Don’t Start Hiring Until You’ve Done This

Hiring isn’t about picking the best résumé. It starts way earlier: figuring out what you actually need today, and who can grow with you tomorrow.

If I were hiring for a new role today, here’s the foundational work I’d do first.

Before You Post the Job, Figure Out What You’re Actually Hiring For

Too many founders/hiring managers hire to solve their immediate pain.

There’s a “job to be done” that isn’t getting done, so you react by writing a job description, posting it, and immediately diving into candidate sourcing.

Figuring out what you’re hiring for should take just as long as recruiting for the role.

Before you even think about posting on LinkedIn, can you answer these questions?

• New skillset or bandwidth boost: Are we hiring to import a new skillset or are we replacing an existing skillset to increase bandwidth for the rest of your team?

• Full-time or part-time: Is this a full-time role or a project that a part-time person can solve?

• Structured role or builder: Do we have the right systems and support in place for this hire to succeed? Or are we hiring someone to build the plane while flying it?

• Which tradeoffs: What tradeoffs am I willing to accept like seniority vs. cost or specialist vs. generalist (because one person can’t do it all)?

Nailing these questions and understanding what you’re looking for will help you find the perfect candidate and make the rest of the hiring process a lot easier.

Know Thyself before you Know Thy-others

You can read a dozen books on interviewing (good starting points are Who: A Method for Hiring, Topgrading, and The Best Team Wins). But…

These aren’t just feel-good values that you put on the wall. They should define a shared vision of life and work.

An Example: LeagueSide

At LeagueSide, we spent several years figuring out the core values that all of our employees shared.

Here were our (s)core values and yes, we called them score values because we did the sports ball:

• Growth mindset: We get better every single day

• Scrappy: We find a way to get things done

• Ownership: We have an owner’s mentality, not a renters’

• Ego-free: We like the right idea, not my idea

• Customer-obsessed: We always do what’s best for the customer

• Team player: We’re the teammate we’d want on our team

These might seem simple, but it took a lot of time to narrow these down and fully define how these values play out in day-to-day work.

After nailing these values, all of our behavioral questions focused on a value. For example:

• Growth mindset: “What’s something you’re passionate about or taught yourself recently?”

• Scrappy: “Tell us about a time when you were scrappy.”

• Ownership: “Tell us about a project where things went sideways. What role did you play in the outcome?”

• Ego-free: “Describe a time you were wrong. How did you realize it?”

These weren’t trick questions—they were mirrors. They helped us look in the mirror and figure out who we are, what we care about, and who we wanted on the team.

Hire for Now, Plan for Later

Yes, you’re hiring to solve today’s burning problem (YAGNI fans, this one’s for you). That’s valid and smart.

But the best hires don’t just put out fires. They grow into fire marshals (I know nothing about actual firefighting).

Here’s the trick:

When you hire someone, think about their trajectory within the company. Map out:

• What will this role evolve into as the company scales?

  • In the interview: Align the role’s trajectory with the candidate’s ambitions

• Will they manage a team? Own a function? Become a specialist or stay a generalist?

  • In the interview: “Given that the salary would be the same, would you want to pursue people management (VP Engineering) or become an expert individual contributor (Chief Architect)?”

• What will success look like after they’ve been in the role a year?

  • In the interview: “What KPIs or metrics have you owned previously?” Does this align with the role?

This doesn’t just help you get clarity. It helps candidates opt in or out. When the right person sees a future at your company, they will go all-in and stay for the long haul.

Talk to People Already Doing the Job

Once you’ve defined the role and landed on what you think the job title is, do your research.

Not the kind you do by Googling “startup PM job description” or asking ChatGPT “what even is a PM?”.

🔍 How:

• Reach out to 5–10 people on LinkedIn who currently have the title you're considering and ask them for advice

• Be honest with them about the company stage and the details of what you need

• Listen more than you pitch

🧠 What to ask:

• What KPIs/metrics do you own?

• What does your day-to-day look like?

• Who do you report to? Which departments do you work most closely with?

• What would you change about your current role or how your role operates within your company?

• What are your biggest challenges in the role today?

• If you were hiring someone on your team, what would you screen for?

Repeat this process across industries because the same job title often means wildly different things depending on the context.

An Example: Product Marketing is not Product Marketing is not Product Marketing

At a healthcare startup, product marketing might be deep in compliance and GTM.

At a B2B SaaS startup, they might be doing win/loss interviews, positioning work, or owning sales enablement.

At different sizes of companies, they may report to marketing, product, or sales.

All of these are very different roles that work very different muscles. Talk to several product marketers at different stages to help you narrow in on who you should be reaching out to when recruiting.

Why This Matters

Getting the job title right for the right industry will pay infinite dividends once you launch the recruiting process. It is arguably the most important part of the process. Here’s why:

When your job description actually resonates with people in the role, candidates self-select in. They think, “Wait, this person gets it.” 

That’s a huge unlock, especially in roles where responsibilities shift depending on the company size, team maturity, or even the industry.

So Did it Work at LeagueSide?

Duh. We hired so many all stars that may not have had the exact experience we needed at that moment, but they grew with the company and invested in us as much as we invested in them.

For that, I’ll forever be grateful.

Thoughts, Feelings, Emotions?

I’d love to hear from you. What has your hiring experience been? What are your biggest challenges? Any hiring tips?

Or just want to say hey? Ping me!