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LeadershipEeke de Milliano (Retool, Stripe)

The Product Talent Portfolio

Build a team of complementary spikes instead of clones of yourself, and hire specifically for your gaps

Difficulty
Moderate
Time to result
~months to results
Steps
3
Confidence
91%

Managers naturally hire in their own image because they value and can assess their own skill sets — but the strongest teams balance a talent portfolio of complementary spikes so the whole is stronger than any individual. Eeke de Milliano runs a recurring self-audit of team strengths and weaknesses and hires deliberately against the weaknesses, pushing leads to hire people who don't look like them.

Origin

Eeke de Milliano, Head of Product at Retool, framed under her broader belief that management is about managing portfolios and funnels.

Core principles

  • 01Managers default to hiring their own image because those skills are easiest to detect and value
  • 02A team of identical spikes is weaker than a team of complementary ones
  • 03Homegrown PMs and outside-hire PMs each bring something the other lacks — balance them
  • 04Balance must hold within every pillar of the org, not just in aggregate

How to run it

  1. 1

    Audit the team's strengths and weaknesses

    Every six months, chart the team you have today and write down all its collective strengths and all its weaknesses as a group.

    Pro tip Make it a fixed personal ritual on a cadence so gaps get named before they calcify.

  2. 2

    Hire specifically against the weaknesses

    Target open roles at the identified gaps rather than adding more of what you already have. Push leads to hire people who don't look like them so balance shows up everywhere.

    Pro tip Balance homegrown PMs (deep product knowledge, strong cultural carriers) with outside hires who bring conventional PM rigor from other companies.

    Watch out Resist hiring in your own image — it feels comfortable and assessable but produces a lopsided team.

  3. 3

    Balance archetypes across every pillar

    Mix execution machines with visionaries, and ensure each product pillar has the complementary skill mix it needs rather than concentrating one type in one place.

In the wild

Retool's homegrown vs. external PM balance

Eeke de Milliano deliberately balances PMs who grew up inside Retool — who deeply get the product and carry the culture but may not have seen PM done elsewhere — against PMs recruited from other companies who bring traditional PM rigor but lack the native Retool 'vibe.'

The blended team covers both product depth and process rigor, making the whole PM team stronger than any single profile could be.

Common mistakes

Hiring in your own image

Because you value and can best assess your own skills, you clone yourself onto the team, producing a group that all spikes in one area and is fragile everywhere else.

Balancing only in aggregate

A team can look balanced overall while individual pillars are lopsided; skipping per-pillar balance leaves specific parts of the org weak.

Is it for you?

Best for

Engineering and product managers building or reshaping a team of five or more

Not ideal for

Tiny teams of one or two where you must hire generalists for coverage, not portfolio balance

From the transcript

it's really tempting as a manager to build a team in your image because you understand their skill sets and you value those skill sets

56:00

the best product teams in my mind have really figured out how to balance the you know the talent portfolio

56:30

I really like to balance product teams with homegrown product managers who really get the product

57:00

I always push the leads to sort of hire people who don't look like them so that you know we have balance everywhere

58:00

I do a little personal exercise for myself every six months where I like sit like sort of chart out the team that we have…

58:00

From the episode

How to foster innovation and big thinking

Eeke de Milliano (Retool, Stripe)