When great people leave, it’s not always because they dislike their job. Sometimes, they leave because another opportunity better fits the future they want. In this episode, Shannon Waller shares a simple question you can ask to learn what matters to your best team members—and help make sure they don’t have to look elsewhere to grow.

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Show Notes:

• Your best team members can become stealable when another opportunity better matches the future they want.
• Don’t assume that long-tenured, high-performing team members are satisfied simply because they’ve stayed with your company.
• Great people can experience “brownout,” gradually becoming worn down even when they enjoy their work, earn well, and have a strong reputation.
• Knowing your team members’ goals for the future helps you spot concerns and opportunities before they become reasons to leave.
• By being curious rather than judgmental when asking about a team member’s future, you can create the psychological safety necessary for them to tell you honestly what they want, what’s challenging them, and what may need to change.
• Avoid entering the conversation with an agenda because people are less likely to give you an honest answer when they feel pressured.
• Ask your key team members regularly, “If you and I are meeting three years from today, what has to have happened personally and professionally for you to feel really happy with your progress?”
• Focus on progress rather than perfection because every team member is the best judge of what would make their future more fulfilling.
• Listen for what team members want in both their personal and professional lives in terms of responsibilities, growth, compensation, travel, family, health, and work pace.
• Regular conversations about your team members’ futures can give you valuable notice of a transition and allow you to plan it together.
• Supporting a talented person’s next step, even if it eventually takes them elsewhere, can create a respectful transition and preserve the relationship.
• Ambitious people want to grow, and understanding how they want to grow helps you create opportunities that keep them engaged.

Resources:

Protect Your A-Players

Unique Ability®

How To Sell Transformation Using This One Question

CliftonStrengths®

Is keeping the peace actually holding your team back? In this episode, Shannon Waller interviews Cal Riley, author of Entrepreneurial Compassion, to explore why caring enough to have hard conversations and getting curious about others’ perspectives can build healthier teams, better results, and a more meaningful entrepreneurial life.

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Show Notes:

• Compassionate leadership isn’t about being soft; it’s about caring enough to take purposeful action.
• The most productive leaders combine entrepreneurial drive with genuine compassion for the people around them.
• Avoiding a difficult conversation may feel nice in the moment, but it’s rarely kind or compassionate in the long run. Being nice means avoiding discomfort; compassion means caring enough to address what’s not working and help someone move forward.
• Leaders earn the right to give honest feedback by first showing real interest in people’s lives, well-being, and goals.
• Self-compassion and self-awareness help entrepreneurs learn from mistakes without letting failure define them.
• Slowing down through reflection, journaling, walking, or quiet time can make you less reactive and more present with others.
• Curiosity creates better solutions because understanding someone’s perspective comes before trying to change their behavior.
• An abundance mindset allows you to support great team members when their best next step is outside your company.
• High-performing teams value both individual capability and a willingness to put the team’s needs first.
• Compassion scales when entrepreneurs model it with their leadership team, who then bring it to the rest of the organization.
• You can’t fake compassion; people can tell whether your concern is authentic.
• One way to take action on this is to ask yourself who in your life needs more compassion from you—and consider whether you’ve been extending that same patience, understanding, and grace to yourself.

Resources:

Entrepreneurial Compassion: An Entrepreneur’s Journey Through Combat, Suicide, and the Discovery of Compassionate Leadership by Cal Riley

Multiplication By Subtraction by Shannon Waller

Inviting Genius by Matthew Abrams

Unique Ability®

CliftonStrengths®

More about Cal Riley

Do you take time to connect the dots for your team, or leave them guessing at the bigger picture? In this episode, Shannon Waller explains why context is one of the most valuable things a leader can give. Learn how a few simple communication habits can prevent confusion and missed handoffs, move things forward faster, and give your best projects more momentum.

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Show Notes:

• Great teamwork starts with context because people do their best work when they understand the bigger picture and where their piece fits.
• Don’t assume people already know what you know; this creates confusion, missed handoffs, and unnecessary frustration.
• Explain why something matters before you dive into what needs to be done so team members can make better, more confident decisions.
• Point out who’s involved, who decides, and who needs to be kept in the loop so nothing gets dropped.
• Ask yourself, “What’s missing here?” before you move ahead because one missing person or detail can stall everything.
• Make introductions and connections for people instead of leaving them to figure out the maze on their own; great leaders remove friction by making the right introductions at the right time.
• The more context you share, the less your team hesitates, second-guesses, or duplicates effort.
• When people feel informed and included, they show up more confidently and take ownership of their piece.
• The goal is not just communication, but momentum: helping the team move faster with less confusion and more ownership.
• Connecting the dots is one of the simplest ways to make teamwork easier, more strategic, and more successful.

Resources:

Don’t Make Me Think by Steve Krug

Unique Ability®