More on Leadership

Joe Procopio
3 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.

Alison Randel
3 years ago
Raising the Bar on Your 1:1s
Managers spend much time in 1:1s. Most team members meet with supervisors regularly. 1:1s can help create relationships and tackle tough topics. Few appreciate the 1:1 format's potential. Most of the time, that potential is spent on small talk, surface-level updates, and ranting (Ugh, the marketing team isn’t stepping up the way I want them to).
What if you used that time to have deeper conversations and important insights? What if change was easy?
This post introduces a new 1:1 format to help you dive deeper, faster, and develop genuine relationships without losing impact.
A 1:1 is a chat, you would assume. Why use structure to talk to a coworker? Go! I know how to talk to people. I can write. I've always written. Also, This article was edited by Zoe.
Before you discard something, ask yourself if there's a good reason not to try anything new. Is the 1:1 only a talk, or do you want extra benefits? Try the steps below to discover more.
I. Reflection (5 minutes)
Context-free, broad comments waste time and are useless. Instead, give team members 5 minutes to write these 3 prompts.
What's effective?
What is decent but could be improved?
What is broken or missing?
Why these? They encourage people to be honest about all their experiences. Answering these questions helps people realize something isn't working. These prompts let people consider what's working.
Why take notes? Because you get more in less time. Will you feel awkward sitting quietly while your coworker writes? Probably. Persevere. Multi-task. Take a break from your afternoon meeting marathon. Any awkwardness will pay off.
What happens? After a few minutes of light conversation, create a template like the one given here and have team members fill in their replies. You can pre-share the template (with the caveat that this isn’t meant to take much prep time). Do this with your coworker: Answer the prompts. Everyone can benefit from pondering and obtaining guidance.
This step's output.
Part II: Talk (10-20 minutes)
Most individuals can explain what they see but not what's behind an answer. You don't like a meeting. Why not? Marketing partnership is difficult. What makes working with them difficult? I don't recommend slandering coworkers. Consider how your meetings, decisions, and priorities make work harder. The excellent stuff too. You want to know what's humming so you can reproduce the magic.
First, recognize some facts.
Real power dynamics exist. To encourage individuals to be honest, you must provide a safe environment and extend clear invites. Even then, it may take a few 1:1s for someone to feel secure enough to go there in person. It is part of your responsibility to admit that it is normal.
Curiosity and self-disclosure are crucial. Most leaders have received training to present themselves as the authorities. However, you will both benefit more from the dialogue if you can be open and honest about your personal experience, ask questions out of real curiosity, and acknowledge the pertinent sacrifices you're making as a leader.
Honesty without bias is difficult and important. Due to concern for the feelings of others, people frequently hold back. Or if they do point anything out, they do so in a critical manner. The key is to be open and unapologetic about what you observe while not presuming that your viewpoint is correct and that of the other person is incorrect.
Let's go into some prompts (based on genuine conversations):
“What do you notice across your answers?”
“What about the way you/we/they do X, Y, or Z is working well?”
“ Will you say more about item X in ‘What’s not working?’”
“I’m surprised there isn’t anything about Z. Why is that?”
“All of us tend to play some role in maintaining certain patterns. How might you/we be playing a role in this pattern persisting?”
“How might the way we meet, make decisions, or collaborate play a role in what’s currently happening?”
Consider the preceding example. What about the Monday meeting isn't working? Why? or What about the way we work with marketing makes collaboration harder? Remember to share your honest observations!
Third section: observe patterns (10-15 minutes)
Leaders desire to empower their people but don't know how. We also have many preconceptions about what empowerment means to us and how it works. The next phase in this 1:1 format will assist you and your team member comprehend team power and empowerment. This understanding can help you support and shift your team member's behavior, especially where you disagree.
How to? After discussing the stated responses, ask each team member what they can control, influence, and not control. Mark their replies. You can do the same, adding colors where you disagree.
This step's output.
Next, consider the color constellation. Discuss these questions:
Is one color much more prevalent than the other? Why, if so?
