More on Leadership

Joe Procopio
2 years ago
Provide a product roadmap that can withstand startup velocities
This is how to build a car while driving.
Building a high-growth startup is compared to building a car while it's speeding down the highway.
How to plan without going crazy? Or, without losing team, board, and investor buy-in?
I just delivered our company's product roadmap for the rest of the year. Complete. Thorough. Page-long. I'm optimistic about its chances of surviving as everything around us changes, from internal priorities to the global economy.
It's tricky. This isn't the first time I've created a startup roadmap. I didn't invent a document. It took time to deliver a document that will be relevant for months.
Goals matter.
Although they never change, goals are rarely understood.
This is the third in a series about a startup's unique roadmapping needs. Velocity is the intensity at which a startup must produce to survive.
A high-growth startup moves at breakneck speed, which I alluded to when I said priorities and economic factors can change daily or weekly.
At that speed, a startup's roadmap must be flexible, bend but not break, and be brief and to the point. I can't tell you how many startups and large companies develop a product roadmap every quarter and then tuck it away.
Big, wealthy companies can do this. It's suicide for a startup.
The drawer thing happens because startup product roadmaps are often valid for a short time. The roadmap is a random list of features prioritized by different company factions and unrelated to company goals.
It's not because the goals changed that a roadmap is shelved or ignored. Because the company's goals were never communicated or documented in the context of its product.
In the previous post, I discussed how to turn company goals into a product roadmap. In this post, I'll show you how to make a one-page startup roadmap.
In a future post, I'll show you how to follow this roadmap. This roadmap helps you track company goals, something a roadmap must do.
Be vague for growth, but direct for execution.
Here's my plan. The real one has more entries and more content in each.
Let's discuss smaller boxes.
Product developers and engineers know that the further out they predict, the more wrong they'll be. When developing the product roadmap, this rule is ignored. Then it bites us three, six, or nine months later when we haven't even started.
Why do we put everything in a product roadmap like a project plan?
Yes, I know. We use it when the product roadmap isn't goal-based.
A goal-based roadmap begins with a document that outlines each goal's idea, execution, growth, and refinement.
Once the goals are broken down into epics, initiatives, projects, and programs, only the idea and execution phases should be modeled. Any goal growth or refinement items should be vague and loosely mapped.
Why? First, any idea or execution-phase goal will result in growth initiatives that are unimaginable today. Second, internal priorities and external factors will change, but the goals won't. Locking items into calendar slots reduces flexibility and forces deviation from the single source of truth.
No soothsayers. Predicting the future is pointless; just prepare.
A map is useless if you don't know where you're going.
As we speed down the road, the car and the road will change. Goals define the destination.
This quarter and next quarter's roadmap should be set. After that, you should track destination milestones, not how to get there.
When you do that, even the most critical investors will understand the roadmap and buy in. When you track progress at the end of the quarter and revise your roadmap, the destination won't change.
Sam Hickmann
3 years ago
Improving collaboration with the Six Thinking Hats
Six Thinking Hats was written by Dr. Edward de Bono. "Six Thinking Hats" and parallel thinking allow groups to plan thinking processes in a detailed and cohesive way, improving collaboration.
Fundamental ideas
In order to develop strategies for thinking about specific issues, the method assumes that the human brain thinks in a variety of ways that can be intentionally challenged. De Bono identifies six brain-challenging directions. In each direction, the brain brings certain issues into conscious thought (e.g. gut instinct, pessimistic judgement, neutral facts). Some may find wearing hats unnatural, uncomfortable, or counterproductive.
The example of "mismatch" sensitivity is compelling. In the natural world, something out of the ordinary may be dangerous. This mode causes negative judgment and critical thinking.
Colored hats represent each direction. Putting on a colored hat symbolizes changing direction, either literally or metaphorically. De Bono first used this metaphor in his 1971 book "Lateral Thinking for Management" to describe a brainstorming framework. These metaphors allow more complete and elaborate thought separation. Six thinking hats indicate ideas' problems and solutions.
