Now What? Podcast

Delegation is one of the most important—and most misunderstood—skills in leadership.

In Episode 26 of the Now What? Podcast, Glenn Sharp breaks down why so many leaders struggle to delegate and what it’s costing them.

This episode builds on Glenn’s recent appearance on the Entrepreneur DNA podcast with Justin Colby, where they discussed how leaders can create scalable teams by developing people and letting go of unnecessary control.

Many leaders hold onto work because of fear—fear that it won’t be done correctly, fear of losing control, or simply because it feels faster to do it themselves.

But there’s a hidden cost:

Opportunity cost.

When you spend time doing tasks that should be delegated, you lose time that could be spent developing your team, improving operations, and leading at a higher level.

Glenn explains how great leaders create people efficiencies by setting clear expectations, improving communication, and investing in training.

He also discusses:

• Why lack of delegation leads to burnout and turnover
• How to identify “bright spots” on your team and use them to train others
• Why promoting people without proper development creates problems
• The importance of transitioning from a player mindset to a coach mindset
• How even elite performers (like Michael Jordan) struggle to make that transition

If you’re overwhelmed or feel like you’re doing too much yourself, this episode will help you rethink delegation and start building a stronger, more capable team.

Justin Colby: The Entrepreneur DNA:

Spotify: https://open.spotify.com/show/0JgbSxIL3gi8M04gg8dMey?si=7862b71c269448e3

YouTube:

https://youtube.com/playlist?list=PLNIBJdVxHPuOzXKdoZ3E0qjbpgAcPxfeV&si=cea6jp8KXu06QNd9

Apple:

https://podcasts.apple.com/us/podcast/the-entrepreneur-dna/id1723959859

Learn more at:
https://readnowwhat.com/

Get the book Now What?:
https://www.amazon.com/Now-What-Promoted-Individual-Contributor/dp/B0FJZRX3TM/

At some point in your career, you may face a difficult and deeply personal question:

Should you stay in your current role… or move on?

In Episode 25 of the Now What? Podcast, Glenn Sharp responds to a question from Justin in Vermont, who is experiencing prolonged stress in a dysfunctional organization. While he values the relationships he’s built, the situation is impacting both his professional performance and personal life.

Before making a decision, Glenn challenges listeners to think differently using the Results Cone and a proven assessment framework: the James Peterson Stress Management Questionnaire.

This framework helps uncover the true source of stress, including two key areas:

• The Disappointment Scale — where expectations of others may be unrealistic, leading to unnecessary frustration
• The Under Achievement Scale — where expectations of yourself may create pressure and dissatisfaction

Glenn explains that stress isn’t always caused by your environment alone.

Often, it’s a combination of expectations, perspective, and how we interpret our situation.

He also shares a personal story from his baseball career, illustrating how redefining success can remove unnecessary pressure and create clarity.

If you’re feeling overwhelmed, stuck, or unsure whether to stay or leave, this episode will help you get to the root cause of your stress and make a more intentional decision.

Learn more at:
https://readnowwhat.com/

Get the book Now What?:
https://www.amazon.com/Now-What-Promoted-Individual-Contributor/dp/B0FJZRX3TM/

Employee turnover can be one of the most frustrating parts of leadership.

You treat your people well.
You invest in their development.
You create opportunities for them to grow.

And sometimes… they still leave.

In this episode of the Now What? Podcast, Glenn Sharp responds to a question from Bobby in Lima about how leaders should think about employee turnover and how to reconcile treating people well while still losing members of their team.

One of the most important leadership lessons Glenn shares is that turnover is not always a problem. In many cases, it’s simply a reality of managing people and building careers. Employees will leave for promotions, new opportunities, or sometimes because they believe the “grass is greener” somewhere else.

Glenn explains that great leaders focus on the one thing they can control: how they treat their people and how well they prepare their team for change.

This episode introduces the powerful leadership mindset of “Next Man Up.” Just like in sports, the next person must always be ready to step in when opportunity appears. That readiness only happens when leaders consistently develop and test their staff.

In this episode, Glenn discusses:

• Why managers must accept that people will leave their organization
• Why turnover is not necessarily a sign of poor leadership
• The “grass is greener” mentality and why many employees regret leaving
• How great managers constantly develop their people
• Why testing and preparing your team ensures someone is always ready to step up

Strong leaders don’t try to eliminate turnover entirely. Instead, they build teams that are prepared for it.

Learn more about the Now What? Podcast and leadership resources:
https://readnowwhat.com/

Get the book Now What? Promoted from Individual Contributor to Manager:
https://www.amazon.com/Now-What-Promoted-Individual-Contributor/dp/B0FJZRX3TM/

Many leaders struggle with the transition from doing the work themselves to holding others accountable.

