World's Greatest Boss

I’m joined by Ivan Alo & LaDante McMillon, co-founders of New Age Capital, a seed stage venture capital firm and lifestyle company that invests in tech and tech-enabled startups that are founded and led by Black and Latinx entrepreneurs. We discuss their journey to launching New Age Capital, common hiring roadblocks they see in the startup world, and what traits they look for in the leaders that they invest in. Ivan and LaDante also touch on how to develop a growth mindset around team building and share tips for how to become a more self-aware and effective boss. 

IN THIS EPISODE, WE TALK ABOUT:

• The reality of capital allocation for Black and Latinx founders 
• How to decide when (and if) you should raise money 
• The most important hires to make early on in your company 
• Ivan and LaDante’s thoughts on bringing on an assistant 
• The number one thing that Ivan and LaDante look for when they’re vetting a startup 

RESOURCES: 

• Can't Hurt Me: Master Your Mind and Defy the Odds by David Goggin
• The Comfort Crisis: Embrace Discomfort To Reclaim Your Wild, Happy, Healthy Self by Michael Easter  

CONNECT WITH IVAN & LADANTE

Learn more about New Age Capital: newage.vc 

Read their blog: keepit100.vc 

CONNECT WITH JACKIE

Follow People Principles: @peopleprinciples

Let’s TikTok: @peopleprinciples

Learn more: peopleprinciples.co 

Visit the Hiring School website: hiringschool.com

Firing is one one the not-so-fun parts of managing a team, but it’s crucial for the success of your business. There are six main signs that it might be time for an employee to leave your company, and I break down how to recognize them and approach performance reviews. I explain how to set up a 30-day improvement plan, investigate why someone has stalled out in their role, and optimize one-on-one check-in meetings. Sometimes people aren’t the right fit and can thrive in a different environment, and I’m sharing the tools to help make that happen. 

IN THIS EPISODE, I TALK ABOUT:

• What to do when the roles and responsibilities of a job has changed 
• Having honest conversations with your employees about your expectations 
• Supporting your staff who want to grow in a different direction 
• How to deal with team members who believe in a different direction for the company or your team 
• Tips for improving your termination process 

CONNECT WITH JACKIE

Follow People Principles: @peopleprinciples

Let’s TikTok: @peopleprinciples

Learn more: peopleprinciples.co 

Visit the Hiring School website: hiringschool.com

Today I am chatting with Ashley Herd. Ashley is an attorney and HR leader with experience in a global law firm and companies including Yum! Brands and McKinsey & Company. She now leads Manager Method®, an HR and legal firm providing scalable employment documents and tools for companies of all sizes, to help employers and employees work together. Listen along as Ashely and I share our advice and tips for hiring remotely!

IN THIS EPISODE, WE TALK ABOUT:

• What to consider when remote hiring
• The things you need to think about when you hire employees in other states
• The opportunities and the challenges of remote working
• The future of laws around remote working

RESOURCES:

Let Me Write That Down: A New Employee's Guidebook: A Guided Journal for Employees New in Role - Manager Method

CONNECT WITH ASHLEY

Ashley on TikTik: @managermethod 

Visit the Manager Method website: managermethod.com 

CONNECT WITH JACKIE

Follow People Principles: @peopleprinciples

Let’s TikTok: @peopleprinciples

Learn more: peopleprinciples.co 

Visit the Hiring School website: hiringschool.com

Today’s episode will make you feel more empowered about figuring out the right time to give feedback to your team and how to do it. It is your job as a boss to give feedback and to have these hard conversations. You want to create a culture at your company where team members, including you, feel comfortable and confident giving each other honest feedback, face to face, and in real-time. Listen along as I share with you my pro tips on how to do this and how to make those uncomfortable conversations a little more comfortable (and of course, constructive).

IN THIS EPISODE, I TALK ABOUT:

• How having constructive, uncomfortable conversations takes practice to get easier
• How putting negative feedback in the middle of compliments is confusing and how to gently be direct, without feeling like you have to soften the blow
• Feedback can be positive and negative, and is how people grow and develop both professionally and personally
• A list of talking points and prompts on how to start your conversation

RESOURCES

Book: Radical Candor

CONNECT WITH JACKIE

Follow People Principles: @peopleprinciples

Let’s TikTok: @peopleprinciples

Learn more: peopleprinciples.co 

Visit the Hiring School website: hiringschool.com

In the world of remote work, a regular one-on-one meeting is so critical and so important to make sure you're keeping in touch with your team members. Not only is it a great way to help you build alignment and help them develop, but it also allows you to get to know them personally, which is strongly valued by staff. One-on-ones give you a set-in-stone place where you share information and communicate honestly and openly with your team members. In this episode, I share my top tips for having effective one-on-ones and prepare you to ask the right questions that will help coach your staff to their own answers.