Similarly, his CoRT Thinking Programme introduced "The Five Stages of Thinking" method in 1973.
| HAT | OVERVIEW | TECHNIQUE |
|---|---|---|
| BLUE | "The Big Picture" & Managing | CAF (Consider All Factors); FIP (First Important Priorities) |
| WHITE | "Facts & Information" | Information |
| RED | "Feelings & Emotions" | Emotions and Ego |
| BLACK | "Negative" | PMI (Plus, Minus, Interesting); Evaluation |
| YELLOW | "Positive" | PMI |
| GREEN | "New Ideas" | Concept Challenge; Yes, No, Po |
Strategies and programs
After identifying the six thinking modes, programs can be created. These are groups of hats that encompass and structure the thinking process. Several of these are included in the materials for franchised six hats training, but they must often be adapted. Programs are often "emergent," meaning the group plans the first few hats and the facilitator decides what to do next.
The group agrees on how to think, then thinks, then evaluates the results and decides what to do next. Individuals or groups can use sequences (and indeed hats). Each hat is typically used for 2 minutes at a time, although an extended white hat session is common at the start of a process to get everyone on the same page. The red hat is recommended to be used for a very short period to get a visceral gut reaction – about 30 seconds, and in practice often takes the form of dot-voting.
| ACTIVITY | HAT SEQUENCE |
|---|---|
| Initial Ideas | Blue, White, Green, Blue |
| Choosing between alternatives | Blue, White, (Green), Yellow, Black, Red, Blue |
| Identifying Solutions | Blue, White, Black, Green, Blue |
| Quick Feedback | Blue, Black, Green, Blue |
| Strategic Planning | Blue, Yellow, Black, White, Blue, Green, Blue |
| Process Improvement | Blue, White, White (Other People's Views), Yellow, Black, Green, Red, Blue |
| Solving Problems | Blue, White, Green, Red, Yellow, Black, Green, Blue |
| Performance Review | Blue, Red, White, Yellow, Black, Green, Blue |
Use
Speedo's swimsuit designers reportedly used the six thinking hats. "They used the "Six Thinking Hats" method to brainstorm, with a green hat for creative ideas and a black one for feasibility.
Typically, a project begins with extensive white hat research. Each hat is used for a few minutes at a time, except the red hat, which is limited to 30 seconds to ensure an instinctive gut reaction, not judgement. According to Malcolm Gladwell's "blink" theory, this pace improves thinking.
De Bono believed that the key to a successful Six Thinking Hats session was focusing the discussion on a particular approach. A meeting may be called to review and solve a problem. The Six Thinking Hats method can be used in sequence to explore the problem, develop a set of solutions, and choose a solution through critical examination.
Everyone may don the Blue hat to discuss the meeting's goals and objectives. The discussion may then shift to Red hat thinking to gather opinions and reactions. This phase may also be used to determine who will be affected by the problem and/or solutions. The discussion may then shift to the (Yellow then) Green hat to generate solutions and ideas. The discussion may move from White hat thinking to Black hat thinking to develop solution set criticisms.
Because everyone is focused on one approach at a time, the group is more collaborative than if one person is reacting emotionally (Red hat), another is trying to be objective (White hat), and another is critical of the points which emerge from the discussion (Black hat). The hats help people approach problems from different angles and highlight problem-solving flaws.

Mike Tarullo
3 years ago
Even In a Crazy Market, Hire the Best People: The "First Ten" Rules
Hiring is difficult, but you shouldn't compromise on team members. Or it may suggest you need to look beyond years in a similar role/function.
Every hire should be someone we'd want as one of our first ten employees.
If you hire such people, your team will adapt, initiate, and problem-solve, and your company will grow. You'll stay nimble even as you scale, and you'll learn from your colleagues.
If you only hire for a specific role or someone who can execute the job, you'll become a cluster of optimizers, and talent will depart for a more fascinating company. A startup is continually changing, therefore you want individuals that embrace it.
As a leader, establishing ideal conditions for talent and having a real ideology should be high on your agenda. You can't eliminate attrition, nor would you want to, but you can hire people who will become your company's leaders.
In my last four jobs I was employee 2, 5, 3, and 5. So while this is all a bit self serving, you’re the one reading my writing — and I have some experience with who works out in the first ten!
