Selling advice was the weirdest thing

List member Alessandro sent me the following and I immediately asked him for permission to share here because it’s such a crystal clear illustration of a super-important concept.

I’ll follow this up with a few comments after, but first, here’s what Alessandro wrote me (shared with his permission):

Hey Philip,

Recently, I’ve been on two calls with two different people to see if there’s a fit to get them on as a case study project.

During the calls, I helped them figure out what their current situation is, what’s their goal, and what could be a possible road map to get there.

I was freaking out. It didn’t feel like I was being useful at all, I was trying so hard not to sound stupid and incompetent, and the feedback I’ve given to them sounded like something anybody could know.

That’s what I thought. But they didn’t seem to notice!

Both of them ended the call telling me how much I had been clear and helpful, and how they were excited to move forward on this path.

Plus, even though neither of those are a good fit for the service I’m trying to promote, I could tell they were hoping they were! They were the ones suggesting things I could maybe help them with!

Now, I didn’t charge for those calls and I don’t know if “selling advice” looks anything like that, but it was the weirdest thing for me. It felt like I was doing nothing for them, while they seemed to be impressed and willing to find ways to work with me.

That’s it, just wanted to share this with you 😉

A bit of context: Alessandro was in the Decision Making workshop in and is now going a great job of doing deep market research into a vertical he may specialize in. That’s why you see him talking about not charging, etc. He’s doing deep market research, so all that stuff is a normal part of the game.

The part I hope you notice is how strange providing advice felt to him at first.

I’ve really struggled to put this into words for you, and in the past the best I’ve been able to do is say “it feels really weird at first to get paid for advice”.

If you’re used to believing that your value is in building stuff for companies, then the first few times you find a prospect who is excited to pay you for your advice, it feels… well, again, Alessandro did a great job of describing what it can feel like.

In fact, I bet lots of you are more used to building stuff for companies and then having your client fight you when you do try to offer advice. This is a by-product of filling a staff augmentation role. When your client is measuring you by coding productivity, anything that threatens that metric is going to be seen as a potential problem, and you offering advice about in-progress software can come across as an obstacle to coding productivity.

One of my goals for this list is to help those of you that are stuck in staff augmentation roles make the transition out of staff aug work (if that’s what you want to do). Now as I’m sure you know, getting paid to help your client make better decisions (my definition of advisory work) comes with additional risks, demands, and responsibilities that staff augmentation does not. So this transition is not right for everybody.

But if it’s something you’re interested in, you’ll probably have to deal with the kind of discomfort that you see Alessandro describing so well above. Just know that this strange feeling is usually very temporary, and it’s a nearly-unavoidable part of this kind of change in your business. You might even think of it as a rite of passage or an initiation ritual on the way to something better.

A quick heads-up that I’m opening up registration for the July cohort of the Decision Making workshop in Specialization School ( soon.

You’ll see me start promoting that quite a bit throughout the first few weeks of June. Two of the 7 seats in this workshop are already spoken for, so if you’re hoping one of the remaining 5 seats can be yours, you’ll want to apply as soon as possible.

Instructions here –>