The 90-Day Onboarding Plan: Setting New Employees Up for Success
Onboarding is one of the most overlooked yet critical processes for ensuring a new employee’s success.
At Proletariat, as we scaled rapidly, we knew that hiring fast also meant evaluating and adjusting quickly. That’s why we implemented structured 90-day onboarding plans, delivered on day one (or even before) alongside our Cultural Communication Guide. This ensured every new hire had a clear roadmap for success.
Check out this template for a 30-60-90 day onboarding plan.
The Goal of a 90-Day Onboarding Plan
By the end of the onboarding period, one of three things should be clear:
The employee is successful in their role and fully ramped up
The role has been adjusted to better fit their skills or the team’s needs
The employee moves on if the fit isn’t right
An onboarding plan removes ambiguity, making these outcomes clear and preventing drift where an underperforming hire lingers without direction or resolution.
Key Objectives of a 90-Day Onboarding Plan
1. Craft Personalized Goals That Align with the Team Strategy
Every role is unique, and job descriptions often don’t capture the full nuance of what success looks like. A great onboarding plan ensures:
The new hire’s goals fit within the team’s broader strategy
The plan adapts to the individual’s strengths while addressing growth areas
The employee understands how they create value early on
2. Prioritize Tasks to Build Early Wins
New employees often feel like they’re “drinking from a firehose” in their first few months. Instead of overwhelming them, sequence tasks in a way that builds momentum:
Start with achievable wins: Give them clear, valuable contributions early on
Gradually increase complexity: Move from simple tasks to strategic ones
Provide structured learning: Direct them to the right resources and people
The goal is to avoid burnout and build confidence through early impact.
3. Set Clear Expectations for Progress
Success should never be vague. By clearly defining what progress should look like at key milestones, both the manager and the new hire can track growth and course-correct early if needed. Here is a general outline for the various onboarding phases:
First 30 days: Learning - focus on absorbing information and initial tasks
Days 31–60: Integration - deeper collaboration and ownership of responsibilities
Days 61–90: Autonomy - fully contributing and delivering measurable results
How to Use an Onboarding Plan Effectively
1. Build the Plan Together
The onboarding plan should be a collaborative effort between:
The new hire (so they understand expectations and contribute to goal-setting)
The hiring manager (to ensure alignment with team objectives)
Other stakeholders (who will work closely with the new hire)
2. Treat It as a Living Document
A static onboarding plan is too formulaic to be useful. The plan should evolve based on feedback and real-world performance. Follow these steps:
Regularly review and adjust the plan
Use check-in meetings at 30, 60, and 90 days to assess progress
Be flexible! If the plan needs adjusting, don’t force a rigid structure
3. Involve the Broader Team
Successful onboarding is not just about ramping up a new hire—it’s about integrating them into the team and broader company culture. Provide cross-team introductions and broadcast early wins and progress to give the new employee positive visibility.
Final Thoughts
The specific structure of an onboarding plan matters less than having one at all. Without a plan, new hires drift, progress is unclear, and retention suffers. The best onboarding experiences give new employees clarity on their role and expectations, provide a roadmap to early wins, and ultimately lead to success within 90 days.
What Do Investors Need to Believe?
A strong pitch isn’t about eliminating all risk, it’s about getting investors to irrationally believe your contrarian idea.
Every early-stage investment is, at its core, irrational. Investors know most startups fail. If funding were purely a rational decision, no one would invest at all. So trying to de-risk every part of your pitch to make it seem perfectly rational is a losing game. The real challenge is choosing the right irrational belief and making investors buy into it.
Define Your Irrational Belief
The best startups succeed not because they eliminate risk, but because they bet on something contrarian that turns out to be right.
Ask yourself:
Are you building an unorthodox product? (a new category that no one believes in yet?)
Are you targeting a counterintuitive audience? (a niche that traditional wisdom says won’t work?)
Are you building the company differently? (breaking conventional startup rules in your approach to hiring, go-to-market, or funding?)
Are you cultivating a non-traditional team? (a team that lacks direct industry experience but brings something else?)
If you can’t identify at least one contrarian angle, you may not be differentiated enough to stand out in a crowded, mature market.
Own the Doubts and Overcome Them
Most founders try to avoid or downplay the skepticism around their boldest claim. That’s a mistake.
If investors are going to doubt something anyway, address it head-on. Show them you already know the challenge and have a plan.
Instead of hoping no one questions your lack of industry experience, explain why it’s an advantage.
Instead of ignoring concerns about a new market, prove why the timing is right.
Instead of brushing off skepticism about a radical approach, demonstrate how it is the only path forward.
De-risk Everything Else
Being contrarian on every axis is a recipe for failure. Even the boldest investors need to see a foundation of credibility beneath the big bet. Many of my earlier post on pitching focus specifically on building credibility, but here are a few ideas to consider:
If your market bet is risky, your team should be experienced.
If your business model is unconventional, your go-to-market strategy should be solid.
If your product is groundbreaking, your execution should be airtight.
If your budget is very low/high, your development plan should be unassailable.
Make it clear that while you’re taking one big bet, you’re removing risk everywhere else. By acknowledging the risky part you are able to credibly say “we know this is risky, which is why we have reinforced these other areas.” The contrast makes it easier for investors to say yes.
Final Thoughts
Don’t shy away from simply wrapping up a pitch by confidently saying “in order to invest, you need to believe X.” It is the contrast of the contrarian idea backed up by all the other de-risked strengths that stack the deck in your favor.
When Pitching, Be Like Gandalf
Pitching investors can feel like an epic journey—full of challenges, uncertainty, and the need to inspire belief in something bigger than yourself. So why not take a page from one of the greatest mentors of all time?
As we enter a heavy season of pitching, here are some lessons I’ve learned—through both experience and a little wisdom from The Lord of the Rings.
1. Be Confident in Your Plan
"A wizard is never late. Nor is he early. He arrives precisely when he means to."
Investors don’t always know the right answer, but they do want to believe that you do. Confidence isn’t about arrogance, it’s about conviction. When Gandalf reassures Frodo that wizards are never late, he’s not just making an excuse. He’s projecting certainty, even in the face of doubt.