First, we'll examine what they do well (and why they're beneficial for startups), then what they don't, and how to hire them.
First 10 are:
Business partners: Because it's their company, they take care of whatever has to be done and have ideas about how to do it. You can rely on them to always put the success of the firm first because it is their top priority (company success is strongly connected with success for early workers). This approach will eventually take someone to leadership positions.
High Speed Learners: They process knowledge quickly and can reach 80%+ competency in a new subject matter rather quickly. A growing business that is successful tries new things frequently. We have all lost a lot of money and time on employees who follow the wrong playbook or who wait for someone else within the company to take care of them.
Autodidacts learn by trial and error, osmosis, networking with others, applying first principles, and reading voraciously (articles, newsletters, books, and even social media). Although teaching is wonderful, you won't have time.
Self-scaling: They figure out a means to deal with issues and avoid doing the grunt labor over the long haul, increasing their leverage. Great people don't keep doing the same thing forever; as they expand, they use automation and delegation to fill in their lower branches. This is a crucial one; even though you'll still adore them, you'll have to manage their scope or help them learn how to scale on their own.
Free Range: You can direct them toward objectives rather than specific chores. Check-ins can be used to keep them generally on course without stifling invention instead of giving them precise instructions because doing so will obscure their light.
When people are inspired, they bring their own ideas about what a firm can be and become animated during discussions about how to get there.
Novelty Seeking: They look for business and personal growth chances. Give them fresh assignments and new directions to follow around once every three months.
Here’s what the First Ten types may not be:
Domain specialists. When you look at their resumes, you'll almost certainly think they're unqualified. Fortunately, a few strategically positioned experts may empower a number of First Ten types by serving on a leadership team or in advising capacities.
Balanced. These people become very invested, and they may be vulnerable to many types of stress. You may need to assist them in managing their own stress and coaching them through obstacles. If you are reading this and work at Banza, I apologize for not doing a better job of supporting this. I need to be better at it.
Able to handle micromanagement with ease. People who like to be in charge will suppress these people. Good decision-making should be delegated to competent individuals. Generally speaking, if you wish to scale.
Great startup team members have versatility, learning, innovation, and energy. When we hire for the function, not the person, we become dull and staid. Could this person go to another department if needed? Could they expand two levels in a few years?
First Ten qualities and experience level may have a weak inverse association. People with 20+ years of experience who had worked at larger organizations wanted to try something new and had a growth mentality. College graduates may want to be told what to do and how to accomplish it so they can stay in their lane and do what their management asks.
Does the First Ten archetype sound right for your org? Cool, let’s go hiring. How will you know when you’ve found one?
They exhibit adaptive excellence, excelling at a variety of unrelated tasks. It could be hobbies or professional talents. This suggests that they will succeed in the next several endeavors they pursue.
Successful risk-taking is doing something that wasn't certain to succeed, sometimes more than once, and making it do so. It's an attitude.
Rapid Rise: They regularly change roles and get promoted. However, they don't leave companies when the going gets tough. Look for promotions at every stop and at least one position with three or more years of experience.
You can ask them:
Tell me about a time when you started from scratch or achieved success. What occurred en route? You might request a variety of tales from various occupations or even aspects of life. They ought to be energized by this.
What new skills have you just acquired? It is not required to be work-related. They must be able to describe it and unintentionally become enthusiastic about it.
Tell me about a moment when you encountered a challenge and had to alter your strategy. The core of a startup is reinventing itself when faced with obstacles.
Tell me about a moment when you eliminated yourself from a position at work. They've demonstrated they can permanently solve one issue and develop into a new one, as stated above.
Why do you want to leave X position or Y duty? These people ought to be moving forward, not backward, all the time. Instead, they will discuss what they are looking forward to visiting your location.
Any questions? Due to their inherent curiosity and desire to learn new things, they should practically never run out of questions. You can really tell if they are sufficiently curious at this point.
People who see their success as being the same as the success of the organization are the best-case team members, in any market. They’ll grow and change with the company, and always try to prioritize what matters. You’ll find yourself more energized by your work because you’re surrounded by others who are as well. Happy teambuilding!
