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.

At the time (back in the 70s) was IBM the best option? Ehh, there were probably some upstarts that could have potentially been much better.

But did that matter to the guy who was putting his reputation or even his career on the line? Nope, not a bit! Fear, uncertainty and doubt led rational people to continually opt for the safe and conservative option.

Today we have a new president.

In the liberal tech world Hillary Clinton was IBM. Would she be the best President? Ehh, probably not. She was the safe & conservative option; with her at the helm the chances of the US self-destructing would have been slim. Instead, America interestingly said that it’s ok with a little fear, uncertainty and doubt, in the form of Donald Trump.

So what will Trump be? Will Trump be the garage upstart that disrupts the entrenched political machine and gets us out of our democratic rut? Or is he just a conman selling us vaporware, that hopefully won’t take the rest of the country down with him?

Let’s all hope it’s the former…

You spend enough time with successful people and you start to notice something. They’re not batting 100%. They’re far from perfect and not too different from the rest of us.

So what’s different? Why do they come across like everything they touch turns to gold?

I’ve noticed a few common traits:

  • They don’t dwell on mistakes other than to learn; they fail fast and move on quickly
  • They promote their wins well leveraging the concept that success begets more successes
  • They appear to be lucky but are more often just taking more at bats than most


At a recent coffee meeting a friend asked about a moving into the startup and technology world. He’s interested in changing careers but not sure how to go about it, if he’d be able to do it successfully, or if he’s crazy for even wanting to switch.

I’ve seen many people make the switch – some successfully and some not as much.

Perhaps the biggest lesson out of the gate is that it’s up to you. Nobody is going to magically transform your career except you!

As Jeff Hilimire says in a related post to new entrepreneurs on their startup ideas:

There is good news and bad news. The good news is, it matters very little what their current idea is for their startup, because EVERYTHING IS DEPENDENT ON THEM PERSONALLY. Then I told them that the bad news was the same…it matters very little what their current idea is, EVERYTHING DEPENDS ON THEM.

Similarly when looking to change your career, the good news is that the control is all in your own hands. The bad news is the same, it’s only in your hands.

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What if, as a Business Analyst, your approach to managing requirements could also apply to managing people? That’s an interesting proposition, right?

If you already have BA skills this makes the transition into a team leadership role easy. And as we’ll see, this management style is also well-suited to get the most out of the young knowledge workers filling up the modern entrepreneurial organization.

knowledge workers
Knowledge workers at work

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What is at the heart of your company’s DNA?

Within the technology industry there’s still a spectrum between marketing and engineering companies. Where does your company lie? It’s an important question to know. The answer impacts nearly all facets of how you operate.

Deep down, are you a marketing company? Does your company calculate its brand value and aspire to top this list someday?

Screen Shot 2015-06-12 at 11.15.46 AM

Or are you an engineering company? It might be obvious, like the team over at Boston Dynamics:

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entrepreneur reading list
That’s what it feels like to be an entrepreneur.

Of course most successful entrepreneurs love to learn. They don’t learn just one thing every day, but rather many things – entire topics – and it happens almost naturally.

And with the interwebs being what they are, one of the best places to learn* is by seeing what other people are doing, have done and then written about online.

*Other places to learn: talking to people in person; just f***ing doing it and learning from your mistakes
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When you break ground on a new SaaS startup it’s easy to set ambitious sales goals.

Pick a number…1,000+ customers, $1mm in annual revenue, a dozen strategic partners lined up by year two. Oh and don’t forget the hockey stick growth.


Forget it. Forget all of that. Those numbers, those goals, they aren’t what you should be focusing on right now.

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Outside the services and solutions world utilization and chargeability have little meaning. Inside a consulting company, however, these two numbers drive your business.

Let’s take a closer look at each.

the beach
found yourself on “the beach” lately?


What Is Utilization?

In short, utilization measures whether your consultants are doing anything. More specifically, is the work they’re doing right now tied back to a particular project of some sort?
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