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.
How Much Money Should You Raise in Startup Funding?
One of the most common questions I hear from founders is, “How much money should I raise, and at what valuation?”
The answer is a balance between what you should raise and what you could raise. Let’s break down how to approach this for the best possible fundraising outcome.
The best outcome is when the amount you should raise to hit the next inflection point for your business is within the range of the amount of money you could raise based on the current market and the company’s past fundraising history.
How Much Money Should You Raise?
The amount of money you should raise comes from analyzing your strategy and determining where capital can accelerate your success. A useful rule of thumb is to raise enough to hit your next major inflection point, plus six months of additional runway—because things always take longer than expected.
Identifying Your Inflection Point
Your inflection point should be a milestone that could double your company’s valuation. This could be hitting profitability, launching a product, or reaching a key metric like ARR (Annual Recurring Revenue) or user growth. Early-stage investors are often looking for signs that your company can achieve a significant valuation bump within 12–24 months, as that helps them raise their next fund.
When you think about how much you should raise, do it in isolation—don’t worry about market conditions or fundraising history just yet. This gives you a clear view of what your business truly needs to succeed, even if the final amount raised differs from this number.
How Much Money Could You Raise?
This is where the current market conditions and your company’s fundraising history come into play. Fundraising norms vary based on factors like company type, market trends, and investor sentiment, creating some guardrails around how much you could raise and at what valuation.
Understanding Market Conditions
The fundraising market is always shifting, so check recent deals in your space for benchmarks. For example, the size and valuation of seed rounds can vary depending on your industry and business model. If your company fits well within an established category, recent funding rounds from similar companies can give you an idea of what to expect.
Cap Table Considerations
Your cap table and previous funding rounds will also impact your raise. Ideally, you want to raise an “up round,” meaning your pre-money valuation should be higher than your last post-money valuation. A general goal is to aim for a pre-money valuation that’s double your previous valuation, and to raise 50% more capital than in your last round.
While it’s possible to deviate from these norms—raising a flat round, a down round, or less capital than before—it makes your fundraising more challenging. Investors will ask why, and you’ll need strong answers ready to address their concerns.
Testing the Market
The tricky part about how much you could raise is that it often requires testing the market directly. You can gather as much intel as possible, but until you start pitching, you won’t know for sure how investors will respond. Be prepared to adjust based on real-time feedback.
Final Thoughts
The ideal fundraising amount lies at the intersection of what you should raise and what you can raise. If the amount you can raise falls well below what you need, it’s time to rethink your strategy. Conversely, if the market allows for raising significantly more than you need, carefully consider whether to take the extra capital or adjust your goals accordingly.
Implementing Radical Transparency
Every team can benefit from radical transparency. By being open with your team, you foster trust, alignment, and accountability—critical elements for any successful startup. Here’s how to implement radical transparency and build credibility as a leader.
The Trade-Off of Radical Transparency
Radical transparency comes with risks. Startups are a rollercoaster, and not everyone wants to be exposed to every high and low. There’s also the chance of a leak or breach of trust when sharing sensitive information. However, the benefits of transparency far outweigh the risks. When you share as much as possible with your team and trust them to use that information, you empower better decision-making throughout the organization.
1. Communicate Clear Goals
Don’t shy away from communicating the key goals that will make or break your team’s success. Boldly sharing big objectives can feel uncomfortable, but it’s foundational to transparency. If your team doesn’t know what they’re working toward, how can they make informed decisions? Every team member should be able to clearly articulate the goals and understand why those goals were chosen.
2. Explain the Decision-Making Process
Transparency isn’t just about outcomes—it’s about the process. There are two crucial elements here:
Clarify Decision Ownership: Make sure it’s clear who the decision maker is. This can feel awkward in some team cultures, but if it’s ambiguous, the entire decision-making process is set up for confusion or failure.
Provide Post-Decision Clarity: After a decision is made, offer full details. Anyone should be able to ask about the process, the options considered, and why a particular choice was made. Even if people disagree with the outcome, they will appreciate understanding how and why the decision came about.
