Let me start by saying this: I am still bad when it comes to delegate work. Not “humble-brag bad,” actually bad, the kind of bad where I end up more frustrated with myself than with the person I handed the work to.
The moment that made me actually sit down and think about this happened this week. A sales rep had just wrapped a discovery call with a prospect and needed to put together a presentation to send over. I opened the deck expecting a clean follow-up to a call that, from what I’d heard, had gone really well. Instead, I got slide after slide that had nothing to do with each other. No thread connecting them. No sense of where it was building to. I remember sitting there, genuinely confused, flipping back and forth trying to figure out what story this deck was even trying to tell.
Here’s where things got interesting. The same rep who built this disjointed mess had handled the discovery call beautifully. Verbally, they could tell a story, build tension, connect the prospect’s problem to a solution, land the point. On paper, none of that translated. And this wasn’t a one-off. I’ve seen this pattern repeat across multiple sales reps over the years: strong verbal storytellers, weak written or visual ones. It’s not a one-rep problem. It’s a skill-gap problem.
The Disconnect Between Speaking and Showing
Talking and writing, or talking and designing a slide are not the same skill wearing different clothes. When you’re on a call, you’re reading the room. You adjust mid-sentence. The story builds itself because you’re reacting to a real person in real time. A presentation has none of that. It just has to stand on its own, slide after slide, with no live feedback loop to save it.
I think this is the part I missed for a long time. I’d hand someone a task, “put together a deck for the prospect” and judge the output without really asking how they got there. I assumed that because someone was good at one form of communication, they’d be good at all forms of it. That’s on me, not them.
Teaching Theory vs. Getting Creative Output
This is the part I keep coming back to, and I don’t think I’ve fully resolved it: you can teach someone the principles of a good sales presentation. Problem, story, solution, proof, ask but none of that is a secret. I can sit a rep down and walk them through the structure in twenty minutes.
But the next-level output, the deck that actually makes a prospect lean in, that doesn’t come from knowing the structure. It comes from creativity. And creativity isn’t something you can hand someone in a training doc. You can give someone the scaffolding, but whether they can build something compelling on top of it is a different skill altogether, and I genuinely don’t have a clean answer for how to teach that part. I’m not sure anyone fully does.
This is where my old instinct used to take over, “just do it myself”. I know what a good deck looks like, I can build one faster than I can explain why this one didn’t work, so why not just take it back? And that instinct is exactly what keeps you the bottleneck in your own team.
The Approach I’m Testing Now
So here’s what I’m trying instead: I’m accepting, going in, that it will probably take four or five rounds before someone produces an output I’m happy with. The whole point is that I’m not just sending the deck back with “this doesn’t work” each time and hoping the sixth try magically lands. I’m trying to make each round sharper than the last, more specific feedback, clearer reference points, narrowing down exactly where the story breaks instead of just saying it’s broken.
I’m in the middle of this experiment right now. I don’t have the tidy “and then it worked” ending yet. What I do know is that the old way, quietly redoing the work myself because it was faster wasn’t actually a solution. It just meant the rep never got better, and I never stopped doing two jobs.