When pitching, you must approach every question with that same level of confidence. Investors are skeptics by nature, and they can sense hesitation. If your plan feels weak, under-researched, or uncertain, they will pick it apart. But remember: you are likely more of an expert in your target market than they are. Own that expertise.
2. Give an Air of Inevitability
"Things are in motion that cannot be undone."
Investors want to invest in unstoppable founders. They know that backing a startup means committing for years. They need to believe that, whether they invest or not, this company is going to succeed—and they’d be foolish to miss out.
A great pitch doesn’t just highlight potential; it makes investors feel like they are witnessing momentum. They should walk away thinking:
"This is happening. The only question is whether I get on board now or regret it later."
Be unstoppable.
3. Listen and Be Coachable
"Faramir, tell me everything."
While investors may not be experts in your exact business, they see everything. They spot patterns across multiple industries, companies, and market cycles. Many of them got into investing because they love working with founders and want to help.
But here’s the key: being coachable does not mean being a pushover.
Great founders listen actively and ask smart questions. They extract value from investors’ insights but don’t blindly follow every piece of advice. The best investors want you to challenge ideas, push back when needed, and show your own reasoning.
4. Investors Invest in Lines, Not Dots
"I am Gandalf the White."
Your pitch is not a single, isolated moment—it’s part of an evolving narrative. Investors rarely write checks after just one meeting. Instead, they track founders over weeks, months, or even years, looking for signs of progress.
Just as Gandalf transforms over time, your company’s story should evolve with each investor touchpoint.
Final Thoughts
A pitch isn’t just a transaction; it’s the beginning of a long-term relationship. Investors invest in people and stories, not just slides and metrics.
Too many founders get distracted by making the “perfect” deck when what truly matters is building belief in yourself, your vision, and your team.
So next time you pitch, channel your inner Gandalf.
Breadcrumb Your Pitch
When creating a pitch, you should think of it as building a breadcrumb trail that leads investors to your vision for the future.
Investors need to believe in an optimistic vision, but great investors are also inherently skeptical. This skepticism becomes even more pronounced when you’re pitching something bold, new, or different—which is critical to stand out in today’s competitive market. To convince them to fund your vision, you must systematically guide them through your logic and make them believe in your version of the future.
What Is a Breadcrumb Trail?
A breadcrumb trail is a storytelling structure where each part of your pitch builds directly on the previous one, leading investors step by step through your reasoning. The goal is to create a narrative so compelling and well-supported that by the time you reach your conclusion, the investor feels there’s no other logical outcome than to invest.
Start with the big picture—why this market matters—and gradually narrow your focus to why your team is uniquely suited to solve the problem. This structure works well with frameworks like OPSANA, which outlines Opportunity → Problem → Solution → Advantage → Next Step → Ask.
Here’s how you might think about it:
If you’re going to start a new company, it should be in X Market.
If you’re going to build in X Market, it should create Y Product.
If you’re going to create Y Product, it should include Z Features.
If you’re going to launch Y Product with Z Features, it should be built by this team.
Each step builds on the previous one, reducing skepticism by creating a clear, logical progression.
A Breadcrumb Trail Example
Let’s use an example of a fictional game company looking to build roleplaying games about dancing on Roblox with their own AI-powered tech stack.
Step 1: If you’re going to start a game company, build on Roblox.
Show the opportunity. Highlight Roblox’s growth, the increasing developer earnings, and why it’s an ideal platform for games right now. Use data to make the opportunity undeniable.
Step 2: If you’re going to build on Roblox, make a roleplaying game.
Roleplaying games have proven success on Roblox. Highlight examples of similar games and their popularity to validate the opportunity.
Step 3: If you’re making a Roblox roleplaying game, it should focus on dancing.
Here’s where you sell the uniqueness of your concept. Share insights on why dancing resonates with Gen Alpha (e.g., stats on how dance trends dominate platforms like TikTok). Highlight the market opportunity, the passion of your team, or the magic of the current experience.
Step 4: If you’re making a Roblox dancing roleplaying game, it should use AI.
Use data to demonstrate why AI will transform this space. For example, refer to stats from the GDC State of the Game Industry survey showing the increasing use of generative AI tools by developers.
Step 5: If you’re using AI, build your own tech stack.
Explain why building your own tech stack makes sense. Whether it’s about cost efficiency, control, enterprise value, or competitive differentiation, make a strong case for why this choice adds value. Highlight any progress your team has made so far.
Step 6: If you’re building this product, it needs this team.
Showcase your team’s experience and expertise. Why are you uniquely qualified to make this vision a reality? Talk about your founder-market fit, previous successes, and shared passion for the product.
Step 7: If you’re going to build this company, you need the right partner.
End the trail by explaining why the specific investor you’re pitching is the perfect partner. Reference their past investments, interests, or thought leadership. Make it clear that you’ve done your homework and that this partnership is intentional.
Why Use a Breadcrumb Trail?
Using a breadcrumb trail structure ensures your pitch flows logically, leaving no gaps for investors to fill in on their own. It also helps you identify weak points in your story—areas where the argument isn’t clear or where evidence is lacking—so you can address them before questions arise.
Even if you don’t use one slide per step, this structure forces you to think through everything an investor needs to believe in order to say “yes.”
Final Thoughts
A breadcrumb trail is ultimately about storytelling. It helps you craft a compelling, step-by-step narrative that brings investors along on your journey and builds their confidence in your vision. By systematically leading them through the opportunity, your solution, and your team’s fit, you’ll create a pitch that’s harder to say “no” to.
Remember, investors are skeptical by nature. Your job is to give them enough evidence at every step to overcome that skepticism. If you can successfully guide them to your vision of the future, you’ll be well on your way to building a successful partnership.
OPSANA Pitch Deck Structure
I have built and seen many pitch decks, and the OPSANA framework is one of my favorites.
While there is no universal formula for a perfect pitch deck (check out the Y Combinator Seed Deck Template), I’ve found the OPSANA framework to be an effective structure. It ensures your story flows logically, builds excitement, and answers the key questions investors will have.