Are the colors for the "what's working," "what's fine," and "what's not working" categories clearly distinct? Why, if so?
Do you have any disagreements? If yes, specifically where does your viewpoint differ? What activities do you object to? (Remember, there is no right or wrong in this. Give explicit details and ask questions with curiosity.)
Example: Based on the colors, you can ask, Is the marketing meeting's quality beyond your control? Were our marketing partners consulted? Are there any parts of team decisions we can control? We can't control people, but have we explored another decision-making method? How can we collaborate and generate governance-related information to reduce work, even if the requirement for prep can't be eliminated?
Consider the top one or two topics for this conversation. No 1:1 can cover everything, and that's OK. Focus on the present.
Part IV: Determine the next step (5 minutes)
Last, examine what this conversation means for you and your team member. It's easy to think we know the next moves when we don't.
Like what? You and your teammate answer these questions.
What does this signify moving ahead for me? What can I do to change this? Make requests, for instance, and see how people respond before thinking they won't be responsive.
What demands do I have on other people or my partners? What should I do first? E.g. Make a suggestion to marketing that we hold a monthly retrospective so we can address problems and exchange input more frequently. Include it on the meeting's agenda for next Monday.
Close the 1:1 by sharing what you noticed about the chat. Observations? Learn anything?
Yourself, you, and the 1:1
As a leader, you either reinforce or disrupt habits. Try this template if you desire greater ownership, empowerment, or creativity. Consider how you affect surrounding dynamics. How can you expect others to try something new in high-stakes scenarios, like meetings with cross-functional partners or senior stakeholders, if you won't? How can you expect deep thought and relationship if you don't encourage it in 1:1s? What pattern could this new format disrupt or reinforce?
Fight reluctance. First attempts won't be ideal, and that's OK. You'll only learn by trying.
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.
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Caleb Naysmith
3 years ago
Ads Coming to Medium?
Could this happen?
Medium isn't like other social media giants. It wasn't a dot-com startup that became a multi-trillion-dollar social media firm. It launched in 2012 but didn't gain popularity until later. Now, it's one of the largest sites by web traffic, but it's still little compared to most. Most of Medium's traffic is external, but they don't run advertisements, so it's all about memberships.
Medium isn't profitable, but they don't disclose how terrible the problem is. Most of the $163 million they raised has been spent or used for acquisitions. If the money turns off, Medium can't stop paying its writers since the site dies. Writers must be paid, but they can't substantially slash payment without hurting the platform. The existing model needs scale to be viable and has a low ceiling. Facebook and other free social media platforms are struggling to retain users. Here, you must pay to appreciate it, and it's bad for writers AND readers. If I had the same Medium stats on YouTube, I'd make thousands of dollars a month.
Then what? Medium has tried to monetize by offering writers a cut of new members, but that's unsustainable. People-based growth is limited. Imagine recruiting non-Facebook users and getting them to pay to join. Some may, but I'd rather write.
Alternatives:
Donation buttons
Tiered subscriptions ($5, $10, $25, etc.)
Expanding content
and these may be short-term fixes, but they're not as profitable as allowing ads. Advertisements can pay several dollars per click and cents every view. If you get 40,000 views a month like me, that's several thousand instead of a few hundred. Also, Medium would have enough money to split ad revenue with writers, who would make more. I'm among the top 6% of Medium writers. Only 6% of Medium writers make more than $100, and I made $500 with 35,000 views last month. Compared to YouTube, the top 1% of Medium authors make a lot. Mr. Beast and PewDiePie make MILLIONS a month, yet top Medium writers make tens of thousands. Sure, paying 3 or 4 people a few grand, or perhaps tens of thousands, will keep them around. What if great authors leveraged their following to go huge on YouTube and abandoned Medium? If people use Medium to get successful on other platforms, Medium will be continuously cycling through authors and paying them to stay.
Ads might make writing on Medium more profitable than making videos on YouTube because they could preserve the present freemium model and pay users based on internal views. The $5 might be ad-free.
Consider: Would you accept Medium ads? A $5 ad-free version + pay-as-you-go, etc. What are your thoughts on this?