3. Deliver Bad News
Transparency isn’t just for good news. Leaders build credibility by delivering bad news openly, honestly, and humbly. Avoiding problems or pretending everything is fine creates a culture of secrecy that prevents teams from addressing challenges head-on. Share the results—good or bad—so the team can learn and grow together.
4. Answer Questions
At Proletariat, we held weekly all-team meetings where leadership answered questions from the company. This can be intimidating for leaders, especially as the company grows, but it’s one of the most powerful ways to build credibility. Answering questions authentically builds trust, and mastering this skill is crucial for both internal and external communication.
5. Avoid Surprises
When people are surprised, it usually means they were left out of the loop. While not every surprise can be foreseen, many can. If you anticipate that an event might shock your team, it’s a sign that you haven’t been transparent enough about what’s happening in the company and how it will affect them.
Final Thoughts
I can’t imagine building a strong culture without radical transparency. By giving your team as much information as possible and trusting them to use it wisely, you build a foundation of trust, alignment, and accountability. While transparency has its challenges, the long-term benefits for your culture and your company far outweigh the risks.
Building a Transparent Decision-Making Framework for Your Team
Delegating decision-making responsibility is one of the scariest tasks for a leader. You can’t be in every meeting or make every judgment call. Empowering your team to make decisions is a superpower that can transform your organization and you can even do it while maintaining “Founder Mode”
The Opportunity in "It Depends"
Let’s start with an example of a common leadership decision: there’s a new engineering feature to build, and you need to decide whether Person A or Person B should do the work. Your first thought might be, “It depends.” Every time you find yourself saying this, it's an opportunity to improve your team's decision-making process. How? By defining a clear decision-making framework and providing transparency into how decisions are made.
Having an explicit decision-making framework won’t guarantee that every decision will be perfect. As you’ll see below, judgment is key when balancing different facets of a decision. However, the more effectively you communicate your framework, the more your team can align with your thought process and make decisions independently.
Decision-Making Framework
Decisions require balancing three core areas.
1. Team/Personnel: What Do We Want to Do?
This focuses on what’s best for the team. The complexity here arises from balancing factors like morale, career growth, individual interests, and skills. A major challenge often lies in the trade-offs between short-term gains and long-term benefits.
From our example, say Person A has expertise in this area of the codebase and has completed similar tasks before. Person A would be happy to do this work but doesn’t necessarily need to. Person B, on the other hand, is eager to learn, but the task would take them longer, risking the project’s deadline. What should you do?
2. Company/Strategy: What Do We Need to Do?
Here, the focus shifts to what the company or project needs to be successful. Success should be defined by objectives and outcomes, but in startups, it often boils down to survival—such as not running out of money.
In our example, allowing Person B to work on the feature could delay the project. Missing this deadline could put the next milestone at risk, and the team just missed the previous milestone. Missing the next milestone will likely greatly hurt the chances of future funding. What should you do?
3. Core Values: What Must We Do?
Core values state what your company is willing to do—or not do—in pursuit of success. Compromising on values can lead to cultural drift, but it’s also important to remember that no team is perfect. If a trade-off is necessary, it’s better to make that decision openly and consciously.
From our example, if your company values hitting deadlines but also prioritizes employee career growth, you may feel caught between conflicting values. What should you do?
A Real-World Example
At Proletariat, this situation might play out like this:
Our company values skill development, but we also can’t afford to miss our next milestone after previously missing one. In this case, I would assign the task to Person A to ensure we meet the deadline and secure funding. If we hadn’t missed the previous milestone, I’d be more inclined to let Person B take on the work and invest in their long-term development.
The Power of Decision Transparency
You won’t always be able to outline every trade-off ahead of time, but that’s where decision transparency comes in. Taking the time to not just communicate decisions, but also explain the why behind them, helps your team understand the framework and improve their own decision-making. At Proletariat, we encouraged the team to ask “why” when they didn’t understand a decision. This fostered a culture of open decision-making, where everyone could learn from leadership’s approach to difficult decisions.
