Leading a team is no small feat. Let alone leading the whole company. I've seen founders of small teams and mid-size teams struggle with this. The time where it was just you coding, designing, doing marketing and selling are things from the past. You progressively and naturally moved into your new role as a manager as your team grew.
No matter if you are still coding or designing from time to time or 'full-time leading', you most likely have conversations and discussions on a regular basis with your coworkers. Questions like 'what are you up to?', 'how is project X going?' or more simply 'how is it going?' help you stay up-to-date. But to better understand your employees, you have to go below the surface of 'how things are going'. How do you know how they are really doing in their role?
“How do you know how your employees are really doing in their role? Don't limit asking questions before they enter or leave your company.”
Isn't it strange that the only times you ask real questions is when your employees aren't your employees yet (or any more)? How do you know how they are really doing in their role? Are they still enjoying the work they do? Does the job still excite them? Is it too overwhelming? Or can they take up more?
Employees know and feel when you actually care about them and are not just concerned with MRR, churn or any other KPI. Don't leave asking the important questions to the very beginning or at the very end.
Use some of these questions to get a conversation going that is not just on a micro level about the job or tasks at hand, but might trigger a conversation that will go beyond the obvious day to day work.
“Employees know and feel when you actually care about them and are not just concerned with some metrics.”
“Is there anything I can help you with?”
This question really helps with reminding employees you are in it together. As a team. That you are not 'just the leader', but there to provide help where possible. Especially if you are a technical founder, it's great for backend engineers to know they can check in with you on difficult situations or tricky obstacles. If you are more of a product person, it's great for the product team to know they can use your experience and knowledge.
“Is there something I can do better?”
Being humble is a great feat. As a human, but more so as a leader. It's impossible to know everything. And it's foolish to assume you never make mistakes. You do and you know it. But you might even make more mistakes, judgement calls or have opinions your employees don't agree with. Take this opportunity to learn about your quirks. Get any misunderstandings out of the way. It's great for your employees to know you are willing to learn from them and are willing to get better at your job. Making yourself vulnerable like this sets a great example for the rest of the company and might help them with rethinking the struggles they might have.
“Are you still enjoying your job?”
So simple, but so powerful. If you build an environment where everybody can be honest about their feelings, you can easily get to know what they think of their job. Don't panic if the answer is they don't enjoy it too much right now. Do get to the heart of it though. Know if it is due to the current tasks at hand and thus temporarily or if it is due to external/personal factors. It's up to you to provide the right guidance to fix these issues they'll have. It's also important to follow-up quickly, say 2-3 weeks later.
Too often managers only ask questions related to the day-to-day tasks, so they never get a real conversation as humans. From the early beginnings of your company, you have to make this transparency and freedom to talk about these things part of your culture. Most people often don't feel comfortable talking about the issues they have, especially with 'their boss'. Set the right example, be humble and use these questions as a guide to get to know your employees better. There's no need to do this every week. But every three months is a perfect guideline.
Photo by William Stitt on Unsplash