The OPSANA Framework
Opportunity → Problem → Solution → Advantage → Next Step → Ask
Each element serves a specific purpose and can span multiple slides if necessary. Here’s how to break it down:
1. Opportunity: Paint the Big Picture
What to Cover: How big is this market? Why should everyone care about it? Why is now the right time to go after it?
Purpose: This section sets the stage and gets investors excited (or teach them) about the potential upside. Use real data to show that the opportunity is massive and worth pursuing.
2. Problem: Define the Challenge
What to Cover: Why has no one capitalized on this opportunity yet? What are the obstacles or pain points?
Purpose: Establish your domain expertise by demonstrating a deep understanding of the market’s challenges. This builds credibility and positions you as the team to solve the problem.
3. Solution: Present Your Vision
What to Cover: How will your product, game or service solve the problem and capture the opportunity? What makes your solution unique?
Purpose: Showcase your concept, demonstrate its potential, and prove how it addresses the identified problem. Be clever and build directly off the opportunity and problem sections. Explain how you will win.
4. Advantage: Highlight Your Edge
What to Cover: What gives your team the ability to execute this vision better than anyone else? This could include proprietary tech, early traction, or a standout team.
Purpose: Build confidence that your company can deliver on its promise and outperform competitors. Explain why you will win.
5. Next Step: Show the Path Forward
What to Cover: What’s the next major milestone, and how will achieving it significantly increase the company’s value? Provide a clear and credible plan to get there.
Purpose: Explain what the investor is buying—a bet on your ability to hit that next inflection point.
6. Ask: Make Your Request Clear
What to Cover: What resources do you need to achieve the next step? Why is this specific partner the right fit to help you get there?
Purpose: Close the loop by making a clear and compelling request. Personalize the ask to the specific audience and convince them they are the right partner to take the company to the next level.
Final Thoughts
There’s no silver bullet for creating the perfect pitch deck, but a strong framework ensures you cover all the key areas that matter to investors. OPSANA helps guide the narrative, starting with the big picture and ending with a focused ask. Each section builds on the last, creating a logical and persuasive story about your company’s potential.
What makes a great demo?
A great demo is critical to raising money or finding a publishing partner but demos are rarely shared publicly.
Below are the demos we created to pitch Spellbreak in 2018.
A successful demo should cover three important topics for potential partners:
1. Quality
A demo must demonstrate that your team can deliver a polished experience. It doesn’t need to be bug-free, but it should run smoothly and reflect the quality bar you aim to hit for the full game. If bugs are unavoidable, consider presenting it as a guided demo where someone from your team controls the experience.
Questions the demo should answer about quality:
Does this team know what it takes to make a high-quality game?
Can this team deliver a high-quality experience?
Do they have high standards for their work?
Are they prioritizing the right things?
2. Innovation
The strongest demos highlight what makes your game unique. While a pitch deck can describe your game’s innovative features, letting partners experience those ideas in action is far more powerful.
Example: Spellbreak
In Spellbreak, our innovation was action spellcasting combat, where players could mix and match elemental spells for unique effects. To highlight this, we created a 5v5 team deathmatch demo instead of a battle royale mode. Battle royales often have downtime between fights, so we chose a faster-paced format to better showcase our core gameplay innovations.
Questions the demo should answer about innovation:
How creative is this team?
Do they have ideas that stand out in the market?
Can they “find the fun” in their concept?
Do they have a culture of iteration, testing, and feedback?
3. Execution
A demo is also a reflection of your team’s production discipline. Delivering a polished, innovative prototype within reasonable constraints shows potential partners that your team can manage risks, iterate effectively, and scale to deliver a full game.
Example: Spellbreak
We built a greybox demo in about three months after a year of iterating on combat mechanics. The prototype evolved significantly—starting as a melee-focused game and pivoting to ranged combat based on playtesting feedback.
For art, we created a visually striking diorama of the game world in just 10 weeks, following a major pivot in style. This demonstrated our team’s ability to adapt quickly while maintaining high production quality.
Questions the demo should answer about execution:
Can this team meet deadlines?
Are their production and development processes disciplined?
How much effort have they put into this?
Final Thoughts
There’s no one-size-fits-all template for building a playable prototype. Each project has unique needs and strengths, and your job is to present them in the best light. By focusing on quality, innovation, and execution, and tailoring your approach to the audience, you can create a demo that builds confidence, reduces risk, and paves the way for a successful partnership.
How to Run an Effective Pitch Process
You should run a disciplined pitch process.
An effective pitch process is all about preparation, communication, and execution. There are a few key parts to the process:
Get a fast “no” - use the Teaser phase to filter down the set of partners to ones that will actually do the deal and then focus on getting several of those partners to a term sheet
Keep partners at the same stage - use industry events as ways to hit many partners in a short window and utilize the process structure to move potential partners along together
Gain leverage and apply pressure - use partner competition and the process structure to get slow movers to make decisions and commit within your preferred timeline
Here is a link to the timeline I used when pitching at Proletariat.
Pitch Process Steps
1. Target Planning
Start by creating a list of potential partners (investors/publishers/strategics/etc). This list should prioritize partners based on fit, identify the right contacts, and determine whether a warm introduction is possible.
2. Introduction
The goal here is to meet with the right person to gauge their interest and determine if your project or company is a fit before moving forward. If you are meeting with a partner for the first time, do the outreach several weeks before you want to send out the teaser materials because it can take time to get introduced.
Make it clear that no bridges will be burned if what you are pitching is not a good fit!
3. Teaser
At this phase you want to both further filter out partners that are likely to pass and gather information to tailor your pitch to each specific partner. That means sharing enough information that a partner can gauge if it is worth hearing the full pitch. This includes details like capital needs, timeline, high level product details and more. Be sure to ask questions at this phase, specifically how the partner sees the project or company aligned with their interests or goals.
4. Pitch/Demo
This is the main event and requires careful preparation. Customize your approach for each partner to align with the information you have gained in the previous steps. I will do several additional posts on making a great pitch deck and a compelling playable.
5. Playtest/Diligence
This phase can often be unpredictable and vary widely between partners. It is important to be responsive and maintain momentum. If one partner starts to move forward towards a term sheet, use that as a signal to push the others towards a decision.
