Journal Prompts

Whether this is your first startup or you’ve done this before, it’s essential to pause and define what success means to you—not just to your investors, customers, or cofounders. Startups are long, winding, emotionally demanding journeys. Without a clear understanding of why you’re doing this and what you hope to achieve, it’s easy to lose your sense of direction or end up chasing someone else’s version of success. Your goals might be financial, personal, impact-driven, or all of the above—but getting honest about them now will shape how you make decisions, build your team, and define trade-offs along the way. There’s no single “right” answer—but there is value in being intentional from the start. Here are a few prompts to get you thinking about what success means to you:

• What is motivating me to be an entrepreneur? Why am I on this journey?
• When I consider the time investment I am about to or are already making in my new venture, what am I most concerned about? Consider personal tradeoffs such as partnership, mental or physical health.
• What excites me about the people I might engage with as I pursue this venture? Consider all types of stakeholders – potential customers, suppliers, strategic partners, advisors and investors.
• Why are employees, coworkers, investors, and/or press bragging about my venture in the future?
• Postventure, what will be my proudest achievements? How did my business impact the world and/or communities I care about?

It’s tempting to dive straight into building—especially when you’re excited about your idea. But skipping or rushing discovery work often leads to wasted time, misaligned teams, and products that don’t solve the right problems. By preparing thoughtfully, you’ll enter conversations with potential customers with clearer intentions, better questions, and a stronger foundation for insight. The more grounded your discovery process, the more likely you are to build something people truly need. As you head into the discovery process, consider the following questions:

• What expertise am I bringing to the discovery process and where are my gaps? How might I fill these gaps?
• Are there any particular barriers that could prevent me from doing discovery work? This could be physical (e.g., accessibility), emotional (anxiety) or financial (cash limitations).
• What is the best way for me to feel motivated when things get hard?
• How will I ask for help when you need it? And who will I ask?

Before digging into interviews and experimentation work, consider what you hope to get out of the discovery process, beyond the tactical insights, and how you will approach some of the challenges you may face. I recommend you journal your answers to the below and, if you have a cofounder, team or coach you are working with, that you discuss your answers together to identify ways you can get support and support each other through the process.

• What do I believe to be true about the demographics of my target personas?
• What are my hypotheses about the problems they face today?
• Of all my hypotheses, which are the most important for me to prove/disprove?
• What experiments will I conduct to validate/invalidate my hypotheses?
• What are areas I know I need to learn more about?
• What industry, geography, or other market segment am I going after?

You’ve talked to potential users. You’ve gathered insights. Now what? It’s time to make sense of what you’ve heard by mapping the customer journey—visually documenting the steps, thoughts, and feelings your target customer experiences as they discover, consider, and use your product. Journey maps and storyboards help you identify what your customer is trying to achieve, where they get stuck, and where there are moments of opportunity or delight. They’re not just design tools—they’re strategic. When used well, they guide product development, marketing, onboarding, and even hiring.

As you reflect on your discovery interviews and experiments, consider these prompts:

• What are the key moments in my customer’s journey today?
• Where are they experiencing frustration or pain? What causes it?
• What opportunities are there for us to address these frustrations or pain-points?
• Based on our findings, what changes or ideas should we prototype, test, or reprioritize?

A startup without a clear vision and a plan can quickly fall into reactive mode—chasing ideas, responding to noise, and confusing motion with progress. That’s where OKRs (Objectives and Key Results) and KPIs (Key Performance Indicators) come in. Used well, they don’t just create structure—they create alignment, momentum, and accountability. The process of setting them helps clarify what matters most and how you’ll know you’re on the right track. It’s not about writing the perfect goal—it’s about making sure everyone is rowing in the same direction. Use the prompts below to define your vision and begin crafting meaningful goals:

• What is our True North, and how do we know we’re still building toward it as we scale?
• What must we achieve in the next 6–12 months to make meaningful progress?
• What are 1–3 top priorities this quarter that will move the needle?
• What will success look like, and how will we measure it? (Be specific.)
• Are our goals ambitious yet achievable?
• How do we ensure we are aligned across the team?

