13 questions I ask my marketing clients (and why)
distilled from 20 years of marketing experience
Since leaving my full-time marketing job in 2018, Iâve done marketing consults for almost a hundred clients. Many of them have had great results: clarified their positioning, grew their followings, got more users/customers for their products, made more revenueâ all without compromising their sense of what theyâre doing. Better still, many of them feel less constrained, see opportunities more clearly, and enjoy their work more.
I write this because Iâm ready to take on more clients (DM me!), and also because Iâd like to consolidate what Iâve learned, and share it freely with others.
Also just to be clear, I donât just bombard people with all of these questions at once. I start somewhere, pay attention to what they say, and intuit what would be the most useful path to take.
1. âWhat do you do, and what problem are you looking to solve?â
This is the question I always open with. I typically already have a sense of the answer beforehand via our DMs or emails, but I ask again so that I can witness them talking through it, because thereâs always valuable meta-information in how they answer.
Occasionallyâ sometimes because of the preparation they had done for the callâ the client will explain things to me more compellingly than theyâve articulated anywhere in their work, which is a huge win right off the bat.
More often, they will stammer and flounder a bit, which is also good because thatâs an opportunity for us to sharpen their thinking and their communications, which benefits every other aspect of their work.
And sometimes there will be a deep sigh, which usually means we need to do some foundational re-organization. This is a larger challenge, but I like it because it can sometimes be far more fruitful that the client expects.
2. âWhat specific outcomes are you looking for? Why? What have you tried so far, what are you thinking of trying next?â
Specificity is the goal. Sometimes clients get tremendous value simply from being persistently challenged to articulate what they actually want. The conversation dispels fog, reveals new pathways, and occasionally even reshapes the whole endeavor.
Hereâs a fictional worst-case runâ every real client has given me better answers than this, but I can still work with this:
âI want things to be better.â
âBetter how?â
âMore customers.â
âFrom where?â
âAnywhere, really.â
âAnywhere is nowhere. Where do you think your next customers are most likely hanging out?â
âMaybe [place]?â
âWhat are you currently doing to engage them there?â
âNot much.â
âWhat do you think they would be engaged by?â
âWell, I supposeâŠâ
When a line of conversation goes dead like this, it usually means thereâs a wrong assumption upstream, ie the client doesnât actually want to work on the problem they said they wanted to work on. Catching this can be worth more than everything else combined, sometimes saving a client years of time they would have otherwise wasted. Someone once paid me twice my fee because they were so relieved to realize this!
If the outcomes are clear and a strategy exists, we look at execution. Whatâs working? What isnât? What to fine-tune? Sometimes thereâs a perfectly good strategy that the client simply isnât following through on. Thatâs worth troubleshooting too, and itâll involve some of the later questions.
3. âHow would you define the expedition youâre on? How can you make people feel good about supporting your expedition?â
Whatever it is that youâre currently working on, youâre asking for peopleâs time, money, attention. How can you make them feel good about giving it to you? Approach this with confidence. Oftentimes the best answer is shaped like an inquiry: the point of an expedition is to Find Out. So what are you looking to discover?
The useful thing about this framing is that it nudges the client towards conceptualizing their work as a gift, as something that is of value to other people.
Perhaps most importantly, it gets them to see themselves as a professional who is in charge of their own operation, rather than a meek craftsperson whose fate is determined by chance and the whims of others.
Few people really think this through, so itâs worth reiterating: it is lucrative to know precisely what makes your audience happy to support you. Most people have only a vague sense of this, so theyâre left hoping someone somewhere will be generous for no particular reason. Once you understand how and why people like your work, you can make it much easier for them to act on that.
The best outcome of this exercise is that the client themselves gets more motivated and energized to go on the expedition that theyâve just defined more clearly.
4. âHow would you describe your current âbrandâ? How do your peers describe you to other people? What do you like and what do you not like about this description?â
Dolly Parton famously said to find out who you are and do it on purpose. Itâs staggeringly good advice if you really follow through on the implications.
People are seldom very rigorous about this. You cannot improve your brand if you donât really know what it is. If the word âbrandâ isnât right for you, we could use other words. Your positioning, your persona, your reputation, the way you are perceived both by others and yourself. These days you can get a useful read on this just by asking an AI what impression your work gives off.
Also, importantly, you donât need to overfit yourself into whatever archetype youâre most similar to. It could be âX meets Yâ, or âX, but also Y, and sometimes Z.â
A concrete exercise that pays off for almost anyone who tries it: Collect instances of how people describe you or your work to others, and analyze the patterns. If thereâs no clear pattern, it usually means one of two things: youâre not yet distinctive enough to stick, or youâre too scattered to be made sense of. Both are solvable.
With the more reticent clients, Iâve often gotten breakthroughs by getting them to consider that everybody, or âother peopleâ (wink wink) begin with stereotypes and assumptions before they get into the details. Alien (1979) was conceptualized as âJaws (1975) in spaceâ. Sylvester Stallone was always getting typecast as a thug, and rather than dispute that, he parlayed that with a âyes, and...â to âa sensitive thug with a soft touchâ, which is at the heart of what made Rocky (1976) one of the greatest movies of all time.
