The 2 Most Important Skills to Start Your Career

There is nothing harder than starting out or starting over. When you are new, it can be difficult to get your foot in the door and make a good impression. It can be hard to tell the difference between incompetence and a simple lack of experience.

Therefore, if you’re just starting out, there are two skills that are essential and will carry you farther than any others:

1) A Fierce Attention to Detail.

Any manager with a new hire has in the back of their mind the questions of, “Can they handle this?” and “How much do I need to keep an eye on their work?” If your manager knows you have an excellent eye for the details, they will be much more trusting in your abilities, knowing that you’ve taken good notes of their instructions, will triple check your work for careless mistakes and won’t do anything to make them look bad.  Building this trust can be the difference between a fast accelerating career with new responsibilities and languishing as an entry-level hire for years.

The longer I’ve been a manager and worked on product teams, the more I appreciate this trait. Over and over again we see the evidence of how the little details are what people notice and love (A great example is how Crashlytics built for Tweets which led to their viral growth). This is at the heart of great craftsmanship.

2) A Hunger to Learn.

Unfortunately, minding the details is not enough to succeed. You must also be eager to learn new skills. The faster you level up, the more likely you are to advance in your career whether always at the same company or at new ones. You need to learn from others and seek out sources of information on your own, which are skills in and of themselves to develop.

Many people in other careers have asked me how to get into product management, which isn’t always easy. However, one of the easiest ways to change your role is to work at a growing company and show how fast you can learn and grow.  This gives a company the confidence to give you more and new responsibilities.

The Combination is the Key.

When you combine an attention to detail with a hunger to learn, you will be unstoppable. Watching for the little details will make you more inquisitive and help you find the hidden gems and little secrets others gloss over. The little details are where life’s curiosities and greatest lessons lie.

As you grow the confidence of others and use curiosity to drive your learning, you will open new doors and build great relationships with others in your field. You are likely to attract great mentors who enjoy watching your development and love sharing stories and lessons to further your learning. They will also become your strongest advocates, either as great references, or the kinds of people that hire you again and again.

What do you think are the most important skills for those starting out?

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Why you should read 100 books

When I was fresh out of college with a internship at E Ink (maker’s of the display screen for the Amazon Kindle) I emailed the founder and then CEO, Russ Wilcox, to see if he would meet with me to give me some advice on entrepreneurship. Lucky for me, he was willing to schedule a meeting before my internship ended. You can read the full story here, but one of the best pieces of advice he gave me during our meeting was simple, yet powerful: Read 100 Books.

At the time it almost didn’t make sense and led to more questions than answers. What books? Why that many? How fast? By when?

I remember frantically writing down a bunch of book titles he started mentioning and then he stopped me and said the important thing was that they were on a diverse set of topics with different viewpoints instead of any specific books. He suggested trying to read 5-10 on categories like sales, marketing, leadership, negotiation, etc.

Mission Accomplished.

5 Years and 4 months after that conversation, I’ve finally hit the number and now looking back, I realize it’s one of the most important pieces of advice I ever received. I would not be where I am today if I hadn’t read as much as I have. Reading 100 books has done all the following for me:

  • Helped me better understand the responsibilities of coworkers (especially important as a product manager and startup founder).
  • Being comfortable in a conversation on just about any subject due to what I’ve read.
  • Rapidly improved my skills in key work responsibilities helping me accelerate my career and avoid costly mistakes.
  • Met other great people who also read regularly.
  • Given me the confidence and framework to help me learn anything.

If you’re reading this, I encourage you to also read 100 books. But realize it’s not about the number, but a routine of reading regularly that will serve you well throughout life.

Here’s my quick advice on how to make it happen and make the most of it:

1) Read what you can apply immediately.

I’ve managed to read a wide variety of books that have helped in my career and I’ve always chosen books based on what my current challenges and interests are. This has helped me apply concepts I pick up as I read a book, usually over the span of 2-4 weeks, depending on the length.

When I was moving to SF to run product at KISSmetrics, I started out with a great book on Product Management, then dove into a few books on design, before finding myself diving into sales, marketing, leadership and strategy books depending on what was happening at work and my personal life. Every time, I found great ways to build on what I read in my life around me which has helped tremendously with retention and understanding.

