The Hiring Playbook I Wish I Had as a First-Time Founder

👋 Hi my name is Roslyn, I’m a 2x founder and executive coach. I help purpose-led founders fall in love with building their companies again. Learn about working 1:1 here.

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Hi there — Happy July! 

I hope you’re balancing out all of your work with some time to rest and enjoy the beautiful weather. 

Remember: you don’t need to earn rest. It’s actually a key ingredient to your ability to level up as a leader, and to navigate your work and life from a more grounded place.

SHIFTING GEARS

After two months of talking about fundraising, we’re shifting gears in July to talk about one of the most complex, important, and rewarding parts of building a startup: building teams. 

For many people (myself included), this is one of the most rewarding aspects of building a startup: creating a culture, hiring great people, empowering them to do more than what you can achieve on your own. 

And, from my own experience as both a founder and an executive coach to founders, it can be the most challenging and emotionally intensive part of building a startup. 

Which completely makes sense because human beings are complex. This means that managing and leading teams is also often the area with the most potential for professional, personal and spiritual growth. 

Personally, as much as I absolutely loved team building at my last startup, I sometimes found it emotionally exhausting, especially because I struggled with parts of me that desperately wanted to be liked and respected, that wanted to keep everyone happy and that held quite high standards for me and my team (and sometimes these parts were in conflict!).

Over the next several newsletters, we’re going to cover both the inner and the outer work of building teams. 

We’ll get into the tactical side — things like how to hire, run 1:1’s and let people go. And we’ll also discuss the personal development side — like how to give direct feedback as a people-pleaser, how to release control in order to delegate as a perfectionist, and how to shift from imposter syndrome to confident, authentic leadership.

Also…

ASK A FOUNDER COACH

I want to help answer YOUR questions on this topic. Feel free to drop any questions about leadership or management — even specific challenges — here. I may feature my response to them in a future newsletter.

Today, we’re starting from the beginning, with how to hire great people. 

Where we go deep on the outer work or the inner work of building a startup.

Hiring in the early stages of your company is one of the most important things you’ll do — and one of the easiest to mess up. In the words of Jim Collins, author of Good to Great, “First who, then what.” That means getting the right people on the bus before you worry too much about where it’s going.

Hiring well isn't just about resumes and interviews. It’s also about self-awareness, energy management, clarity, and courage.

Here’s how to approach it, step by step:

1. GET CLEAR ON WHO YOU ARE (AND WHO YOU NEED)

In the earlier stages, your startup is still an extension of you. Before you rush to hire, slow down and ask:

• What are my unique strengths as a founder?

• What energizes me? What drains me?

• What do I need to let go of so I can step into my next-level leadership?

From there, map out what the business truly needs next. Not just the job title you think you need (e.g., “a Head of Marketing”), but the problem you’re trying to solve. What outcomes do you want this person to own?

EXERCISES FOR DERTERMINING WHO TO HIRE

1. Joyful scope evolution for founders: Audit your time for a week or two and track which tasks are high vs. low impact and energy giving vs. energy draining. Then plot them on a graph to determine which tasks you should be doing yourself vs. hiring for or delegating.

• I’m also a fan of a ‘Zone of Genius’ mapping exercise from Gay Hendricks’ The Big Leap, for a quicker gut check. See below.

• For more on why this step is crucial to building a startup without burning out, check out this newsletter, where I covered this topic in detail.

2. Draw a Future Org Chart

• Visualize your company 12-18 months out

• What roles will exist by then?

• What outcomes must be owned to get there?

• What can be consolidated now, and what needs a specialist?

This helps you hire for the next stage, not just current pain.  

3. Create a Role Scorecard where you define:

• Outcomes: What does success look like in 6–12 months?

• Competencies: What skills/experience will drive those results?

• Cultural qualities: How do they need to show up on your team?

4. Create an “Only I Can” Filter

• Ask: “What are the things only I can do as CEO right now?”

• This clears the way for hires who can:

  • Own critical ops or GTM pieces

  • Free you to focus on fundraising, vision, team alignment

5. Move from "below the line" fear-based hiring (panic!) to "above the line" clarity and ownership (more on that in Apendix A here).

Resource: You can copy my ‘Intentional Hiring for Founders’ worksheet here, which encompasses all of the above activities.

2. HIRE FOR ALIGNMENT, NOT JUST ACHIEVEMENT

A resume is often a lagging indicator. Early-stage hiring should focus less on credentials and more about patterns: how this person thinks, grows, collaborates, and recovers from setbacks.

It can be tempting as an early-stage founder to hire someone that brings credibility to your startup from working at noteworthy companies or attending a prestigious school.

But you’re not just hiring someone to do a job. You’re inviting them into a high-stakes, high-intensity relationship. 

