Hidden Value with David Sherry

Delegation is a challenge for many entrepreneurs. 

You either:

• Struggle to figure out what work to hand off.
• Have a ton of work but don’t know how to communicate what needs to get done.
• Or (less talked about) even feel a little guilty about giving work to someone else...

Delegation, when done right, isn’t a burden—it’s an opportunity to align your team with the highest-impact work.

1. The Telescope Approach: Start big picture

The first step in effective delegation isn’t where you’d expect. I always tell entrepreneurs to start by zooming out—like using a telescope.

A telescope can either give you a wide view of the entire night sky or zoom in on a specific planet or star. When you’re thinking about delegation, start with the widest lens possible.

Ask yourself:

• What is this person’s role?
• What are the most important projects this month, quarter, or year?
• What actually matters most in the business right now?

Before you get lost in the details of small tasks, take a step back and list the top three most important priorities for the business. This helps you delegate work that actually moves the needle, rather than just keeping people busy.

If you already set clear quarterly goals, this gets easier—you already have the right context in place. From there, you can start focusing on what specific work needs to be assigned.

2. Focus on 80%

Once you have the big picture, think about what this person should spend 80% of their time on. This give you a starting context.

Ask:

• What is this person best at?
• Where should they be focused?
• Are they currently aligned with their highest-value work?

If they’re already spending 80% of their time on the right things, then you’re just tweaking the remaining 20%. But if their focus is off, that’s where you need to start making adjustments.

For example, if someone’s role is to lead brand marketing, then ask: What part of brand marketing does the business need most right now? 

Instead of just handing them random tasks, make sure they’re working on what will have the biggest impact.

Delegating small, unimportant tasks effectively doesn’t help if your team isn’t aligned with the most important work in the first place.

Communicating

One last thing—these conversations don’t have to feel heavy or overwhelming. A client of mine recently shared how much anxiety they felt about these discussions. But the truth is, you don’t have to approach delegation conversations with a super serious tone.

Yes, delegation is important, but keeping it light makes the process easier for everyone. Instead of making it feel like a high-stakes, make-or-break situation, try saying:

• “Hey, let’s take 10 minutes to check in on this.”
• “I love a lot of what you’re doing, I just wanna tweak one thing.”
• “I must not have been super clear before—let’s make sure this is aligned.”

This makes people more open to feedback and less defensive. The more relaxed and collaborative you make it, the more effective the conversation will be.

A lot of times, when you’re frustrated with a team member, the issue is actually pretty small. But in the moment, it feels like everything is wrong. They’re probably doing a great job in most areas, but one small detail is off.

Instead of assuming everything is a mess, take a step back and recognize what’s going well. This makes the conversation with your team much more productive:

1. Acknowledge what’s working – “Hey, I love the work you’re doing on X.”
2. Identify the one thing that needs tweaking: “I think we could improve Y a little bit.”
3. Collaborate on a solution – “How do you think we could approach this better?”

This keeps the conversation positive and solution-oriented instead of turning it into a stressful critique.

Here’s a quick recap of how to delegate more effectively:

1. Zoom Out First – Start with the big picture before diving into the details.
2. Focus on the 80% – Ensure your team member is working on the right 80% of their role. 
3. Communicate Big & Small – Most issues are small; recognize what’s working and adjust from there.
4. Keep It Light – Delegation doesn’t have to be a stressful, serious thing.

I hope this helps you think differently about delegation. Let me know—where have you struggled with delegation?

If you’ve ever felt stuck, frustrated, or like you're spinning your wheels despite putting in effort, this might be what's happening beneath the surface….

You might rationally know what you want—whether it’s raising your prices as a freelancer, launching a new project, or taking a big step forward.

But despite your conscious desire, something always seems just out of reach…

The way to recognize subconscious resistance is to look at areas where you're putting in a lot of effort but never seeing the results you want. It’s like hitting an invisible wall. You get excited, you try, you push, and then suddenly, something stops you. You fall back to where you started, and the cycle repeats.

Usually the subconscious makes itself known through strong fear (ah!), discomfort (in the body), or resistance but you can’t rationally explain why it’s there.

Here are a few examples:

• You know you need to raise your prices, but every time you go to send that email, you freeze up.
• You're about to record your first podcast, but seeing yourself on camera makes you feel terrible.
• A casual conversation suddenly makes you deeply uncomfortable, and you just want to leave.

These are signals that something deeper is at play. In the healing and personal development world, this is often referred to as a “trigger”—an unconscious emotional reaction that doesn’t have an obvious logical cause.

Work with your emotion, not your logic.

The good news is that once you recognize this dynamic, you know where to focus your energy.

Instead of trying to rationally “figure it out” (which can be exhausting and often ineffective), shift your attention inward to observe what’s happening emotionally.

1. Pause When You Feel Resistance – When irrational fear or discomfort shows up, don’t ignore it. Instead, acknowledge it as valuable information. Thank you!
2. Stay With the Emotion – Instead of pushing it away, sit with it. Ask yourself, What am I actually afraid of? Usually the fear is deeper and wider than the task at hand.
3. Identify the Conflict – Example: You want to start a podcast, but deep down, you fear being misunderstood or criticized. This is why there’s a “push-pull” effect – we have a conscious desire and an unconscious fear. 

Curiosity and awareness help you detect the bigger pattern at play. Shockingly, whatever is coming up for you right now related to this fear is probably something that is affecting other areas of your life as well. 

Look for your resistance

If you feel stuck in an area of your life—whether it’s business, relationships, or a creative project—start paying attention to where resistance shows up. Often, there’s another voice at the table, one that isn’t rational but still deeply influences your actions.

Find someone to help you identify, map, and learn more about this fear; be it a coach, therapist or just a good friend! 

Have you noticed any recent irrational fear or discomfort holding you back from something important? 

