Ask a silly question, get a silly answer, right?

The fear of appearing silly is particularly severe at the beginning of a client engagement.

Most branding projects involve some sort of stakeholder interview programme and the people involved are generally important: leaders within the organisation, or key customers, or board members. You’re probably meeting them for the first time and if they emerge from their interview thinking you’re an idiot, you’ll face an uphill struggle to rebuild credibility. The pressure not to stuff up can be immense.

An understandable response is to create a detailed discussion guide packed full of insightful, intelligent questions that will reassure your interviewees that you know your stuff and you’ve covered every possible angle. I’ve seen many of these types of discussion guide over the years. Here’s an (anonymised) example:

As far as discussion guides go, it’s OK. For one thing, it has the advantage of brevity: not only are discussion guides that span multiple pages unwieldy, they set unreasonable expectations of the number of questions anyone can cover in a 45-minute conversation (at least, without that conversation morphing into an interrogation). This guide contains around 23 questions, which suggests an average of under two minutes’ discussion per question: that’s not a tremendous amount of depth, so I’d suggest this is at the absolute limit.

It also has a clear structure, which shows that the guide’s author has considered the knowledge gaps that the interviews should help to fill. For reasons I’ll discuss later, this isn’t my preferred structure, but at least we’re not looking at a long list of questions to fire at an interrogee.

A final positive is that (at least some) of the questions are short and open-ended: easy for the interviewer to ask and simple for the interviewee to understand. Sadly, not all the questions are like this. And there are plenty of other things we could do to improve the discussion guide. I tend to follow a number of basic principles.

Firstly, it’s a guide, not a questionnaire

This is a vital distinction: a questionnaire is a comprehensive list of questions you want someone to answer, whereas a guide is a tool for structuring a conversation. A guide will do exactly what it says on the tin: point you in the right direction. But the questions you ask should flow naturally from the conversation. Each person you speak to is likely to have particular areas of interest or concern and it makes sense to let them spend more time and to delve deeper into those areas. So, I focus my guides on two important types of signpost:

  1. Topic areas: these are the building blocks that I use to structure the guide, based on the knowledge gaps I want to fill, and
  2. Key questions: for each topic area, I try to identify an absolute maximum of four simple, open-ended questions to ask (and I aim for as few as possible). As I mentioned above, these questions should be easy to ask and understand (although they may ultimately prove fiendishly difficult to answer).

The number of topics depends on the time available, but as a general rule I try to allow somewhere between 5 to 10 minutes per topic, depending on how difficult or interesting each topic is. So, a 45-minute discussion guide is likely to contain a maximum of six topics and twenty questions. And these are generally the questions I’m absolutely itching to find out the answer to (as opposed to questions I feel I’m expected to ask).

Soften them up with some easy questions, then get into the tough stuff

The example I’ve shared begins by introducing some context (which is good), but then gets straight into a BIG question. There’s no room for rapport-building (which matters), or for gaining any context for the answers to follow. So, prefer to I start with a brief introduction (the stakeholder should already have been briefed on the project and the purpose of the interview, but this doesn’t always happen so it’s best to be prepared), and then I ask the interviewee to provide some helpful context:

  • Tell me about your current role and how the brand fits in.
  • How did you first become involved with the brand?
  • How has your relationship with the brand evolved since?

I also think it’s helpful to understand from the outset what effect or outcome they are hoping the brand project will deliver. The example guide saves this for the end of the conversation, but I think it’s helpful in establishing rapport to understand where the other person is coming from and to give them the opportunity to share what they are hoping to get in return for spending their time with me.

The only way to avoid a stupid question: do your homework

I actually quite like asking silly questions (more on this later). But I HATE asking stupid questions, by which I mean: questions that I should already know the answer to, if I’d bothered to look at the brand and its category. This sounds obvious, but over the years I’ve seen plenty of (generally senior) colleagues think they can simply rock up to an interview, glance at the discussion guide and then crack on. The success of a stakeholder interview doesn’t depend on the intellect or charisma of the interviewer: it depends on their preparedness.

The point is that you’re supposed to be curious.

Which means that you should have studied any available materials. Crucially, you don’t need to have understood everything you’ve seen or read: the interview is an opportunity to probe areas you’re unclear about. I’ve looked through some of my favourite discussion guides and they are peppered with very specific probes, which only make sense if you understand the context:

  • Why focus on health?
  • Transformation: are you sure?
  • Are you counteracting a negative, or working towards a positive?
  • Which brand do people say they work for?

