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&lt;p&gt;One of the most stressful times in a career is losing a job. It can also be quite stressful if you&#39;re on the other side of the layoff. That is, if you&#39;re the deliverer of the bad news, the one having to tell someone they&#39;re about to lose a job. The reason is there&#39;s no easy or best way to tell someone that their services are no longer needed, and there&#39;s no best time to tell someone either. Or is there?&lt;/p&gt;&lt;p&gt;According to Christa Quarles, the CEO of Open Table, an online restaurant-reservation service that seats more than 19 million lunchers and diners a month, there is in fact a best way and time to let someone go. Quarles, the subject of a recent &lt;em&gt;New York Times&lt;/em&gt; &lt;a href=&quot;http://www.nytimes.com/2016/08/14/business/christa-quarles-of-opentable-the-advantage-of-early-often-ugly.html&quot; target=&quot;_blank&quot;&gt;Corner Office column&lt;/a&gt;, has years of experience when it comes to having to terminate an employee&#39;s employment.&lt;/p&gt;&lt;blockquote&gt;The first time I had to fire someone whom I had specifically hired, I was truly sick to my stomach. I fought the idea for a long time, and thought I could mitigate the problem.&lt;/blockquote&gt;&lt;blockquote&gt;And then you start realizing it’s actually better for that person too. The kind thing is saying that you’re not going to be successful here for these reasons, and you want that person to find their better path.&lt;/blockquote&gt;&lt;blockquote&gt;I’ve had to terminate lots of different kinds of people in different roles, and I would say that the minute you know it’s not right should be the minute you do it. And you never regret doing it too soon. You always regret waiting too long. When somebody’s not right, there is addition by subtraction sometimes.&lt;/blockquote&gt;&lt;p&gt;Incidentally, Quarles began her career in investment banking. She worked for Merrill Lynch, Morgan Stanley, and the now defunct but once formidable boutique bank Thomas Weisel before moving on to the C-Suite at Walt Disney and then Open Table. And so, she&#39;s learned a lot more than how to fire someone during her career. For example, she&#39;s also learned the power of vulnerability: how being vulnerable can enhance rather than hurt managerial success.&lt;/p&gt;&lt;blockquote&gt;Early on, especially when I worked on Wall Street, God forbid that you declare any granular weakness, because people would pounce on it.&lt;/blockquote&gt;&lt;blockquote&gt;But the paradox of owning what you know and what you don’t know is that you actually seem more powerful as you expose more vulnerability. I’ve become more comfortable with exposing my vulnerability and not being afraid to go there.&lt;/blockquote&gt;&lt;blockquote&gt;When I give criticism now, I’ll talk about how I failed in a similar situation. I try to humanize the criticism in a way that says this is about an action, it’s not about you as a person. I want to make you better. If somebody feels like they’re in a safe place and they can hear the message, they’re more likely to change.&lt;/blockquote&gt;&lt;p&gt;Another piece of advice that managers and budding managers should steal from Quarles&#39; playbook has to do with how the CEO deals with teams working on new products or services. Quarles likes to use the phrase &quot;Early, often, ugly,&quot; which I&#39;d recommend any manager adopting as his or her own.&lt;/p&gt;&lt;blockquote&gt;The other surprise [of working as a CEO for the first time] was that people were afraid to share things early on. Teams were trying to perfect something before they would show it to me, and they’d waste a ton of time trying to get it to be perfect to show to the C.E.O. So I said, “Early, often, ugly. It’s O.K. It doesn’t have to be perfect because then I can course-correct much, much faster.” No amount of ugly truth scares me. It’s just information to make a decision.&lt;/blockquote&gt;&lt;p&gt;As for how Quarles makes her hiring decisions, she says she looks for the brightness in your eyes.&lt;/p&gt;&lt;blockquote&gt;I am looking for whether your eyes light up when you’re talking about 80 percent of what the job requires. And I always ask, “What kind of work do you avoid doing?” Because there’s always a part of your job that everybody hates. I want to understand what part that is, and I also want to understand what makes your eyes light up. The person who enjoys their job is going to give you 20 times the effort.&lt;/blockquote&gt;&lt;p&gt;And so, it follows in Quarles&#39; world that if you&#39;re ever on the losing-your-job end of a layoff conversation at your place of employment, it&#39;s likely that you&#39;re not a terrible employee; you&#39;re just not enjoying your job all that much. So losing it, while stressful, might not be the worst thing after all. It could just mean that you&#39;re getting closer to finding a job you like, and thus one at which you will thrive.&lt;/p&gt;&lt;p&gt;&lt;em&gt;Follow me on&#160;&lt;a href=&quot;https://twitter.com/vaultfinance&quot; target=&quot;_blank&quot;&gt;Twitter&lt;/a&gt;.&lt;/em&gt;&lt;/p&gt;&lt;p&gt;&lt;em&gt;Follow us on&#160;&lt;a href=&quot;https://www.instagram.com/vaultcareers/&quot; target=&quot;_blank&quot;&gt;Instagram&lt;/a&gt;.&lt;/em&gt;&lt;/p&gt;

Derek Loosvelt

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