http://sheeleyexecutiveconsulting.co/

Sheeley Executive Consulting, 100 S Water St, Watertown, WI (2026)

05/28/2026

Shout out to all who showed up for breakfast and some early bingo.

I love the crossover events like these because it reminds me just how much is going on in right now.

Sure, lots of talk about data centers, energy, and tourism, but most of my conversations today were about connecting people who want to work with companies that want to hire.

Folks, just get out and talk to people. Stop taking headlines at face value and get after it. So much of business is hearing what opportunities are ripe and ready for you to help.

Thanks for crushing it again, Julia QC, Linden Peacy, & Krueger.

Watertown Area Chamber of Commerce
Fort Atkinson Area Chamber of Commerce
Jefferson Area Chamber of Commerce

Jonathan E Sheeley

05/14/2026

Leaders learn from everyone.

Not just authors and gurus.

This morning I was a guest at the for the first event in their new Milwaukee Mornings leadership series — a fireside chat presented by featuring Chef Dan Jacobs of .restaurant and .mke

The Market is one of my wife Nicole’s and my favorite places in the city. It was a great choice for this conversation.

Chef Dan shared five questions he uses to navigate competition — forged in the pressure of and still running his kitchens today:

1. What are they actually asking me to do?
2. How am I going to set myself up for success?
3. Where is the creative opportunity here?
4. Do I have the right tools for this?
5. Am I having a good time?

Five questions that work in a kitchen and in a boardroom.

They work in any moment where pressure is high and the work still has to be worth something.

Dan also said something about Milwaukee that I like: “We’re so cool we don’t even know we’re cool yet.”

I’ve been coming to MKE for work and pleasure for 15 years, and I’ve come to appreciate the way a mid-market city can own its personality with unique options, affordable experiences, and a pace that you can choose. The blend of beautiful history and modern design here teaches a good rule for life: legacy planning draws on the strength and lessons of the past to build new and bold opportunities. You can’t scrap everything and start fresh, but you also can’t preserve it all. Those choices require leadership dexterity and patience.

Thank you to the Milwaukee Mitchell International Airport for presenting, and to the Milwaukee Public Market for launching a series worth showing up for. I’ll be back.

MKE, I’m a fan.

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If you want to develop as a leader, create team alignment, or bring this kind of work to your organization, start with the assessment on my profile.

I’m Jonathan Sheeley, and I turn business leaders into legacy architects.

05/13/2026

"I'm thankful for the permission to change."

I had a conversation with a leader today who is doing the real work of redirecting and leading an organization to higher aspirations and better value to their clients.

Something that stood out to me is the gratitude she expressed for the support from the board she's serving with to adjust, tinker, and assess new initiatives.

It's not that the old way was bad; it just wasn't serving the clientele anymore. So what's she doing?

- Asking stakeholders a lot of questions (inside relational input)
- Assessing what has worked (hard data input)
- Seeking help from an experienced leader (outside but relevant input)
- Enlisting new voices to the table (new and inspired input)

This approach takes time. But it works.

As a leader, having the buy-in from the different layers of a complex organization is critical.

Managers see an issue, decide on change, and expect people to get in line.
Good managers have employees bring issues to them and will hear out their solutions.
Leaders listen, learn, discern, decide, promote, and execute change with their team.

Thanks for the inspiration, Kelly Webster & Oconomowoc Chamber Of Commerce.
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If you want to develop as a leader, create team alignment, or bring this kind of work to your organization, start with the assessment on my profile.

I'm Jonathan Sheeley, and I turn business leaders into legacy architects.
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05/09/2026

Leadership in business is a lot like sailing.

You’ve got to be a little bit crazy to do it well.

Yesterday I was in Sheboygan and took the chance to see the lakefront. i’ve always been enamored with the water. it’s beautiful, wrestless, and calming all at the same time.

Since starting a company, I’ve spent a lot of time thinking about the parallels between business and sailing.

- to sail somewhere, you have to know where you’re headed. if you do the trip twice, it won’t be on the same exact path because the water is always changing.

- to keep a boat on course requires constant attention and redirection.