In the consultancies I’ve worked in, the task of developing a discussion guide has often been delegated to a junior consultant. And this is fine, provided the brief is to digest all available information and then develop a unique guide based on the knowledge we’ve gained. All too often, though, the brief is to copy an existing guide from a ‘similar’ past project. This will get you to an OK guide that will make you look competent, but not a great guide that will help you uncover insights, ideas and opinions with the potential to shape an exciting answer. Inevitably, most discussion guides will cover some of the same basic questions, but if these account for more than half of the questions you ask, the chances are you’re going to have a very humdrum series of conversations.

The best guides are visual

The last thing I want during an interview is to have to scan down a list of questions to find the next subject to discuss. Earlier, I mentioned two types of signpost: I use these to create a more visual form of discussion guide:

I’ve found there are a few advantages to representing a discussion guide this way:

  • It forces me to be disciplined: if a question doesn’t fit in a circle then it’s too long, and if I can’t fit all the themes and questions on a page, there are too many of them.
  • It forces me to think about how important a topic is: most of the time in the above guide is devoted to current perceptions of the brand and its competitive set, because the brand in question hadn’t previously carried out customer research. I focused much more on culture, offer and ambition in the internal stakeholder interviews.
  • It makes it easier for me to leap between topics: conversations flow in all sorts of directions and frequently involve hopping between subjects. With a visual guide, I can strike through a question or topic once I feel it’s been adequately covered – regardless of sequence – and then steer the conversation back to an earlier topic, or to a topic that hasn’t yet been discussed.

Following these basic principles helps me build discussion guides that I find more interesting and helpful than the earlier example. But if I REALLY want to pull out the stops, there’s another principle I like to add to the mix:

Ask silly questions!

The eagle-eyed among you will have noticed that the above discussion guides are timed for 45 minutes. Sometimes, stakeholders are pressed for time and the conversation needs to be compressed into half an hour. And sometimes stakeholders are willing to extend an interview to an hour or more. When that happens, there’s another box of tricks I like to keep up my sleeve… Well… Two boxes of tricks:

The black box, as the gold foil lettering suggests, was created by artists/ musicians/ composers Brian Eno and Peter Schmidt in 1975, initially as separate projects. Both men had started to collect ways to jog their mind whenever they had reached a creative impasse. Brian Eno kept his on a set of cards. Peter Schmidt kept his in a book. And once they realised they had independently arrived at a similar solution to a common problem, they pooled their ideas and released them as a set of cards: ‘Oblique Strategies’.

There are over 100 cards, described as ‘worthwhile dilemmas’. Although I find them very helpful for idea development (‘Be dirty’, ‘Discover the recipes you are using and abandon them’, ‘Faced with a choice do both’), they can also be useful for finding more interesting questions to ask. For example:

  • ‘What to increase? What to reduce?’
  • ‘The most important thing is the thing most easily forgotten.’ So, what’s the most important thing that your brand has forgotten?
  • ‘State the problem in words as clearly as possible.’

Less poetic but more relevant is the grey and yellow box behind.

I first came across The School of Life when I was working with a gym brand that wanted to explore ways to help people exercise their mind as well as their body. In the end, the project came to nothing, but I very much enjoyed meeting the people at The School of Life and they gave me a lovely gift: a box of cards like the Oblique Strategies, except this set was designed to encourage people to talk openly about their relationships. I thought the cards were brilliant.

And then I thought, perhaps the same idea might work for brands?

So (after I’d moved to another consultancy), I worked with some talented writers (Matt Davenport and Will Nicklin) and The School of Life to develop a set of ‘Wild Cards’, which contained more brand-specific prompts. For example:

  • Which person in your business best represents the ideals expressed by your brand?
  • Who or what is your brand’s nemesis?
  • When was the last time you felt truly excited at work?
  • How large a gap exists between your company’s actions and its stated intentions? Why is that?

I still use the cards today. Sometimes as part of a project kick-off session. And sometimes, if I can extend an interview to an hour (or more), I’ll ask the interviewee to scan through the box and pick a card they feel is particularly relevant to the brand in question. Sometimes I give them a pre-selected group of cards or questions to choose from. The cards often take the conversation in all sorts of weird and wonderful directions that no amount of preparation could have anticipated: project stakeholders carry all sorts of unrealised and unspoken opinions, hopes, and ideas that can only be shaken loose by bizarre questions and prompts. What I’ve learned from experience is that (1) these weird (and often silly) questions are generally best introduced at the end of an interview, once rapport has been established, and (2) it’s a good idea to let the interviewee choose which question(s) they want to answer.

Some of the most surprising, rewarding, and enjoyable interview moments of my career have been prompted by these sorts of questions: they are no substitute for a great discussion guide, but they can be a perfect complement.

Ask a silly question, get a sublime answer.

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