What are you letting go of this year?

One question I’ve been asking my coaching clients lately: What are you letting go of this year?

This isn’t about adding to your to-do list. Instead, it’s about clearing the path. Think about:

• 🌟 Mindsets or assumptions that no longer serve you (or maybe never did).

• ⏳ Habits or ways of spending time that aren’t aligned with your goals.

• 🧩 Relationships or commitments that drain your energy.

We focus on what we want to achieve and commitments we want to add. But frequently the real magic of progress comes from removing things that are holding us back.

📈 Your Coaching Homework

This week, pick 2–3 things that might be holding you back. Then, choose one to let go of.

Here are two examples from my own life to spark your thinking:

1️⃣ Letting Go of Perfectionism

I’ve always had a high bar for quality, which has driven many of my successes. But when it comes to content creation, that same perfectionism can slow me down.

Here’s my hack: Instead of writing, I’ve shifted many of workflows to speaking. For some reason I feel less perfectionism while speaking, so now I do a podcast where I can prep and then let it fly, I use audio transcription to get ideas out while I’m walking my dog, and I even use voice shortcuts to respond to some emails. When I shoveled our cars out of the driveway on Monday, I did it while speaking into Fireflies.ai and thinking through my goals and plans for the week. Then when I got back to my computer, I had ChatGPT organize it and prep my week. For me, speaking frees me from over-editing and helps me get ideas out faster. This shift has made me happier and more productive.

2️⃣ Saying No to Group Zoom Calls

I realized that group Zoom calls often drain my energy. While I love in-person workshops, in-person meetings, and one-on-one Zooms, group Zoom calls rarely energize me and frequently drain me.

So, I’ve intentionally reduced them. I’ve stepped back from business lines that relied heavily on recurring group Zooms. It’s not a one-size-fits-all decision (not everybody can do that) and I’m not saying I don’t do these at all, but I’ve greatly reduced the volume and it’s been a game-changer for me.

🌟 Your Turn

Your examples might be totally different—maybe even the opposite of mine! The goal isn’t to copy but to reflect on what’s uniquely holding you back and give yourself permission to let it go.

Clearing space, whether mentally, physically, or emotionally, is what allows the great things to grow.

Happy pruning in 2025! Let’s improve clarity, focus, and momentum by reducing.

Until next time, enjoy the ride.

Boost your team’s engagement with this leadership tactic: behavior labeling

One of the most important traits of a leader is reliability and consistency. People need to know what to expect from you. If you are unpredictable or unreliable, it creates toxicity. Yet great leadership is about building a tool kit of techniques and tactics and applying the right tactic at the right time in the right way. There is a clear dichotomy between using different approaches and being predictable to your team. Behavior labeling is a simple way to ease the tension between these two concepts and increase the engagement levels on your team.

When I was a product manager at LinkedIn, Jeff Weiner was the CEO and even though he wasn’t the founder he certainly acted like one and Reid Hoffman treated him like one. Jeff had strong opinions and was articulate and compelling. So when he said something in a meeting, sometimes entire plans and roadmaps got reprioritized after. When he found out this was happening, he reflected, wrote a blog post, and addressed the whole company about it. He said most of the time he’s just another opinion in the room. He loves products and will share his ideas, but team leads should treat them exactly as they would anybody else’s. The team lead makes the call. The second level was a nudge where he believed he had a sense for the right direction, but it was still somebody else’s decision and he meant that and he wanted them to lead and learn. The third level was executive mandate where he could declare it and people should do it. He would use that sparingly, and only when he had outsize context, prior experience, or there was serious risk or reward involved that warranted that behavior. He also promised to make it clear in every meeting which mode he was in. If he didn’t clarify, it was your job to ask him and get it clarified. He told the company that’s the way he would operate from that point on. It had a huge positive impact because he could use different approaches and people knew what to expect in a specific situation.

Similarly, Scott Belsky (Chief Strategy Officer, EVP of Design and Emerging Products at Adobe) recently talked at the Cornell Product and Tech Leadership Program I helped run. He discussed how he handles design reviews and in most situations, he gives teams the leeway and the autonomy to make their own calls. But some projects cut across products, or have a level of risk or criticality where they have to nail it. In those situations, Scott will tell the team that he is holding himself personally accountable for that product execution and he will be involved, and in the details, and at times driving the decisions and the direction. Sounds a lot like founder mode, right? Yes, but not everywhere all the time just because. It’s applied surgically where it’s appropriate and it’s telegraphed so people know when he’s in that mode and when he’s not. 

One final example is Sarah Liebel. Sarah is an entrepreneurial operator and has helped scale 2 companies from early growth stage through IPO. She shared with me that she has 3 modes: curiosity mode, conviction mode, and commander’s intent. She shares which mode she is in with her teams so they know what to expect. In curiosity mode she is going to ask a ton of questions, but it’s not challenging - it’s clarifying so she can understand the context and the situation. Then she will go into conviction mode and if necessary will leverage commander’s intent to push something forward.

Labeling your behaviors can help both you and your team. For your own psychology, you don’t have to be in conviction mode all the time. It’s appropriate to be in curiosity mode but you may need to timebox that and say in 2 weeks I will have enough context to transition to conviction mode. Externally, when you share how you’re operating and why, it’s an incredible unlock for your team. When you are the leader, you would be amazed how much energy others waste trying to read your mind and predict your behavior. Short circuit that, share your tool kit and tell them what to expect in upcoming projects or situations! It’s easy, you can start today, and it does wonders.

Building a peer group as a startup executive

As you become more senior, the job becomes more lonely. Engineers can go to happy hour, share stories, talk a little trash, and help each other shake off the day’s stress. When you are CTO, you are the only one in the company with that job and you don’t have a direct peer group. You have senior engineers, other execs, and maybe the CEO, but you can’t go to happy hour with 3 other CTO’s from the company and riff on your day because there aren’t others. So you have to reach outside the company to build that peer group.

Targeted peer groups can improve your happiness and performance in a variety of ways:

• Relieving stress - sharing notes and coping strategies with people who have empathy for your unique pressures

• Improving operational decisions - sharing experiences with vendor selections, talent and culture issues, and operational processes

• Improving relationships - discussing how to manage relationships with stakeholders

• Improving your network - getting to know other experts for future opportunities or recruiting

Therefore it is important to build targeted peer groups, especially for new executives. For CEO’s, I recommend YPO. Women may enjoy Chief. Some VC’s have guilds or groups for different functional leaders within their portfolio companies.

If you don’t have built in communities, you can go find them or create them. They can be casual or well organized like Round. Either way, it’s important.

Your homework for today:

1. Think about the unique challenges you face in your role

2. Consider where you want to be in 12 months

3. Review the frequency and quality of discussions you get with like-minded peers

4. If you are satisfied with 3, given 1 and 2, congrats - time for happy hour. If not, find a way to improve it. The communities are there. If you can’t find them, email me and I’ll help 🙂

It’s the end of product management as we know it.

