Why Managing People Is So Hard—and What Small Business Owners Can Do About It

By Kekeletso Nkele, small.news Assistant

Q: So how would you advise someone who’s built a business a little bit bigger and is sort of reconciling these two common growing pains? What’s your advice, or what’s your sort of, what’s your, what does your expertise say we should do in those situations?

A: Management and managing people require different skills. The Peter Principle states that people are promoted to roles where their skills no longer fit.

For many, this shift happens when they start managing a team. Being good at the work doesn’t guarantee skill or enjoyment in managing others. You might simply prefer to do the work and excel at it.

Support and develop managers. Management skills can be learned, even if not all are enjoyable. If someone struggles with management, offer support or consider moving them to an expert role without people management.

The second part is about what to do when you’re at the top and feel disconnected from managers and contributors involved in daily work. It’s hard to stay fully connected. You could spend all your time meeting employees, but have no time for other tasks.

First, set aside 15 minutes once a quarter for one-on-one conversations with colleagues at all levels. It doesn’t have to be often, but it shows they are a priority. It also helps you get to know them and take good notes.

Make them feel they matter, even if you don’t spend much time with them. The second is having all-hands meetings, which I know you do at Silver Lining. Communicate directly with everyone. Problems start when messages filter down through layers, creating misunderstandings. Avoid this ‘telephone game’ by speaking directly.

Q: What is the skill set of a good manager?

A: Good managers have core competencies, not just learned skills. Competencies shape how we manage. Competencies are tough to build. They’re about handling ambiguity and thinking through management challenges.

Several competencies help develop management skills. The first is managing your emotions. You’ll give hard feedback, resolve conflicts, and handle crises. You must keep emotions in check and move forward, even if scared, nervous, angry, frustrated, or excited.

Second, be flexible and adapt to different ways of working. I am still working on giving each team member what they need without treating everyone the same. Flexibility means shifting how you work without feeling drained, though it can be exhausting for some.

That’s the second thing. Third, see both the big picture and the micro details. As a manager, avoid micromanaging. Balance is crucial: know when to go deep, when to pull back, and when to shift.

Q: If you were going to give advice or perspective to a small business owner they’ve got one to five employees. They all report to you, the owner. Your natural competencies are visionary and outward-focused, and maybe in product development, sales, or all the things that take over.
But now you have staff and assumed everything would get easier.

A: What do you do? I’ll say something maybe provocative: hire someone to manage your people. It’s not a crazy idea.

In bigger businesses, there is a CEO who focuses on vision, external relationships, and marketing. Then there is someone focused on internal operations and people management. Obviously, bigger businesses have money and many people to manage.

If you’re a smaller-business founder who knows what you’re good at and what energizes you, hire someone to manage the team. This COO-style person handles people management, so you only manage them, not five people.

Hiring the right manager boosts productivity for everyone. They make the team more effective, justifying the investment.

Q: Would you say their first hire should be a general manager, a generalist with management, operations, and administration skills, who multitasks across functions? Might that be the best first hire?

A: Someone who takes on low-level administrative tasks that waste your time and energy. Sometimes that is the best first hire. That person can often take on more responsibilities over time.

Sometimes the role stays administrative, and that’s fine. For other founders, hiring someone who can handle many tasks and take on projects you’re not good at can work well.

Q: What are you most worried about right now?

A: I’ll speak to my niche. One thing I hear from managers is concern over AI. There are many concerns. Someone recently asked me how to manage AI agents.

I don’t know. There’s so much happening with AI, and jobs are changing quickly. As a manager, especially a small business owner, you must figure out how to use AI, what it’s good for, what it’s not, how people should use it, and how to keep data safe.

Q: Now, all those same changes, what’s hopeful in them?

A: What excites me about managing people is remote work and global teams. This trend has grown for a while. It offers access to talent at affordable prices and gives people the flexibility to live their lives.

We’re still shifting toward healthy work-life integration, hiring people who can work anywhere, travel, and work any hours. There are many opportunities we haven’t tapped. Looking ahead, virtual reality will bring cool things in a year or three. I look forward to that day.

There are many untapped opportunities. We’re pushing further. Virtual reality will soon let me put on glasses and be in a room with my team, drawing on whiteboards and collaborating as if in person, even if we’re halfway across the world.

Q: The risk is in critical thinking and problem-solving, but I thought what you were working on was so interesting. Can you tell us about it?

A: Sure. Several years ago, I was leading a workshop. It was like four hours long.

This motivated me to design a program called micro workshops, which I’ve been doing for several years now, where the idea is you get 30 minutes, and we focus on one key skill.

So the very practical, how do you do it in addition to why it matters, and how to integrate it into your work, and we practice it. And then that’s what you focus on within your team for the next couple of weeks. And then we do another session where we can either build off that skill or introduce something new.

And what’s magical about this is that it’s 30 minutes long. So your attention span is actually focused. It’s highly interactive because you’re practicing the skill.

Q: If you had a magic silver wand, Mamie, and you could wave it right now and you could make one thing true for every single small business owner in the world, what would you use yours for?

A: I wish for each of you to have a team you love working with and who loves working with you, because when you have a team you love and who loves you, you can do magic things together.

Q: How do we support you?

A: All right. Well, I’m going to send you to a website: themodernmanager.com/overview. Cause it’s an overview of everything I’ve got going on right now.

You can find my podcast and some free resources. And then the program I just talked about with micro workshops. And because I just love leading these and supporting teams.

And you can also find a new program I’m kicking off soon called team playbook builder, because teams need to know what you need, and as a business, hopefully, you have these things in place, right? You’ve got to know your mission. Why do you exist?

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