Deciding whether or not to have a cofounder is one of the most consequential early choices you’ll make. A great cofounder can bring partnership, expertise, and experience; a bad one can drain time and create tension that potentially derails the business. Before jumping into a partnership—especially one born of urgency rather than intention—get clear on what kind of cofounder (if any) you need, and whether the match is right. This isn’t just about complementary skills; it’s about shared values, mutual respect, and the ability to work through conflict.

As you reflect on your current situation—or evaluate a potential cofounder—use these prompts:

• Do I want a cofounder? Why or why not? What would I hope a cofounder brings to the table?
• Where am I strong, and where am I stretched too thin? What gaps could a cofounder help fill?
• Do we share a similar vision, work ethic, and appetite for risk?
• How will we navigate decision-making, ownership, and conflict? Have we talked about the hard stuff yet?
• Is this a relationship I’d want to be in when things are hard—not just when they’re exciting?

For joiners considering a role at a startup:

• Do I see alignment between the founders—and does that give me confidence in how the company is being led?
• Am I aware of how major decisions are being made and how I can contribute without stepping on founder dynamics?

When considering the type of company you want to build, its culture, and how it will function as you scale, answer the following questions in your journal and/or perhaps as a diverge<>converge exercise with your cofounder(s):

• What are the core values of our business that I wish to embody no matter how much we scale?
• How committed am I to holding the bar? Will we delay projects or say no to investors if we hold out to ensure we are hiring top talent while creating a diverse workforce and inclusive culture?
• What training will we partake in and/or procedures will we adopt to ensure we maintain the bar?

Every hire you make in the early days helps shape your company’s culture, operating style, and trajectory. The temptation to “just fill the seat” can lead to costly missteps—especially if you don’t yet know what kind of team you’re trying to build. Before you post that job description, step back and think about your organizational needs, what “great” looks like for this stage, and how you’ll ensure that new hires don’t just fit your culture—they expand and enrich it.

Use the following prompts to ground your hiring strategy:

• What kind of company are we trying to build, and how should our hiring reflect that?
• What are our most critical gaps right now in skills, experience, or execution?
• Who should be involved in interviews, and what perspectives should they bring?
• What qualities do we value most in teammates at this stage—beyond just expertise?
• How do we distinguish between “culture fit” and “culture add”? How will we make space for both?
• What should we consider when it comes to salary and other forms of compensation?

Letting someone go is one of the hardest parts of building a company—and one of the most important to handle well. But before jumping to termination, it’s essential to pause and reflect: is this truly a performance issue, or a mismatch in expectations, support, or communication? Founders often wait too long to act—or move too quickly out of frustration. Either path can damage trust, culture, and momentum. Thoughtful separation begins with thoughtful inquiry. Taking the time to ask the right questions can help you clarify whether the situation is fixable, how to communicate clearly and respectfully, and whether parting ways is truly the best outcome for both the individual and the business. Before moving toward termination, ask yourself:

• Is the system failing the person or the person failing the system?
• Is the work itself getting done and/or are metrics being met without compromising quality, impact to customers, etc.?
• What are the downstream consequences of the work not being closely managed by or completed by me?
• Is this an opportunity for me to coach someone who has demonstrated potential and just needs to adjust to our way of doing something?
• Am I the domain expert, or are they?

You can’t plan for every possible legality throughout the life of your startup, but one should at least do an inventory to assess what areas are of most concern such as:

• Have you secured counsel that understands startup land?
• Do you have a cofounder, advisor, and/or employee agreements in place?
• Do you have any truly defensible IP, and if so, have you at least filed a provisional to start the clock on your ownership of this IP?
• What other agreements or regulatory considerations should you plan for, such as Letters of Intent (LOIs) or Terms & Conditions for your product or becoming GDPR or SOC 2 compliant?

