The Problem with Traditional "Hiring"

A Humble Guide (and Checklist) for Hiring Right.

“Hiring is a leader’s most important job. And it’s the easiest to get wrong.”

Every exec says hiring is a top priority. But ask them who’s on their bench, what skill sets they’re missing, or how long it takes to fill a critical role—and many fumble through an answer.

This post is for leaders who want to hire better. Not just faster or cheaper—better. The kind of hiring that scales, adapts, and lasts.

This is a detailed blog. I’m sharing some secret sauce and a link to one of my tools. (scroll down for the link the link at the bottom of the post!)

No time to read? Catch the podcast version below.

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<My Thoughts. My Own Only>

Quick reminder: the above are my thoughts. No one’s paying me to write this—not my employer, not anyone.

I've worked in small startups, mid-size firms, and big tech over the past 25+ years. I ask questions, listen closely, and form my own opinions.

You don’t have to agree. I welcome smart debates. I write this to learn from smart people, regardless if they agree with me or not.

Oh…and if you like this, subscribe below!

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Hire Right—Don’t Just Hire Fast

Hiring the right person slowly is far better than hiring the wrong person quickly. Trust me—I've learned this the hard way.

• Bad fits are expensive — not just financially, but in lost time, morale, and team momentum.

• Training and onboarding take time. If the fit isn't right, you're doubling (maybe tripling?) when they leave or need replacing.

• Culture matters. A wrong fit can poison a team dynamic faster than you think.

So: be deliberate, involve your team and focus on values and mindset, not just skills.

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Here’s my hiring philosophy—developed across four startups, four scale-ups, and more blindspots than I care to admit. I look for mutual fit across 3 dimensions:

1. Aptitude (Relevant & Learned)

• I don’t care if you massively failed at the previous company—I care what you’ve learned. Repeating the same mistake in different roles isn’t growth. It’s a pattern.

• We care about your “How”. So when we ask about past experiences, we’ll want to know: 1) What did you want? 2) Why didn’t you get it? 3) What did you learn?”

“Experience is what you get when you didn’t get what you want” — Randy Pausch

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2. Attitude (Hyper-Realistic & Creativity Smart)

• Intelligence is the ability to adapt to change.

• We look for people who have won of course AND also for people who’ve failed, regrouped, and won.

• Tell me about a plan that fell apart—and how you still moved forward.

“Fall seven times, stand up eight.” — Japanese Proverb

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3. Fit (Company, Team, Then Individual)

• We’re a high-performance sports team, not a family.

  • We’re all in the “people business”. You will get to spend most of your day with your team. Spend time to determine a strong fit with the people. The people you get to work with matters as much (if not more) as the logo of the company you join.

• We’re building around team goals, not individual wins.

  • We don’t hire “brilliant jerks”. We value personal excellence—but it has to lifts the team. No solo heroes. If your success doesn’t help the team succeed, it doesn’t count. Collaboration, communication, and shared accountability matter more than titles or egos. We win together or not at all.

• We think long term. My best hires think in decades, not quarters.

  • I hire with the idea that I’ll get to work with them for 10, 20 years or longer.

  • I’ve worked with and hired many of the same people over decades, across different companies. (I consider that part of my “secret sauce” actually!).

“If you want to go fast, go alone. If you want to go far, go together.” — African Proverb

How Am I Supposed to Hire For That?!

Good question. I’m happy you asked ;). Good hiring is not magic. It’s process. Here is the the 6-step method that’s worked for me. I hope it can work well for you too!

Step 1: Align on Role, Rubric and Questions

I had the opportunity to hire and scale large, multi-disciplinary teams at Microsoft and Google—both during periods of hyper-growth. These companies taught me how to assess talent systematically and at scale.

The model I use now is a hybrid of the best ideas from those systems—with a few of my own learnings layered in.

Here is what a “Rubric” looks like for a Chief Product Officer or Product Leader.