7. Term Sheet Negotiation
Getting that first term sheet may feel like the finish line, but there is much more to go. Follow these steps:
Get a signable deal: Once you receive a term sheet, negotiate to ensure it meets your minimum acceptable terms.
Notify others: Inform other interested parties without disclosing confidential details, prompting them to make a decision.
Negotiate: Once you have a deal you’re happy with, use it as leverage to improve offers from other partners. Communicate clearly and move quickly to avoid hurting relationships.
I will write a future post about managing a competitive process that will go into more details.
8. Long Form/Additional Diligence
This step varies widely by partner. Work quickly and proactively to close the deal, as time kills all deals.
9. Close
Congratulations! Now the real work begins.
Final Thoughts
Preparation is the key to running a pitch process. In the later phases being responsive is critical and having much of the legwork done will make it easier. Stay confident, don’t let early passes drag you down. Approach the process with professionalism and persistence, and you’ll increase your chances of achieving a great outcome.
How to Do Your Annual Self-Review
An annual self-review is one of the most valuable gifts you can give yourself.
Throughout life, we encounter many forms of evaluation—from report cards in school to performance reviews at work. A self-review, however, is different. It’s a chance to reflect inwardly, free from external expectations or judgments. For me, a thoughtful self-review feels like a form of therapy. It helps me practice gratitude for the past year, evaluate my growth, and set a clear direction for the year ahead.
Over the years, I’ve experimented with different tools and processes for self-reviews. Here are some of my favorite resources to guide your journey:
1. The Year Compass
This is my current favorite template for self-reviews. The Year Compass strikes a balance between reflecting on the past year and planning for the next. Its workbook format encourages thoughtful, detailed responses, and I prefer to either print it out or use my reMarkable tablet for writing.
One exercise I love is reviewing my calendar from the past year. It’s like taking a guided tour through the last year, revisiting moments I might have forgotten. While this can be time-consuming, I find it immensely rewarding. I recommend spreading The Year Compass process over several sessions in the final weeks of the year. Taking breaks—especially when transitioning from reflection to planning—is helpful to keep a clear head and not feel rushed.
2. The Personal Annual Review – Sahil Bloom
This is a simple, streamlined approach featuring just seven questions, all focused on the past year. While it doesn’t help with planning for the future, it excels in deep reflection. One question that stood out to me was: “What did I not do this year because of fear?” It challenged me to confront areas where I held myself back and think about how I can overcome those barriers moving forward.
3. Downshift’s Annual Review – Steven Schlafman
New for 2024, this template takes a different approach. Unlike other reviews that emphasize goal-setting and optimization, Downshift focuses on reconnecting with yourself. Its description says it best:
"It’s not about adding more to your plate or finding new ways to optimize yourself. Instead, it’s an invitation to pause, reconnect with who you are beneath the achievements, and discover what emerges when you lead from a place of wholeness rather than constant striving."
While I haven’t tried this format yet, I’m excited to give it a shot this year.
Final Thoughts
The specific format you choose for your annual self-review isn’t as important as committing to the process itself. Reflecting on your journey takes time and effort—especially during the busy end-of-year period—but it’s an investment in yourself that is well worth it.
Here’s to a year of growth and gratitude.
Be Present This Holiday
Don’t miss out on another holiday with friends and family.
We all know the holidays are stressful. I know from personal experience how hard it is to be present during the holidays, especially when the specter of work stress haunts you like the ghost of Christmas future. There are a few things I have learned that can help make working (or not working) over the holidays a little bit easier.
Plan Ahead
Lay out the days and times that you want to be unavailable and focus on spending time with loved ones. Be realistic about what you think you can do and write it down. If your team is working over the holidays (please don’t do this unless you must!), make sure your colleagues know when they can contact you and expect a response. If you know you will need to do some amount of work, communicate it to friends and family so they can set expectations.
Disconnect
Now that you have made a plan to disconnect, you just need to do it. Turn off your notifications, put your phone away, turn off your smartwatch, whatever it takes. Remove the potential distractions and keep them put away. This will give you the space to focus on the here and now and enjoy the time you have.
Don’t Dwell
If something unexpected comes up, deal with it quickly. If it cannot be handled quickly, do not dwell on it. Take the time to write that email, or slack message so it will not be rolling around in your head as a distraction. If at all possible delay any response until a designated work time, especially if there will be extended back-and-forth required to resolve the issue.
If you feel your mind wandering towards work, step away and write down what you are thinking. This will get it out of your head and allow you to be more present to what is around you. You will be amazed at how effective it can be to take 10 minutes in a bathroom to write a note down that can free your mind for a whole evening.
Have a Script
If you know you are going to get asked about work and you don’t want to discuss it, come up with a few responses that will let you redirect the conversation.
Some of my favorite responses to “how is work?”:
“Work is good, I have been spending my time after work doing X.”
“Work is good, I actually have a vacation coming up where we are going to X.”
“Work is good, the other day on the way to work I listened to a really interesting podcast about X.”
If small talk stresses you out, this can be a great way to ease your anxiety.
Don’t Beat Yourself Up
If you get distracted or need to step away to handle something, don’t let it ruin the remaining time you have. It is not easy to disconnect and shed work stress. Be kind to yourself and set reasonable expectations that work for you.
Final Thoughts
There is no right or wrong way to enjoy the holidays. Choose whatever will make you happy and energize for the rest of the year. Managing work/life balance is very personal and you should decide for yourself what will make you happy. I hope that you have a great holiday season.
Interviewing for Curiosity
Curious people make some of the best teammates.
Innate curiosity is a major advantage in any role. Curious individuals seek out knowledge, actively pursue learning, and constantly strive to improve. They’re driven to understand how and why things work and evolve, which often leads to better decision-making and a stronger sense of ownership in their work. Hiring for curiosity means finding people who are not just capable but also deeply invested in growing and contributing to your team.
Below are some of my favorite interview questions to gauge a candidate’s curiosity and their drive to learn.