Money may not be why you started the company—but how you manage it will make or break it. Early financial decisions set the tone for discipline, transparency, and long-term viability. Even if you’re not the “finance person,” you still need to understand where your money is going, who’s accountable, and what assumptions your budget is built on. This isn’t just about bookkeeping—it’s about staying in control of your runway and being ready for whatever comes next.

Use these prompts to check your financial foundations:

• What is my relationship with money and does it differ from my cofounders (if applicable)? How will this impact how we make financial decisions?
• Who owns the day-to-day financial operations of the business? Are roles and responsibilities clear?
• Do we have a business bank account—and a backup, in case of delays or market issues?
• Do we have a budget that reflects the reality of our business—including any non-obvious costs (e.g., lab equipment, regulatory fees, seasonal swings)?
• How often will we review cash flow, and how will we make spending decisions?
• What financial tools or advisors might we need to stay ahead of surprises?

Raising capital can be both empowering and distracting. Before diving in, get clear on why you’re raising, what kind of investors you want at the table, and whether your business is truly ready. Fundraising isn’t just about getting money—it’s about forming long-term relationships and creating a rhythm of communication and accountability. If you do raise, you’ll need to juggle investor conversations while still running the business—and prepare for what comes after, like board meetings and updates.

Use the following prompts to assess your readiness and approach:

• Do we need to raise money now, or are there other ways to achieve our next milestones?
• Do we have a venture-backable business?
• What type of investors are we looking for (angel, VC, strategic)? What do we want beyond capital (such as partnerships or advice)?
• Who will lead the fundraising process, and who will keep the business moving while we do?
• How will we evaluate investor fit—values, track record, ownership expectations?
• How are we thinking about our valuation, terms we care about (non-negotiables) and what subsequent rounds might look like?
• If we take on outside capital, how will we structure board meetings and investor communication?

Having a great product isn’t enough. How will people hear about it? Why will they care? And what will make them come back? Your go-to-market (GTM) strategy should reflect who you’re building for, how you want to be perceived, and where you’ll find early traction. It’s also a place to start setting performance expectations—because GTM isn’t a one-time launch; it’s a series of learnings that guide future growth.

As you shape your GTM strategy, consider these questions:

• What do we want our brand to signal to early customers?
• Where are our customers already looking for solutions, and how can we meet them there?
• What marketing, sales, or partnerships will help us reach our audience most effectively?
• What metrics (conversion rates, engagement, referrals) will show us we’re gaining traction?
• How are we thinking about pricing—and how might it evolve as we learn more?

Great startups balance what they’re building with how they’re delivering it. One “stool” represents product, engineering, and design—focused on creating something new. The other stool—product, sales, and support—focuses on getting that product into the hands of real users and understanding how it’s performing in the wild. When these two efforts are siloed, you risk shipping things that don’t work—or failing to adapt when they do. But when they’re in sync, you create a tight feedback loop that fuels smarter decisions and faster iteration.

Use the prompts below to reflect on how these teams can work better together:

• Do we have strong communication between the teams building the product and those supporting or selling it?
• What mechanisms (standups, shared tools, feedback rituals) help us stay aligned on user needs?
• How do we prioritize input from sales and support without derailing long-term plans?
• Are we tracking and sharing the right data—usage, performance, satisfaction—to inform decisions?
• Where are we seeing friction or handoff failures between innovation and delivery?

There are three specific foci in this chapter: How you communicate with various stakeholders, how you handle crises and how to deal with conflict. The prompts below cover each:

Stakeholder Communication:

• Who are the key stakeholders in my startup right now (e.g., team, cofounders, investors, customers), and what do they most need to hear from me?
• Am I communicating with each group proactively and transparently—or only when something’s urgent or going wrong?
• Where might I be under-communicating or assuming alignment without checking?
• Where am I struggling the most when it comes to some communication (e.g., pricing with customers or changing strategies with investors)? How can I get help improving these harder conversations?
• What regular rhythms (e.g., all-hands, investor updates, customer check-ins) can I establish to build trust and keep people informed without overwhelming them?

