top of page

Leadership interviews - Unearthing brand insights

You only know what you know. At the start of a branding project, one of the most important things I believe a leadership team can do is verify their assumptions or explore the truth of the situation through good insights.

In most of my recent projects this leads to me ‘virtually’ interviewing a number of audiences to uncover the truth of where the brand is - both in terms of the context of today and in regard to the opportunities for the future. This is done in a multi-dimensional way by listening to different audiences from both within an organisation (across divisions and regions) as well as without by connecting with customers.

Uncovering what people really think and really believe is a task often overlooked. But without this how can you know what the gap looks like between where we are and where we want to go? Also how do you know that your picture of things is right? What if it’s skewed by overly ambitious points of view? What if your team have fallen into the trap of looking at the situation from within the ivory tower and not from without. The echo chamber that is a team (be that a leadership team or a business division) and the reality, importance and relevance of the ideas being championed may be radically different.

It’s vital therefore to discover the truth.

Once armed with this truth, as a strategist I can go back to leadership and hold the mirror up - positively challenging any assumptions to ensure that any new direction is grounded in the realities of the day - not in wishful thinking. Not even in my own opinion.

But how do we find out and uncover what people are really thinking and doing? One way is through quantitive data - surveys, tracking, feedback data and the like. This can indeed have its place. Often these data points will tell us what. Rarely do they tell us why. The why is often vital. So, as a consultant I find that there is huge value in me, rolling up my sleeves and setting up interviews with real people to ask them the real questions that hopefully will enable me to get a good grasp on the realities of where the brand is right now. And I've done hundreds so I'm hoping what I share here will have some value to you.

In this short series of posts I hope to reveal how I go about this amongst four key groups

  • Leaders

  • Customers

  • Staff

  • Partners

Today we’re going to think about the first group. Leaders.

Working with business leaders

I like to interview leaders individually before bringing them together into a workshop. I find leaders in most businesses really interesting people. Driven, successful and often very confident. My work will eventually see me get these people in a room to collaboratively make decisions and align. But at the start of an engagement where my initial discovery work is being done I’m more interested in getting to understand them, their personal ambitions, what makes them tick, their challenges and, perhaps importantly I’m keen to build rapport with them.

Strategy is all about making complex and often uncomfortable decisions in times of uncertainty. Although I’ll come up with a strategy, the people ultimately making the decisions and living with the consequences will be the leaders. Therefore taking the time to carefully reflect and listen to them is important. It’s also essential to ask “the simple questions” and not just accept things on face value. Interviews allow that work to begin positively. Ultimately you want your brand strategy to align and unite a leadership team so they more forward with purpose - inspired and engaged. This might not be how they start the process and so understanding where the disunity is is an important aspect of the work.

The initial discovery interviews are a great way to meet leaders and, on top of understanding where they are coming from also seed in concepts around brand which help them to see the value of my work. Most leaders are super passionate about their part of the business. That could be a business function or business unit that they oversee. Therefore it is not hard to get them talking on this. The bit that they sometimes need help with is connecting their world to the wider business and the objectives of the whole. Thats why brand strategy is super powerful. It should bring alignment. So that everyone is pulling in the same direction. So that their work ladders up into something bigger, more inspirational and more impactful. This message is perhaps the most important one I often find myself seeking to land in-between my questions to them.

Depending on how questions are worded though you can help to get them to think about brand without even realising it - for example simply by asking questions from a customer perspective rather than a commercial perspective. There is huge value in this to ensure that as a strategist I’m helping to shift mindsets.

A few other tips: Leaders are always time-strapped so its important to stick to the allocated time (usually 30-60 mins). These people often do not suffer fools lightly - so although some light humour and personality is a good idea, keep the conversation focused on the task in hand. It’s also important to take notes and write them up for later reference if needed. As projects progress this can be very helpful.

Discovery questions to ask leaders

So what kind of questions should a strategist be asking in the early stages of a brand strategy project? What follows is my framework that drives the flow of the conversation. It’s important to appreciate I will not ask a leader all of these questions but might cherry pick ones from each section depending on how the conversation goes.

As I see it its helpful use a simple flow - I like to use a past / present / future framework sandwiched with an opening and closing. Here’s a rough overview:


Always frame the conversation in a way which explains why you re doing it and why it will be helpful to the process. Always frame the conversation in a way which explains why you re doing it and why it will be helpful to the process. Thank the leader for carving out the time. Be open and genuinely curious.


  • Tell me about you and the work you do?

  • How did you come to work for the company and why did you join?

  • Do you know why and how the company began?

  • What would you say your key skill-sets were?

  • What initially attracted you to the brand?

  • How long have you been in post and whats the history been up until this moment?

  • Why do you do what you do?

  • When you think of the role the brand has played in the past what are you most proud of?


  • How many people are in your part of the business and who reports in to you?

  • What are your main responsibilities?

  • What are your current goals?

  • What are the main challenges you face?

  • Whats keeping you at the company?

  • How do you believe customers perceive the brand? How do you know?

  • Whats working well at the moment?

  • Where do you think the brand could add more value for customers right now? What needs to be better?

  • Who would you say are our biggest competitors?

  • Why do customers buy from us?

  • What main problem do you feel the brand solves for its customers?

  • What are the benefits in solving this for the customer?

  • What would happen if we didn’t solve this for the customer?

  • What one thing would you change in our offering if you could?

  • On a scale of 1-10, how satisfied are you with how things are in the business? Why?

  • Do you have a strategy at the moment and is the organisation aligned to that strategy?

  • Whats currently keeping you up at night?

  • Why does the brand exist (beyond making money?)

  • Do you think the brand presents itself in a clear way to customers? If not what do you think is most confusing?

  • What is it that we promise customers?


  • When you look at the next 5 years + what big industry trends are coming down the track?

  • What role do you see the brand playing in that future?

  • How do you see brand strategy helping to make this a reality?

  • What needs to change in the company to ensure it is relevant for the future?

  • What will happen if we don’t make this change?

  • What is your current plan to improve things?

  • How do you see brand thinking helping you?

  • What are your ambitions for the future, both personally and for the organisation?

  • In the future what is it that you believe this brand should be famous for?

  • What’s the biggest challenge to you achieving your ambitions? 

  • What achievements would you be most proud of if the brand could accomplish them?


To close its always important to thank the leader and explain whats going to happen next. I usually ask for their permission to send them any follow up questions via email this is very important to increase the chances of engagement if I need to gain deeper input on key insights. I also find this final question REALLY helpful:

  • What should I have asked you but haven’t!

This end question allows them to go weapons free on any key issue which is on their mind. It’s often this question where they open up on whats really where their focus is.

So, there is a guide for interviewing leaders at the start of a brand project following a simple flow of past / present / future. I hope you can see the value of structuring an interview like this and for conducting leadership interviews to enhance brand strategy work and I do hope this guide will be helpful to you.

Next time we’ll look at interviewing key customers. Watch this space!

Best wishes in your ambitions to unite your team and build a powerful brand.


bottom of page