Original post available here

Mickey Mellen
2 years ago
Shifting from Obsidian to Tana?
I relocated my notes database from Roam Research to Obsidian earlier this year expecting to stay there for a long. Obsidian is a terrific tool, and I explained my move in that post.
Moving everything to Tana faster than intended. Tana? Why?
Tana is just another note-taking app, but it does it differently. Three note-taking apps existed before Tana:
simple note-taking programs like Apple Notes and Google Keep.
Roam Research and Obsidian are two graph-style applications that assisted connect your notes.
You can create effective tables and charts with data-focused tools like Notion and Airtable.
Tana is the first great software I've encountered that combines graph and data notes. Google Keep will certainly remain my rapid notes app of preference. This Shu Omi video gives a good overview:
Tana handles everything I did in Obsidian with books, people, and blog entries, plus more. I can find book quotes, log my workouts, and connect my thoughts more easily. It should make writing blog entries notes easier, so we'll see.
Tana is now invite-only, but if you're interested, visit their site and sign up. As Shu noted in the video above, the product hasn't been published yet but seems quite polished.
Whether I stay with Tana or not, I'm excited to see where these apps are going and how they can benefit us all.

Henrique Centieiro
3 years ago
DAO 101: Everything you need to know
Maybe you'll work for a DAO next! Over $1 Billion in NFTs in the Flamingo DAO Another DAO tried to buy the NFL team Denver Broncos. The UkraineDAO raised over $7 Million for Ukraine. The PleasrDAO paid $4m for a Wu-Tang Clan album that belonged to the “pharma bro.”
DAOs move billions and employ thousands. So learn what a DAO is, how it works, and how to create one!
DAO? So, what? Why is it better?
A Decentralized Autonomous Organization (DAO). Some people like to also refer to it as Digital Autonomous Organization, but I prefer the former.
They are virtual organizations. In the real world, you have organizations or companies right? These firms have shareholders and a board. Usually, anyone with authority makes decisions. It could be the CEO, the Board, or the HIPPO. If you own stock in that company, you may also be able to influence decisions. It's now possible to do something similar but much better and more equitable in the cryptocurrency world.
This article informs you:
DAOs- What are the most common DAOs, their advantages and disadvantages over traditional companies? What are they if any?
Is a DAO legally recognized?
How secure is a DAO?
I’m ready whenever you are!
A DAO is a type of company that is operated by smart contracts on the blockchain. Smart contracts are computer code that self-executes our commands. Those contracts can be any. Most second-generation blockchains support smart contracts. Examples are Ethereum, Solana, Polygon, Binance Smart Chain, EOS, etc. I think I've gone off topic. Back on track. Now let's go!
Unlike traditional corporations, DAOs are governed by smart contracts. Unlike traditional company governance, DAO governance is fully transparent and auditable. That's one of the things that sets it apart. The clarity!
A DAO, like a traditional company, has one major difference. In other words, it is decentralized. DAOs are more ‘democratic' than traditional companies because anyone can vote on decisions. Anyone! In a DAO, we (you and I) make the decisions, not the top-shots. We are the CEO and investors. A DAO gives its community members power. We get to decide.
As long as you are a stakeholder, i.e. own a portion of the DAO tokens, you can participate in the DAO. Tokens are open to all. It's just a matter of exchanging it. Ownership of DAO tokens entitles you to exclusive benefits such as governance, voting, and so on. You can vote for a move, a plan, or the DAO's next investment. You can even pitch for funding. Any ‘big' decision in a DAO requires a vote from all stakeholders. In this case, ‘token-holders'! In other words, they function like stock.
What are the 5 DAO types?
Different DAOs exist. We will categorize decentralized autonomous organizations based on their mode of operation, structure, and even technology. Here are a few. You've probably heard of them:
1. DeFi DAO
These DAOs offer DeFi (decentralized financial) services via smart contract protocols. They use tokens to vote protocol and financial changes. Uniswap, Aave, Maker DAO, and Olympus DAO are some examples. Most DAOs manage billions.