How do you work with your subconscious fears?

The idea that one day your business will be "stable" and free from uncertainty is a myth. Markets shift, customers change, and what worked yesterday won’t necessarily work tomorrow. There is no finish line where you finally “made it” and get to stop adapting.

The real safety net? Trusting yourself to respond.

Instead of forcing yourself to fit into an old model, it’s time to evolve your business to fit YOU.

I remember having a phone call with Paul Jarvis (Author/Creator) and we were talking about his newsletter, which I was an avid reader of. I told him how much I was impressed by his consistency and quality.

“Oh,” he said. “I just spend a few days at the beginning of the quarter writing and scheduling about 3-4 months’ worth of emails.”

“You can do that?!” I asked.

For Paul, his workflow meant batching and scheduling, but to the outside, it looked like extreme willpower. To him, it probably felt like a short burst of focus and then leisure to think about other aspects of his business.

It’s easy to look at others and think they possess some type of magic we don’t have. But when the “trick” is shown, we see that it was our perception that was false. We just didn’t see the possibility.

In working with Founders, sometimes all I do is simply point to the potential that someone wasn’t able to see for themselves. It’s obvious when you know it, and yet it remains frustratingly hidden when you don’t.

The first step to making something happen is seeing that it’s possible.

Some people look at magicians and leave confused, amused, or annoyed. 

Others ask the magician to learn and then practice their sleight of hand…

I have a client who went from $5k months to $10k and then $50, $100k+ months.

Here’s what I noticed along the way: He’s still him, and yet the way that he sees his work has changed drastically at each step. He’s embraced a change of role, and a change of leadership; how he serves his clients and what problems he solves for them.

Each change in revenue was preceded by an unlock, you could feel it happen in our conversation.

Suddenly it was no longer about him doing the work, but finding others to help. Suddenly it wasn’t about just hiring others, but creating new products. Suddenly, his business was about client experience, and now how much value he creates for his network.

This is the seamless process that happens when you are entering a growing market with a high propensity for flexibility and complexity.

And of course it doesn’t seem so seamless at all. Each block in thinking is caused by what previously worked, and it’s hard to change roles. It takes a small ego and a big desire to learn.

If you don’t know where to start, here’s a question to consider;

• How has your role changed, even though technically you still are the same title?
• If you could promote yourself, what would your new title be?
• How can you start doing some of that work, today?

Business growth comes from leadership growth and change.

I’ve been practicing meditation again, now through a new App called “The Way.” 

It’s been teaching a simple framework for noticing more about how our minds work. 

What can you do about being stressed, having anxious, coming back into the present?

The framework is very useful for getting yourself out of your head and back into the present. It all starts with awareness and noticing – catching yourself getting out of presence. There are so many different ways that we stop being present.

So it helps for you to get a basic understanding about how you, specifically, leave the present moment:

Presence/Out of Presence:

• Audio/Past: We remember a conversation that we were having (and maybe cringe about it). 
• Audio/Future: We’re practicing a conversation that we’re going to have.
• Audio/Present: You’re hearing something in the room you’re in, right now.
• Visual/Past: We see images of some past event or person.
• Visual/Future: We are imagining how we’ll act, we’re in a fantasy of the future.
• Visual/Present: You’re seeing the room you’re in, the color, the texture. 

Etc.

Those senses, those same senses that were distracting you become an anchor to getting present again. 

Talk about a counter-intuitive move! 

Start by “labeling” what you’re noticing. Understand a bit better and get curious about yourself in this way.

And, you can download the app the way if that's helpful to you. 

What helps you get outta your head and back into the present? 

If you’re stuck selling, ask yourself if you’re trying to prove the value of what you do to someone else.

The biggest misconception of sales and selling to clients is that you’re convincing someone to buy from you. This manipulative view leads to poor processes and poor outcomes. 

It’s very unlikely this potential client values what you value.

This is where the manipulation shows up in attempts to correct this misalignment.

(rarely works).

Instead, see if you can learn what your client values.

Become a detective to understand how they see what they need and want.

Become a partner to them in creating or capturing that need together – and ask yourself how you can help bring them to that better future faster, easier, or more artfully.

Even that is not enough.

Your job isn’t even just to deliver and meet expectations but to go beyond them.

The best client relationships go beyond the initial scope into an even more expanded and valuable future.

Selling is the art of transformation. 

The faster you identify what transformation is needed, the faster you can start delivering value to your clients.

There’s a subtle lesson as to why our best thinking arrives in the shower. It’s a multiple of effects all happening at once.

The first is that you’re not intending to think about anything in particular. This “release” from our problem-solving mind seems to allow to actually… solve problems for you. But done in a holistic manner that skips the direct logic of pouring energy through the known problem space.

The second is the heat. You’re relaxed. You’re no longer in the rush or the stress of the day and that gives your system a chance to calm down. Strangely, the calm also works well for solving big problems in simple, effective ways. Stress as a stimulus may give your work more distance, but perhaps not more depth.

Third, is the sound. There’s a white-noise effect, a hum of the water pressure and splash of the droplets. Attuning to this sound, you center yourself unconsciously into a type of meditative state. This meditative state anchors to sound, the consistency of it allows you to drop into a more open state giving you some separation from your thoughts.

You can take a few lessons from this confluence of factors – that you have a system of senses that are all intelligent. That your mind-based logic is only one system and is a blunt tool.

That your environment matters for your consciousness and your experience of being.

And – that turning away from something is also a useful method for working through something.

Explore why many people get their best ideas in the shower and what it reveals about problem-solving. Discover the role of relaxation, white noise, and a calm environment in fostering insights. Learn how stepping away from intentional thinking and engaging all senses can lead to holistic solutions. Share your own experiences and methods for finding the best answers in the comments.