Everything is a remix, and even if the creator doesnât see it that way, the audience will still interpret her work through the lens of what theyâve seen before. Being sensitive to this can make all the difference between being appreciated and being ignored.
5. âWhat constraints are you operating under? Which of these are actually real, and which can we dismantle or bypass?â
Everybody is constrained, and so my clients are, too. And if youâre trying to do anything substantial at the edge of your ability, your constraints are going to reveal themselves. Some constraints are hard ones, like chronic health conditions. But some constraints can be conceptual, or even entirely imagined. Itâs very worthwhile to do an audit of your constraints, because youâll always find that you have more room to maneuver than you assumed.
A common constraint Iâve encountered is the fear of posting cringeâ which is totally understandable and even good, since it protects the work from certain kinds of failure. But people often overcorrect on this and become stiff and lifeless. Here it helps to have a precise conversation about what makes a work lively or not, compelling to whom, cringe to whom, etc. This reveals the fear to be more specific and more manageable than it seems.
A related and rampant constraint I encounter is what Iâll call âthe ghost of TEDâ. People seem to have internalized the assumption that youâre supposed to present your work like a polished TED talk: a neat origin story, carefully choreographed beats, a tidy conclusion. But thatâs just one way to communicate. Itâs not the only way, and for many people itâs not the right way. The ghost can be dispelled.
An important thing to understand here is usually that polished keynotes and performances are âlate stageâ outcomes, and not how things start out. So people tend to mistakenly compare themselves against the others at dfiferent stage of development, and worse, they often try to emulate the later stage, which distracts them from doing what would actually get them to the next stage.
(Iâll bring this up again later because itâs important.)
6. âWhatâs your best stuff? How are you currently presenting it? Could you present it better?â
Most clients already have better material than theyâre making visible. When I look through websites and blogs, I typically find a lot of unnecessary detail up front and the most interesting stuff buried or scattered. As David Ogilvy said, when youâve written your headline, youâve spent 80 cents of your dollar.
The same applies to stories. Most people have anecdotes they tell in person that land really well, and still havenât gotten around to writing up or recording. Sometimes getting that one story into a shareable format is worth more than everything else we discuss.
The Ghost of TED shows up here too: people keep assuming that packaging a story means producing something formal. It usually doesnât. Some of the most effective versions of this are informal chats, a friendâs podcast, an impromptu talk recorded on a phone, even in someoneâs car. If weâre talking about writing, it doesnât necessarily need to be a crisp landing page. Ray Dalioâs book Principles was previously a PDF that itself looked like it grew out of a bunch of emails and notes.
Assemble good things and make them accessible, and donât worry too much about the polish layer on top until you know it works. Look again to the Apple I.
7. âWhat on your todo list are you afraid to do?â
Itâs not even that you ever have to do them, but examining it can be very revealing about yourself and the situation youâre in, or think youâre in.
Sometimes the scary thing is high-value and de-risking it is straightforward: preparation, a sanity check from someone you trust, a smaller first version. Inspiration tends to arrive in grandiose forms, rudely indifferent to your constraintsâ but you donât have to manifest the final form on day one. Lady Gaga played parking lots before she did the Super Bowl.
Sometimes, though, even after youâve right-sized the task, itâs still just scary. For some people the parking lot isnât meaningfully less terrifying than the stadium. Thatâs a different problem, and it connects to the question of core motivations, which weâll get to in #9.
8. âWhat are you conflicted about?â
Being conflicted is normal, even healthy. The problem is that performance pressureâ to ship the next post, close the next sale, push the next updateâ creates an incentive to suppress conflict rather than examine it. This works until it doesnât. Suppressed conflict becomes internal friction, and enough internal friction becomes mysterious stuckness.
If youâve been head-down long enough, you may not even perceive the conflict anymore. Which is precisely when itâs worth stepping back and articulating it properly. Sometimes doing this reveals a path through. Sometimes it reveals that certain tasks youâve been grinding on are actually irrelevant to what you care about. Either way the result is more clarity, and sometimes Iâve seen this lead to products becoming more honest and opinionated, which tend to resonate more with the people theyâre for.
Everyone is conflicted, and itâs almost always better to name the conflict than to pretend it doesnât exist.
9. âWhat do you love about your work? What do you really enjoy? When are you most in flow?â
This is especially important to talk about if the client is coming to the session with a weary energy, but itâs always relevant even if they arenât. Because itâs difficult to artificially manufacture enthusiasm for doing something difficult. And we can usually safely assume that whatever it is thatâs blocking them from reaching their goals is something difficult for them to overcome, otherwise theyâd already have done it!
Itâs not sustainable to expect to do something that you donât want to do, or donât like to do. Le Guin said that love doesnât sit there like a stone, it has to be remade like bread. And it is the love you have for your work that will keep you going when things inevitably get tough. All happily married couples know that they have to spend real quality time together. And all marriage therapists will ask questions like, âWhat made you fall in love with each other?â Because there has to be something good worth fighting for. And this applies to everything. What are you fighting for, and why?