2) Get good recommendations.

Not all books are created equal. In fact, most books are pretty terrible, especially business books. There are gems out there though, so it really pays off to ask others who read what the *best* books are they’ve read on a subject. This has saved me tons of time on books that aren’t worth my time. This is why I made a list reviewing of all the books I’ve read  and some of my all time favorite books for entrepreneurs here. You’ll also occasionally find posts about books that CEOs like Jeff Bezos has his leaders read, which are usually great.

3) Build a routine of reading.

I read on public transportation. First it was riding the T in Boston and now MUNI around SF. I love this for so many reasons:

  • It gives you something to look forward to even when a bus commute might be lengthy.
  • A book won’t get stolen like your cell phone might be when you have it out as you play Angry Birds/check Facebook, etc.
  • It gives you bite size chunks of reading as most rides are 10-30 minutes…just enough for a chapter or two.
  • A book is a great way to get just a little bit more personal space on a crowded bus.
  • It’s a great warm up and cool down to your work day if you read during your commute.

If that’s not an option for you, build a routine around it in some other way. Maybe it’s 20 minutes before you go to bed, while you eat breakfast or perhaps audio books while you drive to work. It is the routine of always reading something that will carry you through that many books over the years.

4) Carry your book around with you.

Nothing sparks a conversation like someone noticing what you’re reading. Often those that notice read a lot too, which is a great way to make friends and you can get more recommendations for books from them. This also means that if a friend is running late, you always have a productive way to fill the time.  I brought Dale Carnegie’s “How to Win Friends and Influence People” with me to Bootstrap Live and ended up talking with Andrew Warner and the guy next to me about how much we all loved it.

5) Write all over your books.

Despite working in technology, I still prefer physical books in my hand. I underline, I highlight and dog ear all my books. Something about it helps me with retention of what I read. Even if you prefer to read on a tablet or Kindle, be sure to take notes and challenge yourself to think about how to apply what you’re reading. It helps a lot to review books you’ve read before when you have that subject come up. It’s amazing to me how often past events line up as examples (or counter-examples) of something I’m reading. I’m always sure to take a moment to consider it and write it down in the book.

6) Always make progress.

Life doesn’t always go as hoped or planned. There are times of frustration and stagnancy both personally and professionally in all our lives.  I’ve found one of the best things for me is knowing that no matter what is happening in my life I’m always learning because of what I’m reading. I can always look back and see progress there.

It has also helped that when I’ve had down times, if I read something related to it like a book on happiness or successfully navigating your 20s, I’m actually being proactive about the problem and getting advice from someone great who took the time to research and write a book about the subject.

Remember, this is not a race. The point of reading all these books is to absorb all the ideas and skills shared in the books, not race to the end.

I’ve heard some people like to skim books and think that doing things like reading the opening and closing paragraphs of a chapter and reading headlines in the chapter is enough. They’re either reading the wrong books or missing out on some deep lessons.

As a wise man once said, “Anything worth doing is worth doing well.” It is the journey to 100 books that I both enjoyed and grew tremendously from…not the milestone of specifically 100 that matters to me; I haven’t stopped reading and won’t anytime soon. My Amazon Wishlist is longer than ever (please suggest the best books you’ve read in the comments!) and I can’t wait to learn through more great books for the rest of my life.

3 Books Every Investor Should Read

As an entrepreneur, when I consider the ideal investor I would like to have, it’s a lot more than someone with money. I want them to have characteristics like:

  1. Able to make smart bets: Investments are largely made when it’s too early to tell with certainty who or what will win in a market. 
  2. Add value and insights: This is more than replaying personal war stories and biasing from your own experiences.
  3. Asking good questions: Someone who pushes founders to take a step back and recognize the things that matter often comes more from asking questions than providing answers.

Being great at those three things is no small task. Fortunately, there’s been some great books written that can supplement the knowledge and know-how of even the most veteran entrepreneur or get a new investor off on the right foot. These are books I’ve read and re-read because they’ve providing so much value to me and I believe can specifically help investors as well.

The Innovators Dilemma by Clayton Christensen

Disruption is a brutally abused word in tech these days. Clayton Christensen brings it back to reality and explains how it really works in this classic written in the 90s (and has arguably gotten better with age).