In Episode 23, Glenn Sharp answers a question from Robert in California, who is working 90 hours a week while his two leads are operating at only 60–70% capacity.

The real issue isn’t effort.

It’s mindset.

Glenn explains why leaders must shift their thinking before they can change the behavior of their team. Simply telling someone they’re now part of management doesn’t work.

You must train them, invest in them, and hold them accountable.

In this episode, you’ll learn:

• Why proactive leadership beats reactive management
• How the Results Cone helps leaders focus effort where it matters most
• Why you must align expectations with your boss first
• How the Leadership Coaching Scorecard helps structure leadership development
• Why thinking three years ahead changes your leadership strategy
• The Birthday Cake method for developing managers
• How the Accountability Ladder helps new leaders transition from friend to boss

If you're overwhelmed doing everything yourself, this episode will help you start building the leaders your organization needs.

Learn more at readnowwhat.com

Get the book Now What? on Amazon:
https://www.amazon.com/Now-What-Promoted-Individual-Contributor/dp/B0FJZRX3TM/

Growth is exciting.

But expansion can quietly damage the very operations that made you successful in the first place.

In Episode 22, Glenn Sharp responds to a question from Elise in Orlando. Her company is preparing for a major acquisition, and her operations team — overseeing 10 locations across Florida — must develop a solid integration plan before the agreement is signed.

The question is simple:

How do you prepare for expansion without hurting your current performance?

Glenn walks through the leadership principles that protect your “home base” while positioning your team for growth.

In this episode, you’ll learn:

• Why proactive planning always costs less than reactive recovery
• How the Results Cone applies to expansion strategy
• Why rumor control is critical during acquisitions (and how poor communication once led to a 15% workforce loss)
• Why you must test your people now — before expansion stretches your leadership capacity
• How to think from the perspective of the company being purchased
• Why involving your team early builds ownership and reduces resistance
• How to protect your core operations when top talent is pulled toward new growth

Expansion without structure creates chaos.

Expansion with preparation creates opportunity.

The episode closes with a preview of Episode 23, where Glenn tackles how to hold managers accountable without damaging morale.

Learn more at readnowwhat.com

Get the book Now What? on Amazon:
https://www.amazon.com/Now-What-Promoted-Individual-Contributor/dp/B0FJZRX3TM/

Micromanagement is frustrating.

Especially when your boss is a good person — but constantly involved in even the smallest details of your work.

In Episode 21, Glenn Sharp answers a question from Michael in Cincinnati about how to deal with a micromanaging boss without damaging the relationship — or your career.

Instead of reacting emotionally or staying silent, Glenn introduces a proven framework from Crucial Conversations: the STATE Method.

Before addressing the issue, Glenn explains why you must first shift your paradigm.

What pressure is your boss under?
What might he be worried about?
What’s happening from his perspective?

Then, use STATE:

• Share your facts – Stick to observable behavior, not accusations.
• Tell your story – Explain how the behavior impacts you.
• Ask for others’ paths – Invite your boss to share their reasoning.
• Talk tentatively – Avoid absolutes that trigger defensiveness.
• Encourage testing – Ask genuine questions instead of trying to win.

Glenn also explains the difference between:

“What” skills — what you say
“How” skills — how you say it

Because in crucial conversations, tone determines whether your message will be heard.

If you’ve ever felt micromanaged — or worry that you might be micromanaging someone else — this episode provides a clear, professional path forward.

The episode closes with a preview of Episode 22, which explores leadership challenges when purchasing another company.

Learn more at readnowwhat.com

Get the book Now What? on Amazon:
https://www.amazon.com/Now-What-Promoted-Individual-Contributor/dp/B0FJZRX3TM/

Great managers don’t pass information along.

They filter it.

In Episode 20, Glenn Sharp answers a coaching question from Jeannette about one of the most practical leadership concepts from Now What? — being the “strainer” for your team.

Jeannette admits she doesn’t feel naturally creative and struggles to simplify complex messages from corporate leadership so her team can understand them.

Glenn explains why this isn’t about creativity — it’s about responsibility.

It’s your job as a leader to simplify.

In this episode, you’ll learn:

• Why communication and influence are managerial responsibilities — not personality traits
• How the “Results → Thinking → Behavior” framework applies to communication
• Why forwarding corporate emails directly to your team is a leadership mistake
• How to filter and translate messages into relatable language
• The powerful Reese’s Egg story — and how breaking a goal into simple, personal terms transformed results
• How to use bright spots and high-potential employees to help influence others
• Why situational discussions beat reading emails
• How to “shrink the change” to reduce resistance
• Why influence means speaking in terms your audience understands

Glenn shares real-world leadership stories, including a corporate sales mandate that seemed impossible — until it was simplified and reframed into something employees could actually achieve.

