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4 Tips For Hiring An Effective Leadership Team–From Founders Who’ve Been There


leadership team

The question, “What makes a great leader?” has no easy answer. Preconceived, idealized notions of how a leader tends to look, speak, or act usually don’t hold up in the real world.

Depending on the company, the guy wearing an expensive suit and a severe demeanor may actually do more to alienate a team than motivate them. 

But the tenets of a startup demand an answer to this question. With high expectations and a shorter runway for scaling the business, startups have to quickly install real leaders in management and executive positions—people who can organize and motivate in equal measure. 

Truthfully, no business can afford to continue cycling through leaders while trying to find the perfect fit. Chaos at the top doesn’t just trickle down; it cascades. It’s simply that a startup has less time to get it right. 

With that in mind, here are a few of Minutes’ top contributors on what they’ve learned about building a great leadership team.

Matthew McFarlane

Look for good writing skills—regardless of the position (Jaleh Bisharat, CEO of NakedPoppy).

Jaleh Bisharat

I’ve found that one of the most interesting predictors of success is being a good writer—even if the job itself doesn’t require much writing. For this reason, I emphasize hiring good writers and encourage team members to prioritize writing skills. Almost every time I’ve broken the “hire good writers” rule, I’ve regretted it.

For the past 25 years, I’ve asked for a writing sample from job candidates. I don’t request they create something new (because I think it’s important that job candidates not have to complete anything resembling “free work”). Any piece of writing is useful, as long as they wrote it entirely on their own.

Read more here.

Ask open-ended questions to gauge cultural fit (Heidi Zak, CEO of ThirdLove).

It can be difficult to tell whether or not someone will be a good cultural fit during an interview. So, you have to be very careful not to lead them with your questions. Smart people (the type you’re interviewing, hopefully) will read into your questions and alter their answers to fit what you want to hear.

Instead, ask broad, open-ended questions like, “How do you go about communicating with your team?” or “Tell me about how you work cross-functionally at your current company.”

That type of question doesn’t give them an opportunity to mirror something you’ve already told them, and the answers you get will be much more revealing when it comes to deciding if this person is the right cultural fit.

Read more here.

Vet candidates for perseverance in the face of adversity (Ed Michael Reggie, CEO of Funeralocity).

There are a few things you can spot on a resume or in a candidate’s employment history that are quite telling. Like, for example, whether a candidate has a habit of job-jumping––which is definitely a red flag.

In making these initial hires, you want people who have experience building something big over the span of at least five years. That kind of experience shows several important things: the new hire likely has emotional intelligence; they’ve likely reported to (and succeeded under) several different people; they’ve figured out how to roll with the punches; and, perhaps most importantly, they’re persistent. They won’t quit on you when the going gets tough. 

Read more here.

Build a leadership team that isn’t afraid to experiment (John Monarch, CEO of ShipChain).

There’s not always a clear path to the solution. Sometimes, you have to experiment. High-potential leaders understand this need and are willing to jump into the weeds to try new approaches and test out unproven ideas

When hiring a leadership team, I check for this skill by noticing when a manager sees equal or better results from solving a problem their own way. If a mistake is made once in a while as a result of this approach, that’s okay. Having the desire to experiment, and seeing innovation as a result, is much more important than the occasional slip-up.

Read more here.

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