Questions for Curiosity
1. Our industry changes so fast. How are you keeping up with it?
This is a great way to open the conversation. Look for responses that show the candidate believes that staying informed is part of their job. Ideally, they’ll share specific sources of information—newsletters, forums, podcast, industry events—and explain how they integrate learning into their routine. A detailed answer suggests they’re proactive about keeping up with change.
2. Tell me about a time when you questioned an established process or approach.
This question uncovers how the candidate approaches analyzing systems and identifying areas for improvement. Pay attention to what motivated them to question the process: Was it a genuine desire to understand and improve, or something else? It’s also helpful to see if they maintained an open mind while addressing the issue.
3. When was the last time you challenged an assumption or belief you held? What prompted you to question it?
I like this question because it combines curiosity with self-reflection. It offers insight into how candidates reassess their own beliefs, seek out new perspectives, and grow as professionals. Look for examples where the candidate embraced discomfort or uncertainty as part of the learning process.
4. If you could ask an expert in your field one question, what would it be?
This question can reveal how much thought the candidate has put into their field and what gaps in knowledge they’re eager to fill. If they struggle to answer, follow up by asking about individuals or companies they admire and why. If they’re unable to name anyone or articulate why they admire them, it could signal a lack of curiosity.
5. What was the last work-related topic you were interested in learning more about?
Specificity is key here. Look for responses where the candidate dives into a particular subject or skill, showing their passion for going deep into the details. If they “nerd out” on the topic, it’s often a sign of someone who takes pride in their work and finds joy in mastering their craft.
Bonus: Is there an area outside your day-to-day role that you’re interested in learning more about?
This bonus question provides insight into the candidate’s broader interests. Candidates with curiosity beyond their immediate role often make stronger teammates because they better understand the challenges faced by other disciplines. In fields like game development, where cross-disciplinary collaboration is crucial, this can be a significant advantage.
Final Thoughts
Curiosity is an often-overlooked trait when hiring, but it’s directly linked to a candidate’s growth potential and intrinsic motivation. Curious people don’t just do the work—they love the work. They bring fresh ideas, adapt to change, and inspire their teams to do the same. By focusing on curiosity during the interview process, you can identify candidates who will grow with your organization and help it thrive.
The Impact of Gratitude on Culture
On the eve of Thanksgiving I wanted to share some of my favorite articles on gratitude and the impact it can have on culture.
How to Cultivate Gratitude, Compassion, and Pride on Your Team
I love this article and this research because it focuses on how to build grit on your team. I think grit is one of the most valuable traits in an employee and teammate. This article goes into how having grace with team members can promote more patience and perseverance and how expressing gratitude plays an important role.
“Work from my lab, for example, shows that people induced to feel grateful show double the patience when it comes to financial rewards. They’re twice as willing to forgo an immediate smaller profit so that they can invest it for a longer-term gain. In a similar vein, people made to feel pride or compassion are willing to persevere more than 30% longer on challenging tasks compared to those feeling other positive emotions, such as happiness, precisely because pride and compassion induce them to place greater value on future rewards.”
Being a good boss isn’t easy—here’s how to get better
While not just about gratitude, this article touches on how to become a better manager through four simple “human practices”. I think all the advice in this short article is valuable but I like how it highlights the importance of authenticity when expressing gratitude.
“Celebrating small achievements helps people face larger challenges and sets up a positive dynamic where everyone wants to do better. But don’t overdo it. People can tell when their bosses and senior leaders are just following a script without truly meaning what they say. Hone the ability to feel genuine thankfulness and express it in a heartfelt way.”
The Science Of Gratitude: How Thankfulness Impacts Our Brains And Business
In a results oriented culture it can be difficult to build in strong recognition loops for employees. This article is a good reminder to me that recognition is critical to team success, but also that expressing gratitude can be a good way to ensure employees feel recognized.
“Gratitude is closely linked to employee recognition—and there is an overwhelming amount of research that shows how recognizing employees leads to positive outcomes.”
Final Thoughts
Practicing gratitude and building it into team culture have clear benefits. I hope this was a reminder to be thankful. Have a great Thanksgiving for those in the USA.
Using Decision Transparency to Build Trust
Hiding the details of a decision reflects a poor team culture and weak leadership.
In contrast, decision transparency—being open about the decision-making process before and after a decision is made—is a cornerstone of building trust within a team.
Making tough decisions is one of the most critical responsibilities of a leader. These decisions often involve unclear outcomes, high stakes, and difficult trade-offs. In many cases, no matter the outcome, some team members may be disappointed. Decision transparency doesn’t eliminate disagreement, but it fosters trust by showing that decisions are made thoughtfully and with integrity.
Why Decision Transparency Matters
Transparent decision-making ensures that even if someone disagrees with the outcome, they can understand how and why the decision was made. This helps build a culture where team members trust their leaders and feel confident in the process, even during challenging times.
How to Implement Decision Transparency
Whether you're navigating an upcoming decision or explaining one that has already been made, these key components will help foster transparency:
1. The Decision Maker
Clearly identify who is responsible for making the decision. Leadership often means owning the final call, so if you’re the decision-maker, embrace that role and communicate it to the team.
If the decision is delegated to someone else, explain why that person is the right choice.
In hierarchical organizations, clarify how you were involved if the decision was made by someone higher up.
For collective decision-making processes, outline who was involved and their roles.
2. The Process
Detail the steps taken to reach the decision.
Describe what information was gathered, the analysis conducted, and the factors considered.
Highlight the effort invested in making the best possible choice. This reassures the team that decisions aren’t made arbitrarily, but with careful thought and consideration.
3. The Outcome
Communicate the final decision clearly and precisely.
Share what the decision means for stakeholders, and clarify if further approvals or steps are required.
Explain how the decision will be implemented and outline what’s needed from the team to move forward.
4. The Reasoning
Explain why the decision was made.
Highlight the key factors that tipped the scales and the rationale behind prioritizing those factors.
Share any trade-offs and the reasoning behind those choices, so the team understands the broader context.
Final Thoughts
Decision transparency isn’t about avoiding conflict or pleasing everyone—it’s about building trust. By showing the thought process behind tough decisions, leaders demonstrate respect for their team’s intelligence and input. Even if team members disagree with the outcome, they’re more likely to support it when they understand how and why it was made.