IN THIS EPISODE, I TALK ABOUT:

• How in the world of remote work, a regular one-on-one meeting is so critical and so important to stay connected to your staff
• How you can train your staff to save non-urgent questions for your 1:1s and avoid numerous emails
• How to get out of the habit of answering questions for your staff and solving their problems for them, and instead help each of your team members come to solutions on their own
• How to make sure 1:1s go beyond a status update and into honest conversations around an employee's performance and their development goals

CONNECT WITH JACKIE

Follow People Principles: @peopleprinciples

Let’s TikTok: @peopleprinciples

Learn more: peopleprinciples.co 

I recently read a study that found 11% of people change their minds after signing an employment offer. There are so many factors that go into that, but how can you help your new hires feel excited and solid in their decision so that they don’t back out before the first day? I’m sharing my top five tips for creating a seamless onboarding process, including how to prepare beforehand and what to do during their introduction week. I share stories of processes that I’ve seen work really well (and some...not so much), and what I recommend for virtual onboarding. 

Listen in to learn more about how to create an efficient and effective onboarding process. 

IN THIS EPISODE, I TALK ABOUT:

• How to give your new hire an opportunity to prepare for their first day 
• My favorite way to kick off the first day and set expectations 
• My recommendation for how often you should be meeting with your new employee during their first week 
• Ideas for getting the company together to introduce the new team member 
• Why I like the employee ‘buddy system’ 
• Tools for getting your training videos, SOPs, and industry information organized before your new employee starts 
• Why you should schedule 30, 60, and 90-day check-in meetings immediately 

CONNECT WITH JACKIE

Follow People Principles: @peopleprinciples

Let’s TikTok: @peopleprinciples

Learn more: peopleprinciples.co 

In last week's episode, I mentioned that paid parental leave is something that’s becoming more of a table steaks benefit during the hiring process. No one knows that better than today’s guest, Allison Whalen, the co-founder and CEO of Parentaly, a business service that helps companies improve the experience of paid parental leave, so that employees feel supported and businesses thrive. 

We discuss why and how small businesses can and should offer paid parental leave to their team, and how offering paid leave helps boost employee happiness, engagement, and retention. Allison explains how to set up a plan so that paid family leave doesn’t impact the bottom line of a small business, and offers solutions to the two major concerns that she sees business owners struggle with when it comes to establishing a company protocol. Plus, Allison shares exactly how she’s handling her own upcoming maternity leave and takes us through her team’s process of ensuring a seamless transition while she’s away. 

IN THIS EPISODE, I TALK ABOUT:

• How Allison has seen the ​​paradigm shift around paid parental leave, especially for non-birthing individuals 
• What the current standards and trends are when it comes to paid family leave 
• Some of the major business benefits of offering paid parental leave, especially for smaller teams 
• Allison’s thoughts on having a part-time ‘welcome back month’ 
• How to create a culture where employees feel comfortable being transparent about their pregnancy or plans to start a family 
• The importance of defining your communication plan and boundaries before going on parental leave 

CONNECT WITH ALLISON 

Learn more on the Parentaly website: parentaly.com 

Follow Parentaly: @parentaly 

Connect with Allison on LinkedIn: Allison Whalen 

CONNECT WITH JACKIE

Follow People Principles: @peopleprinciples

Let’s TikTok: @peopleprinciples

Learn more: peopleprinciples.co 

As a small business owner, offering benefits to your employees can feel a little bit intimidating and costly. I break down the different benefits you should consider offering, including health insurance, paid time off, retirement solutions, and other perks that really help you stand out to potential employees. 

I share some simple tools to help get started with setting up a health insurance plan and determining how much you want to contribute. I get into some of the pros and cons of lump sum versus accrued paid time off, and what I recommend small business owners offer for federal holidays. I also give a sneak peek into next week’s episode, which is going to have a more in-depth look at paid parental leave. 

