A mentee of mine has a fortunate dilemma – too many job offers – so she reached out to me asking for advice on how to trim down the list. Great question!

Here are a few questions you can ask to try and find product/market job/market fit.

1. Ask yourself, would you be a user of the product?

If you would use the product, dog-fooding will be much easier and you’ll have much more customer empathy. And frankly you’ll be more excited to go into the office every day.

2. Ask yourself, are there people you can learn from?

Everyone, even great leaders like Musk, Bezos or Jobs, have an opportunity to learn more. And one of the differentiating factors between good and great leaders is that great leaders embrace continual learning. Look for a company where there are good mentors and senior leaders that can help you grow.

3. Ask the employer for key company metrics.

Ask to see things like revenue growth, churn, LTV, user counts, engagement, etc. This will not only give you a sense for the health of the business but also show you what type of metrics they value. Do they care about top line numbers (e.g. sales $$) or are they more focused on engaging customers? This will also help you vet whether they are a data-oriented company. I’d raise a warning flag for any company that isn’t willing to share some key data points or even worse, doesn’t have any to show.

4. Ask the employer what success is in your role.

It’s important to level-set expectations so their version of success should align with what you’re looking for out of the employment relationship.

5. Ask yourself, is the leadership team experienced?

All else being equal I recommend working with a team that’s already “been there & done that”. Yes, first-time leaders and entrepreneurs can be successful, but the odds are lower. Unless you’re specifically looking for a high-risk, high-reward opportunity seek out seasoned teams that will provide more stability.

6. Ask the employer if they have product/market fit AND why.

Note that the answer doesn’t have to be “yes”. The important thing is that the leadership can confidently articulate whether they do or not, how they know, and what they are doing to achieve product/market fit (if they haven’t reached it yet). Similarly, you’ll want to ask yourself what stage of company you want to work for. Do you want to be part of the team that is still finding product/market fit, do you want to help scale a company that has fit, or do you want to join a mature, well-oiled machine?

7. Ask the employer who the competition is.

This will help tell you how good of a market the company is in. If there are no competitors this is a warning flag. If there are dozens of competitors, how does the company plan to differentiate itself?

8. Ask the employer what their funding situation is.

What is the company’s runway and how much risk is there that you won’t have a job 12 months from now?

Of course there are many other considerations like the people, culture, work environment, commute, and on and on. However I’ve found that most people are already asking those questions. The thoughts above are often overlooked yet can be the most important to determine how successful and how happy you’ll be at your next job.

You’ve likely seen something like this at the New York Times, Wall Street Jornal, HBR or one of countless other online news and content sites.

I’ve only got 9 article remaining – better make them count!

Making readers subscribe to online content is broken

This isn’t about trying to avoid paying for content, but rather a simple exercise in scale.

When newspapers were the norm you had a handful to pick from in town so there wasn’t an issue choosing the one you liked the most and subscribing to it. You might have even been an overachiever and had a weekend subscription to the WSJ or USA Today too!

The model of the internet, however, gives us the wonderful benefit of the long tail. We no longer only have two or three papers to choose from, but rather thousands and thousands of papers, blogs and more. And that’s an incredibly good thing! The problem now is that there’s too much choice, presenting a separate problem of finding the content you want.

Enter newsletter aggregators. I see a new one pop up every week. Possibly my favorite, Hacker Newsletter, perfectly exemplifies why online article subscription doesn’t work. This past week’s newsletter contained links to articles from 43 unique sites.

Three Cases Against Online Content Subscriptions

1. It’s simply not financially reasonable nor logistically a pleasant experience to manage subscriptions to even a fraction of those 43 sites.

2. Perhaps more importantly, especially as we’ve learned in the US with our last Presidential election, when you get your content from a single source you get trapped in a Filter Bubble. We should make it easier for people to expand their perspectives, not the opposite.

3. Again looking at our last election’s issue with Fake News, I have a suspicion that when you pay for content you subconsciously become more likely to believe it without critique or skepticism.

To be sure these are businesses that need to bring returns to their shareholders, but a content subscription model in an online world is the wrong way.