Crisis Management:

• Have we defined clear, shared criteria for what constitutes a code green, yellow, or red situation—and do team members know how to escalate appropriately?
• Do we have a directly responsible individual (DRI) assigned for different types of crises, and does everyone understand their role when something goes wrong?
• How do we communicate during a crisis—internally and externally—and are we prepared to adjust that strategy based on the severity and impact?
• After our last crisis (big or small), did we do a proper retrospective? What would we do differently next time—and have we updated our plan accordingly?

Managing Conflict: If you are experiencing conflict with a team or individual, ask yourself the following questions, and based on your answers, devise a plan to resolve the conflict or consider asking a coach, therapist or mediator to help facilitate a tough conversation.

• Could there be a situation I am unaware of that is creating this tension?
• How am I complicit in the situation I say I don’t want? [hat tip Jerry Colonna]
• Am I asking the right questions?
• Am I putting off dealing with conflict because I want to win, fear hurting feelings, or some other reason?

As your company grows, so must your leadership. What once required your hands-on involvement will increasingly require you to step back, delegate, and trust others to take the lead. This transition can be emotionally tricky—letting go of control, redefining your role, and helping early team members adapt to new layers of management. Scaling well means learning to separate what needs to get done from how it’s done, and creating a culture that empowers others without losing your core DNA.

Reflect on these prompts as you consider how to scale intentionally:

• What are the key responsibilities I need to let go of in order to lead at the next level and how am I setting up my team for success?
• How will I support early team members as we layer in more experienced talent?
• What rituals or behaviors will help reinforce a culture of trust, innovation, and ownership?
• Where do I still feel the need to be “in the weeds,” and what can I do to create a psychologically safe environment for me to do so?
• Are we building the systems and structure (processes, tools, roles) to grow without breaking?

Founders wear all the hats—and it’s a heavy load. The constant switching between product decisions, team dynamics, investor conversations, and personal obligations can take a toll. Burnout isn’t a badge of honor; it’s a warning sign. Learning how to protect your time, prioritize your energy, and ask for help isn’t just good for your health—it’s essential for your leadership. The most effective founders build a support system early: coaches, therapists, peers, and boundaries.

Use the following prompts to reflect on your well-being and work-life balance:

• What activities or responsibilities drain me the most? What energizes me?
• What do I HAVE to do, WANT to do, and know I am GOOD AT?
• How am I setting (and protecting) time for rest, reflection, and non-work priorities?
• Do I have people—coaches, therapists, advisors—I can turn to for support and perspective?
• What early signs of burnout do I recognize in myself, and how do I respond to them?
• If I were leading this company for the next 10 years, what would I need to change to stay healthy and present?

At some point, every founder faces the question: Should I keep going—or is it time to exit? Whether you’re contemplating an acquisition, acquihire, IPO, or even a shutdown, this is one of the most emotionally and strategically complex decisions you’ll make. It’s not just about what’s possible—it’s about what’s right for you, your team, your investors, and the vision you set out to achieve. The right path forward often requires letting go of ego, revisiting your original goals, and considering what success looks like now, not just when you started.

Use these prompts to explore your exit readiness and options:

• Why am I considering an exit now—and is it coming from a place of strength, fatigue, or something else?
• If I imagine life after this exit—emotionally, financially, and professionally—how do I feel?
• Have I explored the full range of options (e.g., raising more money, restructuring, bringing in new leadership) before deciding this is the best path?
• What are the implications of each option—for my cofounder(s), team, investors, and customers?
• Who do I trust to help me think this through clearly—with both realism and empathy?

Refer to this blog post for more detailed frameworks to process your transition regardless of the path to exit.