As an investor this is critical so you can call BS on an entrepreneur that claims they’re disruptive, but really are hopeless. This book will help you understand not only how to recognize disruptive technology in its earliest days, but what it means to get in the market, grab a position and successfully grow and take down the incumbents. Benjamin Tseng, a Bay Area VC, has a great post also discussing the value of this book for investors here.

Investor Scenario: A founder claims they have a disruptive innovation and are telling you about their immediate mass market plans, The research in Christensen’s book will help you guide them a better approach or to pass on the deal.

The Master Switch by Tim Wu

Over the past 100 years, communication platforms have dramatically changed and evolved. During this time, we’ve seen the emergence of the telephone, radio, television, email, the internet and more. Without fail, every time one of these new mediums emerged, they fought an uphill battle to eventually win the market.

This book goes perfectly hand in hand with Innovator’s Dilemma by walking you through how many technologies were slowly commercialized and changed the world. By the time you get to the end the patterns will be impossible to miss and priceless to match against what you see in new markets emerging (some of which you hopefully can invest and place strong bets on).

Investor Scenario: A founder has a transformative technology. Knowing the patterns of past innovative companies, you can help them anticipate resistance they may face both in the market and legally.

Tribal Leadership by Logan, King & Fischer-Wright

A book on culture to go hand in hand with two on innovation cycles? Absolutely. While there are other books out there I’ve rated higher on culture, none are more powerful for an investor.

You only get a limited amount of time with a founder and their team, so knowing how to quickly tell the difference between a strong team culture and one struggling is huge. What makes Tribal Leadership special is how it helps identify the key words that you can listen for to tip off how a company is really doing. 

Armed with this information, you can help a founder get back on track if some of the team has issues.  It can also help you decide if you should pass on an investment that looked good otherwise; a motivated, excited team will be significantly more productive, work longer hours and help recruit the best talent. You need those for the characteristics for a company to hit deadlines and win the market.

Investor Scenario: You visit one of your investment’s offices. If you overhear employees talking about their excitement for the mission, they’re operating at a high level. If instead they’re complaining about how much their work or a project sucks, you may want to ask the founder some questions.

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Unfortunately, many business books are a complete waste of time. Luckily, gems like the 3 books above exist and help tremendously to educate us, change our perspectives and diversify our knowledge on important subjects. I’d love to hear any great book recommendations in the comments for investors or entrepreneurs.

How to Become a Better Leader Instantly

Whether building a career at a large company or starting your own, if you want to advance and grow, soft skills like leadership are just as important to develop as hard skills like programming languages and sales tactics. Despite being a species evolved to live and work in groups, most of us struggle to effectively communicate with and motivate others. This is unfortunate, given how important and helpful a skill it is to master.

I’ve been studying leadership for a while and there are many techniques for motivating and effectively working with others. Many take some practice and skill. Fortunately, there are a few things you can do to very quickly develop your skills, which I was reminded of as I was recently reading the excellent book, “Fierce Conversations: Achieving Success in Work and Life One Conversation at a Time.”

One tip in particular stood out as something I’d heard many times before and I realized it’s the single easiest, yet important tactic to learn:

Give specific praise regularly

Animal trainers around the world know the best way to train animals is through rewarding good behavior. Just think about the last time you were at Sea World and the seals and dolphins got fish and other treats after each trick they did.

While humans are much more complex creatures, we still like rewards, just often in a different form: praise. Because this praise is written or verbal, the key is to be specific.  Don’t just say, “Good Job.” Instead, you’ll want to pull out exactly what was good so they know to do it again. Some simple examples could be:

  • “Great work on the folder feature, Susan. I really like how you made your code clean and easy to follow with comments explaining each section of the code.”
  • “Your report on quarterly earnings was great, Tom. Your graphics were perfect for explaining to the board how we recovered from the rough month.”

After praise like that, I guarantee you that Susan will continue to comment her code and keep it clean and Tom is much more likely to keep investing time to make great graphics for his reports.

This type of praise is powerful for a few reasons:

1) People want to feel appreciated.

Assuming you like your job even a little bit, you want to do good work. There are parts where you’ll put in extra effort. People just want to be recognized for that hard work and that will motivate them to do more of it. Think back to a time someone thanked you for a great job on a project you slaved over for weeks. Give others that feeling.