My Cornell colleague Josh Hartmann and I recently spoke at a Cornell keynote about the rapid changes that have hit the tech world and how CEOs, CPOs, and CTOs are adapting. Let’s break down what tech leaders are doing and how you can think about evolving your product organization.

We have seen market crashes, most recently in 2001 and 2008. We have also seen several platform shifts: PCs, internet, cloud, and mobile. But we are on truly rare ground right now. A pandemic obliterated prior assumptions about office space, the market crashed, with SVB as a kicker, and we are on the precipice of a new platform shift with AI. All. At. Once.

So product management as we know it is done. It’s time to adjust our thinking, quickly.

One trend in the market is the revival of the General Manager role. This position has been around for a long time. It means running a P&L, including all costs that go into making and selling a product: product, design, engineering, marketing, sales, and operations. During the past ten years, many tech companies have used functional org designs with product, engineering, and design teams that report to their own executives without arbiters at the director or VP level who control resources cross-functionally. GMs were occasionally used in international teams or new ventures but rarely in core product development teams. In the functional model, P&L “ownership” is dispersed. During times of abundance, this org design works well because it optimizes for product decisions, tech tradeoffs, and distinct product, engineering, and design cultures. The big downside is that cross-functional decisions such as pricing changes, headcount changes, reorgs, or strategic shifts take longer because they require intense cross-functional negotiations. During times of abundance, those decisions can be slow and it is merely a nuisance. During times of scarcity, slow decisions will cause failure. We have been in abundance for 10+ years due to the incredible business models at big tech companies such as Meta and Google and the nearly endless venture capital fueling startups and growth companies.

Welcome to times of scarcity. It is now increasingly important to make hard tradeoff decisions rapidly. Creating GM roles or morphing other roles into GM roles is one tactic. I’m seeing a revival of the GM at tech companies and I like it.

It’s not the only way. AirBNB is doing something totally different. There has been a lot of talk about AirBNB implementing an Apple-style product marketing manager role that blends product and marketing. But listen to Brian Chesky carefully in his interviews; you see several key points many people are missing.

AirBNB’s efficiency is mind-blowing. They have less revenue and profit than companies like Google, but their Free Cash Flow per employee is in a league of its own. AirBNB has natural tailwinds because marketplace models at scale are highly profitable. But it’s still a remarkable example.

So what should you do in your org?

First, figure out who the decision-maker is in any given context or domain and lean into it. Great companies tend to be politically dominated by a specific function, usually driven by the founders' personalities. At Meta and Google, engineering runs the show. LinkedIn is product-driven. Apple and AirBNB are design-driven. Costco is operations-driven. The problem with these cultures is that dominant functions create the feeling of second-class citizens. Google PMs know they’re not the most important people in the room. But the advantage is giving somebody access to the accelerator and removing other people’s access to the brake pedal so you can move fast.

In today’s world, you better move fast. Figure out who should have the reins for specific decisions, and let them move.

Roles and responsibilities are frequently fuzzy, especially between product and other functions. An hour spent clarifying roles and responsibilities is a very high-leverage hour. Determine what artifacts must be created (roadmap, positioning statement, pricing page, etc.), what decisions must be made, and what activities must happen. Then make sure you have a function that clearly owns each.

Decisions need to be made by people close to the problem, with overall strategic context. If people on the ground make decisions but don’t fully understand the company’s strategy and investment areas, they won’t make the best decisions, and that’s not their fault. In contrast, ivory towers with execs making decisions on problems they don’t intimately understand will lead to failure and culture rot. So ensure your communications flow effectively; it’s the WD-40 for effective decisions. In today’s market, making difficult decisions with limited information quickly will give you the velocity you need to win.

If you have comments or questions or are taking a different approach on your team - shoot me a note!

Improve your team’s retention with structured career conversations

When I joined LinkedIn’s product team in 2012, I encountered a distinct approach to career conversations. It began with an upfront acknowledgement: “You are unlikely to work here for the rest of your career. Great, now that we addressed that we can be honest and discuss your true career goals.” This candid perspective, ingrained by Reid Hoffman, was based on a philosophy that employees join for a tour of duty to get the team from Point A to Point B. Completing this tour is important and leaving midway is a failure. But you should be open about your long-term aspirations and after each tour ends you have earned a discussion about your next career move, whether that be within LinkedIn or somewhere else.

While more common now, this was cutting edge in 2012. If a product manager aspires to become a venture-backed CEO, they might require more exposure to sales, even if not directly related to their current role. Ironically, the more marketable you make people externally the longer they stay because it means they’re growing.

Here are several tactics for engaging in these career conversations with your direct reports. It can be enlightening at times and uncover a deeper level of conversation around where your team members want to go, where they perceive they are growing and where they may feel stalled or blocked.

1. Proactively schedule a 30 to 60-minute conversation about their career

Avoid scheduling this during a crisis or before a significant deadline. Find a moment when you can step back from everyday tasks and focus solely on career-related topics. You may need to conduct a regular 1:1 meeting within the same week to discuss urgent matters separately, enabling both of you to be focused and present during the whole conversation. If possible, consider holding this conversation over coffee or a meal.

2. Share a document for them to fill out before you meet

Here is the format I use.

While simple, it can be challenging for many to complete. So, stress that this document is a dynamic work-in-progress and bringing a super rough draft for the first conversation is fine. Encourage them to start jotting down their aspirations and strategies for achieving them. Just as product success needs a roadmap, career success demands explicit goals and strategies.

3. Start with the long-term

Begin with a conversation about your direct report's long-term goals, both personal and professional. Choosing a 5-year horizon breaks some of the tension, especially if they are not accustomed to sharing their career ambitions with their manager. This timeframe seems distant enough to foster openness, yet near enough to require a specific plan. This dialogue can reveal a lot about their aspirations, how they feel about their career progression, and the types of challenges that will keep them engaged. It’s remarkable how often managers discover that a team member may depart in order to seek specific experiences or challenges when those can be readily facilitated internally with minimal adjustments. All because the manager asked and listened.

4. Discuss balancing individual aspirations and organizational objectives

Seek a balance between your team member’s passion and their job responsibilities. Ideally, most tasks align with both their goals and your needs. Acknowledge that 20% of the role may not cater to their interests, but it’s crucial for success in the job. Conversely, 20% of what they need for their career goals may not align with your objectives. That’s also OK and enables you to make room for them to engage in projects or side activities that stimulate the right types of learning and growth.

If the gap between job requirements and their personal goals is too large, it’s better to identify that, address it, and discuss it rather than leave it to fester. If the gap is closable in the short term, which it usually is, then you can collaborate on defining and bridging the gap.

5. Listen intently

These career conversations are invaluable for understanding how to best support your team. Make an effort to minimize distractions by switching off your phone and quieting your internal chatter. Truly immerse yourself in the conversation, listen to the ideas that are clearly articulated and guide them as they try to express ideas that are still incubating. If they haven’t yet defined precise career objectives, your assistance in discovering and refining those goals can be empowering.