It’s designed to test at least 6 capabilities:

1. Product Insight
   → User empathy, end-to-end thinking, product design under constraints

2. Analytical Ability
   → Market sizing, data interpretation, defining and using success metrics

3. Leadership
   → Cross-functional influence, resilience, stakeholder alignment

4. Craft & Execution
   → Prioritization, MVP strategy, go-to-market awareness, technical depth

5. Strategic Insight
   → Growth frameworks, monetization strategies, market positioning

6. Behavioral Fit
   → Past examples of conflict resolution, accountability, team impact

The above can easily expand to other roles in tech but I’ll let you come up with your own for each of the discipline you’re hiring for.

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Step 2: Build Your “Question Bank”

It’s always useful to have a set of “go to questions” the team can use. It makes the interview more systematic. It also will allow to compare notes when evaluating candidates’ answers to the same questions. Here are some examples:

1. Product Insight

• "Tell me about a time you built something users didn’t initially ask for—but ended up loving."

• "Describe how you balanced user needs with technical or resource constraints."

2. Analytical Ability

• "How would you estimate the market size for [product or feature]?"

• "What’s a metric you chose to track success—and how did it influence your roadmap?"

3. Leadership

• "Tell me about a time you aligned multiple teams with conflicting priorities."

• "Describe a moment where you faced major pushback—what did you do?"

4. Craft & Execution

• "Walk me through how you defined the MVP for a new product or feature."

• "What’s a time when your execution plan didn’t go as expected—how did you adjust?"

5. Strategic Insight

• "Tell me about a strategic bet you made. What was the rationale and the outcome?"

• "How did you position your product against competitors?"

6. Behavioral Fit

• "Tell me about a conflict you’ve had on a team—how did you handle it?"

• "When have you had to hold yourself accountable for a failure?"

You can manage the whole thing in an online sheet (and even ask your team to add some of their favorites!).

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Step 3: The “Hiring Grid” (My Secret Sauce)

Alright—you’ve got the rubric. You’ve defined the role. You even have a list of precise questions every interviewer should ask.

Now what?

Before you post a job description, pause. Most leaders jump straight to writing JD copy or pushing roles to recruiting. That’s a mistake.

Here’s what I do instead: I build what I call the Hiring Grid. It’s the blueprint. A pre-job-description exercise that defines what great looks like—before we write a single line of the JD.

The Hiring Grid forces clarity. It aligns stakeholders. And it saves everyone time.

Here’s what you should have answers to:

1. What keywords appear in the best candidates’ resumes and profiles?

   1. Examples include: Analytics, Data, GTM, Leader, Sales, Partners, Customers…etc

2. What professional attributes are we looking for?

   1. Examples include: Leads without a title, gets stuff done through others, influences effectively, thrives in ambiguity, both coach and player…etc

3. What personal attributes matter most?

   1. Examples include: Detail-oriented, entrepreneurial, energetic, self-starter, collaborative, mature focus on impact over activity, self-motivated…etc

4. What will this candidate’s primary responsibility be?

   1. Examples include: Drive cross-functional programs that scale GTM strategy and execution…etc

5. What will their key deliverables be?

   1. Examples include: Shipped initiatives, operational frameworks, organizational clarity…etc

6. Who will they work with the most?

   1. Examples include: Customers, Product Managers, Sales, Partners…etc

7. Who will they work with the least?

   1. Examples include: Engineering, QA/Test (though technical appreciation is still valuable)…etc

8. How do we measure success in this role?

   1. Examples include: Leads complex programs to completion—early and under budget. Brings structure, drives change, and adds clarity to chaos…etc

9. Examples of great candidates?

   1. Insert LinkedIn URLs of 2–3 ideal profiles…etc

10. What companies might they come from?

    1. Company X, Y, Z…etc

11. Any companies we prefer NOT to hire from?
    Yes. Despite overlap in skillsets, past hires from Company X, Y, Z…haven’t been the best fit for this role.

