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.
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.
@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
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.