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Questions to ask in your Head of Design interview

Image by Jon Tyson

When I was searching for design leadership roles, I kept a list of questions to use in interviews. They split neatly into four key areas:

  1. The type of role on offer
    Not all head of design roles are created equal

  2. The current state of design
    Is this a renovation project or caretaker moment?

  3. The overall direction of the org
    Am I joining in war time or peace time?

  4. The hiring manager
    Who is the person that will have the most influence over my time here?

I tend to ask most of these in the initial recruitment team call to see if it’s worth exploring any further, but I think it’s also valuable to ask multiple people the same questions to uncover different answers from different seniorities, teams and tenures.

These questions always sit alongside the standard stuff e.g. location, travel, package etc. They have helped me find great roles and avoid some terrible decisions. I hope they’re useful to you too.

1. The type of role on offer

What type of leader is needed? Different types of leaders are needed depending on the many aspects of the where the role came from, why it’s vacant and what expectations have been set. Some HoDs are expected to clean up a team, whilst other HoDs are needed to build a team from scratch. Each type of role will suit a different type of leader. These questions will help you understand what type of role this will be:

Is this a new role? (If so why are you creating it now?
If it’s not new and has someone left, why did they leave?)

This is usually my lead question. It helps me determine if expectations have already been set for the role by someone else.

Is the team in a high growth phase? (If not, is it a reduction/streamlining phase?)

I try to get an early indication of what the core challenge will be inside an organisation. If it’s high growth I will undoubtedly be doing lots of hiring and org design, whereas if its in a streamlining phase, I’ll more than likely be looking for cost savings and cutting back people or processes.

Is this a time of change (e.g. new owners and/or exec team, new direction)?

Has something spurred a change in the org that has lead to the role? When a business has undergone (or is still undergoing) seismic changes there will be lots of choppy waters ahead. Big change can take years to shake out. What you sign up for today may not exist next month — perhaps for the better.

Is this ‘hands on’ or pure management?

Sadly there’s still quite a lot of HoD roles being advertised that expect IC work. In my experience this is usually an indication of low-level design maturity and lack of investment in the design discipline. Player-coach roles are a good stepping stone for new managers, but ultimately not tenable.

2. The current state of design

What is the health of the design org today? I want to know if I’m signing up for a major renovation project or if I’m joining a group with a high functioning team with a grasp on the business benefits of design.

What’s the relationship like with the product, tech, marketing and sales teams?

Hopefully there is a mutual respect between teams, but this question will help me understand if I’m going to be repairing relationships.

Which team has the most influence on design?

I’m looking for red flags with this one. Does the sales or marketing team currently have a heavy hand on the design process and do I want to be the one who challenges this?

Why wasn’t this role filled internally?

I love asking this one to different people around the business. Not only does this gives me an indication of the team’s reputation but it also guides to me on the abilities in the current team.

What’s the biggest challenge the team has faced last year?

Hopefully there is nothing unexpected here. Usual answers may be levels of resource or strategic direction. Tread carefully if the answer is more fundamental e.g. ‘technology’ or ‘relationship with marketing’.

How do you measure the impact of design?

Do they in fact measure the impact of design? If not then you may spend lots of time and energy proving its value around the org.

What does the tech/product leadership want from a design peer?

Again this is a great indicator of the health of the design discipline. In my experience it’s a good sign when the Head of Tech and/or product have clear needs and demands.

3. The overall direction of the org

Am I joining in war time or peace time? There’s lots of crossover with the first area, but here I’m specifically looking for challenges in the business that will shape the HoD role.

What is the path (and time) from a concept to launch?

This is vital for me. I asked this at every interview and strongly advise all designers and design managers to do the same. If the route from design to launch is very long and very complex, buckle up for a frustrating ride.

Is there a Chief Product or Design Officer in the exec team?

Another indicator of the maturity of a business. I personally avoid companies with Chief Digital Officers. In my experience they are legacy players where design plays a minor role.

Who do you count as the biggest competitor?

Is the company leading, chasing or disrupting? This question can help you uncover what kind of environment you’ll be playing in.

Biggest challenge for the business?

Are finances an issue? Is the market shrinking or is some outside influence going to shake the ground the business is built on?

4. The hiring manager

Never forget that interviews are a two-way process. Don’t be afraid to delve into the hiring manager. As a hiring manager, you’d be surprised at how few people ask anything about me or my management style, so I always have some probing questions at hand when I’m the interviewee.

How do you handle stress?

Are you a shit umbrella or a shit funnel?

Tell me about your journey through {company name}?

Have they just started and if so, what’s it been like for them? If they have a long tenure it’s good to know if it has met their ambitions.

If in 3 months time, it’s all gone wrong, what happened?

A nice little ‘pre-mortem’ style question to flesh out expectations and fears.

What does progression look like from here?

I want to know if I do well in this role how it will develop, how they will invest in me and what opportunities could open up for me.

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