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Given that I literally spend most of my time these days speaking with other consultants, one of the things I notice most is how lonely building your own consultancy can be.
Unlike most businesses, running a boutique consultancy in Data & AI is very unique in that the product and the person running the show are the same (i.e. you).
What that means is that every decision that gets made for the company to grow is literally a battle with yourself. From which (and how many) clients to take, to how projects get delivered, to what tools you use, is a constant battle between your ambition and your indecision.
To be honest, I would’ve never guessed how big a factor that is for most consultancy founders until I started seeing it first-hand.
When I started my company, I wanted a way to show people how I can help them navigate those challenges in a low-pressure setting. To do that, I had a genius idea to offer 90-min mini-workshops where I could talk to you about the problems keeping you from growing your shop to where you wanted it to be:
“I don’t know how to attract the right clients.”
“I’m not sure if I have time to even pursue solving many of my problems.”
“I don’t know how to get paid what I need to grow.”
“I’m not sure how to hire the correct people for the skillsets I lack.”
And as I began doing more of them, I realized how much that setting had in common with your standard “therapy” workshops - so that’s literally what I started calling them.
A “Therapy” Session, in all its glory
The problems I end up with folks in these sessions are pretty varied: Some are personal, some are professional, but all of them are keeping each of these consultancy founders from being able to take the next step they want.
The problem is that many of us are too proud to admit we need the help, so I’m glad to be able to provide this free service to others who need it.
And while, to be clear, I AM NOT A PROFESSIONAL THERAPIST OR MEDICAL PROFESSIONAL and will never try to be, one of the cooler parts of my job has been learning what exactly the issues are that are keeping each of you from building the company you want, and providing you the context you would never otherwise get if you tried to brute-force the problem by yourself.
So what exactly does a Therapy Session look like?
Check it out in this demo video:
A typical session usually has 4 parts:
You tell me literally the entire set of issues getting in your way, followed by a deep-dive discussion on why each of them is stopping you today.
We discuss the broad goals you have to solve those (and where you’d like help).
I help you prioritize the challenges from activity #1 based on two factors:
How impactful solving that problem is (i.e., how much it matters to your consultancy)
How complex (in terms of money, time, effort, and technology) it will be to solve that problem
(if you need help to solve them) We talk about what solving them together would look like from a timing, cost, and effort perspective
And that’s it!
What usually happens is that we’re discussing those challenges you face, we also end up expanding the conversation into basically everything that goes into solving those, and the conversation changes from just a simple discussion of what bothers you to a real deep dive into why those problems exist in the first place.
So if there are issues you feel stuck on in growing your consultancy that you could use an external perspective for, sign up here and let’s talk about your problems! It’s all free!
The Meme Team: Running your shop like Kool-Aid Man
The other big lesson of running these therapy sessions is that every Data & AI consultancy basically runs on this vibe:
OH YEAHHHHH
What I mean by that is that you don’t realize how much every consultancy you know is run basically via duct-tape and bubblegum until you talk to them.
Every process, strategy, and decision is made through a combination of intuition, luck, and pure Kool-Aid Man-branded determination.
And as you may imagine, that’s not very sustainable.
The only reason I’m telling you this is to say if you’re building a consulting shop and you’re reading this, you probably need to spend more time on formalizing everything about how your company runs.
How you find clients (and how they find you).
How you interact and sell to them.
How you hire the right candidates.
How you run your team.
How you deliver projects.
Everything needs to be deeply understood and systematized first, so you can turn it into something useful for your growth later.
Trust me on this one.
This is Fine: The Show About Your Fuck-Ups
A week ago, I promised you a very special announcement - so here it is: the very first episode of my new series called This is Fine!
As a refresher, the story behind it is that for many years, I’ve noticed that we consultants tend to talk pretty freely about the amazing things we do, but never about the things that go wrong - all the fuck-ups that really teach us how to get better at our jobs.
So for this show, we’ll be talking about the real big learning moments of so many cool consultants’ careers, highlighting not only the stories behind what happened to them, but also what they learned, how they apply those lessons daily today, and what you can learn from them if you were in their shoes.
This time, I’m joined by Dylan Anderson, a long-time data consultant and founder of DA Ecosystem Advisory, a boutique Data & AI consultancy just like yours!
Two years into his consulting career, Dylan was juggling three projects across three partners: delivering way above his pay grade, burning late nights, and convinced he had it under control. Except he really didn't.
And by the time a partner called him in to ask why things were slipping, it was already too late to course-correct quietly.
So to celebrate our first episode, Dylan is here to walk us through the moment his career hit a wall, and what it actually taught him about showing up as a great consultant, covering:
Why "I thought I was still doing a good job" is the most dangerous thing you can tell yourself
The skill nobody teaches you early enough: how to say no (and communicate up)
What changed after that moment, and how he now creates the psychological safety he never had
Why the hard stuff is where the real consulting education happens
Check the full video on my YouTube channel above, and let me know if you’d like to participate in a future episode!
The Secret to Understanding Your Client’s Pain
The surefire way to measure how real your clients’ AI pain is
When you’re scoping or selling AI work, every single one of your clients will tell you their problems are a 10. Existential. Unheard of. Unsolvable, even. You and I both know they’re more like a 3.
Look, I’ve been there: we all want to close the lead and win the work, so we let urgency inflate the pain diagnosis.
But to be honest, not all pain points are created equal, and treating a 3 like a 10 is how you end up with a scope that creeps to death and a margin that somehow turned negative 6 months into the project.
To prevent this, I like to use the same frameworks doctors use when I build a discovery workshop for other AI consultancies: rate your pain from 1-10.
It splits the pain into pretty neat categories:
1 = Your classic AI FOMO (we heard we need to do this, so we want to)
3 = Unimportant nice-to-haves (that won’t really move the needle efficiency, cost, or revenue-wise)
5 = Real problems but safely deprioritized (no matter how relevant they might seem)
7 = Time-sensitive problems for critical verticals or teams with immediate business impact.
10 = Existential. The business will literally fall apart if we don’t build this.
There aren’t ever that many 10s, and that’s the whole point.
So when you want to scope or structure an AI build project sustainably, step 1 is confronting your client about whether the problem they think is a 7 is actually a 3 that feels existential because their boss said so.
Get that answer right, and your timelines, margins, and ability to sell more deals also get exponentially better.
You’ll thank me later.
What’s Next?
Next week, I’ll be doing a deep dive into every consultancy founder’s favorite topic: positioning!
Make sure to join as I explain the secrets to uniquely defining your market, what makes you different as an AI consultant, and much more!
Get in Touch
If you’ve brute-forced your boutique Data & AI consultancy and feel like you need an external perspective to get unstuck, I’m here to help!
Get in touch to learn more about how I enable Data & AI consultancies to sell, deliver and scale more effectively through my workshops. If you haven’t already, visit my:
Website (where you’ll find a lot more details about my work and how it comes together)
LinkedIn Page (where I post every day with many of the same lessons shared here)
YouTube (for deep dives, tutorials, and fun stories from my work with clients)
And let’s chat more about where you’re struggling with your consultancy!
Otherwise, thank you so much for reading, and see you next week!
P.S.: A reminder that if you enjoyed this newsletter, you should click this ad so my cats will stop threatening to crash all my work calls if I don’t buy them new toys 🤣
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