When leaders communicate decisions clearly and openly, they not only strengthen trust but also set a standard for accountability and integrity within the organization. Transparent decisions pave the way for better alignment, stronger culture, and ultimately, a more resilient team.
Crafting a Fundraising Narrative
Fundraising is all about storytelling. But when you are early, what story is worth telling?
At the Seed and Series A stages, when tangible traction may be limited, the strength of your narrative is the only thing you have. This narrative should be centered around the unique discoveries your team has made—insights that, although not widely known yet, hold the potential for significant impact and value. A successful fundraise narrative intertwines these valuable discoveries with a realistic, actionable plan to capitalize on them, demonstrating how additional funding will be the catalyst for growth.
Types of Discoveries
Your narrative should illuminate the insights and breakthroughs you have discovered in these four critical areas:
1. Founders/Team
Showcase why your team is distinctively qualified and ideally suited to win. The discovery here is the team itself: a unique blend of skills, experiences, and perspectives tailored to seize the opportunity at hand. Highlight previous successes, relevant expertise, and the shared vision that sets your team apart. Focus on founder-market fit, which is often something deeper than just professional experience, and go beyond the resume.
You want investors to walk away from the pitch feeling like they deeply understand the motivations and super powers of the team.
2. Opportunity/Market
Present the market potential your team has discovered. This could be an emerging market catalyzed by external factors or an established market ripe for disruption due to competitor complacency. The key is to convey the size and accessibility of this opportunity and how your team is positioned to capitalize on it.
This is a chance to show the depth of subject matter expertise on the team. Teach the audience something about the market they didn’t already know. This will build credibility for the team and help prove out the viability of the business.
3. Product/Tech
Discuss the groundbreaking product or technological innovation your team has developed. This discovery should address a tangible moat that the team has developed that other companies do not have.
If you have built something already, show it. If you have not built it yet, explain why no one else has, and how you plan to be the first. Give the audience a chance to see how the experience and capabilities you highlighted with the team can work in action.
4. Go-to-Market/Distribution
Reveal your unique approach to market entry and distribution. This could be an innovative sales strategy, a novel distribution channel, a unique partnership model, or deep knowledge of the customer.
Use this opportunity to be clever. Show how you are not just building a product, but an actual business. Explain in detail how other companies have attempted to do this, and how you will do it better.
Final Thoughts
You don’t need to have a discovery in every area. Focus on the discoveries that feel like true outliers. You are better off building a narrative around one very strong point than spreading it across several mediocre ones. Investors look for things that stand out and break patterns, you will lose credibility if you attempt to pass off something mundane as a groundbreaking discovery.
Be ready to iterate on this story as you start to tell it. Watch for reactions as you pitch and see what is resonating with the audience. Continue to focus on the areas that get the biggest reaction. Practice the narrative and build your skill as a storyteller, it will certainly make you a better communicator and leader.
Bottom Line Up Front - How to Write Better Emails
Stop saying “Hi!”
Effective communication is essential to building a strong company culture. At Proletariat Inc., our Cultural Communication Guide included specific guidelines for email that helped improve clarity and efficiency—especially as we scaled and remote work increased during the 2020 lockdowns.
For a long time, we didn’t have a formal email structure, but as our team and volume of emails grew, it became challenging to separate important messages from the noise. This led us to establish an email protocol that was direct, purpose-driven, and clear.
How to Write Better Emails
Our approach was inspired by the Harvard Business Review and adapted to fit our needs.
1. Bottom Line Up Front (BLUF)
Start with the main point. Summarize the purpose of your email in one concise sentence at the very top. Avoid lengthy introductions—get straight to the important details to respect the reader’s time.
2. Subject Line Keywords
Use subject line keywords to categorize each email’s purpose, ensuring the reader immediately understands the intent. Only use one keyword per email thread; if you need more than one, consider splitting the message into separate emails. Here’s the breakdown:
[Feedback]: You’re seeking feedback, and it’s optional. Specify the response deadline to avoid late feedback impacting decisions.
[Action]: You’re requesting action from the reader. This usually involves a specific deadline and is often time-sensitive.
[Info]: You’re sharing information that doesn’t require a response—purely informational.
[Request]: You’re requesting a decision or permission. Be sure to specify the date by which you need a response.
3. Set a Clear Timeframe
Indicate any deadlines directly in the email. If it’s urgent, add “URGENT” to the subject line and follow up with a direct message or in-person check-in for prompt action.
4. Structure and Tools
Keep it organized and concise. Use bullet points, lists, and concise sentences instead of long paragraphs to improve readability.
Direct action with @mentions: Tag individuals with the “@” symbol to clarify what each person needs to do in response, making it easier for everyone to see their responsibilities.
How to Respond to Emails
If you need more than a day to respond, acknowledge the email and provide an estimated response time. This helps maintain clear communication and sets expectations for follow-up. Create a culture around the expected response time to emails. If you are on a email thread with multiple people but follow up and close the loop through a different channel (chat, meeting, etc) be sure to respond back to the group and explain that this is resolved.
Final Thoughts
While this email structure worked well for us, each company may need to tailor it to fit its unique culture. Defining and training your team on an effective email style is worthwhile to improve communication, ensure clarity, and save time across the board.
How to Conduct Effective Reference Checks
Every hiring manager should make time for reference checks, especially for leadership roles or those heavily requiring soft skills.
While interviews offer insights into a candidate’s background and skill, they only provide one side of the story. Reference checks provide an external perspective, allowing you to make more informed hiring decisions. I recommend asking candidates for references and also seeking out objective references they may not directly provide.
Before diving into questions, do some quick research on each reference’s relationship with the candidate, how long they worked together, and their professional connection. This allows you to focus the conversation more productively. Schedule at least 30 minutes to ensure plenty of time to ask questions and fully hear what the reference has to share.
Top 5 Reference Check Questions
Why do you think the candidate chose to leave your company?