6. Help them set measurable goals and actionable next steps

Let them steer the discussion, it’s essential that they feel ownership over the plan. But hold them accountable for creating a plan. Often, the initial attempt can be challenging and require iterations. That is natural, but ensure that they progress towards a plan with specific goals and action steps that you both agree on. Someone eager to hone their storytelling skills might find public speaking or improv classes useful, but never had an accountability partner to help them make it happen.

7. Schedule a follow up

Completing a significant project or "tour of duty" should prompt another round of conversation about future possibilities. Reflect on the milestones achieved and discuss what comes next. If there isn’t a specific milestone, then mark a date 3 or 6 months from now for a follow up. 

Engaging in career conversations with your direct reports paves the way for relationships founded on mutual understanding, support, and growth. The key is to be proactive, receptive, and sincere during these discussions. It will go a long way in cultivating a dynamic and motivated team where high performers are inspired to stay and do their best work.

Getting the right input, at the right time, from stakeholders

As you get more senior in your career, it is common to underestimate the importance of people and process. I found this out the hard way while leading a product team at Flatiron Health. I was in charge of driving the process for setting our Objectives and Key Results (OKRs). In my first quarter, I began the process with a drafted version of the OKRs, aiming to provide a foundation for the development team to build upon. I saw this as a mere kick-starter, not something carved in stone. However, the reaction was: “What!? You didn’t even have the respect to ask our opinions before setting the goals?” The team felt dis-empowered.

With this lesson in hand, I approached the next quarter with a different strategy. I came to the OKR meeting with a blank whiteboard and invited everyone to participate as we drafted the OKR’s from scratch. Yet, this approach backfired too. “What!? Our PM doesn’t even know where we’re going? We’re screwed.” The team felt directionless.

The third quarter I approached the OKR setting with drafted objectives, but not KRs. I made it clear that these were preliminary suggestions with tons of room for input based on our fundamental strategy. The “Goldilocks” approach finally resonated.

While this example is specific to setting OKRs with a development team, the principle holds across many decision-making situations. It's impractical and detrimental to seek input from everyone on every decision. But a crucial element of leadership is carefully deciding whom to involve and when in any meaningful decision. Some people need to provide input. Some people need to be informed. Some people, hopefully very few, have true veto power. When making a decision, it will go a long way if you not only focus on the content (the right decision) but also the process:

1. Share the fact that you have an important, pending decision with the right people. The goal at this stage is to collect the proper data, facts, opinions, and inputs.

2. Collect and process the inputs.

3. Analyze and draft a decision.

4. Share your analysis, in draft form, with a select group for pressure testing.

5. Make the decision.

6. Share the decision, along with the reasoning, broadly.

7. Follow through and execute on the decision.

Early in your career, getting the right answer is the most important thing. As your responsibilities grow, having the right process can be even more important because that leads to people in the organization supporting your decision and enabling your success. If you want further content, Gokul Rajaram’s 20 minute video on decision-making is a high leverage use of time.

Does a product manager need domain expertise?

If you don't understand your industry, you can't be successful. If you are an industry veteran that's too steeped in tradition, you become less capable of innovation. So what's the real deal with domain expertise? First, let's be specific. You can break domain expertise down into your understanding of:

1. The industry: key players, competitive dynamics, regulatory issues, supply chain, talent

2. The customer: characteristics, behaviors, motivations, goals, key challenges

3. The product: technical design, value prop, key features, customer experience

4. The problem: entertaining, saving time, making money, improving performance

Within these areas, it is easy to conflate knowledge and skill. Knowledge is knowing what a neural network is. Skill is the capability to build a deep learning model that produces results for your business. Knowledge is required but not sufficient. Skill is where you truly differentiate yourself.

In my experience, skills at solving a specific type of problem are the most critical. Steven Spielberg is an expert at entertaining.  I would bet on him being successful in any medium as long as the fundamental premise is developing rich characters and stories to entertain an audience. Tim Ferriss, on the other hand, is an expert at improving performance. He does it across domains like entrepreneurship, investing, sports, cooking, and politics. But it's always about identifying behaviors that improve results. Great product managers hover around similar problem types, whether it's saving companies time and money or connecting and entertaining consumers.

Understanding the customer is also wildly important. World-class product experiences are anchored on empathy for the user. It takes time to build this empathy and knowledge. However, if you have the skill to perform effective user research - then you can accelerate the learning curve and learn new customers more rapidly.

Product is a mix. You need deep knowledge and specialized skills to build a self-driving car or develop a new cancer drug. But I have found most software products to be readily learnable once you understand the basics.

Industry is a tricky dichotomy. You can't succeed in a complex regulated industry, like financial services or healthcare, without knowing the market's dynamics. On the flip side, radical innovation tends to come from industry outsiders who aren't steeped in the old ways, i.e. Stripe, AirBNB, Uber, etc. So there is a risk/reward tradeoff. Being an insider increases your chances of success, but reduces the chances of outlier success. Being an outsider increases your chances of hitting a home run, but increases the likelihood of complete failure.

As a product manager, I recommend you think carefully about where you want to build your expertise over time, especially in regards to problem type. Early in your career, focus on breadth so you can build a baseline and experiment. Once you find the area(s) where you have the highest combination of passion and ability, go deep! That's how you go from good to great.

How to triple your LinkedIn profile views

I started KeithonCareers 10 years ago and ever since I have recommended that people write publicly. Cogent writing is a great proxy for cogent thought. So if you can articulate something interesting and share it, people will find it, be impressed, and want to talk to you. The career ROI is huge. You don't have to do it perfectly. You don't even have to do it often. I have had more career opportunities that started by people finding my blog than I ever would have imagined. That's with only publishing 6-12 posts per year.

My personal struggle is that I have many ideas for posts, but I'm a perfectionist and not a natural journalist. So writing a blog post can feel like work and take a long time. Separately, attention spans are only getting shorter. So I decided to launch an experiment. Instead of adding my ideas to a growing list of "future blog post ideas," I would just write down the fundamental idea and share it on Twitter and LinkedIn (without the full post). So I used a free Buffer account, set up a queue to post once at 9:30am and once at 4pm. Whenever I came up with an idea, I would write it in Buffer on my phone, queue it up, and then ideas would automatically publish on a relatively steady basis.

I posted resume and interview tips.

I posted cultural observations.

And I posted a few things that might just strike a chord with people.

After 1-2 weeks, I saw a few things happen:

1. Some posts really resonated, some didn't. I wasn't able to predict in advance which were which. So it was a great way to test ideas before investing in a long-form post.

2. I had a few interesting conversations in the comments.

3. My LinkedIn posts got 10x as many views as my corresponding Twitter posts. With Twitter's 280 characters being much more restrictive, I found that posting on LinkedIn and using up 300-500 characters was my best bet (LinkedIn accepts more but the point of this was to keep it brief).