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Daniel Vassallo
3 years ago
Why I quit a $500K job at Amazon to work for myself
I quit my 8-year Amazon job last week. I wasn't motivated to do another year despite promotions, pay, recognition, and praise.
In AWS, I built developer tools. I could have worked in that field forever.
I became an Amazon developer. Within 3.5 years, I was promoted twice to senior engineer and would have been promoted to principal engineer if I stayed. The company said I had great potential.
Over time, I became a reputed expert and leader within the company. I was respected.
First year I made $75K, last year $511K. If I stayed another two years, I could have made $1M.
Despite Amazon's reputation, my work–life balance was good. I no longer needed to prove myself and could do everything in 40 hours a week. My team worked from home once a week, and I rarely opened my laptop nights or weekends.
My coworkers were great. I had three generous, empathetic managers. I’m very grateful to everyone I worked with.
Everything was going well and getting better. My motivation to go to work each morning was declining despite my career and income growth.
Another promotion, pay raise, or big project wouldn't have boosted my motivation. Motivation was also waning. It was my freedom.
Demotivation
My motivation was high in the beginning. I worked with someone on an internal tool with little scrutiny. I had more freedom to choose how and what to work on than in recent years. Me and another person improved it, talked to users, released updates, and tested it. Whatever we wanted, we did. We did our best and were mostly self-directed.
In recent years, things have changed. My department's most important project had many stakeholders and complex goals. What I could do depended on my ability to convince others it was the best way to achieve our goals.
Amazon was always someone else's terms. The terms started out simple (keep fixing it), but became more complex over time (maximize all goals; satisfy all stakeholders). Working in a large organization imposed restrictions on how to do the work, what to do, what goals to set, and what business to pursue. This situation forced me to do things I didn't want to do.
Finding New Motivation
What would I do forever? Not something I did until I reached a milestone (an exit), but something I'd do until I'm 80. What could I do for the next 45 years that would make me excited to wake up and pay my bills? Is that too unambitious? Nope. Because I'm motivated by two things.
One is an external carrot or stick. I'm not forced to file my taxes every April, but I do because I don't want to go to jail. Or I may not like something but do it anyway because I need to pay the bills or want a nice car. Extrinsic motivation
One is internal. When there's no carrot or stick, this motivates me. This fuels hobbies. I wanted a job that was intrinsically motivated.
Is this too low-key? Extrinsic motivation isn't sustainable. Getting promoted felt good for a week, then it was over. When I hit $100K, I admired my W2 for a few days, but then it wore off. Same thing happened at $200K, $300K, $400K, and $500K. Earning $1M or $10M wouldn't change anything. I feel the same about every material reward or possession. Getting them feels good at first, but quickly fades.
Things I've done since I was a kid, when no one forced me to, don't wear off. Coding, selling my creations, charting my own path, and being honest. Why not always use my strengths and motivation? I'm lucky to live in a time when I can work independently in my field without large investments. So that’s what I’m doing.
What’s Next?
I'm going all-in on independence and will make a living from scratch. I won't do only what I like, but on my terms. My goal is to cover my family's expenses before my savings run out while doing something I enjoy. What more could I want from my work?
You can now follow me on Twitter as I continue to document my journey.
This post is a summary. Read full article here

Eitan Levy
3 years ago
The Top 8 Growth Hacking Techniques for Startups
The Top 8 Growth Hacking Techniques for Startups

These startups, and how they used growth-hack marketing to flourish, are some of the more ethical ones, while others are less so.
Before the 1970 World Cup began, Puma paid footballer Pele $120,000 to tie his shoes. The cameras naturally focused on Pele and his Pumas, causing people to realize that Puma was the top football brand in the world.
Early workers of Uber canceled over 5,000 taxi orders made on competing applications in an effort to financially hurt any of their rivals.
PayPal developed a bot that advertised cheap goods on eBay, purchased them, and paid for them with PayPal, fooling eBay into believing that customers preferred this payment option. Naturally, Paypal became eBay's primary method of payment.
Anyone renting a space on Craigslist had their emails collected by AirBnB, who then urged them to use their service instead. A one-click interface was also created to list immediately on AirBnB from Craigslist.