The episode reinforces that great managers don’t amplify noise — they reduce it.

They translate complexity into clarity.

The episode closes with a preview of Episode 21, featuring a challenging leadership question from Michael in Cincinnati.

Learn more at readnowwhat.com

Get the book Now What? on Amazon:
https://www.amazon.com/Now-What-Promoted-Individual-Contributor/dp/B0FJZRX3TM/

The move from manager to director isn’t just a bigger job — it’s a completely different one.

In Episode 19, Glenn Sharp responds to a question from Jimmy in Charlotte, a successful manager of 9 who’s being considered for a Director role overseeing 60 people with five direct reports. It’s an exciting opportunity — but also a stretch.

What changes at this level?
What skills actually matter?
And how do you prepare for leadership at a higher altitude?

Glenn explains that success at the director level comes down to two core capabilities: Vision and Influence.

In this episode, you’ll learn:

Why you can’t stay in the weeds as a director
How the Results Cone changes your focus from doing to developing
Why you don’t need to know everything — but you must see what others don’t
How creating a Mission / Vision / Values framework builds alignment
Why goal-setting must begin with the end in mind
What it means to develop people who can replace you
Why “Don’t bring me problems — bring me solutions” builds ownership
The powerful succession question: “Who ya got?”

Glenn shares practical frameworks and mindset shifts that help leaders move from tactical execution to strategic influence — and explains why delegation and leadership development are no longer optional at this level.

The episode closes with a preview of Episode 20, featuring a question from Jeannette in Chicago about being a “strainer” for your team and filtering what reaches them.

Learn more at readnowwhat.com

Get the book Now What? on Amazon:
https://www.amazon.com/Now-What-Promoted-Individual-Contributor/dp/B0FJZRX3TM/

In this episode, Glenn Sharp addresses a challenge many managers face but rarely talk about openly: how to develop high-potential employees without losing them.

Glenn responds to a question from a listener in Plymouth who manages a smart, ambitious employee that has clearly outgrown his current role. The employee is capable, motivated, and bored — and the manager is worried about losing him if the next step isn’t handled correctly.

Glenn explains why high performers don’t leave because of a lack of opportunity — they leave because of a lack of clarity and development. Promoting someone too fast or without preparation often creates bigger problems than it solves.

You’ll learn:

• How to approach a high-potential employee who’s getting bored

• Why understanding what the employee really wants matters more than assuming

• The Birthday Cake Method for development, from foundation to readiness

• How to give a realistic picture of leadership before promoting someone

• Why high-potential employees must prove readiness, not assume advancement

• How the Situational Leadership model helps identify development gaps

• Why expectations and accountability must be revisited throughout the process

• How and when your boss should already know who your top performers are

Glenn reinforces that developing high-potential employees is intentional work — and when done well, it keeps your best people engaged, challenged, and growing.

The episode closes with a preview of Episode 19, which focuses on the transition from manager to director and how leadership expectations change at the next level.

Learn more at readnowwhat.com
Get the book Now What? on Amazon:
https://www.amazon.com/Now-What-Promoted-Individual-Contributor/dp/B0FJZRX3TM/

Burnout doesn’t happen overnight — it builds quietly, one frustration at a time.

In Episode 17, Glenn Sharp addresses burnout head-on after responding to a listener question from Tampa. The listener describes working for an unapproachable boss, receiving unclear direction, and feeling increasingly frustrated and depleted — to the point of burnout.

Glenn explains why asking for help is the right first step, and why burnout is often driven by perspective, boundaries, and control more than workload alone.

In this episode, you’ll learn:

• Why changing the way you think about a situation can reduce burnout

• How to compartmentalize work so it doesn’t consume your health or relationships

• The “Bubble” concept — what deserves your emotional energy and what doesn’t

• Why focusing on control and influence matters more than replaying the past

• How burnout often signals the need for relief, not avoidance

• Why difficult conversations are necessary — and avoiding them makes burnout worse

Glenn shares powerful stories, including a CFO whose overwork nearly destroyed his health and personal life, and explains how reclaiming boundaries helped him regain control.

The episode closes by reinforcing that burnout is often a signal that something needs to change — and previews Episode 18, which will explore what to do when high-potential employees feel stuck due to limited growth opportunities.

Learn more at readnowwhat.com
Get the book Now What? on Amazon:
https://www.amazon.com/Now-What-Promoted-Individual-Contributor/dp/B0FJZRX3TM/