Let Your Employees Ask Questions

This post initially started off with the ludicrous title, “Entrepreneurs Need to Recognize Their Employees Aren’t Entrepreneurs, Because if They Were, They Wouldn’t Be Employees”. But not only is that way too long, as Megan and I were working through it, I realized it also isn’t entirely true. In my own career, I’ve been an employee several times, and I’d still very much consider myself an entrepreneur. And I’m sure there are plenty of employees out there in the world who would love to be entrepreneurs, but are biding their time working for someone else for one reason or another.

But it does underscore a larger point, that employees often shouldn’t be treated like entrepreneurs. The number one complaint I get from founders about early employees is that they require too much hand holding. The second most common complaint is that they aren’t comfortable enough with risk.

In a lot of ways, management style is like love languages. If you prefer to be managed a certain way, you’ll probably manage others in that same way. So if you’re an entrepreneur who doesn’t like being micromanaged and wants to figure it out on your own, you’ll expect the same of your employees. In some ways, that’s good (see my blog post about the what and why vs the how). 

But you also have to recognize that as a founder, you’re empowered to fuck things up. If you spend three months chasing a market that turns outs to be a dead end, nobody is going to fire you. You own the place. If someone does that at a large company, they’re maybe getting fired. And your employees will bring that reticence to your startup. So, early on, plan on providing feedback and answering a lot of questions about how you want things to get done.

When you hire someone, you need to give them time to earn trust. Not just with you, but with themselves. Employees need to feel like they have a safe environment to make mistakes, and in order to feel that they need guidance. You need to take some time to step into their shoes, tell them how you would do things, and let them know that while they are free to make other decisions, it’s best to talk them through first.

For your first ten employees as a founder, you not only have to be very clear on the why and the what, but you have to be comfortable occasionally venturing into the how too. You have the context of the entire company all in your head, but no one else can read your mind. So, for a bit, overcommunicate.

I have always struggled with this. When I hire someone, it’s because I don’t want to be responsible for that work anymore. So when an employee starts asking me questions, I immediately go to “why did I hire this person if I’m still going to do all the work?” First, that’s such a short-sighted perspective. Second, I’m abdicating my responsibility for communicating how we make decisions at NewCo. Good founders take the time to walk employees through decision making and great founders tie those decisions to company values.

If an employee asks you a question about how you want something done, it doesn’t mean they don’t know how to do the job. It means they don’t know how YOU want the job done. Too many founders assume that questions mean an employee doesn’t know what they’re doing, and then stop giving them work in hopes they’ll eventually quit or become so useless the founder will have no choice but to fire them. 

Don’t fire them. Don’t put them on probation. Just answer the question, and move on. Eventually your hires will know as much about their area of the company as you do and then you’ll probably suddenly feel out of the loop and unnecessary. Startups are hard 🙂

— Eric Marcoullier


Like I said above, I have always sucked at managing people. I’ve always been a “get out of my way and let me figure shit out on my own” kinda person and I empathize with every founder who complains that they have to answer yet another questions from their new salesperson or product manager. I mean, why can’t they just figure it out already?!?

But that’s a pretty shitty way to manage someone who just wants to succeed for you. And more often than not, we just need to be reminded that the reason that employee is asking questions is because they want to do it the right way. For you.

If you could use an occasional reminder that your employees are probably tirelessly working to help you build your company, give me a shout. Hit me at eric@marcoullier.com or my coaching site.


(Photo by Egor Ivlev on Unsplash)

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