Get this right—and everything downstream (job description, interviews, onboarding) runs smoother, faster, and with far fewer surprises.

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<Subscribers Only>

I’ve build an easy-to-use online spreadsheet with the above. If you want access to it, register here.

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Step 4: The Hiring Process

By now, you’ve got clarity. You’ve built the Hiring Grid. The Job Description can be built (I hope you’re using templates and AI for that!).

Now comes execution—and it has to be as disciplined as your product launches.

I run the hiring process in three phases:

Phase 1: Selection

The hiring manager and recruiter sit down with the completed Hiring Grid.
We agree on must-haves, nice-to-haves, and no-go’s.

No “we’ll know it when we see it” nonsense.
If we can’t define what great looks like, we’re not ready to hire.

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Phase 2: Initial Screen

The recruiter sources three promising candidates who match the Grid. The hiring manager conducts a 15–20 minute fit screen with each. This is not a deep-dive on product. This is about:

• Values alignment

• Cultural fit

• Communication style

• Motivation

You’re looking for vibe, not validation. The real interview discussions come next.

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Phase 3: Interview Loop

Candidates who pass the screen go into a structured loop of five interviews.

Each round maps to your rubric capability:

1. Product Insight

2. Analytical Ability

3. Leadership

4. Craft & Execution

5. Strategic Thinking

Order doesn’t matter. Consistency does.
Interviewers are aligned on what they’re evaluating—and use the structured rubric to assess.

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Step 5: Decision-Making

Once three candidates have completed the loop, convene the Hiring Committee.

This is not a scorecard readout. It’s a pattern recognition conversation.
What did you learn about each candidate across dimensions?

Look for signal consistency—or contradictions. Surface blindspots. Don’t rush.

If two or more finalists look strong, bring them to your division leader, GM, or CEO for a final conversation (this is “as appropriate” interview I was referring to earlier).

This isn’t about rubber-stamping. It’s about alignment on expectations, chemistry, and the leadership bar.

Bonus: Hiring Is Also Training!

The hiring process doesn’t just filter talent.

It allows you to federate your team around what what excellence looks like. When they proudly go through the process and hire the right fit, they walk away clearer on what great leadership means at your company.

You’re doing more than just building a team. You’re reinforcing a standard.

This is why systematic execution matters.

This last “unexpected” benefit will be your team’s “X-factor”. And by that, I don’t mean the show. I mean something hard to teach or quantify but that significantly will amplify your team’s impact.

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Step 6: Reference Checks

Let’s be honest: reference checks are awkward.

They’re often treated as a formality—or worse, a rubber stamp. But they’re actually one of the most high-leverage steps in the hiring process. Here’s how to run reference checks.

1. Provide Context
   Don’t open with “Tell me about them.” Instead, explain the role and responsibilities, the KPIs (what they deliver and how they lead) and Who they’ll work with most—and least. (Hint, Hint…use the Hiring Grid!)

2. Get Oriented

   Understand the reference’s POV. Ask:

   1. How do you know the candidate?

   2. What was your working relationship?

   3. How often did you interact?

3. Look for Patterns
   Now ask questions that uncover real insight:

   1. What’s their superpower?

   2. How do they handle conflict?

   3. What advice would 10x their impact?

   4. Why this job, now?

   5. What might they fear in this role?

   And don’t hang up before you ask my favorite reference question of all time:
   “What didn’t I ask that I should have?”

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I hope you found this post and hiring grid useful.

I will be writing next about coaching teams and retaining talent. I’ll cover concepts like:

• “Zone of Excellence” (TLDR; the job of a leader is to understand his teammates’s “superpower” and create the best environment for them to exert it)

• “Organizational Design” (TLDR; don’t design around existing structure and org chart. Design around needs and ambitions).

If you have any thoughts on these topics, please drop them in comment.

And if you liked this, remember to subscribe and share it with friends!