4. My LinkedIn profile views went up exponentially (see featured chart at the beginning).

5. A number of people reached out to me, folks I haven't met and would like to, and people I know but haven't talked to in a long time.

The results were super valuable. I'm just instigating interesting conversations, but if you're looking for a job - you should consider posting to LinkedIn. In 300-500 characters, you can get surprising results. Every chief marketing officer has a Facebook strategy, an Instagram strategy, and a SnapChat strategy. I still don't think they have LinkedIn strategies, which means the content feed isn't completely saturated yet. But the demand for content is there. So take advantage while the getting is so good. It's seriously underrated.

To see my future career tips and observations - follow me on LinkedIn.

A product manager's list of things to read, watch, and listen to

I have spent 19 years building products, teams, and companies. Along the way, I have read, watched, and listened to a LOT of content.  Here are some of my favorites.

Books on Business Leaders and Creators

• Steve Jobs by Walter Isaacson

• The Everything Store: Jeff Bezos and the Age of Amazon by Brad Stone

• Delivering Happiness: A Path to Profits, Passion, and Purpose by Tony Hsieh

• Pour Your Heart Into It: How Starbucks Built a Company One Cup at a Time by Howard Schultz

• The Billionaire Who Wasn’t: How Chuck Feeney Made and Gave Away a Fortune by Conor O’Clery

• Buffett: The Making of an American Capitalist by Roger Lowenstein

• The PayPal Wars: Battles with EBay, The Media, the Mafia, and the Rest of Planet Earth by Eric M. Jackson

• Hit Refresh: The Quest to Rediscover Microsoft's Soul and Imagine a Better Future for Everyone by Satya Nadella

• Shoe Dog: A Memoir by the Creator of Nike by Phil Knight

• Steven Spielberg: A Life in Films by Molly Haskell

• Built from Scratch: How a Couple of Regular Guys Grew the Home Depot from Nothing to $30B by Bernie Marcus, Arthur Blank, and Bob Andelman

 Books on Leadership and Management

• The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers by Ben Horowitz

• What Every BODY is Saying: An Ex-FBI Agent’s Guide to Speed-Reading People by Joe Navarro

• The Charisma Myth: How Anyone Can Master the Art and Science of Personal Magnetism by Olivia Fox Cabane

• Primal Leadership: Learning to Lead with Emotional Intelligence by Daniel Goleman, Richard Boyatzis, Annie McKee

• Never Eat Alone and Other Secrets to Success, One Relationship at a Time by Keith Ferrazzi, Tahl Raz

• Executive Presence: The Art of Commanding Respect Like a CEO by Harrison Monarth

• Leadership Lessons of the Navy SEALs: Battle-Tested Strategies for Creating Successful Organizations and Inspiring Extraordinary Results by Jeff Cannon

• Make your bed: Little things that can change your life...and maybe the world by William McRaven

• The Making of a Manager: What to Do When Everyone Looks to You by Julie Zhuo

• The Power of Moments: Why Certain Experiences Have Extraordinary Impact by Chip Heath, Dan Heath

• The Coaching Habit: Say Less, Ask More & Change the Way You Lead Forever by Michael Bungay Stanier

• The Trillion Dollar Coach: The Leadership Playbook of Silicon Valley’s Bill Campbell by Eric Schmidt, Jonathan Rosenberg, and Alan Eagle

• The Dichotomy of Leadership: Balancing the Challenges of Extreme Ownership to Lead and Win by Jocko Willink and Leif Babin

• Extreme Ownership: How U.S. Navy SEALs Lead and Win by Jocko Willink and Leif Babin

 Books on Productivity

• The 7 Habits of Highly Effective People: Powerful Lessons in Personal Change by Stephen R. Covey

• The Effective Executive: The Definitive Guide to Getting the Right Things Done by Peter Drucker

• The Power of Habit: Why we do what we do in life and business by Charles Duhigg

• Getting Things Done: The Art of Stress-Free Productivity by David Allen

• The Willpower Instinct: How Self-Control Works, Why it Matters, and How to Get More of It by Kelly McGonigal

• Atomic Habits: Tiny Changes, Remarkable Results by James Clear

• Make Time: How to Focus on What Matters Every Day by Jake Knapp, John Zeratsky

 Books on Product Management

• The Lean Startup: How Today’s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses by Eric Ries

• Inspired: How to create products customers love by Marty Cagan

• The 4 Disciplines of Execution: Achieving Your Wildly Important Goals by Sean Covey

• The 4 Steps to the Epiphany: Successful Strategies for Products that Win by Steve Blank

• Lean Analytics: Use Data to Build a Better Startup Faster by Alistair Croll

• Sprint: How to Solve Big Problems and Test New Ideas in Just Five Days by Jake Knapp, John Zeratsky, Braden Kowitz

• Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration by Ed Catmull, Amy Wallace

 Books on Sales and Marketing

• Crossing the Chasm: Marketing and Selling High-Tech Products to Mainstream Customers by Steve Blank

• The Art of Persuasion: How to Influence People and Get What You Want by Juliet Erickson

• Rainmaking Conversations: Influence, Persuade, and Sell in Any Situation by Mike Schultz, John Doerr

• Building a StoryBrand: Clarify Your Message So Customers Will Listen by Donald Miller

• On Writing: A Memoir of the Craft by Stephen King

• Building a Story Brand: Clarify your message so customers will listen by Donald Miller

 Books on Startups

• Venture Deals: Be Smarter than Your Lawyer and Venture Capitalist by Brad Feld, Jason Mendelson, Dick Costolo

• Do More Faster: TechStars Lessons to Accelerate Your Startup by Brad Feld, David Cohen

• The Art of the Start: The Time-Tested, Battle-Hardened Guide for Anyone Starting Anything by Guy Kawasaki

• Rework by Jason Fried, David Heinemeier Hansson

• The Messy Middle by Scott Belsky

• Angel: How to Invest in Technology Startups - Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000 by Jason Calacanis

• It Doesn't Have to Be Crazy at Work by Jason Fried, David Heinemeier Hansson

• Bad Blood: Secrets and Lies in a Silicon Valley Startup by John Carreyrou (just for fun, incredible story)

 Books on How to Think

• Fooled by Randomness: The Hidden Role of Chance in Life and in the Markets by Nassim Nicholas Taleb

• Freakonomics: A Rogue Economist Explores the Hidden Side of Everything by Steven Levitt, Stephen Dubner

• Awakening Your Ikigai: How the Japanese Wake Up to Joy and Purpose Every Day by Ken Mogi

• Principles: Life and Work by Ray Dalio

• Sapiens: A Brief History of Humankind by Yuvan Noah Harari

 Websites and Blogs

• Techmeme (simple aggregator)

• Business Insider

• TechCrunch

• Jason Lemkin: Saastr

• Tomasz Tunguz

• Dharmesh Shah: On Startups

 Email lists

• Axios Pro Rata (venture capital, private equity, M&A)

• Axios Media Trends

• Seeking Alpha Wall Street Breakfast (financial markets)

• Fitt Insider (business of health and fitness)

 Videos

• Bloomberg Technology (available on Bloomberg TV or web)

• Pando Monthly Fireside Chats (no longer published, includes some oldies but goodies)

• Both Sides TV

• Google Ventures Workshops

 Podcasts

• Bloomberg Technology

• This Week in Startups

• Motley Fool Money (financial markets)

• A16Z Podcast

• How I built this

• Tim Ferriss

• Masters of Scale

• Naval Podcast

3 metrics to see if a job is right for you

When considering a job opportunity, you might rely on gut instincts or you might create a spreadsheet and rank 10 different factors. Whatever you do, here are 3 things you should think about that you might not be considering.

