I learned this from founders outsourcing the one main skill they need to build
“There’s nothing like a done-for-you service.”
That’s what I thought as I sat, decompressing after a difficult conversation with a client.
I helped this founder line up sales conversations for their new product.
We started off the engagement with clarity. Everything was in place. I built out the outreach sequence and brought him along the journey each step of the way. He seemed like he was onboard. Very eloquent about the problem we were solving and articulate. I thought “this guy will kill it on sales calls.”
A few weeks in, I realized he was avoiding the work entirely. So I cornered him on a call.
To his face, I was frank. I told him he wouldn’t see the ROI on this initiative, if I can’t get him on a call. He responded “I’ve been quite busy and I thought this would be more of a done-for-you service.”
As we wrapped up our engagement, I sat with him on a call to write responses to emails and think through how to respond to LinkedIn DMs. That’s when it dawned on me. He just wanted some handholding through one of the hardest things – maneuvering uncomfortable conversations that come with selling and putting yourself out there.
I realized there are some things you can’t fully outsource.
Avoiding uncomfortable conversations now will only cost you later
You can’t outsource dealing with human friction.
No technology, positioning sequence, and messaging can fully solve the friction of building trust.
On the call with that founder, I realized that the value was sitting there with him, giving pointers, being a soundboard. Not necessarily because I was providing things he couldn’t think about on his own. But if he was on his own, he might overthink it, and worse, decide to get off his seat and “get back to it” another time.
That other time usually doesn’t come.
He needed the accountability to sit there to do the work or pay more to get it all done for him.
Resistance always shows up. It’s become more apparent to me that you have to work through it to learn the texture of this friction. You can’t outsource your own growth.
It’s like wanting someone to go to the gym for you.
When it comes down to a form of growth that requires communication – selling a product, writing a book, building a community – a lot of resistance comes from the fear of the social ramifications of one’s actions.
“What will the person on the other side think about me reaching out to them?”
That’s the question in that founder’s mind when he was struggling to do sales.
I saw the same response when I worked with writers and authors.
When you write words on paper, you’re exposing how you think. In your head, you’re constantly asking “Will people take me seriously? Will they find me out as an imposter? Will they finally realize I am not as smart as I think I am?”
The more these questions appear, the more likely you are to stand up from your seat and not write.
Zooming so far into the future about a consequence that has not yet happened.
Writers call it “writer’s block.”
Founders and business owners call it “clouded vision.”
I call it the fear of being an outcast.
Hey Ya. Listen up.
That’s why a founder would want a “done-for-you service” so he or she does not have to put their face on an endeavor that might fail.
Everywhere I go these days, I see someone building an AI SDR, or AI employee. They say they are using it for productivity, in reality they just don’t want to deal with the messiness of human interactions.
If you choose this unfortunate path, you’ll keep trying to outsource a skill that you should be learning. This will eventually cost you because you’ll have to pay someone else to do that valuable skill for you.
The founder that fully outsources sales will lose deals because in the early stage of a business, people buy the founder’s vision, enthusiasm, and personality, not the product. If you don’t get in front of people, you don’t stand out.
If you’re a writer that would rather outsource all your writing to an LLM to sound smart, you’ll be average like everyone else without a unique perspective.
Even worse, sales predators will continue to sell you courses, packages, and “done-for-you services” so you don’t actually learn a skill and continue to rely on them for results.
I could have been one of those sales people. I could have hit my client with an “upsell” that would cost them 3x what they were already paying me. But that would be creating a dependent relationship that serves neither of us.
The reality is that learning to overcome this friction is not a one-time thing. It’s a continuous practice.
So how do I develop this practice moving through friction?
The system I’m testing to overcome resistance:
Here’s what I’m learning on the practice ground: Most people are more interested in showing off the outcome than showing up to do the actual work.
The best leaders I’ve met show up to focus on solving critical human problems. A lot of times, this cannot be outsourced.
With the client that I was working with, we got to a fork in the road when he told me he wanted a “done-for-you service” after the fact. He was ready to leave results on the table. We had to have an uncomfortable conversation about how best to use our time left on the contract. That’s how we spent the last third of the engagement in 1-hour working sessions, executing, staying on zoom while we finished our work, and viola – we got results.
There was no shortcut to avoid the discomfort.
Discomfort isn’t always a bad thing. It can be a sign that you’re growing.
Over the years, I’ve learned to move past that discomfort with a simple system.
Here’s how I’d experiment with a system to move forward:
Use the 5-day rule: if there’s a task that you keep saying “I’ll do it tomorrow” and you’ve done that for 5 days. There’s a deeper issue that hasn’t been addressed. It’s either not a priority or there’s something blocking you.
Ask the consequence question: “What social consequence am I scared of that’s stopping me from doing this task?” The funny thing is that when you ask this question out loud and answer it, sometimes the answer itself feels silly.
Do 15 minutes on the 6th day: The easiest way to start doing something as a habit is to make the first step easy and easily achievable. 15 minutes is all you need. Do it early in the morning, set a reminder, sit down, and do the task until the timer stops.
Get accountability: To stay consistent with it, get another human being to keep you accountable. This could be a family member, a peer doing the same thing, or a coach (for instance, I reached out to my coach when I had a sticky situation with a client. My coach had seen this several times. They framed how to think about it.)
This system can be applied to anywhere you find resistance – sales, writing, job search.
Closing Reflection:
Teaching someone to catch a fish is way more valuable than helping them catch one.
With founders and authors I work with, the real win isn’t the sales convervations we can book, it’s when they say “Thanks Nifemi, I can do this on my own now.”
Transferring an intangible skill like overcoming the resistance to do sales is valuable. But even more important, for the person learning the skill it is usually unavoidable. The more you avoid the social friction that comes from putting yourself out there, the more you accumulate costs.
You get over it by developing a system that makes it easy for you to get to it.
So this is the question I have for you today:
“What’s the one uncomfortable conversation you’ve been avoiding that, if you had it this week, would change everything?”
Yours truly,
Nifemi
P.S. If you read this far, can you reply with one word to describe a skill that you want to learn but feel a lot of resistance to? I read and reply to every message.