2) The absence of praise will be felt.

When someone does subpar work and you give no praise, they will notice and want to work harder to seek your praise they previously enjoyed. On the other hand, if you don’t praise people regularly, they are less likely to continue to put in the extra effort on projects. We have all had those moments where we went the extra mile on something and were disappointed when no one noticed. Chances are, you didn’t do it again for that boss or coworker. Don’t be that kind of manager.

3) People want to be noticed.

Especially in the startup world, it’s easy to take great work from your team for granted. Everyone just ships feature after feature, marketing content over more content and keeps grinding. This is also why celebrating wins as a team matters; it’s an opportunity to recognize both the collective efforts of the team and specifically who made major efforts to help the team get there. This is the key to making people feel like they’re “part of something bigger” that draws so many to the lower pay and longer hours of startup life.

Can you remember the last time you praised each member of your team? Were you specific with them or just a vague, “Good job”?

This is just one of the awesome tactics you’ll learn in the book, Fierce Conversations. It covers many excellent topics and will help you understand how to have productive and often difficult conversations effectively with others in both your personal and professional life. I scored it a 9 out of 10 on my ratings scale and highly recommend it.

Lessons in Innovation from the Biographer of Jobs, Einstein & Franklin

Walter Isaacson has written the biographies for some of the greatest inventors of the last 300 years in Ben Franklin, Steve Jobs and Albert Einstein. He spoke at the National Book Festival in Washington DC and I serendipitously stumbled upon his speech on CSPAN2. It was so amazing, I wanted to share it all with you as I found it is on Youtube here:

I highly encourage you to watch the whole thing, but I wanted to highlight two things that stood out to me.

Simplicity is a spiritual quest.

Especially in the tech scene and product world, we talk about simplicity like a Holy Grail of sorts and with good reason; a truly simple product has many advantages in the market and a strong likelihood of success. I think Isaacson captured this very well in his talk when he said,

Walter Isaacson on Simplicity

Often I find myself getting caught up in building something that is infinitely flexible and covers a million use cases and it makes me forget the essence of what I’m trying to build.

Spirituality comes into play because this requires faith; I have to believe that by sticking to the core of what I’m doing and ignoring some attractive features, I’m building the right product. It also reminds me of the effort required to get there; the first few iterations are unlikely to get to perfection. Instead, it is the dogged pursuit of simplicity that helps find the essence of what I’m really trying to create.

Tying these concepts together, and sharing how Einstein and Franklin thought about simplicity in addition to Jobs is a fascinating insight only the biographer of all 3 could do.

You have to be YOU.

After a question from the audience at the very end of the video, Isaacson covers the most important lesson I think we all need to remember as we read all the tech blogs and study successful people:

“Don’t try to just copy any one of them. Biography is understanding our world, our values and how you might apply them in your life.”

No matter who I’m studying or learning from, I try to see what I should learn from them to build on who I am, not try to be them. I will never pull off the design instincts and asshole of Steve Jobs nor the curiosity and mathematical brilliance of Einstein, but I know I can learn skills and approaches from them that will make the best version of me.

My Philosophy on Reading Books

I read a lot of books. For the past 3 years, I’ve averaged finishing a book every 2-3 weeks (thanks to this post inspiring me). Through all this reading, I’ve learned a tremendous amount thanks to a specific philosophy I’ve had on what I choose to read.  Since I just published the organized list of all the books I’ve read and recommend, I wanted to explain how I arrived at this list. These are my strategies when choosing how and what I read:

  1. Only read for purpose – I read books on subjects I want to learn about (i.e.: non-fiction only), so reading is about education not relaxation or escape for me.
  2. Stick to highly recommended books – I ask trusted friends, mentors and observe leaders in tech for books to read. I hate wasting time on a bad book, so I work hard to ensure anything I read isn’t a waste. This is why I include a section in my books list on books not to read.
  3. Read to solve current problems or satisfy current interests – This helps me quickly apply whatever I read to challenges I’m facing in my work and/or personal life.
  4. Write in the margins – If I don’t write down the ideas sparked in reading, I won’t remember nor apply them. It also makes it easier to revisit concepts I found interesting in any book I’ve read.
  5. Read in small bites – I read when I’m on public transportation, which generally means 15-30 minute bursts. This ensures I have plenty of time to think about each concept I read about and absorb as much as I can. Credit to Leo of Buffer for expanding on this subject here.
  6. Share – When I learn interesting concepts or a great book, I share it. The subsequent discussion with others leads to even more learning.

