This is another one of those questions that I get from entrepreneurs quite often. It's also a problem I struggle with myself, even after two decades of being an entrepreneur with multiple successes and failures.

How do you efficiently fill the gaps for the skills your startup doesn't have?

The funny thing is -- that's rarely how the question comes to me. And I get it. If you're going to be an entrepreneur or a startup leader and attempt something no one has ever done before, you're going to need a pretty strong ego. That same ego is going to stop you (and me) from putting a hand up and saying, "I suck at this skill. What do I do about that?"

Here's what you do.

Should You Hire a Professional?

The question about filling skill gaps almost always drops in my lap disguised as a strategic hiring decision. In other words, the startup doesn't have in-house resources to get to the next level -- maybe software development, maybe sales, maybe accounting, whatever. So the company needs to bring in a pro, and it doesn't have the available funds to do so.

Does that sound like your startup? Because it's almost every startup. Including my own.

Last week, I got a question from a startup CEO about the right time to seek professional design for the company's app

The app is still in MVP, but generating revenue and adding customers at a good clip. While the CEO didn't see any evidence of the "rudimentary" (his word) design turning away potential customers, he felt like it was only a matter of time before the startup's ugly app began to stunt growth. 

He was not wrong, but from everything I could see, it wasn't time to press the (expensive) panic button and bring in design professionals. Not yet. His product worked. It did what it was supposed to do. It solved customer problems. 

So here was my question back to him:

Why aren't you doing the design yourself?

Why Entrepreneurs Don't Do Obvious Things That Can Grow Their Business

I've seen too many promising startups fail because tech founders wouldn't pick up a phone and cold call sales prospects, or because sales-oriented founders spent way too much money outsourcing overbuilt software development, or because introverted founders preferred to work alone and stagnate rather than talk to strangers in search of their first hire. 

Don't get me wrong. Design is hard. Anyone who tells you that anyone can design an app interface has never designed an interface for a successful app. I'm not great at design. But in the decades that have passed since I launched my first ugly product (which eventually got acquired), I've taken it upon myself to get pretty good at design.

Because I had to. 

And this is the paradox. When entrepreneurs come up against a skill they don't have experience with, they tend to just not do it. What they should be doing is rolling up their sleeves and taking their best hack.

Here's why.

One of the reasons it's so hard to be an entrepreneur is because when it comes to the success of the venture, we're the only ones with the right answers, whether that's in sales, technology, finance, or whatever. 

We may not be able to offer hands-on expertise in certain areas, but at the very least, we need to get involved and make sure that the result of the effort lives up to our vision. In almost every area of business today, there are tools that will execute most of the hands-on tasks for you -- all you have to do is provide the strategy and make the decisions.

At every startup, and in every facet of its business, there is no single person who knows that strategy and is equipped to make those decisions better than the person in charge. 


If you want to be a successful entrepreneur, get good at everything, because you only have to be the expert at applying all that everything to whatever it is your startup does.