonal skills, we are, for the most part, on our own. And, that’s a big miss because it is in our interest to focus first and foremost on our intrapersonal skills.

Interpersonal and intrapersonal skills are analogous to personality and character. There’s a saying that personality opens doors while character keeps doors open. That’s just one way of saying that the best long term indicator of your ability to build trustworthy relationships is your character.

Or, put another way, your interpersonal ability is only as good as your intrapersonal ability in the long run.

The 100 year career

Oxford university scientists expect us to live to be 100+ with many routinely expected to reach 150 years. Working life will, thus, last well into 70s, 80s and even past 100. How might we approach a career if we knew it was going to last 100 years?

Here are six ideas –

  • Regardless of the career you choose, approach learning like a chef. When you learn something, focus on building the skill to reason from basic ingredients/first principles. Learning how to learn is a high RoI skill because you will need to learn many different skills over a 100 year career.
  • You don’t have to prove anything to anybody for a really long time. Judging your success in 25 years will be like awarding the NBA title to the team leading the score in the first quarter. Again, we’re talking about 25 years.
  • Retiring early is a misnomer. Instead, if you want a way out of your lucrative but uninteresting career, look to get wealthy enough by your desired age so you can spend the next few decades working on ideas that interest you. And, if this path is avoidable, you may want to consider it. Also, if you’re a university administrator, I hope you’re planning out your continuous learning curriculum.
  • It will help to find work you enjoy or feel passionate about. A great way to do that is to get incredibly good at whatever you are doing. We love things we are good at.
  • Your biggest performance improvements will come from improving your attitude. A growth mindset that allows for openness to new ideas will be your biggest asset.
  • Don’t let a setback in your next expected raise or promotion get to you. You’ve got time. :-)

Of course, these ideas apply just as nicely to any career. Maybe we should adopt them regardless?