I hope that this episode clears up some common misconceptions about employee benefits and sparks inspiration about what you can offer your employees, regardless of how big your team is. 

IN THIS EPISODE, I TALK ABOUT:

• Simple ways to provide health insurance benefits when you only have a few employees
• Different types of paid time off, including vacation, sick, and unlimited 
• An overview of retirement solutions 
• Why more and more companies are offering a health and wellness stipends 
• Benefits to consider if your team is mostly or all remote 

RESOURCES MENTIONED 

• Gusto
• 
  

CONNECT WITH JACKIE

Follow People Principles: @peopleprinciples

Let’s TikTok: @peopleprinciples

Learn more: peopleprinciples.co 

When most people think of work culture, their mind goes to happy hours, gifts, and other incentives. But work culture goes so much deeper than that一it’s who you hire, how you communicate, build trust, and make decisions. I believe that a blend of in-person and remote work is here to stay, so I’ve been doing alot of research on how to cultivate collaborative, inclusive, and thriving online teams. 

I share what my experience was like being an HR executive during the early days of the pandemic, some of the things I would do differently in hindsight, and what I plan to do when I build a remote team. I explain how to create a solid internal communication plan, foster visibility across teams, set up core working hours, and plan in-person get-togethers. I also break down what soft skills to look for in potential employees when hiring for a remote position. 

IN THIS EPISODE, I TALK ABOUT:

• The importance of building trust and how to do it with your team online 
• Some less commonly discussed pros and cons of working remotely 
• The importance of creating agreements and protocols around communication
• What ‘all hands’ and ‘stand up’ meetings are and when they’re appropriate 
• The top three things to look out for when you’re hiring someone remotely 

RESOURCED MENTIONED: 

• Owl Labs State of Remote Work study 
• We Work Remotely  
• Rituals for Virtual Meetings: Creative Ways to Engage People and Strengthen Relationships 
• The Holloway Guide to Remote Work 

CONNECT WITH JACKIE

Follow People Principles: @peopleprinciples

Let’s TikTok: @peopleprinciples

Learn more: peopleprinciples.co 

I’m joined by business coach and entrepreneur Jess Glazer to talk about her transition from a burnt out solopreneur to a visionary business leader. We discuss why setting up systems before you hire is so critical, how to truly delegate as a leader, and what it looks like when your ego is in the way of your own success and ability to scale. Jess breaks down her experience with bartering and shares what she would do differently when it comes to her first hires. We also chat about how to keep tabs on your employees without micromanaging them and what she does to cultivate a strong team culture.  

IN THIS EPISODE, I TALK ABOUT:

• Key indicators that you need to hire an employee 
• Why you should have a contract in place with everyone you work with, even if there isn’t money being exchanged 
• The top reasons why so many entrepreneurs are slow to hire 
• Simple tools to help you articulate your systems
• Why passing off your to-do list to an assistant isn’t always the most effective solution for getting stuff done 

RESOURCES MENTIONED

• Rocket Fuel: The One Essential Combination That Will Get You More of What You Want from Your Business by Gino Wickman and Mark C. Winters
•  

CONNECT WITH JESS 

Follow Jess on Instagram: @iamjessicaderose

Learn more: jessglazer.com

Watch the Harness Your Coaching Superpower Workshop 

CONNECT WITH JACKIE

Follow People Principles: @peopleprinciples

Let’s TikTok: @peopleprinciples

Learn more: peopleprinciples.co 

GUEST BIO 

A former celebrity personal trainer and elementary school teacher, Jess Glazer turned her once “cute side hustle” into a multi-million dollar business in under 2 years. 

Since leaving her elementary school teaching job in 2017 she has hired a team of incredible heart-centered leaders, served hundreds of clients, helped create over 11 million dollars in revenue for those clients and is committed to helping 100 entrepreneurs create 7-figure impact driven businesses (9 down, 91 to go!)

As a result of donation/awareness she and her husband built & opened a school in Ghana, Africa with Pencils of Promise. 

She’s been featured in The Wall Street Journal, Forbes, Yahoo Finance, The Today Show, Good Day New York, The New York Post, Shape Magazine.

Her mission is to cause a ripple effect and inspire change for generations to come; making a massive impact and leaving a lasting legacy beyond her singular actions.