This question offers valuable insight into the candidate’s motivations and career aspirations. It can also provide the other side of the story if the exit from the previous company was at all contentious. I prefer to work with people who do their best to leave places in good condition and not burn bridges.Is this person one of the top 5 people you’ve ever worked with? Why?
Ranking forces specificity and offers a clearer sense of how this candidate measures up. I find this more insightful than simply asking if they’d work with the person again, as it provides a more direct assessment. If a candidate provides a reference that does not absolutely put them in their top 5 that is a red flag.What’s one area this person improved in while working with you?
I put a lot of weight on a candidate’s ability to grow and adapt. This question can reveal how quickly they enhance their value on a team. It’s often helpful to follow up by exploring the process they undertook to improve and how much help the team or company provided.Can you give an example of a time they made a difficult decision or tackled a tough problem?
This question is essential for assessing resilience and problem-solving. It’s important to hear about specific challenges the candidate handled, which reveals their grit and determination. I really look for an example of the candidate doing a hard thing that helped the team or company succeed.What was the best thing about working with them? And the most challenging?
Unlike traditional strengths and weaknesses questions, this phrasing highlights the candidate’s impact as a teammate. It can reveal aspects of their work style, personality, and how they interact and communicate with others. I love to hear that a candidate is a joy to work with because of their positive attitude, which often has nothing to do with their skill in the role.
BONUS: What did you learn from them, and what did they learn from you?
I love this question because it often brings out unexpected answers. It reveals the candidate’s openness to feedback and their potential for growth. I want to work with people that are coachable and love to learn, but also enjoy teaching others.
Final Thoughts
While connecting with multiple references can be time-consuming, it’s almost always worth it. If you’re undecided on a hire or choosing between multiple strong candidates, extra reference checks can provide the clarity you need. Asking similar questions across multiple references and candidates will help you gather a broad set of insights to make the best decision.
Culture Communication Guide: A Critical Tool for Cultural Onboarding
Every team should have clear communication guidelines that are taught and enforced for all employees.
You should have a cultural communication guideline document that lists out the channels your team uses to communicate and how each team member is expected to use them. Check out this example from Proletariat. By clearly defining how the team should communicate it becomes easier to enforce the cultural norms you want and accelerates how quickly new team members can onboard into the culture.
Culture is often defined as “a series of unwritten rules that everyone knows and follows”. Why do these need to be unwritten? They don’t! Please write them down, especially when it comes to how your team communicates with each other.
What should be in a Cultural Communication Guide?
For the guide to be useful it should include at least three sections. The value of the guide is in the details. By reading this document every employee should be on their way to becoming a great communicator with the rest of their team.
1. Choosing the Right Communication Channel
Teams often use multiple channels—email, Slack, meetings. Clearly define which type of communication belongs where based on message content, urgency, and response needs.
2. Communication Channel Usage Guidelines
Once a channel is chosen, the guide should outline how to use it effectively. This includes setting expectations for tone, timing, format, and best practices for emails, meetings, and other interactions.
3. Examples and Best Practices
Include examples to show the guidelines in action, making it easier for employees to understand and follow.
How do you use a Cultural Communication Guide?
The two primary uses for this guide will be with existing teams and with new team members. For existing teams this should be used for creating consistency and agreement on how the team wants to communicate. For new employees it should be part of their training and onboarding.
At Proletariat we would include this guide as part of the employee handbook, send it to new employees when they started, and also give a presentation covering these details as part of their onboarding.
It is up to company leadership to decide how to enforce these guidelines. The way these are enforced, and how strictly, is also a major reflection on the culture of the team. Do not define these rules and then decide to not enforce them!
How do you make a Cultural Communication Guide?
Crafting a document like this should be a group effort with feedback from the full team. If there is no agreement on ways to communicate, use the creation of this guide to find compromises. The process of choosing how the team will communicate is a great step to improving efficiency across the team.
The best way to start making this guide is to simply write down all the ways the team communicates now. Taking stock of the current communication practices of the team sets a good foundation for discussion around what areas of team communication are working well and what areas could be improved.
This should be a living document, something that is updated regularly as your team grows and changes. I have found that certain communication styles can work well when a team is small but fall apart when a team is big.
Naavik Podcast - How Studio Culture Fuels an Exit
I recently had the pleasure of joining the Naavik Podcast to dive deep into a topic I care deeply about: studio culture and its impact on success. Hosted by Alexandra Takei, we explored the question: What is culture, and why does it matter?
In this episode, we discuss the culture we built at Proletariat, the lessons I learned along the way, and how a strong team culture can be a driving force behind company success. I had the chance to talk about the definition of culture, who is responsible for setting and maintaining it, and actionable tactics leaders can use to build and nurture a thriving culture within their teams.
Over the course of our hour-long conversation, we dove into Proletariat’s core values and how they evolved as the company grew. We also touched on how values need to adapt in response to a company’s changing needs and goals. We even talk about the difficult tradeoffs of investing in culture when a company is simply struggling to survive. If you’re curious about how culture can fuel growth, retention, and success, this episode is for you.
How New Leaders Can Earn Trust Quickly
Whether you’re stepping into a startup as a non-founder leader or hiring your first executive as a founder, it is critical to build trust quickly.
Create a Trust Building Plan
One of the most effective ways to build trust is through a clear plan with frequent check-ins that encourage transparent discussion. At Proletariat, we used a 30-60-90 day structure, focusing on two key aspects.
The Two Pillars of Leadership Trust
Leaders often have two core responsibilities: tasks (the tangible work they produce) and decision-making.
Tasks: This involves skill, execution, and communication. It can range from crafting a presentation to delivering complex projects involving large teams.
Decision-Making: This is about identifying choices, gathering information, assessing possible solutions, managing differing opinions, and ultimately choosing the right path.
Building Trust Through Tasks
To build trust through tasks an individual needs to consistently meet or exceed expectations over time. When creating a trust building plan consider the following:
Communication: A new leader should set clear expectations and create a communication plan that existing leadership and the new leader can use to keep everyone on the same page.
Skill and Competency: New leaders need to build credibility within their team and show that they can apply their skills within the context of where the company is today. Existing leadership should highlight areas where those skills are most needed.