In fact, sometimes the people that are drawn to prominent companies and ivy league schools are more risk-averse and invested in being right or “the best”. You likely need someone who is resourceful, resilient and comfortable with uncertainty, making mistakes, failing and being wrong.

So ask yourself:

• Can I be radically candid with this person?

• Do they share the same values around communication, learning, and ownership?

• What’s their tolerance for uncertainty and failure?

• Are they lit up by the mission?

Radical Candor by Kim Scott advises: be direct, be kind, and don’t sugarcoat what startup life actually looks like.

3. BUILD A PIPELINE, NOT JUST A JOB POSTING

Most great early hires don’t come from cold applications. They come from networks, referrals, and authentic conversations about what you’re building. Finding aligned talent is an active process, not a passive one.

Here’s what you can do:

• Tap your community. Let your investors, advisors, and peers know exactly who you’re looking for — and why it matters. Sometimes investors have a job posting website or newsletter to share hiring opportunities from their portfolio companies.

• Show what and how you’re building. Post content that reflects your company’s culture and founder journey online. People are drawn to transparency and authenticity.

• Always be recruiting. You don’t need to be in “official” hiring mode to plant seeds with people you respect and admire.

• Do your own sourcing. Don’t just post the job description on LinkedIn and wait to see who applies.

  • Set your criteria for a certain role. 

  • Create a candidate pipeline in a spreadsheet (here’s a template).

  • Turn on LinkedIn premium and set aside an hour or two to search for people with the right experience and indications of cultural fit. 

  • Write a compelling outreach message asking them to hop on a call to learn more about the opportunity and company.

If the thought of outreach makes you feel uncomfortable, remember: you’re not bothering people — you’re inviting them into something meaningful.

4. INTERVIEW WITH INTENTIONALITY

Skills can be learned. But qualities like self-awareness, resourcefulness and coachability are non-negotiables, especially in early stages.

Before you interview someone, make a list of the top soft skills you believe are necessary to succeed in the role you’re hiring for and then write interview questions that deliberately test for these skills as well as alignment to organizational values.

For example, if you’re interviewing for self-awareness, curiosity & learning velocity, ask questions like:

• Tell me about a time you received tough feedback — how did you respond?

• What kind of environments bring out your best work? What throws you off?

• What’s something you’ve changed your mind about in the last year?

Listen for emotional intelligence, humility, and growth mindset — qualities that are essential for enduring the volatility of startup life.

5. CREATE A HIRING PROCESS THAT REFLECTS YOUR CULTURE

Your hiring process conveys your culture. Are you clear? Respectful of time? Communicative? Do you follow through on what you say? Do you act in alignment with your company’s values throughout?

The experience you give candidates now sets the tone for your future team. Build a simple but thoughtful process:

• Clear job scorecard (what success looks like, key competencies, cultural qualities)

• Create a candidate pipeline & resume review based on job scorecard 

• A few meaningful interviews (behavioral and values-based)

• Paid project or working session that demonstrates their capabilities, problem-solving and/or creativity (optional, but helpful for key roles)

• Debrief and alignment among decision-makers

Always close the loop. Kindness and professionalism go a long way.

6. DON’T IGNORE THE “ENERGY”

Check in with your intuition or “gut feeling”. How do you feel after time with this person? Expanded or contracted? Energized or drained?

This is your nervous system talking. Your body often picks up on things your mind misses.

Slow down enough to listen, and make a note of it in your interview notes. 

7. CHOOSE TEAM OVER TALENT

In Good to Great, Jim Collins explains that the right people aren’t just “the best” — they’re the best for your team, at this moment in the company’s growth.

Don’t over-index on flashy résumés. Look for partners, not saviors.

TL:DR: The clearer you are about who you are, what you need, and how you want to build, the easier it is to find the people who are ready to build it with you.

WITHIN RESOURCES

If you’re a founder who’s hiring, I created these resources just for you:

• Intentional hiring worksheet for founders: to help you decide what work to keep for yourself and what to hire for.

• Candidate pipeline template: Use this for proactively sourcing candidates.

READ

• While perhaps more known for his books Good to Great and Built to Last, I personally love Beyond Entrepreneurship 2.0 by Jim Collins on all things building teams with intention and heart. Many of the sentiments from this book are reflected in today’s newsletter.

• Scaling People is a practical and empathetic guide to being an effective leader in high growth environments, written by Claire Hughes, an executive from Stripe and Google.

• 1:1 Coaching: If you’d like a partner in navigating the growth edge of team building (or building a startup in general), you can book a free coaching consultation.

• Let’s be friends: If you want to see the BTS of building Within and receive more tips and ideas on building with integrity, connect with me on LinkedIn and Instagram.

• Finally, tell me how you liked this newsletter. I read every piece of feedback.

Thank you for reading and being a part of the Within community.

With love,
Roslyn 💚