Up, up, and away: Finding jobs that maximize learning

You’re a high achiever — fresh out of school, early in your career or just looking for a new transition. Startups seem like the place to be for you.

You have a plethora of options in front of you — Startup A offers you free lunches and $200,000 a year. Startup B says shoes are optional and offers yoga classes for your dog. Startup C lets you casually namedrop how you had dinner at Mark’s place and he totally took your soy allergy into account.

All these are things that startups throw at you to hire the best talent, and are nothing compared to the real value working at startups — learning.

Kyle Tibbits defines rate-of-learning as:

The velocity at which you are aggregating new insights and deploying them in ways that build value.

Learning, especially early on in your career benefits you the same way saving for retirement early does — it compounds over time.

Credit: Kyle Tibbits

That steep rate of learning sets you up for a completely different level of success more than a 5% raise in compensation does.

These are 3 things I have identified that lets you know which companies will provide you with the highest rate of learning:

1. Immediate / quick feedback
2. Clear indication of success or failure
3. Optimal task difficulty

1) Immediate or quick feedback

Have you ever learned to play an instrument? If yes, you’ve known pain. You sound awful. You screech, neigh and fumble your way through Ode to Joy, trying to not awaken the dead with your ungodly dissonance.

But with practice, you get better. The reason is feedback. When you hit a note wrong, you hear it instantly. That feedback that you’ve messed up lets you know what you need to fix.

The same principle applies to your career. Want to gain mastery as a designer? You need to hear those flat notes.

A company with rapid iteration and shipment cycles lets you see the results of your work quickly. Those results let you know if you’ve done something right or wrong.

Repeated cycles of feedback help you internalize what works and what doesn’t. Repeat that dozens of times and you develop an instinctive, subconcious level of expertise — one where you start rising above the minutia of execution, and can attack more complex problems.

So, if you want to accelerate learning, you want rapid feedback cycles. What does this mean in practice?

A design role at an early stage startup can mean it takes a long time to ship your work and see the results. A job at a consultancy or agency where you can’t get feedback from the actual execution of your work also limits feedback on your work.

Questions to ask when you’re interviewing: What’s the cadence of shipping new features? How long are sprints or product cycles? Typically, how long do you take to ship a new feature?

2) Success Metrics

So, we want to see results fast. Got it. But what do we do with the results?

To understand the results of your work, you need to clearly identify what constitutes a success and a failure. If you don’t know what you’re aiming for, you’ll never know if you’re doing a good job.

Metrics for success in your work can be quantitative (retention, conversion etc.) or qualitative (customer satisfaction, bug reports etc.). But they must be clearly defined and, more importantly, measurable.

Having the right metrics to measure the results of your work is crucial in maximizing learning.

Say you are trying to re-engage your user base. The number of users engaging in your product’s core action: that’s feedback. Your CEO saying “make the button bigger”? Also feedback. The first one measures the actual success of your work. The second one does not.

Companies that are able to articulate clearly defined, specific and measurable metrics for each project are great places to maximize your learning early in your career. Teams who are unable to articulate their goals and metrics are red flags.

Questions to ask: What were the metrics that you looked at for the last feature you shipped? How do you measure or track these metrics? How would we measure my success at my role?

— — — — — — — — —

Secondly, ownership. The success or failure of the work you did should be largely attributable to the work you did. If you work at large companies that do big and bundled product releases, the success/failure metrics becomes part of a collective effort of ten other features and teams. Early in your career, this makes it hard to figure out what the results are telling you about your work.

Questions to ask: What does a typical product release look like? How big are the teams? Who/which team owns this metric?

3) Optimal task difficulty

Another key step in growing and learning is finding a job where your skill level matches the challenge level of the job.

Okay, fine. Here’s what I mean. By matching your skill level to be optimal to the challenge of the job, you are more likely to have wins than losses.

Success leads to more success. Doing well in your job gives you confidence in the work you do. It makes the work you do more enjoyable — and it keeps you motivated.

But Lakshmi, what about the hustle? Isn’t being successful all about failing repeatedly until you hit massive success?

Nope. Small repeated wins matter. Here’s why.

When you take on a job that you’re under qualified for, you’re setting yourself up for constant failure. Failures are great opportunities to learn. But when you are out of your depth, you won’t even know why you failed. You need to understand the failure to actually learn from it. Failure that you can’t understand also leads to more dissatisfaction.

I’m not saying take a job you are over-qualified for. You still want a challenge that stretches you, but is reachable enough to keep you motivated.

For example, if you’re just starting out, a very early stage company still trying to figure out product-market fit presents a more complex challenge than you can probably handle.

Questions to ask: What’s the biggest problem you are currently trying to solve? What kinds of tasks do you have in mind for me to work on?

Startup jobs are hard, and they have steep learning curves. Another way to ensure that your job isn’t overly challenging is to look for places with mentors. Someone who is more experienced is more able to make strategic big picture decisions. They take out some of the uncertainty from the equation, making the job more optimally challenging for you.

Jobs with very little mentorship (because you’re the only member on that team) make it harder to course correct. You’re more likely to fail, and not even know why.

Questions to ask: Are there other senior members on my team? How many members are on this team?

—

Conclusion

While it may be easy to be swayed by free lunches and dog yoga, a high rate of learning is what’s going to set you up for success in 5 or 10 years time.

If you liked this article or found it useful, I’d appreciate a ❤.

I publish regularly on Medium, so follow me if you want to read more!

Thank you to Kannan Chandra and Nick deWilde for your help with this article!