To entice potential single people looking for love, Tinder developed hundreds of bogus accounts of attractive people. Additionally, for at least a year, users were "accidentally" linked.
Reddit initially created a huge number of phony accounts and forced them all to communicate with one another. It eventually attracted actual users—the real meaning of "fake it 'til you make it"! Additionally, this gave Reddit control over the tone of voice they wanted for their site, which is still present today.
To disrupt the conferences of their main rival, Salesforce recruited fictitious protestors. The founder then took over all of the event's taxis and gave a 45-minute pitch for his startup. No place to hide!
When a wholesaler required a minimum purchase of 10, Amazon CEO Jeff Bezos wanted a way to purchase only one book from them. A wholesaler would deliver the one book he ordered along with an apology for the other eight books after he discovered a loophole and bought the one book before ordering nine books about lichens. On Amazon, he increased this across all of the users.
Original post available here

Ben Carlson
3 years ago
Bear market duration and how to invest during one
Bear markets don't last forever, but that's hard to remember. Jamie Cullen's illustration
A bear market is a 20% decline from peak to trough in stock prices.
The S&P 500 was down 24% from its January highs at its low point this year. Bear market.
The U.S. stock market has had 13 bear markets since WWII (including the current one). Previous 12 bear markets averaged –32.7% losses. From peak to trough, the stock market averaged 12 months. The average time from bottom to peak was 21 months.
In the past seven decades, a bear market roundtrip to breakeven has averaged less than three years.
Long-term averages can vary widely, as with all historical market data. Investors can learn from past market crashes.
Historical bear markets offer lessons.
Bear market duration
A bear market can cost investors money and time. Most of the pain comes from stock market declines, but bear markets can be long.
Here are the longest U.S. stock bear markets since World war 2:
Stock market crashes can make it difficult to break even. After the 2008 financial crisis, the stock market took 4.5 years to recover. After the dotcom bubble burst, it took seven years to break even.
The longer you're underwater in the market, the more suffering you'll experience, according to research. Suffering can lead to selling at the wrong time.
Bear markets require patience because stocks can take a long time to recover.
Stock crash recovery
Bear markets can end quickly. The Corona Crash in early 2020 is an example.
The S&P 500 fell 34% in 23 trading sessions, the fastest bear market from a high in 90 years. The entire crash lasted one month. Stocks broke even six months after bottoming. Stocks rose 100% from those lows in 15 months.
Seven bear markets have lasted two years or less since 1945.
The 2020 recovery was an outlier, but four other bear markets have made investors whole within 18 months.
During a bear market, you don't know if it will end quickly or feel like death by a thousand cuts.
Recessions vs. bear markets
Many people believe the U.S. economy is in or heading for a recession.
I agree. Four-decade high inflation. Since 1945, inflation has exceeded 5% nine times. Each inflationary spike caused a recession. Only slowing economic demand seems to stop price spikes.
This could happen again. Stocks seem to be pricing in a recession.
Recessions almost always cause a bear market, but a bear market doesn't always equal a recession. In 1946, the stock market fell 27% without a recession in sight. Without an economic slowdown, the stock market fell 22% in 1966. Black Monday in 1987 was the most famous stock market crash without a recession. Stocks fell 30% in less than a week. Many believed the stock market signaled a depression. The crash caused no slowdown.
Economic cycles are hard to predict. Even Wall Street makes mistakes.
Bears vs. bulls
Bear markets for U.S. stocks always end. Every stock market crash in U.S. history has been followed by new all-time highs.
How should investors view the recession? Investing risk is subjective.
You don't have as long to wait out a bear market if you're retired or nearing retirement. Diversification and liquidity help investors with limited time or income. Cash and short-term bonds drag down long-term returns but can ensure short-term spending.
Young people with years or decades ahead of them should view this bear market as an opportunity. Stock market crashes are good for net savers in the future. They let you buy cheap stocks with high dividend yields.
You need discipline, patience, and planning to buy stocks when it doesn't feel right.
Bear markets aren't fun because no one likes seeing their portfolio fall. But stock market downturns are a feature, not a bug. If stocks never crashed, they wouldn't offer such great long-term returns.