Cultivating and Maintaining an Outcome-Oriented Culture
Every team aspires to be successful, but success isn’t about staying busy—it’s about delivering specific outcomes. Cultivating an outcome-oriented culture is a big challenge, and maintaining it as a company scales is even tougher. I wanted to share some steps leaders can take to do this within their teams.
What is an Outcome-Oriented Culture?
An outcome-oriented culture prioritizes results over activity. It’s a mindset where the focus is not merely on the tasks completed or the time invested but on the tangible impact those efforts produce. In an outcome-oriented organization, every action, strategy, decision, system, and process is aligned with the goal of driving meaningful outcomes. This often necessitates rethinking not just the team’s goals, but also how team members are incentivized, recognized, and rewarded.
Steps to Cultivate an Outcome-Oriented Culture
Define Clear Outcomes
The foundation of an outcome-oriented culture is a clear definition of what success looks like. This involves setting specific, measurable, and achievable goals that are in sync with the organization’s broader objectives. These outcomes must be communicated throughout the organization so that every team member not only understands what they’re working toward but also why it matters.
Look out for goals that are actually just outputs (like "ship a new feature on time"), too short-sighted (like "make $1,000"), or too broad ("build something customers love").
Align Tasks with Outcomes
Once outcomes are defined, it’s crucial to ensure that every task and decision is aligned with these goals. The key is to create a direct line of sight between daily activities and the desired outcomes. If someone is working on something but they don’t understand how it helps achieve a target outcome, they should be empowered to not do it or deprioritize it. This is why transparency on goals and ensuring that the team understands the underlying "why" is so important.
Measure and Share
An outcome-oriented culture is not about tracking outputs—such as the number of tasks completed—but about measuring the impact of those tasks. Regularly reviewing performance against the desired outcomes keeps the organization on track and allows for real-time adjustments. This data should be openly shared across the team—keeping results under wraps because they might be seen as "bad news" only detracts from the focus on achieving real results.
Reward Results, Not Effort
To maintain an outcome-oriented culture, it’s essential to reward results rather than effort. While effort and hard work are important, they should not be the primary basis for recognition or compensation. Instead, rewards should be tied to the achievement of the target outcomes.
This is incredibly challenging to execute well and requires a culture that fosters psychological safety and allows for the occasional failure. It’s easy to veer into extremes, potentially creating a mercenary culture where risk-taking is not valued or incentivized. Balance is key.
Final Thoughts
Cultivating and maintaining an outcome-oriented culture is not a one-time effort; it’s an ongoing process that requires commitment from everyone in the organization. By focusing on clear outcomes, aligning activities with goals, empowering teams with transparency, measuring what matters, and rewarding results, organizations can create a culture that not only drives success but also sustains it over time.
In the end, an outcome-oriented culture isn’t just about getting things done—it’s about getting the right things done and ensuring that every effort leads to meaningful, impactful results.
Interviewing for Grit
I love working with gritty people. The best teammates I’ve ever had displayed a tremendous amount of grit. Every team wants to hire people who have grit, but it can be very difficult to determine from a short candidate interview. I wanted to share my favorite interview questions to test for grit.
Hiring is one of the most challenging and critical responsibilities of any leader. Mastering the art of interviewing is crucial, though it’s only one part of a comprehensive hiring process (I’ll cover reference checks and other aspects in a future post).
For those unfamiliar with the concept, grit, as defined by Angela Duckworth in her book on the topic, is a combination of perseverance and passion for long-term goals. It’s a trait that often distinguishes those who succeed in the face of adversity from those who don’t. If you haven’t read her work yet, I highly recommend it.
1. What is the most challenging thing you have ever accomplished at work?
With this question, you’re looking for more than just someone who shows up and does their job. The ideal candidate has taken on difficult challenges because they were driven to achieve something meaningful. Look for answers that involve learning new skills, driving organizational change, or stepping outside their comfort zone to accomplish something significant. Passion for their work often correlates with their willingness to tackle tough projects.
Be wary of answers like “firing someone” or “layoffs.” While these are undoubtedly hard tasks, they don’t necessarily reflect grit in the context we’re discussing. Grit involves perseverance in a challenging environment over an extended period, not just the ability to handle difficult situations (although an ability to do hard things is good too).