Maker DAO was one of the first protocols ever created. It is a decentralized organization on the Ethereum blockchain that allows cryptocurrency lending and borrowing without a middleman.
Maker DAO issues DAI, a stable coin. DAI is a top-rated USD-pegged stable coin.
Maker DAO has an MKR token. These token holders are in charge of adjusting the Dai stable coin policy. Simply put, MKR tokens represent DAO “shares”.
2. Investment DAO
Investors pool their funds and make investment decisions. Investing in new businesses or art is one example. Investment DAOs help DeFi operations pool capital. The Meta Cartel DAO is a community of people who want to invest in new projects built on the Ethereum blockchain. Instead of investing one by one, they want to pool their resources and share ideas on how to make better financial decisions.
Other investment DAOs include the LAO and Friends with Benefits.
3. DAO Grant/Launchpad
In a grant DAO, community members contribute funds to a grant pool and vote on how to allocate and distribute them. These DAOs fund new DeFi projects. Those in need only need to apply. The Moloch DAO is a great Grant DAO. The tokens are used to allocate capital. Also see Gitcoin and Seedify.
4. DAO Collector
I debated whether to put it under ‘Investment DAO' or leave it alone. It's a subset of investment DAOs. This group buys non-fungible tokens, artwork, and collectibles. The market for NFTs has recently exploded, and it's time to investigate. The Pleasr DAO is a collector DAO. One copy of Wu-Tang Clan's "Once Upon a Time in Shaolin" cost the Pleasr DAO $4 million. Pleasr DAO is known for buying Doge meme NFT. Collector DAOs include the Flamingo, Mutant Cats DAO, and Constitution DAOs. Don't underestimate their websites' "childish" style. They have millions.
5. Social DAO
These are social networking and interaction platforms. For example, Decentraland DAO and Friends With Benefits DAO.
What are the DAO Benefits?
Here are some of the benefits of a decentralized autonomous organization:
- They are trustless. You don’t need to trust a CEO or management team
- It can’t be shut down unless a majority of the token holders agree. The government can't shut - It down because it isn't centralized.
- It's fully democratic
- It is open-source and fully transparent.
What about DAO drawbacks?
We've been saying DAOs are the bomb? But are they really the shit? What could go wrong with DAO?
DAOs may contain bugs. If they are hacked, the results can be catastrophic.
No trade secrets exist. Because the smart contract is transparent and coded on the blockchain, it can be copied. It may be used by another organization without credit. Maybe DAOs should use Secret, Oasis, or Horizen blockchain networks.
Are DAOs legally recognized??
In most counties, DAO regulation is inexistent. It's unclear. Most DAOs don’t have a legal personality. The Howey Test and the Securities Act of 1933 determine whether DAO tokens are securities. Although most countries follow the US, this is only considered for the US. Wyoming became the first state to recognize DAOs as legal entities in July 2021 after passing a DAO bill. DAOs registered in Wyoming are thus legally recognized as business entities in the US and thus receive the same legal protections as a Limited Liability Company.
In terms of cyber-security, how secure is a DAO?
Blockchains are secure. However, smart contracts may have security flaws or bugs. This can be avoided by third-party smart contract reviews, testing, and auditing
Finally, Decentralized Autonomous Organizations are timeless. Let us examine the current situation: Ukraine's invasion. A DAO was formed to help Ukrainian troops fighting the Russians. It was named Ukraine DAO. Pleasr DAO, NFT studio Trippy Labs, and Russian art collective Pussy Riot organized this fundraiser. Coindesk reports that over $3 million has been raised in Ethereum-based tokens. AidForUkraine, a DAO aimed at supporting Ukraine's defense efforts, has launched. Accepting Solana token donations. They are fully transparent, uncensorable, and can’t be shut down or sanctioned.
DAOs are undeniably the future of blockchain. Everyone is paying attention. Personally, I believe traditional companies will soon have to choose between adapting or being left behind.
Long version of this post: https://medium.datadriveninvestor.com/dao-101-all-you-need-to-know-about-daos-275060016663