Time machine for your career

Q: How did you manage to cram 8 years worth of PM experience in 3 years? Can this only be done working at a startup?

Believe it or not, it’s possible to do in any setting. The right startup provides some built-in support, but anyone can accelerate their career with the right tools.

Decoupling experience from a number of years exposes an uncomfortable truth: most time is spent learning haphazardly, if at all. Time gives you the opportunity to take more swings, but many swings are taken in utter darkness.  

To change this, we need to examine the core building block of learning: the feedback loop. The value of this loop is captured in an equation: speed x clarity.  

Speed is how fast you iterate. Clarity is how well you extract signal from the noise. You need both to make the feedback loop valuable.

I didn’t know this when I started, but the equation was stacked in my favor.
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The ladder of feedback

Clarity is my favorite variable because it’s almost always within your control.  

I’ve found there are three different rungs of feedback which sharpen your clarity:

1. Pinch: tells you what to fix (e.g., spend more time validating your idea)
2. Nudge: tells you what went wrong (e.g., new subject line tanked conversion)
3. Outcome: tells you how something is doing overall (e.g., MVP is underselling)

The newer you are, the more value you get from starting at a lower rung. Because the ladder is skill-specific, you may need pinches in one, but nudges in another.  

Pinches show you how to bridge the gap between where you are and where you could be. Between working at Bain and Faire, let’s just say I’ve received plenty of pinches. 

Not every environment is a boxing ring though. Some people shy away from pinching you in fear that it will come off as a punch. Make it easy for them to share openly:

• Start with what you’re working on (e.g., I want to get better prioritizing my to-dos. I notice you’ve mastered this, and would appreciate any advice)
• Make it low-risk (e.g., I want to better support you, so let me know how I can be helpful)  
• Be specific and timely (e.g., I feel like I came off defensive in that meeting. What’s your take? What could I have done better?)

A side benefit to getting this feedback is that you’ll never be surprised in a performance review. 

The pitfall, however, is that it’s subjective. People may not always be right, but they usually have a point. Try to understand that point, and decide whether to take action. This is why it’s best to work with people you admire. Their feedback inevitably molds you into a version of them.  

If you’re new, it helps to take some action even if you disagree. Other people may have more context, and will stop giving you feedback if you’re not taking it to heart.  

Sometimes you’ll get contradictory feedback. On my first project in consulting, my manager told me I was too confident and needed to qualify my responses. I did as I was told. On my next project, another manager told me I needed to be more confident.

With time, you’ll develop your own compass.
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Untangle market feedback

Nudge and outcome feedback tend to be more objective because they come straight from the market. You’re no longer in the land of opinions, but that means you need to exercise more judgment to interpret what’s happening.

Let’s look at a classic dilemma: the product flopped. Was it because the strategy was doomed, or the execution was poor? Because awareness was low, or conversion was low? Because feature X sucks, and we should’ve pursued feature Y instead?

Without a thoughtful plan and metrics in place, the answer is usually “We have no idea! Back to the drawing board...”  

To avoid wasting an expensive effort, list out your riskiest assumptions, and find ways to ideally test and de-risk each one.  

When we embarked on an odyssey to overhaul how 1M+ products were categorized on Faire, we wanted our suppliers to give us every piece of valuable information on the product. This was the perfect answer, but not the de-risked answer. 

What if the expensive overhaul did nothing? Instead, we scoped down the problem and had the most popular products tagged by an external party. It gave us an imperfect but workable dataset to test the new experience.  

Once we saw it was driving incremental dollars, we stepped on the gas and brought our suppliers into the fold. We also did excruciating pre-mortems, reviewing the hundreds of new category pages manually. If it failed, it would not be for lack of quality execution.  

When you’re tackling something new, try phasing out your work to get more nudges. While it takes more time upfront, when it’s high-stakes, slow is smooth, and smooth ends up being fast. Nudges will also build your pattern recognition for making sense of outcome feedback. 

Clarity makes every feedback loop count. Don’t spin into oblivion.
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Move with purpose

Your pace of learning is also set by how quickly you and your team can do a full cycle. While you can be a bar-raiser, some patterns are hard to break.  

Startups are generally synonymous with speed. It’s one big race against time. But not all startups are made equal.  

Those that have just found product market fit are ideal because they are no longer drunkenly walking in the dark. Something is working. They want to grow it, and find new things. You get both speed and clarity. I boarded the Faire rocket ship right before takeoff.  

Newborn startups will give you plenty of speed, but often not a lot of clarity. The market feedback will be harder to interpret without a clear set of customers.  

Big, well-organized companies will give you clarity, but not a lot of speed. They are careful to protect what’s been built, and have hired legions of people to guard every piece of territory.  

Big, dysfunctional companies will give you neither. They’ve lost their way, and before long, you probably will too.
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You don’t need permission

While it helps to be on a rocket ship, your fate is not sealed by who you work for. The harder but perhaps more rewarding path is to come up with a personal learning plan.  

You can learn from UX examples, marketing examples, and this newsletter. You can build products in your free time. You don’t need permission to learn at your preferred pace. When it comes down to it, we are all in a race against our own clocks.