Skill to ego ratio

Your speed of learning is one of the most important factors in your career. Reid Hoffman says that “many people with 20 years of experience really have 1 year of experience repeated 20 times.” You want to avoid that fate by continuously learning, which means being around highly skilled and motivated people. But highly skilled environments usually have the egos to match. I have seen this personally, both on Wall Street and in Silicon Valley. On the flip side, there are places that are humble but unskilled. That sucks too, for different reasons. Measure the balance between these two factors. Flatiron Health and LinkedIn are two of the best places I’ve worked at and they both have great skill to ego ratios. I won’t tell you there are no egos. I would be lying to you. But for the caliber of talent they have attracted, the level of humility is impressive. A strong skill to ego ratio creates an invigorating and fun environment.

Compensation to autonomy ratio

Compensation matters. So does your ability to turn off devices and be a human, whatever that means to you - be it training for a marathon, picking up your kids from school, or watching Netflix on a Tuesday. What people screw up is thinking about those concepts in isolation. One job might pay more but not let you work from home on Fridays. Another might be super flexible but not give you the compensation you’re looking for. Your ideal outcome will vary throughout your life, but always consider compensation and autonomy in tandem. Every ounce of autonomy that somebody takes from you is a huge cost. Don’t forget that.

Your excitement for the mission

Answer this question: “On a scale from 1-10, how excited are you about the mission?” Let’s be honest, the true daily tasks of most jobs are hard and boring. So you have to be motivated. Maybe what motivates you is helping kids. Maybe it’s being on a high performing team with the competitive spirit of pro athletes. Whatever it is - ignore everybody else and go deep on what energizes YOU. If you find a 10, it will change your life.

Stand for something greater than yourself

My grandfather, Robert Grasty, was 16 years old when Pearl Harbor was bombed in 1941. Like the patriots of his era, he went straight to the Navy after his 18th birthday to voluntarily enroll. He was rejected due to a foot surgery. They said he couldn’t wear the boots. He was off the hook. But instead of going back to his life, he went to the Army. He was rejected again. So he kept trying until he successfully became a sailor for the US Merchant Marine. Not only did he choose to serve, he banged on doors until somebody said “Yes, you can risk your life for your country. Let’s get started.”

He recently passed away at 93 years of age. There are few World War II veterans left with us today. So let’s take some lessons from their generation as we pave the path for our own future.

Build for the long-term

My grandfather put himself through engineering school at Virginia Tech and then spent the meat of his career, 25+ years, at General Electric. He had a successful career and spent a good portion of it building jet engines. None of it was easy and nothing happened overnight. In today’s world, it’s easier than ever to find a new job or make a change. Personal autonomy is important and I have taken full advantage of that in my own career. I don’t think 25-year tours of duty should be the norm anymore. But we have to remember that it takes time to build things that matter. You don’t build a jet engine in a two-week sprint. You don’t win World War II in a single year. We need to mix the freedom, autonomy and creativity that is thriving in today’s workforce, with the idea that committing to things and building for the long-term matters. Because it does.

Invest in your family and community

Strong families and relationships don’t happen by accident. They happen because you invest in them and make them happen. At one point in his career, my grandfather was running a large manufacturing plant. His son, my uncle Peter, came to visit. Peter had been living on a commune, with the full hippie hair and dress code to match. Peter didn’t exactly fit in at my grandfather’s office, especially during times when there was serious tension between large corporations and the counter-culture movement. But my grandfather didn’t worry about other people’s opinions, even though his reputation and relationships were the key to his livelihood. He marched Peter in the front door, introduced him to the managers, and gave him a full tour. This sent a clear message, to Peter and to the team members at the plant, that family came first. My grandparents, like many from their generation, were constantly investing in their family and their community. Whether it was renting a lake house for family vacations, spending time with their church, coordinating dinner groups, or getting involved with local organizations, they brought people together.

Reach across the aisle

My grandmother, who inspired a post about building a successful career and a successful family, was a devoted democrat. She was actively involved with democratic activities and land conservation issues in New Hampshire. My grandfather was a staunch Republican. Yet they shared fundamental values and built a lifelong partnership, 63 years of marriage, and a loving family. I remember my dad asking my grandfather how many times their votes cancelled each other out in elections. My grandfather smiled and said “I don’t know. I never asked her who she voted for.” I assume he was half joking, but the message stuck with me. You can put politics aside in light of something greater than yourself. In a world that is increasingly politicized and partisan, let us remember that we can build relationships, organizations, and families across political barriers. It may not be the default. It may not be easy. But it is more important than ever.

Stand for something greater

It is hard to imagine what the world would be like without the sacrifices people made in World War II. What legacy will we leave for generations after us? I am not asking you to quit your job and join the peace corps. But think about your impact. Do things that make the world a little bit better. Build organizations that endure. Build real relationships with good people. Reach across an aisle or two. Stand for something greater than yourself.

In loving memory of Robert Alvin Grasty (1925-2018), US Merchant Marine (1943-1946).

Should I be an employee at a top tier company or a leader at a startup?

It’s a career choice you may have to make. The answer will be highly personalized, but here are some key things to consider.

Big company = learn your function. Startup = learn to build companies

If you want to learn to be a great software engineer - join Google. If you want to learn how to build a company - join a startup. I spent 3 years as CEO of a startup and learned 10x as much about company building as I learned in 2 years at business school and many years working at big companies. After that experience, I worked at LinkedIn. At LinkedIn, my product management skills grew more quickly because I was surrounded by training opportunities and people with deep product expertise that made me better. If you want to learn expertise in a function - go with a reputable company in your field because they are phenomenal training grounds. If you want to learn how to build something from scratch, get outside the comfort zone of giant companies.

Do you want a gold star on your resume from a top talent brand?

