How would you evaluate a product before joining a company as their PM?

Hello Friends,

I’m in talks with the COO of a company about joining them as their Product Head. I’ve got a long list already, but what questions would you ask to gather data so you can evaluate where the product is today, identify potential opportunities for the future, identify potential red flags and risks.


  • B2B company working with SMBs.
  • Has been around for ~10 years, bootstrapped and profitable,
  • ~80 employees/10 people on design/eng team. That entire team would report to me.
  • CEO had been de-facto product manager but realized he doesn’t have enough time to do that justice.

@NatalieSmith, What makes this role interesting? This is the question you should ask yourself and the person your into talks with. Well, that’s where you can start from.


I’d ask the COO what their strength is — are they an executional, strategic, or visionary leadership style?

  • None of these are bad, but if you’re the Head of Product, you need to know if you’re the right counterweight to them. 2 visionary leaders won’t go well, and 2 executional leaders will work for awhile, but burn people out without a ‘why’
  • Then go ask others who report to the COO what role they think the COO is, and what roles they play. Does the COO have a good sense of their own strengths?

Similar to the above, I’d also ask for a recap of the last exec meeting — it’s helpful to know if that meeting is combative, if decisions actually get made after discussions, etc. As a Head of Product, those people will be your peers, not your team, so your relationship with them is going to be paramount.


I forget who mentioned this before, but a walkthrough of the last feature release from idea inception to release to follow up is a good way to hear how the sausage is actually made. Definitely helps to ask about surprises and learnings along the way.


I’d ask about his personal / company values to figure out if I can work with him.
And I’d ask about what part of the product process he’s planning to hand over to you 100% vs still be involved in. Realistically, he won’t give you everything at least in the beginning.


@Natalie, remember that the first product manager always dies on a hill. :wink:


@Heather, that’s my favorite.

@Ahmad, I literally just did that but would love to hear more about this from you

@Donovan, @Mario, @Samantha, Thanks for your inputs, really helpful and got me thinking. Thanks


This article is a fun one.

I’ve been there a few times
For me it comes down to

  • where is the company in their growth curve
  • what type of product work do they need for the foreseeable future
  • autonomy

When I say type of product work I refer to

  • feature work (enhance and develop new features)
  • growth work (getting the most out of the existing product - retention, monetization acquisition)
  • PMF expansion work (adapt product to new markets or new product lines)
  • scaling product work (infrastructure work to be able to deliver value at scale)

@Ahmad, this article is absolutely incredible. Thank you. I just came off a disappointing end to a first PM experience and I wish I had read this 18 months ago.
Still would have done it, and still will pursue this opportunity, but there’s great content in here to help keep my eyes open for


@Ahmad, Great article. I totally stumbled into a first PM role and yeah, so much I wish I knew.


This post by Casey Winters can be helpful to uncover some risks:


Failure Mode #2: Does the Expertise Match the Type of Product Work Needed?

The red flags for me when I read the background @Zachary Cohn

  • are you the first PRoduct leader? Why has it been 10 years ? That’s too long. Where are the dead bodies?
  • What is the vision for the next period?
  • How much does the CEO see himself getting involved in the product?
  • Where does he see the biggest challenges in the product and team going forward ?
  • How involved is he currently with that 10 person team? Is he involved in issues directly or is is he doing a more supportive style

If he’s personally still doing PM work and not continuously letting go with his team what makes you think he’ll let go with you


Some good answers here.
My 2 cents as I just had an interview with a CEO of a similar company this week for a head of product role (managing 1 PM and growing a team). Figure out phase of the product/company:

  • What’s the strategy for the next 1-2y? Is it geographical expansion? Segment expansion? (best slide I know of regarding product strategy is attached from Tami Reiss)
  • What’s the biggest challenge for the company regarding that strategy? Is that challenge marketing oriented? sales oriented? product oriented?
  • What’s the unique value of the product vs. competition and how does that come in with regards to the strategy?

Figure out how the COO sees the role:

  • What’s the biggest challenge of the product and why is it a challenge?
  • What do you feel needs to change with regards to how the company does product management?

Figure out the COO’s view of how to give you decision autonomy

  • Which decision autonomy level would the COO not give up ever and which decisions autonomy levels will he give to you. And for which of those would he still want to be part of the process etc. It’s always a grey area so this subject is the most difficult to figure out and you’ll never get a direct answer. You need to use your spidey senses for this one. Great slide by John Cutler about decision autonomy levels here

Ask many follow up questions to get beyond the buzzwords and understand what those buzzwords mean to the COO. Ask for real examples that happened in the past.

1 Like

This thread made me think of this article which I loved where April Underwood talks a lot about joining Slack when the previous head of product was, well, the CEO, and how to manage that transition

This topic was automatically closed 180 days after the last reply. New replies are no longer allowed.