Execution: Successful execution shows grit, team building and problem-solving. When creating a plan be sure to focus on what exactly great execution looks like. Start with tasks that are likely to succeed to help build momentum.
If a task fails, conduct a post mortem to understand what went wrong and set up the leader for future success. Trust is easily lost through a few failed tasks.
Building Trust Through Decision-Making
To build trust through decision-making an individual needs to consistently make “good” decisions based on the organization’s decision-making framework.
Decision-making is about applying a consistent framework that balances team needs, strategic goals, and company values. I recently wrote a post diving deep into how to delegate decision making which discusses this framework.
A trust building plan should lay out how decision-making can be phased over time to give the new leader more and more autonomy as they learn to use the decision making framework. Clear communication on when a new leader should get additional approval, and how much transparency they should provide in the decision-making process, or any other key factors, will help ensure success.
If a wrong decision is made it is critical to post-mortem that decision and fix any issues or misalignment.
Final Thoughts
I know that I trust a new leader when I can delegate a responsibility to them and have full confidence in the outcome. It’s when I can trust them to make decisions, knowing they’ll either choose the path I would have or find an even better one. Trust isn’t built overnight, but through a consistent approach to tasks and decisions, leaders can earn the confidence of their team and set the foundation for long-term success.
Delegate with Autonomy Using Commander’s Intent
Successful delegation hinges not only on the individual leader’s capabilities but also on the prevailing team culture. Cultivating an environment where effective delegation thrives—allowing team members autonomy in decision making and the opportunity to grow without being micromanaged—is a deep topic.
A concept that I love from the US Military is known as Commander’s Intent. Simply defined: it is the end-state of the battlefield if the mission is a success. In a business context, this means the leader articulates a detailed vision of the end-state for a successful project to the team but allows the time to define the plan and path to that end state. This approach requires the team to not only devise with their own plan but empowers them to make decisions without the need to go all the way up the chain because a clear final goal has been established
Implementing Commander’s Intent
Below are several concrete steps to use this process when kicking off a project.
1. Define End-State Success
Clearly define what success looks like for the project through objectives and outcomes. An Objective is a desired goal that is both inspirational and easy to understand. An Outcome is a measurable want, need, or change from the current state.
2. Set Constraints and Requirements
Identify the constraints and requirements of an end-state victory provides the guard rails for the team to start problem solving and establishing a plan of action. Constraints are limitations or restrictions on any plan or process to reach the desired end state. Requirements are any necessary conditions for the end-state victory.
3. Determine Anti-Goals
Define what failure looks like. This helps to clarify what success does not entail and assists in avoiding undesired end-states. Anti-goals include scenarios where the outcomes and objectives might be met, but the project is still considered unsuccessful.
4. Question and Redefine
Ensure the entire team understands the Commander’s Intent. Any potential judgment call or unclear circumstance should be brought up and discussed. Each of the previous steps will work better as open dialogs. If they are prescribed ahead of time, it is critical to allow for discussion and redefinition before commencing the project.
Final Thoughts
The Commander’s Intent is explicit intent. This end-state definition is shared widely and clearly to the entire team. Explicit intent alone is not enough to properly deliver successful results, implicit intent is also required. Implicit Intent is the culture of the team, the rules of engagement, the norms and values the team wants to uphold along with any habits that allow them to function
5 Great Interview Questions for Leaders
It is hard to hire great leaders and managers. Below are five of my favorite questions to ask in an interview to help you identify strong leadership candidates.
Unlike many individual contributor roles, management and leadership positions can be particularly challenging to evaluate in an interview setting. A conversation is just one piece of the puzzle. In addition to interviews, I highly recommend conducting thorough reference checks and ensuring you have a well-structured onboarding plan for new hires—two topics I’ll cover in future posts.
In a previous post, I discussed how to hire for grit. Beyond grit, there are several qualities I look for when hiring managers and leaders: the ability to make sound decisions, clear and effective communication (especially when delivering bad news), a results-oriented mindset over political maneuvering, and a high degree of self-awareness.
1. How do you define a high-performing team?
This is a strong first question because it opens the door to follow-up inquiries. Here, I’m looking for candidates who can articulate not only how their team achieves results and meets goals but also how they balance company success with individual and team growth. It’s also a good opportunity to assess their views on culture. You can dig deeper by asking how they’ve contributed to creating an environment where high-performing teams can thrive.
2. What steps do you take to deliver difficult news that you know will upset your team?
This question often reveals a lot about a candidate. It’s not uncommon for interviewees to seem visibly uncomfortable while answering, as delivering bad news is one of the hardest parts of management. What I listen for here is a commitment to transparency and accountability. Bonus points go to those who can explain how they foster a resilient team culture—one capable of processing and responding to challenging news.
3. How would your team describe your leadership style and strengths as a manager?
This question provides two key insights: first, the candidate’s level of self-awareness, and second, a baseline for comparison during reference checks. While there isn’t one "right" leadership style, I want to see that the candidate has put thought into their leadership approach and can articulate what makes them effective. Leaders who are intentional about their craft tend to be the ones who grow and adapt the most successfully.
4. Describe a situation where you’ve had to manage your own emotions effectively to prevent the team from feeling demoralized or negative.
It is common to ask how a leader motivates their team, but I find that learning how they avoid demotivating their team is often more insightful. This is especially true in passion-driven industries like game development, where many people are naturally motivated to do great work. In this answer, I want to hear evidence of self-awareness and a thoughtful, considered approach to communication.
5. How would you handle a high-performing team member who is consistently late to work?
I love this question because it challenges the candidate to think beyond rigid policy enforcement and into the realm of personalized management. If their answer is, "I’d tell them to be on time or face the consequences," I often follow up with, "What if they say they work best later in the day?" The best responses delve into the nuances of individual management, balancing team culture and performance expectations with the needs of top performers.
Final Thoughts
Hiring great leaders and managers involves far more than just asking a few well-crafted questions, but these five have proven to be some of the most insightful over the years. When interviewing leadership candidates, think about your company’s culture and what kind of leaders will thrive within it. Remember that interviewing is a skill and you should constantly work to improve your ability to do it well.