How to Hire Product Leaders, by Chief Product Officers!


Rupert Jupp

By Rupert Jupp, Managing Director

As many companies find, product leadership roles can be very challenging to hire. Once they are eventually appointed, many leave prematurely for reasons that are so easily avoided.

At Princedale Partners, we believe that part of the reason for this is a general lack of understanding of how to accurately assess product leaders in interviews. This is understandable, as they often report to and are interviewed by the CEO, rather than a fellow product expert.

This lack of technical expertise gives rise to misplaced assumptions around what the role is designed to achieve and what it is specifically responsible for, which in turn creates the false expectation that it can be a silver bullet hire.

To help solve this, we asked some of the most well-respected Chief Product Officers what questions they ask in interviews to get inside the mind of the candidate, and why they ask them – they are below and we hope you find these useful.

But first, some background: Princedale Partners specialise in three core areas which includes Digital Product leaders at the Chief and VP level. Over the last few years we’ve been retained by clients across the consumer sectors, including Retail, Energy, Fintech, Marketplaces, PropertyTech, Travel and Media.

To ensure product hires are both appointed with ease and teed up for long term success, we invest significant time upfront to tailor the hire to the client’s specific organisation – considering stakeholders, business structure, ambition and attainable goals. We also bring in Chief Product Officers to help in these interviews.

Companies reluctant to invest this time upfront – working on assumptions instead – shouldn’t consider recruiting this role. We often see great product leaders leave businesses prematurely because not enough thought and understanding has gone into the hire from the outset. 

Should you wish to explore the ways in which we can help you scope this role or others in our sweet spot, please get in touch and let’s arrange a conversation.

Rupert Jupp
Managing Partner, Princedale Partners

Question 1:Tell me about a digital product which for you created a “wow” moment, what role did you play in creating it and what was the outcome?
Question 2: What could this product do next to further improve experience, what failures did you have along the way and what did you need to change to make it work?

Question 1: What is the best team you have worked with and led, and why?

Looking for their understanding of what good looks like, their role as a leader, the relationships between team members and what they did to sustain it.

Question 2: What is the most challenging situation you have found yourself in, what did you do and what were the results?

Looking for the depth of issue they have a had to handle, how they analysed it often reveals depth of affinity to data, or organisational awareness and again their leadership approach.

Question 1: Describe what your current company does.

Can they really clearly articulate who the customer is, what the need is and how they solve that need.

Question 2: How do you deal with conflict? 

I look for people who are obsessive about transparency and can easily articulate. If they can’t, no hire.

Question 1: What was the scope of your previous Product role?
Question 2: How strategic versus execution focussed have you been?

Do they evidence getting their hands dirty, or do they just sit and define a vision and get their team to execute?

Describe a scenario in our business and describe what dimensions you would consider and what would inform your scoping & decision making approach.

This is a great one to test out how logical and rational the person is – and how the individual can deconstruct how to deliver value in the soonest possible time.

How do you know a product is well designed?
How do you practically translate a customer need into code? What is a product development process that works?
Give me some examples of really tough product decisions and how they impacted the P&L.

The role is hard to recruit because you need to balance three highly different skills that rarely exist in a single person:

  1. Design – to know what great looks like, to have empathy with customers to uncover their real unmet need.
  2. Technology – because you need to translate that very creative output into something very clear that a coder can code
  3. Business – because you need to show to the business how the thing fits with the company’s purpose and will make financial sense