When I was in business school, there was a successful serial entrepreneur who had started and sold multiple companies already. But he had never worked at a company he didn’t start. So he went to a prestigious consulting firm after business school, in part to prove that he could pass somebody else’s talent bar and play well with others. He didn’t have to do that, especially if he wanted to work in startups for the rest of his career. But he believed that gold star on his resume would make him more marketable in the future. It’s a good mindset to at least consider, especially early in your career. If you’ve done nothing but work at giant companies, startups might raise an eyebrow and wonder if you can handle an environment without lots of support infrastructure. If you’ve only done startups - big companies will wonder if there is a reason why you’ve never worked at an established company. You don’t want to float around for no reason, but there is something to be said for experiencing work within big companies and small companies. It helps you develop a wider range of skills and helps you learn where you truly thrive.

Find clever people, spend as much time with them as possible

This one is orthogonal to company size. Big companies have lots of teams and they’re not all created equal. Research the team you’ll be joining. Do they inspire you? Would they push you to get better at the things you want to improve at? Drew Houston, Dropbox CEO, says “You become the average of the 5 people you spend the most time with.” Find people you want to spend time with, regardless of company size, and spend time with them.

Most importantly - keep learning

There are many different ways to invest in your personal growth. You can learn an entirely new function (i.e. switch from marketing to product), learn a new market, learn a new customer, learn a new technology, or you can go from individual contributor to team leader to org leader. The vector of learning that is most exciting to you and most valuable for your career is a personal decision. But make that decision with care. Sometimes switching between big companies and small companies can help you grow in a direction that you are prioritizing for the next phase of your career. Sometimes it will help you collect a gold star that pays dividends on your resume, or give you raw early-stage experience that will make you tougher when you get back to big companies. Regardless of where you go - make sure you keep learning. That’s the most important factor in your career.

How to join projects that get you promoted

Eric Schmidt famously told Sheryl Sandberg "If you’re offered a seat on a rocket ship, don’t ask what seat. Just get on." He was talking about companies, and specifically Google. But the advice goes for projects as well. Every company has a Project X or two, where Project X is a high-flying initiative that senior leaders are heavily invested in and closely watching. We all want to live in a perfect meritocracy that is 100% fair. But let's be honest - working on Project X is good for your career. So what does it take to get on Project X?

Before you start, write down your goals

If you run hard and fast, but you're going East and ultimately decide your goal is West, well guess what? That was a waste of time and energy. So don't prematurely jump for the sexy project. Write down what you love, what you hate, and what you want to be doing in 5 years. As best as you can. Then use that as a guiding light to find your Project X, something that is a company priority with lots of upside but also aligns with your long-term goals. If you're reading this post, you probably have an idea of a project you'd like to work on some day. I'm going to give you a guide for getting there.

Just ask

After identifying your goal, you need to find the decision-maker and talk to her. In some cases, this will be your direct manager. If it's not your direct manager, you should talk to your manager first and have a general career conversation to prevent surprises. The earlier you are in your tenure, the more you need to present this as a "long-term exploration" of something you may want to do some day. The longer you have been on your team, the more right you have to discuss shorter-term next steps in your career. Once you have your manager's OK, set up time to talk to the decision-maker. In this case, I'm defining decision-maker as the person who can say "yes, let's have you join this project." If it's not clear who that is, start asking until you figure it out. It's possible that multiple people need to say yes, which is more complicated, but let's assume it's one. Now politely ask this person for 15 minutes to discuss your career interests. They'll know you're ultimately asking for something and that's OK. This process is all about honesty. When you talk to her, clearly describe your long-term interests, your skills, and the role you would like to play on Project X. Then, don't ask to join the project yet. Ask her what she would need to see, now or in the future, to believe that you would be a good fit. This gives her a low risk way to be completely honest, which is important because you need to get the truth. It's easy to ask for the role and trigger a response like "well, we don't have any openings right now so come back in six months" when inside she's thinking "you can't do this role because you've never worked with enterprise customers." Getting that real feedback is critical. It gives you something specific to work on. If you're lucky, maybe she'll be ready to have a conversation about joining the project now. You don't know unless you ask.

Create a plan to bridge the gap

If asking was all it took, then congratulations you can stop here! Otherwise, take the feedback you got and create a plan. Start with what success looks like, perhaps proving to senior leadership that you can effectively work with enterprise customers, and then work backwards. What specific skills do you want to invest in? What would it take for others to believe in you? There is reality and there is perception. Both matter. You need to change reality by building your skills and experience. You also need to change perception by thinking carefully about how you can prove this to other people. For example, "customer-facing skills" is fuzzy. But closing deals is not. If you are able to close three complex deals that increase a product's revenue by 10%, that is a proof point you can lean on. Think carefully about proof points when you're preparing your plan. What measurable milestones do you want to hit over the next quarter?

Build a reputation

While working toward your goal, be methodical about building a reputation. If you want to eventually change teams, working on things that have cross-cutting impact across the company will help you build a reputation that transcends your current role. I have seen PM's host monthly forums where product managers share learnings and best practices from recent product launches. I have seen engineers start hackathons at companies that weren't used to thinking that way. If you are willing to do most of the work and it doesn't cost the company much money, you can make it easy or unnecessary to get approval. Even small, seemingly random things can make a lasting impression. Maybe there is no shared holiday calendar so that your team knows when people are out of the office. Maybe the coffee maker is broken. Find something that is broken and fix it and people remember. They really do. It's part of building your reputation as somebody who makes things happen. It should go without saying, but also make sure you crush it in your current role. Explore new things, but always deliver on your current responsibilities and keep a strong and honest relationship with your manager. That's usually a pre-req to unlocking new opportunities.

Pull it all together

In summary, there a few things that are important to get on your company's next rocket ship. Make sure the decision-maker knows you're hungry and ready. Get specific and actionable feedback about how you can get there. Crush it in your current role, make an impact beyond your responsibilities, and create a detailed plan. Then march toward your milestones and make it happen. Project X might be closer than you think.

What skills do you need to become a product manager?

People frequently ask what it takes to become a successful product manager. I tell them all the same thing. To start with, you need a basic level of skill across a wide range of topics.

• Engineering

• Design

• Marketing

• Sales

• Data and analytics

• Strategy and prioritization

• Communications and leadership

Then, to become world-class you need to build superstar skills in one or two areas. These one or two areas will be highly dependent on your personal interests, your natural-born skills, and your experience.

As you invest in your superstar skills, it becomes increasingly important to find a product, a market, and a company where flexing those specific muscles pays outsized dividends. Each company is politically driven by a different function and it’s important to keep that in mind. At Apple, for example, design and marketing run the show. At Facebook and Google, engineering drives everything. At Salesforce, it’s all about talking to customers. As you grow in seniority, it becomes more and more critical to be the right PM for the job. The top PM at Instagram might completely fail at Amazon Web Services and vice versa.

So build the base skills then carefully select areas where you want to develop your personal edge. For more on this topic check out A product manager's list of things to read, watch, and listen to.

4 words to live your career by

Building a happy and successful career takes time and energy. Try focusing on these four words to guide you in the right direction.

Honest

First, be honest with yourself. It’s amazing how easy it is to lie to ourselves. When you’re excited or upset, think carefully about your motivations, your loves, your fears, and your biases. We all have them. The more you understand them, the more effective you will be.

