THE BLOG
08/08/2014 03:05 pm ET Updated Dec 06, 2017

How to Hire the Wrong People and Fail, Sometimes, Repeatedly!

Part of being an entrepreneur (be it in the nonprofit or for-profit sector) is learning from your mistakes -- improving every time, so that each move you make is forward, each failure a lesson that when taken to heart will promote growth. Part of that learning curve is asking the big questions, and then acting upon the answers.

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So here's one that's been bugging me for a while: Why is it that some truly amazing social entrepreneurship ventures never get off the ground? Or why do some concepts and programs with every reason to succeed and thrive only achieve a modicum of success, and then die?

It took some time, but I finally have an answer, and it all comes down to the way we build our teams at the outset.

Hiring Up

I know what it's like to pour your heart and soul into something only to have it flop. There have been a few ventures in my past that all had the ability to explode and grow and scale and sustain themselves. While they all were somewhat successful, they never reached their full potential.

I was devoted to and passionate, but still getting burnt out. In some cases I had teams of people working for me, but none of them could take the ball and run with it. None of them were helping take things to the next level. Why?

And one day, during my afternoon walk, I stumbled on the similarity that a lot of the people I had hired under me had one thing in common, they were all in sorts of professional transition. Then, in a moment of astounding clarity, it hit me: In each case I had put together a team of people to help support the project, but I had gone about it all wrong. I had never sought to hire anyone that I felt was smarter than I was (yes, I am embarrassed). Or more skilled. Or more connected. (Not to say none of them were, of course, but it wasn't something I consciously sought out as part of my criteria.)

So I was often in a position when I had to delegate, I had to direct constantly, which meant there was no time for me to do what I really wanted to do or to focus on bigger picture and strategy. And when this happened, everything eventually fell apart.

Facing Fears

I can't believe it didn't occur to me sooner, honestly. No one has ever sat in a meeting, excited about a new venture, clapped their hands together and said, "Great! Now let's put together our D team!" Of course, everyone wants an A team - a group of people as connected and qualified as you are, ready to rock your new project into the stratosphere.

So why isn't that what we get? What gets in our way? I actually think it's fear and ego (which we'll discuss more in a moment), disguised as practicality.

Starting something new is scary, particularly in the nonprofit sector. How will you get your message out, generate revenue, provide for payroll? These are legitimate concerns, but they shouldn't become scapegoats.

But those "hard" concerns aren't the only things that get in our way. "Soft" concerns, like insecurities that make us need to be the smartest in the room, in control of every little detail and minute task (if you're the CEO, do you really need to be OCD about printing & organizing name badges?) - even though letting them go will free up our time for other things.

It's an unsustainable practice, one that is doomed to lead to failure in the grand scheme of things.

Proceed With Passion

Ever heard the saying about how it takes twice as long to fix something done incorrectly as it does to do it right the first time? It applies here.

There's so much at risk with a new project, and risk makes us nervous. But when you have an idea so amazing it's worth following through, it's also worth the risk to invest in a good team early. Because if you don't you'll be too bogged down in the day-to-day to start over later.

So, you want to build an A team right out of the gate. But what should you be looking for?

First things first: Decide the top two or three things that you really value and will not deviate from. For me it came down to two key elements: ability and passion.

Ability - My driving process right now is I want people smarter, brighter, more involved than I am in the specific and narrow context of the scope of the job. If I want someone to take over certain aspects to free me up, I want them to be ready to dive in without needing extensive training - aside from getting acclimated to the environment and overall vision.

Here are some other key considerations:

  • They need the right skill set, i.e., no less than 70% of what you're looking for - you're building a top performance team, not hiring interns
  • Their qualifications have to match; they need to know the sector, the field and the players, and possess both the hard skills and soft skills to handle the job
  • They should have competing and complementary skills - able to take on the tasks that you don't excel at or don't enjoy
It's not about handing off grudge work. It's about balancing things out to keep the entire team strong. Because then you get to focus on the things you do best and are most passionate about; and so does everyone else.


Passion - So you've got a few people with that 70%. They've got the ability, but that doesn't make them a match for your team. Because it's not just about ability, it's about passion. In other words, just because someone can type 95 words per minute, doesn't mean they would love a job typing all day.

To get a real sense of your prospects, you want to ask unique questions that cue you into what parts of the job will fulfill them. We'll talk more about this in part two.

The bottom line is you want people who are passionate about the job and the sector you're involved in. They have to want to be there, not just be marking time while they figure out what else they want to do. You're not looking to just sustain - you're looking to build something that lasts.

To that end, be comfortable saying no. Because if ability or passion aren't a match, it's not going to work anyway. This is something they've figured out at 3D interactive training company Heartwood:

"We've learned that if there's a task someone dislikes, they don't do the best job. AND we've learned that there's always someone out there who really enjoys doing that hated task. (Yes, always.) If one day someone realizes 'I used to like doing this, but don't anymore' - they are required to speak up.

Why? It affects quality. And quality is VERY important, especially if you want to master your niche area and eventually make a larger difference in the world, i.e., matter."

When you open yourself up to this kind of approach, you will naturally attract the right people. So decide what your deal-breakers are, and next time I'll share just how to make that A team a reality.