2. Tell me about a project you worked on that failed or didn’t get the outcome you hoped for.
This question gives insight into how a candidate deals with setbacks—a key component of grit. Listen for ownership of the failure, the lessons learned, and what they would do differently in the future. The candidate’s response should reveal a sense of determination and resilience, showing that they can pick themselves up, learn from the experience, and push forward.
Be mindful of candidates who deflect blame or offer vague explanations. Gritty individuals tend to reflect deeply on their failures and view them as opportunities for growth.
3. What is something you are trying to improve or get better at, either personally or professionally?
This is one of my favorite questions because it reveals not only how gritty the person is but also what drives them. Look for genuine enthusiasm and a clear plan for improvement. The best candidates often have long-term goals they’re working toward and can share stories of both setbacks and progress along the way.
If a candidate isn’t trying to improve in any area, it’s a major red flag. After they respond, dig into the details of their plan. Do they have a methodology? Some of the grittiest people I know are passionate about the process of improvement itself. Their diligence and commitment to growth are strong indicators that they’ll continue to develop and apply new skills in the future.
Bonus Question
If the candidate is an individual contributor: What traits do you look for in great teammates?
If the candidate is a leader: What are the most important traits you look for when hiring?
This is a great chance to hear if they also value grit. Do they recognize the value of optimism, determination, and perseverance? Who they want to work with will give you an idea of how they see themselves.
Final Thoughts
Identifying grit during an interview isn’t just about asking the right questions—it’s about listening carefully to the answers and probing deeper when necessary. By focusing on these questions, you can better assess whether a candidate has the perseverance and passion to thrive in your organization.
Four Types of Traction to Help you Fundraise
Using Traction in Your Pitch
In the Pre-seed, Seed and even Series A stages, showcasing traction that surpasses that exceeds market expectations is not just advantageous—it's crucial. An exceptional metric can often be the focus of your fundraising narrative, providing a concrete proof point of your company's standout performance. There is a constantly fluctuating market that investors will use to gauge specifics like if a company is ready to raise a new round and at what valuation. Investors base this market off of several factors like the state of other companies that have raised recently (current market rate) and the competition to be involved in a company’s round (deal heat).
Four Types of Traction
For most companies there are four different types of traction. Raising when you have an outlier metric on at least one of these will make the fundraise go much better. The further down this list, the more risk that has been taken off the table, so the better the outcome.
Warning: Only highlight truly outlier metrics in your pitch! It will look bad to investors if you show a slide with 2000 people in your Discord server and say, “our fans love us.” Remember, every detail you expose in your pitch invites judgment from the audience (more on that in a future post).
Demand
This encompasses indicators like your waitlist size, social media following, and community engagement metrics. Gaming and consumer companies that have tens or hundreds of thousands of rabid fans ready to throw money at them is a great signal. For B2B startups, a substantial waitlist of companies eager to use your product can significantly de-risk market size and product demand assumptions. Leverage publicly available competitive data to benchmark your performance and highlight your standout achievements in this area.
Growth/Scale
This refers to your user or customer base and, importantly, the quality of these users or customers. Demonstrating growth is a step closer to achieving product-market fit. In the consumer sector and in gaming, a large user number can be impressive, even if they don't monetize. For B2B startups, the emphasis should be on either the number of customers or the caliber the customers. While achieving outlier status in user/customer numbers before a growth round may be challenging, it can be effective.
Retention
Retention metrics offer a deeper insight into product-market fit, indicating not just initial interest but sustained engagement with your product. For consumer and game companies, early retention rates (Day 7, Day 30) are primarily used as predictors of long-term user engagement (Day 180, Day 365). I consider a strong Day 30 number to be the best possible form of traction for any game. In the B2B space, good indicators are not just lack of churn, but proof of renewal.
Revenue
The best possible traction is revenue. It is the holy grail and the major step to proving out product-market fit. If you are pre-Series A and have an outlier retention metric I would argue you may not need to raise a round at all. As mentioned before, having a small amount of revenue is not worth mentioning. It is easier to explain that while you’re making some revenue now, it is not a major focus, than it is to act like you’re excited about a few thousand dollars coming in.