Second, be proactively transparent. Being honest is more than telling the truth when somebody directly asks you. If you go out of your way to educate people about what’s going well, what’s not, and what is at risk, you can proactively avoid a lot of problems.

Third, be open about your concerns and provide constructive criticism. Look at people who are extremely successful and you will frequently find this behavior. They give honest feedback, but do it in a constructive way so people can improve. If the train is about to go off the rails, you want somebody on your team who will raise their hand and tell you. Be that person, it pays off.

Kind

Kindness matters. The trick here is to carefully weave it with honesty. It’s easy to be honest and abrasive. It’s also easy to be kind and avoid criticism. It’s extraordinarily difficult to be kind and constructive at the same time. But if you can perfect this art, it will pay dividends throughout your career. If people know they can come to you for the brutal truth, but get it in a way that doesn’t attack them - you will become a trusted adviser.

The flip side is that you have to let go of the idea that you will make everybody happy. It is not possible. It is possible, however, to be honest and have the best intentions. If you are open, honest, and constructive then you can sleep well at night and accept the consequences. You will always miss something. You will always make somebody upset. That’s OK. It really is. It has to be or you will never make meaningful progress in this world. But have the best intentions.

Disciplined

The devil is in the details. Get your shit done. Send out status updates. Read the document before the meeting. Go the extra mile to close a deal. In the short-term, 9 out of 10 actions will go unnoticed. But people catch on and you will earn a reputation for being gritty and reliable. In the long-term, your results will speak for themselves. Success is 99% perspiration. Strategy doesn’t separate companies and careers. Execution does.

Clutch

There is something magical about having somebody you can count on in the most critical situations. Pick your favorite sports analogy, whether it’s Tom Brady, Derek Jeter, Simone Biles, or somebody else. If you aspire to 10x your market value, you should aspire to be disciplined, prepared, and reliable. Poise under pressure is a result of consistent grit over an extended period of time. When you become the clutch player, you become a true leader.

Preparing for a phone screen

Prep your physical space

If you might invest years of your life at this job, take the extra 15 minutes to make sure you’re ready for the interview. Plan exactly where you are going to take the call. That means privacy, little background noise, and either a landline or good cell phone reception. Also, have your resume handy along with a pen or laptop to take notes.

Rehearse your intro

Research shows that most interviewers make their decision within the first five minutes of an interview. This means you need to rehearse your opening. Again. And again. And again. Trust me. It’s work, but it is critical. The phone screen is similar to your resume, think of it like a movie trailer. Your goal is not to tell your whole story on the phone, but to entice them so they want to bring you on-site to see the rest. I recommend describing yourself in two to three unique sentences. Then use the rest of your conversation to prove those sentences true. Also be clear about what you’re skilled at, what you’re excited about, and how this role fits into your career goals.

Review your resume and ask yourself questions

Pretend you are the interviewer. Now read your resume and for every project and every bullet, see what questions come to mind:

• What happened after you launched Project X?

• What made this project a success?

• What would you do differently next time?

• What does this mean?

• What role did you play on that team?

For each story, decide how strong your answer is and how relevant it is to your two to three sentences. If it’s a strong project, rehearse your response and discuss it proactively during interviews. If your answer is weak or not relevant, consider deleting the bullet.

Research your interviewer

Knowing your audience gives you a leg up. So ask politely when you’re scheduling the interview if you can have the name and role of the person interviewing you. If they decline, leave it there. But asking once is fine. If they give it to you, use your research skills across the web to learn everything you can. You might pick up tidbits about what they look for, what they’ve done, what they’re working on, what hobbies they have, or where they went to school. You will not change any fundamentals, but you can tune your answers and conversation points so that you’re more likely to connect with the person.

Write down questions for them

The interview process is as much for you as it is for them. Picture yourself in this role. Would you be happy? Would you be successful? What factors about the company or the role would change the answers to those two questions? Turn those thoughts into detailed questions for the interviewer and write them down. It’s your life and your career, make sure you know what you’re getting into.

6 ways to blow a job interview without realizing it

You say:

I’m not feeling challenged in my role.

They hear:

My boss is giving the most important projects to other people and there is a reason for that.

Alternative:

I have gotten everything I can out of this role and am ready for something bigger. So I am exploring opportunities internally and externally and this role sounded really interesting.

You say:

No, I haven’t had a role like this before.

They hear:

I want to get hired, but there’s a large chance I can’t do the job.

Alternative:

I haven’t had this exact role before, but it looks like the key components are A, B, and C. A and B are exactly what I’ve been doing on Project Z, let me tell you about it. C is something I’ve been working on recently and am excited to learn.

You say:

No, I don't know much about your products - an overview would be great.

They hear:

Choosing a job is one of the most important decisions in my life and I chose not to do my homework before this interview. If you hire me to run a project, I won’t do my homework then either.

Alternative:

I looked through your website, read your annual report (if the company is public), and saw some articles about Project X. But I can only tell so much from the outside so I would love to hear more.

You say:

I am really passionate about Education (insert appropriate market). No, I’m not interviewing at similar companies - just this one.

They hear:

If I truly had passion for Education, I would know a bunch of interesting companies and be exploring jobs at several. That means I’m either lying about my passion or lying about where else I’m interviewing. Neither option is good.

Alternative:

I’ve been excited about this space for awhile. I think companies X, Y, and Z are also doing interesting things so I’m looking at companies like them as well. But I’m particularly intrigued by this role for the following reasons.

You say:

Sorry I’m a few minutes late. The traffic/train/weather/etc. was terrible this morning.

They hear:

I am not reliable. This is one of the most important meetings I will have this year and I did not plan my day to make sure I’d be on time. When you have a critical deadline, it’s 50/50 that you can count on me.

Alternative:

Barring true emergencies (family situation, car accident, etc.) don’t be late! Seriously. If your trains and traffic are unreliable, get there an hour in advance and do work at a nearby coffee shop. If you are out of town and staying at a hotel, scope it out the night before so you know exactly where to go in the morning. Attention to detail matters. If you can’t arrive to an interview on time, why should they trust that you can deliver projects on time?

You say:

No, I don't have any questions.

They hear:

If I was curious, I would ask a lot of questions. If I cared about the work environment, the team, and the product strategy, I would ask a lot of questions. But I have no intellectual curiosity and a low bar. So I have no questions. I just want a job.

Alternative:

Ask great questions! This is part of the interview. Identify the key things that matter to this business and drill in to learn more and see if you want to work there. You don’t need different questions for every single interviewer. It’s OK to repeat your questions and get multiple perspectives from different people. It’s not OK to have no questions.

3 keys to simplifying your product design

Building a product customers love is about making it simple and compelling.  Here are 3 keys to getting it right.