- to be on the water is to be working hard and enjoying the process. It’s hard fun.

- to sail a ship, you must know enough about the boat and the trip to be able to get there safely.

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I’m Jonathan Sheeley—I turn business leaders into legacy architects. You’re business isn’t just a vehicle for income, it can be an asset for your family, your team members, and your community.

if you want that for your company, DM me and we’ll talk about what that would look like for you.

04/27/2026

Most leaders know their org chart.

Fewer know their sphere of influence.

The org chart tells you who you manage and who manages you. Your sphere of influence tells you where your character, your reliability, and your judgment are.

There are three distinct layers worth understanding.

The vertical layer is the one most people recognize — your direct reports and your direct supervisors. These are the relationships the structure enforces. The real question isn't whether those relationships exist, but whether you're actively investing in them or simply relying on the org chart to hold them together.

The peer layer is where leadership gets tested and developed.

Your peers sit at the same level as you, often doing entirely different work, and you have zero positional authority over them. You can't assign them tasks. You can't pull rank. If you want them to shift tactics or buy into a direction you're driving, your logic has to connect to the mission. Your relationship has to carry weight before the conversation starts.

This is where a lot of leaders stall. They've learned to manage down. They haven't learned to lead sideways.

The general layer is where people know about you when your name comes up in a room you're not in. It's built through consistency — doing your work with fidelity, keeping your commitments, being the same person regardless of who's watching.

It also functions as the seedbed for everything else. Your general influence should be opening doors you haven't approached yet.

One more thing worth saying: the sphere of influence concept has been used to keep people in their lane and out of the conversation. That's a misapplication. Used well, it's a tool for becoming more intentional — about who you're responsible to, whom you can serve, and where your growth is actually happening.

The sphere isn't a boundary. It's a responsibility.

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If you want to develop as a leader, create team alignment, or bring this kind of work to your organization, start with the assessment in the comments.

I'm Jonathan Sheeley and I turn business leaders into legacy architects.

04/24/2026

Most business owners have a sense of where they want to go.

Very few have developed the skill of articulating it in a way that moves their organization.

Vision isn't just a statement. It's a leadership capability. The ability to see a future state with enough specificity that others can picture it, believe in it, and orient their work around it.

That ability to cast a compelling vision and communicate it consistently is one of the highest-leverage things a leader can develop.

It changes how teams make decisions. It changes how culture forms. It changes what the organization is willing to attempt.

When vision is present and well-articulated, leaders spend less time managing and more time building. The organization moves toward something, instead of just moving.

This is the work I love most. And it's where I've seen the most significant shifts in the leaders I work alongside.
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If you want your work to have meaning beyond your time, start with the link in the comments. Let's see what the Legacy Leadership Architecture can do for your work, your family, and your community.

I'm Jonathan Sheeley | I turn business leaders into legacy architects.

04/24/2026

Real leadership can feel like an extra.

Busy executives can be under insane pressure. From their clients, direct reports, family, community, and themselves.

And in the noise of all the external voices vying for their resources, the long-term aspirations suffer. Because 15 years from now is hard to visualize. You want to know what next quarter holds, or even next week!

So why does it feel like it's so hard? Because real leadership takes extra effort. It's not passive. It's not an add-on. Real leadership requires excellent time-management, focused boundaries, and saying "no" a lot.

If you feel like your role as a leader is hard, don't assume it's a problem. Ask yourself this: is it hard because of the work, the people, or the responsibility?

If your industry is hard, your leadership will be hard. Good. Not an issue. Do good/hard work.
If your people are hard, first look at whether you're communicated, guiding, mentoring, and developing them. If you aren't start there before complaining.
If your responsibilities feel hard, you probably just understand them correctly. Lean into it. Everyone benefits from this.

Leadership is difficult but it doesn't have to be lonely, meaningless, or soul-sucking.

You can lead and have great family relationships.
You can lead and build an incredible team.
You can leave the community you live in better than you found it.
You can leave a legacy.

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If you want your work to have meaning beyond your time, start here: https://www.sheeleyexecutiveconsulting.co/assessment. Let's see what the Legacy Leadership Architecture can do for your work, your family, and your community.