What about Acquisition Cost or Session Length or …
There are a number of other metrics that teams can use to fit into their fundraising narrative. I believe the ones listed above do the best job of showing progress towards product-market fit. If you think you have a truly outlier metric that reinforces your fundraising narrative, use it.
Metric vs. Momentum
Remember that the trajectory towards achieving these outlier metrics can be just as compelling as the metrics themselves. Demonstrating consistent month-over-month growth across any of these dimensions is a strong signal to potential investors. Conversely, a declining metric can raise concerns so be careful how you position your current traction.
A Practical Guide to Improving Feedback Communication
TL;DR: Use a feedback framework to better communicate with your teams. Break your feedback into categories and set expectations for how recipients should use the feedback and how to respond. Consider a three tiered system, called DFN:
Direction (requiring action)
Feedback (requiring response)
Note (requiring no response or action)
Direction/Feedback/Note Framework
As the Proletariat team scaled I wanted to stay involved with the product and design teams. During product reviews or creative meetings I considered myself a member of the product or design teams, not the CEO of the company. My title would have more weight than intended and it often led to an offhand comment I made becoming a high priority task. That is not what I wanted. I needed a shorthand way to give feedback that would convey priority and required action or response.
The DFN framework is not something I can take credit for, but I did use it many times. I found categorizing my feedback was helpful for both the recipient and for me. I would categorize feedback like this verbally, written, and visually, like on screenshots. When providing written feedback, I would color code the categories to make it even easier to understand.
Direction
This is the most forceful category of feedback. Direction requires a change or action, typically in a specific way. When I would give direction I would always include a suggestion on the action to be taken. The recipient of direction is not required to take that suggestion but follow the direction given and make an adequate change.
Example: “This area of the map is too open, it should be more enclosed. Consider adding some additional trees and reduce the width of the path. We want the player to feel claustrophobic.”
In this example it is acceptable if the recipient comes back and says “I don’t want to add more trees, but I will create a ledge here.” If that still satisfies the goal of making the player feel claustrophobic then it worked.
It is not acceptable for the recipient to come back and say “I don’t want the player to feel claustrophobic here”. If there is a disagreement at that level, it requires a deeper conversation on the vision for this area of the game. If I was frequently giving direction to the same person it was an indicator of underlying disagreement or misalignment on the vision.
Feedback
This is the most common category of feedback I would give. This does not require a change or action, but it requires a response. I would sometimes provide a suggestion as part of this feedback, but not always. The recipient is allowed to push back on the feedback directly or to find their own way of addressing it. Either way, it requires a response and follow up.
Example: “This jump is really hard to make. Should these ledges be closer together to make it easier?”
The recipient of this feedback can simply push back on changing the distance of the jump if they think it is the right choice. However, a follow up conversation was needed for the individual to make their case. I would tend to allow people on the team the freedom to make their own calls with this category of feedback. That would change if this feedback was given by multiple people or in cases where we had data to indicate a change was needed.
Note
The last category of feedback is what I would consider coming from a player or user. This is how I felt as a player, not as a developer. Notes rarely would include suggestions and do not require a change, a response, or a follow up from the recipient. This is for the recipient to consider and internalize on their own.
Example: “There are not enough power ups in this area so I spent a lot of time frantically searching for health packs.”
This is a note because it may be intentional and what the designer wants the player to feel. It might also just be a gut reaction from a single play session. I would trust the individual to get notes from many people on the team, distill it down, and use it to help them improve their area of the game.
Final Thoughts
A feedback framework like this one is only valuable if it improves communication across the team. It should be one tool leaders use to cultivate the feedback culture they want in their creative, design, and product teams. If you can’t describe the feedback culture for your creative/design/product team, it may not have one, and that is the first place to start.
This specific feedback framework may not work for your team or culture. Find a structure that allows the team to provide feedback that doesn’t overwhelm, contradict, or confuse the recipient and ensure the recipient knows how they are expected to respond.