How do you decide what books to read? What motivates you to read?

Leadership Lessons First Time Entrepreneurs Forget

While building Greenhorn Connect, I’ve spent a great deal of my time with young and first time entrepreneurs.  If there’s one thing I’ve come to appreciate, it’s the absurd odds stacked against any of us succeeding; there’s just so much that you have no idea about and need to quickly learn.

You could spend years learning just one small subsection of your duties like SEO, analytics, customer development, copywriting, design, fundraising, product development, development architecture or simply great coding, but the demands of startups says you need to become competent and relatively adept at all of those and more.  Amongst all those hard skills, I didn’t even mention leadership, which I think is the most underrated skill to develop as a young entrepreneur.

Leadership is a bit different, because it’s a soft skill; it’s not as easy to measure as the success of your marketing campaign or the elegance and functionality of your code.  However, it’s an immensely important skill and one with more long term value than becoming an expert in any one of the aforementioned hard skill areas; if your goal is to build a company with more than yourself as an employee, then you’re going to be leading others.  As you grow, you’ll be leading more people and spending less time on any of the individual skills you used in the early days and much more on communication, vision and goal setting and coordination across teams.

As I’ve learned through my own errors and in talking to other young entrepreneurs, I’ve noticed there are 2 major concepts most of us don’t recognize that are absolutely critical to leading your team even when you only have one or two employees:

1) Your employees don’t work for you; You serve them.

Having employees means that you’ve been able to convince others to work with you on your idea.  Appreciate the incredible feat that it is.

However, do not think that because they work for you that they are now enlisted to your dictatorship. You need to involve them in core discussions, listen to their ideas and feedback and cultivate a culture of appreciation and shared passion.   A happy, engaged employee is 5x as productive as a frustrated, stymied or sad employee.  This ebbs and flows, so you really need to watch for it on a daily basis.

Showing appreciation for those that work for with you is not optional; you cannot over-recognize their best efforts.  At the same time, it is a balancing act.  There are times for the carrot and other times it is best to lead them with a stick.  Each employee will respond differently, so it’s a skill that requires fine tuning for everyone you work with.   Personally, as much as I love a good reward, I value constructive criticism significantly more; I’d much rather hear how I can do even better next time than dwell on what went right. Unfortunately, what I, you, or anyone else prefer is completely different than the next person you hire.

I constantly feel humbled by the fact that I have a team helping me make Greenhorn Connect a success today.  I do everything I can to make sure Pardees and Ian know that and have learned well the power of having excited, motivated people helping you fulfill your vision. An hour spent cultivating your employees will pay you back exponentially.

2) Uncover and fix problems when they’re small.

With all the hustle and constant activity buzzing around a startup, it’s easy to overlook small problems. Don’t.

When problems are small, solutions are small as well. When problems grow up, then it takes big, dramatic solutions to overcome them. If it’s an interpersonal issue or a major team issue, then suddenly that small issue can lead to someone having to be let go.

Catch problems when they’re small by reading your employees;  look at their face and posture, and if an employee seems down or upset…asking them if something is up and if you can help has huge immediate and long term benefits.

Conflicts and small issues are often simple misunderstandings or honest mistakes. Tackling them head on breeds a culture of accountability and openness to healthy criticism.  When you get your team in this habit, it becomes much easier to avoid major problems, because they never get that big.  Having a discussion about firing someone is a much more dramatic discussion than talking to an employee about a minor issue that may have caused conflict or hurt the company.  Nip problems in the bud and encourage your employees to do so as well.

This post may seem like stating the obvious, but theory and practice are two very different things.  Just like hard skills require practice and active use to become sharper, leadership skills like the issues above require active diligence to become adept at them. Ask yourself how your team is doing at managing these issues; I bet there’s times you’ve noticed your team’s mood affected productivity or a problem grew larger than it should have and caused trouble.

Have you learned these lessons the hard way? What key leadership skills do you think first time entrepreneurs need most?