Itâs strangely rare that anybody is already spending most of their time in the zone where theyâre enjoying themselves the most. Almost half my clients will admit to something like, âIâm working on A, B and C. I love doing C, it makes me come alive.â And I ask, so C is the first thing you do each day, right? And they go, âOh, no, I donât really... it happens here and there sometimes.â I ask, âIs that because A and B are critically important and need to get done first?â And they go, âOh, none of these things are more important than the other, I just kinda respond to whatever comes up.â
So, thereâs an obvious opportunity there for them to to enjoy their work more, which has all sorts of benefits. Anything that produces good energy is good for morale, and colleagues and customers and investors pick up on that. We all want to be part of something wonderful.
10. âWhat are your aesthetic inspirations?â
What marketing has appealed to you as a consumer? What are your favorite movies, musicians, advertisements, products? I ask these in part because I enjoy hearing the answers, but also if we have any shared references, that can let us go much deeper much quicker. They also reveal a lot about what someone actually responds to, which is useful information for figuring out what they should be making.
A more expansive version of the same question: if you were a media mogul, what would you produce or invest in? Suppose youâre a record label, a publishing house, a film studio. Whatâs in your catalog? What artists are you signing?
People tend to answer this one freely because it feels hypothetical, but the answers are usually quite revealing. Thereâs often a clear sensibility in there that isnât showing up anywhere in their actual work, and that gap is worth examining.
Aesthetic doesnât necessarily have to mean pretty or fancy. You could prefer something thatâs simple, austere and so on. The challenge is put together something that is coherent and compelling to the people that you want to engage.
11. âWho are some people youâd like to be mutuals/peers/collaborators with?â
Who would you be most excited to do some sort of collaboration with? Why exactly? Everybody typically has some sense of the kind of people theyâd want to have in their lives.
Oftentimes people in fact are already acquaintances with people they admire, but feel like they donât want to impose, or to risk any awkwardness. I think this is natural and even healthy, but it shouldnât be that it stops you from trying. Rather, you can take it as a challenge to make a worthwhile effort.
You can think of any endeavor as a kind of group projectâ even if itâs just a solo operation, youâre still collaborating with your past and future selves. And the quality of peers you manage to involve in your operation, whether as cofounders, employees or customers, will have a very big impact on the quality of the project. So it is always very worthwhile to think about whoâs the next person youâd want to get involved with, and what adjustments you might have to make to make them want to be involved.
Sometimes just thinking through âhow can we make this become inviting for the right kind of person to want to get involvedâ ends up leading to changes that invigorate the project tremendously, which benefits everything.
12. âIf you could hand off your entire operation to a clone of yourself, and trust that they will manage it skillfully and enthusiastically, what would you like to do next?â
After taking a vacation, resting, clearing your head â what do you think youâd do next?
A lot of my clients are struggling with the tension between stewarding something that has been successful, with trying something new that theyâd like to be doing. They might be so burdened by the current thing that they havenât even allowed themselves the space to articulate what the next thing might be.
But the very reason they were successful in the first place was because of the playful energy they had that theyâre now suppressing. And this self-suppression ends up casting a dark cloud on everything else.
So sometimes, just having some sense of possibility of what they might want to do âeventuallyâ, âwhen theyâre doneâ, can be eye-opening, relieving.
(As I revisit this, it really is striking to me how much of this rhymes with what happens in so many marriages.)
13. âHaving thought through all of these things together with me, what do you think is the most compelling thing to do next?â
This is roughly how I close my sessions. Sometimes over the course of the session it becomes very clear that thereâs one very important thing to do, and we focus on that. Sometimes there might be multiple things, which is fine too.
All of this said, the most valuable thing I do for my clients isnât anything I tell them or ask them. The most valuable thing I do is pay attention. I look at not just what they say but how they say it. Sometimes theyâll recite a spiel (about what theyâre âsupposedâ to do, for eg) but I can see that they donât really care about what theyâre saying. And sometimes there are moments where they light up, get excited, start gushing. Sometimes theyâll hesitate before saying something, and digging into the hesitation is where all the magic is.
Oftentimes I ask them to tell me their backstory, why theyâre doing what theyâre doing, how theyâve helped their customersâ and then I reflect back to them what resonates with me, and the result is messaging thatâs more earnest, lively, effective.
Want me to help you? You can book a consulting call with me today!
(Make sure to also DM me and/or email me so that we can each do a little preparation beforehand to make the most of our time, and make any additional arrangements if neccessary. đ€ )
how much do you charge for this? I think I'm struggling with asking people to pay upfront because I often don't know how much help I can give them. I usually can give them a lot of insight even on just the first interaction. And I have enough of a portfolio now of things that I helped blowing up that I have a lot of people who want to work with me, but many are early stage startups that don't yet have funding
If i take a client and work with them for 4 weeks, and I get them a $10k contractor, how much should I charge?
Vs if I talk to someone for 1 hour, create 1 tweet for them, and they get a $250k investment
This piece is so dense with signal, it took me like two hours to finish reading because my brain needed breaks to deal with all the noise that resonated out of me. I have more things to enact now