I'm Jonathan Sheeley | I turn business leaders into legacy architects.

04/17/2026

Now offering the Legacy Leadership Assessment.

Many assessments show you what kind of person you are, and that’s good to some extent . My assessment gives you a snapshot of your current leadership maturity. I engineered it so you can take steps forward in action and direction. If you want to know how you score on the six domains of leadership take the 15 minute quiz.

Sheeleyexecutiveconsulting.co/assessment

04/15/2026

This year, I've finished 7 books.

Titan: The Life of John D. Rockefeller, Sr.
Traction by Gino Wickman
The Talent Code by Daniel Coyle
The Screwtape Letters by CS Lewis
A Tale of Two Cities by Charles Dickens
The Hobbit by JRR Tolkien
The Lord of the Rings by JRR Tolkien

Then I spent way too much time counting how many books I've read since graduating from college.

It's well over 100. I love reading. It's a simple pleasure that we forget is a privilege of our time.

It's not just about reading to learn. Though I do think there's something important about picking up a framework or a new way of thinking.
It's about understanding people better.

Stories from different eras carry more than their plot. You pick up vocabulary, inside jokes, and cultural connections. You find the problems that have never changed — the ones that cross every era, every culture, every industry. And when you know a story that someone else knows, conversations flow.
A mentor once challenged me to read broadly if I wanted to be able to talk with anyone. It's probably the best single piece of advice I've ever received.
Here's what I've carried into my work from it: people crave the same things: connection, to be understood, to belong to something. If you can see your clients through that lens, it changes how you lead and how you serve.

As you can see, I've been a bit heavy in the novels this year so far. Part of that comes from a season where I am working a lot and need a brain break. But coming off of Traction and The Talent Code, I have lots of work to do on my business.

Here are 10 that have impacted me the most professionally:

Mindset by Carol Dweck
Dare to Lead by Brené Brown
The Motive by Patrick Lencioni
Creativity, Inc by Ed Catmul (Founder of Pixar)
Living Forward by Daniel Harkavy & Michael Hyatt
6 Types of Working Genius by Patrick Lencioni
Turn the Ship Around by L. David Marquet
Free to Focus by Michael Hyatt
Building a StoryBrand by Donald Miller
10x is Easier than 2x Dr. Benjamin Hardy & Dan Sullivan

What are some of your favorite books? Did you start loving books or have to get accustomed to reading as a leader?

04/13/2026

The best growth comes from an accurate view of today.

Last month, my mastermind was talking about growth, but couldn't always pinpoint where they wanted to mature. Talking growth and legacy is good, but where do we start?

So I built something that exposes your leadership mindset, capacity, and structure. And then I realized everyone I work with needs the same thing.

That's how the Legacy Leadership Assessment came to be.

Truthfully, I love assessments. Probably more than most people. But most of them stop at the snapshot. Here's where you are. Here's your profile. Here's a color or an avatar or a four-letter code. Then you're on your own to figure out how to apply it to your life.

The Legacy Leadership Assessment is designed to do something different. It shows you where you are and what it looks like when you're firing on all cylinders in that area. Not a prescription. A picture of the standard — so you can see the gap and decide what to do with it.

It measures 6 dimensions of leadership:

Vision & Strategic Alignment + How clearly your purpose and direction is articulated & expressed.

Leadership Clarity & Decision-Making + How confident, consistent, and distributed leadership is at the top.

Team Cohesion & Culture + The health, trust, and adaptability of your team across generations.

Leadership Development & Bench Strength + Whether your organization can grow leaders from within.

Operations & Scalability + Whether your systems and structure can run and grow without you.

Growth Readiness & Leader Sustainability + Whether the leader and the business are ready for the next stage.

When you finish, you'll get a scorecard across all six. You see where you're strong. You see what areas are costing you.

Ten minutes. Built for leaders who are serious about the long game.
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If you want to develop as a leader, create team alignment, or bring this kind of work to your organization, start by taking this assessment.

I'm Jonathan Sheeley | I turn business leaders into legacy architects.

Sheeley Executive Consulting

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