1. Clarify your value prop

Your value prop should be crisp. Who are you serving and how do you make their lives better? I suggest summarizing your product in the following form: We provide solution X to user Y by doing Z. For example, Patagonia provides high quality active gear to people who love the outdoors using sustainable and ethical practices. They have a big organization with a lot of products. But you can summarize their value prop and purpose in one sentence. The cleaner your value prop, the more loyal your fans.

2. Define goals for specific user actions

These goals should be unique to your product. When Chamath Palihapitiya was put in charge of the growth team at Facebook, Mark Zuckerberg gave him a mandate to grow the user base. But “Growth” was an impossibly broad topic. So they did research and identified a milestone of “7 friends in 10 days.” If a user joined Facebook and connected with 7 friends in the first 10 days, she was likely to become a daily user and invite her friends. If she joined Facebook but fell short of that milestone, she was more apt to churn. This gave the team something tangible to rally around: let’s build products and onboarding experiences that help people find their social network in the first week. Chamath joined Facebook when they had less than 10M users and left when they had close to a billion.

Focus on what you want your users to accomplish. Get this right and everything else falls into place.

3. Reduce cognitive load

Cognitive load is the energy required for a user to absorb information and make a decision. It takes customers more time to understand your product than you think. That’s why it is so important to get out and test your product in the real world. You are not a valid test. You think about your product every day and focus on every detail. If you run a social network, your customer might see your app while waiting in line at a coffee shop, talking to 2 friends, and pulling out her wallet. If you build software for doctors, the physician might see your screen while talking to a patient, ordering a prescription, and flagging down the nurse to check on lab results. People are busy and distracted, so design with the expectation that you will never have your customer’s full attention. Cognitive load is about more than just your product, it is about everything your customer faces.

Here are some places to look for cognitive load:

Navigation bars. People love to copy navigation bars from other companies. “They have X, Y, and Z so we need X, Y, and Z.” Don't fall for it!  Did Google copy the Yahoo! homepage? Design simple flows that lead to the outcomes you want. Then delete everything else.

Calls to action (CTA). If you want users to add an item to their shopping cart, make the button bright and obvious. Then remove buttons that aren't important. Don't ask users to do three things. Ask them to do one.

Word count. Count the words on every page and tighten your copy. Tell the same story, but with fewer words.

Onboarding flows. Don’t ask your user for a ton of information up front. Get started easy and onboard them over time.

Simple product design in the wild

Facebook vs. MySpace: There was a time when MySpace was bigger than Facebook. But MySpace had a fatal flaw. Designing your MySpace page was a complex task involving add-ons and custom html. Setting up a MySpace profile came with huge cognitive load. Facebook, on the other hand, made every profile page the same. When you join, you only have to do 2 things: upload a photo and find your friends.

In ‘N Out menu: In ‘N Out Burger is famous for having exactly 4 food items on its menu: fries, hamburger, cheeseburger, double double. That’s all! Four items, plus milkshakes and sodas. Compare that to McDonald’s and see what you get.

Apple product line: According to Apple lore, there used to be a table in the Apple design studio and every product the company sold had to fit on that table. If the product line got too big, it was time to trim down and simplify.

Diapers.com vs. Amazon: Amazon bought Diapers.com (aka Quidsi) for $550M because Diapers.com was giving Amazon a run for its money in baby supplies. One key reason was simplicity. Diapers.com gave parents a simple way to have diapers, wipes, and baby supplies delivered to their house every month. That’s it. Keep it easy. Keep it simple. Trust me, if anybody is under cognitive load it’s new parents! So this simplicity paid off. Even the URL was easy to remember.

Biggest loser competition: When I was on the product team at LinkedIn, our head of product ran a biggest loser competition. He challenged us to see which team could remove the most unnecessary stuff from their products. Everybody wants to add features and add products and add complexity. Yet the best products are great because they’re simple. It is extremely difficult to remove live functionality from a product. There is always somebody who will yell at you for taking away that feature. But having the discipline to prune your products helps create long-lasting franchises.

It is easy to create complexity. It is hard to create products that are simple and compelling. But it’s worth the effort.

Why your product should evoke emotions

There was a famous food test where critics were given three meals: chicken, grilled chicken, and Tuscan-seasoned balsamic chicken. The Tuscan chicken got the best ratings. But there was a twist. The three meals were identical except for the name. The critics’ brains literally told them that the Tuscan-seasoned balsamic chicken was tastier than the identical “grilled chicken.” The name evoked positive emotions that changed their physical experience.

This is an important concept to remember when designing product experiences. Let’s use Starbucks as an example. Starbucks customers love getting to work in the morning feeling like they are powerful and ready to take on the day.  Nothing evokes that emotion like striding down the street holding a caffeinated beverage in a signature Starbucks cup. On the flip side, Starbucks customers hate when days get long and stressful. Therefore they love having a sanctuary where they can take a 15-minute break in the afternoon. Think about the music, the smells, the baristas, and the entire environment inside a Starbucks. It is designed to evoke emotions so when you sip your coffee, it feels like the best part of your day.

Think carefully about your customers. Figure out what they hate and what they love. Then take advantage of that to evoke emotions and win their loyalty. If people buy your product because it’s rational, you can win for now. If people buy your product because they love it, you can win for a lifetime.

One thing you should never do when applying to a startup

There is something in the startup world, and elsewhere, that I see all the time.  It seems like the right thing to do, but there is no better way to kill your chances: the generalist pitch.  Here is a quote from an email I got recently: "I would be open to any position that would allow me to gain valuable experience and grow within the company.”

I see this a lot and I NEVER see it work.  Here is the problem.  This describes what you want.  It doesn't describe what the company wants.  The company wants a marketer who has been fine-tuning their marketing skills for years and an engineer who loves coding and can talk database optimization for hours.

I like to compare it to a football team.  You might come in and say "I just want to play football."  But in reality there are 2 job openings:

Lineman: You need to be strong, aggressive, 6'6" and 350 pounds.  It doesn't matter if you can run fast or catch the ball.

Wide receiver: You need to be lightning fast and have great hands.  It is not important how well you block or tackle.

It doesn't matter which one you want to be, but it is important that you commit to one or the other.  Anybody who says "I'll do anything you have" has already tipped their hand that they can't compete against the linemen or the wide receivers. My philosophy is to commit to being a wide receiver or a lineman, build the relevant skills, and then go hunting. Let's say you go to 10 teams. 5 won't have an opening for that position and won't meet you (which is fine), 5 will have a relevant opening and meet you, 3 will seriously consider you, and 1 will give you a job offer.  Alternatively, you can optimize for the initial conversation and say you'll do anything. Then all 10 will meet with you but 0 will hire you. So go for the kill and optimize for 1 job offer vs. 10 conversations. It's OK if you don't know precisely what you want to do for the rest of your career, but the more you focus and describe how you will make the company better, the higher your chances.

Don't say you'll do anything.  Tell them how you will help them get more customers (sales/marketing), improve the product (product/design/engineering), or run the company (recruiting/operations/etc.).