When you’re confident you know exactly who you need to hire…

…it’s often because you’ve already filled in the blanks in your mind:

• “I need a Head of Marketing.”

• “I need a senior designer.”

• “I need a technical cofounder or engineer.”

But early-stage founders rarely mis-hire because they choose the wrong person. They mis-hire because they choose the wrong problem to solve.

The danger isn’t uncertainty — it’s false certainty.

You’re not alone in this. Everyone gets swept up in confidence, urgency, vibe, and fear of falling behind.

The truth about hiring for the right problem

You don’t hire a role. You hire a solution to a specific next milestone.

The issue is that most founders define the role before they define the milestone.

They think:

“This is the person I need.”

When the real question should be:

“What milestone am I trying to reach, and what skill set gets me there most effectively?”

Because “Head of Marketing,” “Growth person,” and “Product marketer” are not interchangeable. They solve different problems, at different moments, with different outcomes.

Until you define the milestone, your role definition will be based on guesswork, familiarity, or the last good conversation you had — not the business need.

A few grounding prompts

These help uncover whether you’re solving the right problem, or just hiring a role you’ve latched onto.

1. What is the next milestone I need to reach in the next 60–90 days?
If the milestone is unclear, the role is premature.

2. What outcome must this hire create for that milestone to happen?
Outcomes reveal skill sets. Titles confuse them.

3. What thinking have I already done to clarify the problem?
You don’t need to know everything — but you can’t outsource all the thinking. You need enough perspective to guide direction, decisions, and judgment.

4. Am I choosing this role because I like the person or because their skills map directly to my milestone?
Founders get blinded by charisma, confidence, pedigree, and “startup energy.” Don’t mistake good energy for good fit.

5. Could a consultant, contractor, intern, or part-time specialist achieve this milestone better than a full-time hire?
Not every milestone requires a salary. But — and this is important — avoid the opposite trap: Don’t force your product into templates, tutorials, or generic advice that doesn’t fit your use case. Templates are a bridge, not a long-term solution.

6. Do I understand the difference between the roles I’m considering?
Example (and this matters):
A growth marketer ≠ social media manager ≠ product marketer ≠ lifecycle marketer ≠ SEO specialist.
Choosing wrong wastes months and money.

These questions force clarity. They bring you back to the business problem — not your assumptions.

A moment when founders choose the wrong role

A founder thinks:

“We need a Head of Marketing.”

Why? Because growth feels slow, the title sounds impressive, and the candidate seemed sharp.

But the real milestone is:

• “We need 50 early beta users,” or

• “We need better messaging,” or

• “We need a converting landing page.”

A Head of Marketing doesn’t solve these problems. A generalist growth contractor or a product marketer does.

This is how founders hire the wrong problem.

A moment when founders choose the right role

You’ve built your website and flows using templates. You’ve validated demand. You’ve hit the limits of DIY design or no-code patterns.

Now:

• your team is blocked without UX direction

• you need custom UI for the next feature

• your brand needs consistency

• you’ve created mood boards, examples, and clarity on what the experience should feel like

This is when a designer — contract or part-time — is the right hire. Not because “a designer would be nice,” but because your next milestone requires custom design thinking.

Templates → validation → clarity → specialist.

That’s the correct order for software founders.

Before you hire anyone, do this work

This is what ensures you’re hiring for the right problem:

• Document your current process

• Clarify what’s working and what isn’t

• Identify the decisions only you can make

• Define the milestone and the outcome

• Collect inspiration, examples, flows, or benchmarks

• Understand where templates start failing you

• Make sure the problem is clear enough that someone else can execute

You still need to hold the vision. You still need to know the direction.
You don’t need technical or marketing mastery — but you do need perspective, clarity, and judgment.

Evaluation

Even when you get the role right, evaluation matters. Early hires must be able to:

• explain complex ideas simply

• translate their craft into language you understand

• articulate why their work matters

• connect their work to your milestone

• ask clarifying questions that show alignment

• avoid hiding behind jargon

If you’re confused and they can’t clarify — that’s a red flag. Communication is a skill. If they can’t communicate clearly to you, they won’t collaborate well with your team.

(We’ll go deeper into evaluation in its own question.)

A calmer way to move forward

Pause.
Name the milestone.
Define the outcome.
Identify the problem the business must solve next.
Then choose the role that best solves that problem — not the role you assumed you needed.

Clarity first. Role second.

When you hire for the right problem, the right person becomes obvious.