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The 5 Times Leaders Need to Be Saying Yes Leaders, more than most, tend to noodle a long time about the implications of a 'yes' before letting it pass their lips.

By Jon Elvekrog

Opinions expressed by Entrepreneur contributors are their own.


Leaders, more than most, tend to noodle a long time about the implications of a "yes" before letting it pass their lips.

People like hearing yes almost as much as they fear saying yes. Hearing it is validating. Saying it commits you to something. Leaders, more than most, tend to noodle a long time about the implications of a "yes" before letting it pass their lips.

But there are five instances where I think leaders over-noodle and should be getting there more freely.

1. Yes to the unplanned.

Just because you're not hiring doesn't mean you're not hiring. The traditional way of hiring – which we use 99 percent of the time -- is to assess a gap in the organization, define the role, seek candidates, choose the best and fill the gap. But some of the best hires are people you meet when you're not looking -- and who may not be looking themselves. When you meet someone who makes you think expansively about your business, who shows you areas of expertise you haven't considered, who can turn the mirror on your processes in a way that reveals new angles (and they feel the same about you), hire that person and figure out the role that suits them.

2. Yes to transparency.

Let's be real: Everything is not great all of the time. Whether out of a culture that fetishizes positivism, out of fear of seeming vulnerable, out of a desire not to worry our employees and clients, we sometimes gloss reality. But I think morale comes from trust and trust comes from honesty.

I share our board reports in an all hands meeting every quarter. We talk about ups and downs. We don't hide when someone leaves the company, and we discuss why -- to the extent we don't infringe on anyone's privacy. We talk about our business challenges so that everyone is focused on what the business needs. By saying yes when our people want to know how we're doing, we have built a strong sense of shared purpose. And when your practice is to share the bad news, your people are that much better able to trust and rejoice in the good news.

3. Yes to the occasional, transformational moon shot.

Your engineers have been huddling for several weeks. That's not unusual, but for the last week, your head of sales has been in there with them. Finally, they come to you with an idea for a new line of business. It won't risk current revenue, but it will take a significant resource commitment. Plus, it is not core to your current business and comes with no guarantees of success. But your chief revenue officer's feeling is that if the stars line up, it could be big business.

I often counsel against being distracted by tangential good ideas. But if you're in good shape and sales are rolling, say yes -- and not because you expect success. Do it because it's good to let your teams know that the white space exists for them to innovate imaginatively. They should know that their very best ideas will be supported. Otherwise, they will learn to stop having them. And if, by chance, that moon shot takes off… well, then you may well own a moon.

4. Yes to real life.

Startup culture is filled with the trappings of fun and respect. Whether it's gummy bears, beer Friday, Waffle Wednesday, on-site gyms, catered meals, outings to ballgames, these sort of experiences can provide a company bond. But those are trappings, not life. While the trappings exist to make work a more pleasant place, say yes to things that enhance life, too. When someone needs to leave right at five on Tuesday because they're learning guitar, you're supporting their soul. When you see someone has been working very late every day, thank them for their commitment and tell them to sleep in the next day. Gummy bears are not an intrinsic human need, so say yes to the balance we all need, and it will come back to you in healthy, open employees.

5. Yes to the convincing case that you are wrong.

Lead with your vision, conviction and strategy out in the open every day. And when someone suggests that your strategy is wrong, your conviction misguided, your vision blurry, hear them out. Most of the time, they will not have spent 24 hours a day thinking through the business the way you have, and you will be able to show them where their understanding is incomplete. But if you can't do that, if their argument is bulletproof, say yes and invite them to help you rethink things, because they are probably your most valuable employee.

Jon Elvekrog

Co-founder and CEO of 140 Proof

Jon Elvekrog is the co-founder and CEO of 140 Proof, a social-ad platform company. With his co-founder, Jon developed 140 Proof's patented content-matching technology to harness the massive, growing data set of the "Broad Interest Graph" and match consumers with relevant brand recommendations. 

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