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. :-)

Getting feedback on your regular meeting

If you can avoid your regular meeting, cancel it. This is particularly true if your regular meeting has just become a status update meeting.

How to tell if you need feedback: If >10% of the attendees are typing away on their laptops instead of paying attention, you likely have an ineffective meeting on your hands.

How to ask for feedback: “What will it take for this meeting to get 100% engagement from everyone present?”

Typical causes of meeting failure: Lack of alignment around purpose and lack of preparation and follow up.

While it is easy to diss regular meetings, it is also important to remember that a thoughtful and well run regular meeting can be a powerful driver of context, learning, and belonging within a team.

The commencement speech problem

Many of us picture commencement speakers giving variations of the “Take more risks, work hard, do good” speech. The good news is that the proportion of speeches that contain such advice seems to be going down. Understanding why is useful for all of us as we often end up giving others advice from time-to-time.

The trouble with generic advice is that it doesn’t work for a large group of people. Some people need to take more risks while others don’t. Some folks need to work harder to earn their privilege while others need to be careful about avoiding burn out. Such advice is easy to give – but is generally flawed because it is either self serving (quit college and start companies so I can invest in the best of them) or designed for people similar to the advice giver.

While the best advice is given once you understand a person and their proclivities, that doesn’t scale. The better approach, then, is to focus on principles. For example, a career principle might be to – invest in understanding yourself and use that understanding to make better decisions and develop good judgment.

The challenge with principles is that getting to them takes considerable thought – the sort that should be a pre-requisite to giving advice.

(H/T Julia Galef, Shripriya Mahesh for notes/discussions on this)

Ask advice better – replace the generic question with a hypothesis

The typical approach to asking for advice is to ask generic questions like – “how can I get a job in xx?” or “how can I do well in my x admissions interview?” 

Aside from being hit and miss if you are the person asking these sort of questions, they can be very frustrating if you are on the other end of these questions. They showcase no thoughtfulness and feel formulaic.

A better way is to replace this question with your hypothesis or approach. For example, you could lead with – “I realize it is challenging to make the switch to xx. But, my research points to other folks who’ve done it by doing yy. So, as a first step, I plan to do yy. Second, I am thinking about taking a course on the side or working on a side project to prove I can do it. I’m curious to hear your feedback on my plan?” 

This simple change in approach can have a magical effect because it showcases your preparation and thoughtfulness. In conversations where people don’t know each other well (and, let’s face it, we don’t have such conversations with people we know well), showcasing interest works much better than saying “I am interested.”

Show, don’t tell.

How to: Better brainstorming with private collection

Most brainstorming exercises are acts of “public collection” of data. We put a question on the board and ask everyone attending our meeting for ideas.

Brainstorming, when done well, can be a really fun and energizing exercise. But, it turns out that brainstorming is rarely done well. A small minority of people tend to dominate air time and the shy folks stay out of the discussion altogether.

A simple tweak that helps brainstorming is “private collection.” This involves giving everyone in the room post its or pieces of paper, a few minutes of time and encouragement to write down their ideas.

As a moderator, when you open up the floor for brainstorming, you know for sure that everyone has ideas. So, you can now facilitate the discussion to ensure everyone’s participation.

Brainstorming sessions succeed because of the diversity of ideas on show. Diversity, in turn, can be encouraged by good session design.

This meeting will be a success if

“This meeting will be a success if…”

“The purpose of this meeting is…”

“The 3 things we absolutely need to get done in the next 30 minutes are…”

“We’ve gathered here as a group to…”

There are many variants of the same idea – set up a meeting with the purpose upfront – and it doesn’t really matter which one we pick.

But, ensuring every meeting we participate in starts with quick alignment around the purpose is likely one of the best things we will do for our long term meeting effectiveness.

A short prep checklist for your next interview

I’ve been speaking to folks who are in the process of preparing for interviews lately. While I have a long post on the topic, I thought I’d put together a short prep checklist.

When you prepare, consider allocating time among 4 types of questions –

  1. Why industry (15% of your time): Industry questions target your perspectives on the industry you are applying for. Ideally, you are interviewing for an industry you are interested in and this part of your preparation just involves synthesizing what you think based on recent news, blog posts and events.
  2. Why company (15% of your time): Company related questions typically judge culture fit and understanding of the context the company operates in. For the former, clearly understanding cultural norms and values (in companies that say they care about this) helps a lot. Amazon, for example, expects you to know their 14 leadership principles. And, for the latter, reading an analyst report or two that gives you a sense of the competitors and prospects can help a lot. If the company is public, reading their recently quarterly or annual filings is a must-do.
  3. Why role (40% of your time): There are 2 important variants of role questions –
    • Do you understand what the executives in your function think about? (less common but interesting and important)
    • Do you know what you would do/what skills you would need in your first day? (this is the most common variant and is typically tested using a case which simulates a real problem to test how you approach problems)
  4. Why you (30% of your time): “Why you” questions also typically ask two questions –
    • Would I like to work with you? (file this under the ambiguous “culture fit”)
    • Do your skills overlap sufficiently with the skills required for the job? (Understand the top 3-4 skills required and ensure your behavioral stories call these out – this is particularly important if you are switching careers)

Interview panels focus on different aspects of these 4 questions for various interviews. The “why role” and “why you” specific questions tend to be asked across interviewers.

I hope this helps.

PS: There’s a lot of luck involved in admissions or hiring. I hope you choose to learn from your experience either way and keep going, growing.