Admitting that you have no idea what you're doing

Most entrepreneurs aren't qualified for their jobs--including about 100% of the first timers.

Many times, they get backed just because they're smart people working in an interesting area.  Sure, they had a demo or a prototype or something, but investors know the product will change. 

What they're really betting on is your ability to learn--and that starts with your willingness to admit the following:

"I don't know what to do."

At the Northside Festival this year, Dennis Crowley admitted in his session with Jerry Colonna that one of the toughest challenges that he has faced as an entrepreneur was having everyone looking to you, counting on you, investors betting on you--and feeling like you're supposed to know everything.  Sometimes--a lot of times--he said, you have to admit that you don't know what to do, but that you're going to find someone smart who knows the answer.

I was talking to an entrepreneur the other day, and I asked, "Do you feel like you have a good idea of how you should be spending your time?"

She looked at me as if I had just asked to take a ton of bricks off her shoulders and told me she didn't--but she said it with an enormous sigh of relief in that by asking, I was making it ok.

And in fact, it is ok--particularly when you're not a technical founder, it's not always clear what your next step is in the early going.  Even if you are on the technical side--you may never have managed before, nor been responsible for so many aspects of the product development at one time.  The next move isn't easy for anyone when it's the first time they've ever done something.

The solution?  Start asking a lot of questions.

Find people who seem to know what they're doing--whose companies have acheived success.  Ask them if they feel like they spend their time wisely and how they allocate tasks among the founding team.  What do they do day in and day out? 

One of the best ways to improve how you spend your time is coming up with a routine.  Tim Ferriss recently blogged about the power of routines to help focus you on the things that matter, while not getting you bogged down on the things you don't:

"I’ve always suspected that we start each day with a limited number of decision-making points that, once depleted, leave us cognitively impaired. This is part of the reason that automating minutiae, adopting rituals, and applying creativity only where it’s most valuable (e.g. not deciding what to eat for breakfast) is so important to me."

Routines, however, come after you've defined roles--and for a CEO, that's sometimes not obvious.  Chances are, you have an incomplete team, so you're doing multiple jobs.  How do you handle Product on Tuesday, Hiring on Wednesday, and Fundraising on Thursday--especially when you don't always have control over your own calendar and find yourself depending on others to make time for you?

The answer to how you in particular should spend your time is twofold:

  1. Consult with your investors, advisors, and peers and where they thing you need to focus your energy--and get on the same page about the balance between near term and long term goals.  Don't be afraid to ask, "What am I supposed to do?"
  2. Empower and support your team to achieve way more than they thought they were capable of--so that they can take a lot off your plate.

That's pretty much it, because you really only have two options as a team to finish all the things you need to get done.  To close the gap between all you want to do and all you can do, you need to focus on few things, and get better at doing more or them, because time is finite and you can't make more of it.

How do you get better?

  1. Get a mentor or a coach--someone that understands firsthand what you're doing and ideally has done your job.
  2. Be a continuous learner--take classes, and read books and your profession and best practices.
  3. Set personal learning goals for yourself so you have some way to measure if you are improving or not.
  4. Share your execution problems with others to get feedback on how you can improve.  

Remember, it's never too late to ask.  I've been there--for the last six months of my startup I really had no idea how to save it.  I made random calls to people I thought should buy it, with no success.  I tried pitching business development ideas, coming up with marketing ploys.  None of it was effective--yet I often worked late nights because I felt like I should, even though I knew what I was doing wasn't moving the needle.  I never thought to tell anyone, "I have no idea what to do right now."

In hindsight, I feel like I might not have gotten to that point if I said that way at the beginning as well.  I certainly think there are a lot of aspirational entrepreneurs that have gotten all excited about the pitch and the upcoming launch and aren't totally clear what happens after that.