Startup CEOs: Screw Your Strengths

You’ve beat the odds and created a product that people love. You have some traction. Hopefully you’re even growing like a weed and hockey sticks abound.

You built a team to help you scale up the business and seal your success… But secretly you’re struggling.

You know you should be better about delegating, but everything just seems easier to do yourself.

And I bet you hate giving feedback, too. Maybe you’ve been putting off that “your fired!” conversation with that bad hire for weeks, even if it’s hurting your team and their ability to get shit done.

Maybe you don’t communicate or give regular updates to your team (you’d rather do a couple tweaks the product).

Or you forget to ask your team about their weekend and whats going on in their life. You tell yourself its because you have to get the latest numbers out to your investors or calm down that angry customer.

You hope people are happy and with you for the long haul, but you really have no idea. Since you hate giving negative feedback, you probably hate getting it, too.

Leadership and Management is Hard

If what I’ve just said hits home (even just a little bit), you’re not alone.

Fred Wilson Says:

Starting requires an idea/inspiration, a team, some technical skills, the ability to iterate on the MVP and find product market fit. That’s hard for sure, but what happens after you find product market fit is even harder. That’s called building the company and building the business. And that is where I have seen all founders struggle.

Delegation, performance coaching, firing people, consistently communicating your vision and progress and building personal relationships with your team are some of the most crucial aspects of leadership and management…

They’re also friggin’ hard. And the skills, behaviors and habits required to do them well don’t come naturally to too many technical founder/CEOs.

They Say “Play to Your Strengths – Eliminate Your Weaknesses”

If you want to be the best you can be overall, there is plenty of research supporting the idea that you should play to your strengths and minimize the impacts of your weaknesses.

They say that if you focus on your strengths, you’ll have a much better chance of seeing meaningful improvements to your skills, abilities and competence.

If you’re a manager at a fortune 500 company or developer #25 at a startup, the advice makes a lot of sense. But what if you’re the kind of person who took an idea and made it something real that people love?

I Say “Screw your Strengths. Start Developing Your Weaknesses.”

If you’re a great programmer and you love programming, do you really need to actively try focus on being a better programmer? Not really. Doing and practicing things you know and love  have a funny way of earning a spot in the busiest of schedules.

Getting out of the building and talking to customers was painful, but you did it anyway. You did it because you knew that the only way to build a real business was to get feedback from actual customers.

The only reason you’re a startup CEO is because you overcame weaknesses and pushed through the pain to get where you are today. Confronting your weaknesses won’t stop once you get traction.

And it only gets harder as you turn the product that people love into a real, sustainable business.

As your team grows, you also must grow as an entrepreneur, a manager and a leader… But not everyone makes the cut.

The biggest wins come from founders who are able to transition from successful founder to successful CEO.

This post is the first of many in a series on how you can grow up with your startup. In future posts we’ll cover many topics, including:

  • Why is the transition from product founder to business manager so hard?
  • Can I learn how to be a great leader?
  • What is the best way to figure out what skills to develop first?
  • And… How do you know if your company is as strong as you think it is?

I’ll be posting a new article in the series every few days.  Every post will be supported  by a combination of the latest research in the industrial psychology literature and practical, real-world examples. I’ll keep writing until all angles have been exhausted.

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My employees reviewed me, and I kind of suck.

Happy Cog CEO Greg Hoy got some feedback… Here’s what he learned:

Well, the results are in, and you know what? Mine kind of suck. They weren’t off-the-charts horrible (there were a few “best boss ever” comments that gave me a Michael Scott kind of feeling), but there were way more “needs improvement” marks that I ever anticipated. Because I anticipated none. And some of the comments people left was like chewing aluminum foil. My first reaction was surprise. Then defensiveness. Maybe a bit of anger. I thought things like, “Well, Steve Jobs had issues, but Apple turned out just fine. It’ll be ok, Greg. Grab a beer.”

Feedback hurts, but you need it to grow.  Any sort of meaningful change always begins with awareness. 360 Feedback is a great, and safe, way to learn what you need to work on.

Another great way is by doing an employee engagement survey. The results will tell you similar, yet very different, things. 360 feedback is when people you work with all take the same survey to give you an idea of your strengths and “development areas”. Engagement surveys are sort of like 360 feedback on your company instead of you.

I’m giving away a free engagement survey called insight. If you’re interested in what you can do to keep your employees happy and productive, you can learn more about it at

Remote Working Works

HP recently pulled “a Yahoo!” by ending their remote working arrangements with employees. Justin Jackson had this to say about the Yahoo move:

The only time a manager should fear a flexible workplace is if they’ve hired the wrong people. If you’ve broken Rule #1, all bets are off. It doesn’t matter what kind of office you have; mediocre people create mediocre results.

A few years ago our lead developer  had an opportunity to move to Australia for a 3 years, all expenses paid. His partner received an incredible job offer in Sydney for a three year contract and her employer was willing to pay for him to go with her (we’re in California).

It was an uncomfortable decision, but I gave my blessing. And then he did everything he could to make sure it worked out perfectly. That meant he had to work mornings and evenings with a break in the middle of the day every day to keep his internal customers happy and the team on track. He made it happen.

He’s back in the US now and everything worked out fine. I agree with Justin. Our team is currently scattered all over the world and it doesn’t bother me one bit. If you have great people, and you’re able give them the support they need, remote working works.

Why Your Startup Needs to Obsess Over Culture

Alex Turnbull, CEO/founder of Groove, gets It:

But we also have unique opportunities that our larger cousins don’t have: we’re agile, company-wide changes don’t take nearly as long to test and implement, we’re working from the ground floor, which puts us in a position to build the entire foundation of a great culture from scratch, setting ourselves up for success as we scale. It’s a lot harder to build a culture at a big company where employees are more set in their ways.

I couldn’t have put it any better myself. This is why I started this blog and developing some tools to help startups establish and build great companies with great cultures.

Build a Team that Ships

Naval Ravikant, founder of AngelList, designed his team to function without middle managers.

Here’s what we do:

  • Keep the team small. All doers, no talkers. Absolutely no middle managers. All BD via APIs.

  • Outsource everything that isn’t core. Resist the urge to pick up that last dollar. Founders do Customer Service.

  • People choose what to work on. Better they ship what they want than not ship what you want.

  • No tasks longer than one week. You have to ship something into live production every week – worst case, two weeks. If you just joined, ship something.

  • Peer-management. Promise what you’ll do in the coming week on internal Yammer. Deliver – or publicly break your promise – next week.

  • One person per project. Get help from others, but you and you alone are accountable.