Jessica Zwaan discusses hiring for culture fit in a customer-driven engineering team. Jessica has a background in people, operations, legal and talent and worked as an advisor and mentor to many different start-ups, including Soundcloud, Allplants, Aula, Wonder and MyTutor. She is currently the Chief Operating Officer at Whereby, a fully remote video conferencing platform that works directly with developers who are developing any kind of application, website, tool, or product that requires video conferencing or meetings built into their software.

Jessica Zwaan
Hi Jessica, welcome to the CTO Craft Spotlight Q & A. Thank you for speaking at the CTO Craft May 2022 MiniCon. Firstly, how do you think tech leaders even begin to look at their culture?

In my view, you’re building, or should be building, two products. One of them is the product you’re selling to your customers, and the other is the one you are selling to your candidates.

If you consider the culture and your team or your company as a subscription product. Every month, all your team members choose whether or not to continue to subscribe to that work experience, employee experience, culture and team, etc.

If someone decides to hand in their notice, they essentially sever that subscription with your product. So, when you’re taking that mindset, it is generally much easier for engineering leaders, product leaders and commercial leaders to think about how to build a team when they’re wearing that product hat.

That’s a really interesting way to look at it. So, how does an organisation stand out when it comes to culture?

If we’re thinking about your culture as a product, then all the different companies out there form a marketplace and employees have this vast, vibrant marketplace full of different types of cultures and companies that they can go and work for, and yours is just one of them.

So, the best way to stand out in the marketplace is to have an opinion, know what kind of company you’re building, and be doing a really good job. That means you’re going to be attracting the types of people that will help you strategically, and it also means that you’re going to be retaining the kinds of people you want to continue to subscribe to your culture because they are a good fit for you.

Do you think an organisation’s culture is made up of more than just values, and if so, what does it include?

Values are a really interesting point because values are just one part of what a culture is, especially when you’re just thinking about things like empathy, values, integrity etc., as these things are very subjective. People have different opinions about what they are.

The way that I like to think about it is again using this culture as a marketplace analogy:

  • Is the person we are speaking to a part of our key market?
  • Is this the person we want to attract and subscribe to our product every month?
  • Is this the kind of person that will attract other people to subscribe, which will help our team get value out of their subscription?
  • Is this the key demographic; is this the right person for our subscription products?
How would you suggest that organisations discover these things?

The first thing is to consider ‘What kind of company am I actually trying to build?’

You need to understand what you are trying to build in this marketplace of culture, and it’s a mix of many things:

  • Organisational goals and objectives
  • Your product and market
  • Values and shared principles
  • Your ways of working
  • The performance and behavioural expectations of your team

These things all encompass what organisational culture you are trying to build. Different individuals will be attracted to different organisational cultures as there are many things that some people might find really difficult or uninteresting in your cultural marketplace, but they might love in someone else’s.

For example, I worked at Goldman Sachs, which is a very specific culture. Goldman Sachs is obsessively good at refining the kind of culture they are building, and you know what you’re going to get; some people love it, and some people hate it, and that’s totally fine. Goldman Sachs knows who they are in the marketplace for culture.

In your opinion, how do you work out who will be attracted to your culture?

If you think we’re just a nice place to work, or you feel you have “taken” the best parts of other cultures and workplaces you’ve experienced, you need to be more clear about what you are hiring for cultural fit. Again, going back to the marketplace, consider who will walk past your market stall and say, ‘This is the place for me, and I want to subscribe here.’

To do that, you need to answer a series of questions and be opinionated to make some decisions. Of course, there are no right or wrong answers to many of these things, but consider if you are trying to build a highly skilled company with high volume? As it’s challenging to do both of those things, you need to have an opinion.

For example, are you looking for people with PhDs, or are you looking for boot camp graduates, or are you looking for a really lean small team with high impact, or are you looking for a really broad and large team?

  • Are you flexible and T-shaped?
  • Are you highly specialised?
  • Are you central or distributed in your decision making and how transparent are you going to be?

The point is, you have to understand all of these trade-offs so that if you bump into somebody along the way who sees your high skills, lean remote team and says, ‘I’ve got a bit of broad experience, I really love working in an office, but I love your product, so will I fit?’ you can say they are not the right fit for you, as you because you’ve decided on all these trade-offs and what’s the right fit for you.

So, how would you design your organisation’s trade-offs to review whether the person is a member of your key market?

We have six organisational design principles at Whereby:

  1. Biased towards top talent – this is what we do at Whereby to consider the trade-offs because we’re biased about top talent, as we want the top talent from the marketplace in every area of the organisation.
  2. Lean – we don’t hire for the sake of hiring, and we don’t hire anyone in administrative roles.
  3. T-shaped – we want people to have the right T-shaped roles.
  4. Flexible – it’s really important these principles work well together. For example, if someone’s hyper-specialised in web RTC, which is what Whereby is built on, but has no interest in flexing, unfortunately, it will be a no from us. And the reason is that our org design principles require this flexibility in this T-shaped operating model to be successful. That’s what keeps the rest of our team happy and thriving, so we can’t break away from that.
  5. Diverse and inclusive – we make sure that this is the heart of everything we do.
  6. Tech-enabled – this is really useful for other teams outside of engineering and for us means we don’t hire people whose job is to fill in spreadsheets; if there’s no clear path to something more engaging, more flexible, more T-shaped with more career progression. If this is the case, we’re not going to hire that job.

This is really what drives all of our decisions alongside our values and we consider this when opening new roles, promoting, changing organisational or operational process design. Everything. This is the fabric of so many of our leadership decisions.

These principles are really helpful, but can they be applied to other organisations?

In terms of your own company, think about these trade-offs and figure out who your product is and who you want to be buying it. There’s no right or wrong answer, only a right or wrong answer for your culture and organisational design ambitions. Don’t copy what other organisations do because they will have their own market stall they’re building. Have your own truth and stand by that.

One of the areas to think about for a trade-off is employee skill versus leverage. For example, high skill is like PhDs, and high leverage might be the individuals who touch 20% of your revenue every time they do something at work.

What this helps you do now, and aspirationally (for example, where you want to be in five years), is figure out what is actually part of your culture. This is how you want to attract people and what you should be assessing for.

Really think about, what are the essential organisational characteristics of your team today and in five years and are you assessing these throughout the process or are you just focusing on values etc.

How would you suggest an organisation uses its principles in the hiring process?

Work backwards through your principles to see if someone is a member of this key market.

For example, ask in your interview process:

  • Diversity and inclusion: ‘What does someone who cares about DEI look like?’
  • Sensitive situations with honesty: ‘When was the hardest time you’ve had being honest?’
  • Safe feedback: ‘How do you nurture an attitude of psychological safety around feedback?’
  • Having constructive conversations: ‘At what point do you find you’re not in dialogue, or that you’re not talking about the original issue at hand?’

Make a big list of interview questions that align with your organisational principles and your values. Think about what a good answer would be to your questions. But codify this for your team because it’s subjective. What might be a good answer to somebody who hasn’t got a lot of experience interviewing looks very different to somebody who deeply cares about all these principles?

Finally, can you recommend a book or a podcast that every technology leader should read or listen to either in the space of coaching, learning and development or leadership in general? 

I suggest everyone read through blogs and articles written outside of their field. Product management and marketing have some great content. I subscribe to First Round Review and read everything published by Brandon Chu.

I’m also writing a book all about People Operations and Culture as a Product – keep an eye out for the publisher Kogan Page!


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