When an Employee Wants to Quit, You're Much Better Off Helping Him or Her Make the Transition One sign of a very well-run company is when employees can tell their boss they need to move on, without being shoved out the door.

We've all been there. You realize the role you're in is no longer working for you. You want to start looking for another job, but you don't feel like you can have an open, honest conversation with your manager without being let go. We've all heard stories about colleagues who attempted to be honest with their boss about looking for other opportunities and were terminated because of that conversation.

At the handful of early-stage tech companies where I've worked, I've seen a negative cycle occur when it comes to employee termination and resignation. When an employee is dismissed by their employer, the employer only pays them through the end of the next pay period. I've seen multiple women in their early 20s let go and given just two weeks of pay. They had student loans and little to no savings, and they were put in a very uncomfortable position.

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If it's the employee who is quitting, the employee makes the decision that they want to leave, but instead of having an honest conversation with their boss about it, they lie. They spend 10 percent of their time interviewing -- we've all faked the doctor's appointment -- and the employee ends up doing themselves a disservice by not spending an adequate amount of time looking for the next best opportunity. The employee can spend months in a disengaged state and then when they finally quit, they give two weeks notice, leaving their employer with an inadequate amount of time to properly backfill the position.

To solve for this, I put a policy in place at my company, Spotted, when we were very early stage and had only five or so employees. The policy outlined that if any of our employees decided that Spotted was no longer the place for them, or if I decided that for them, we would agree to have an open, honest conversation about it. They would get two months full pay where they could spend 50 percent of their time looking for another job. Furthermore, we would work together on crafting a shortlist of companies that they were most interested in, and I would help set up introductions for them and act as a positive reference.

Since we started this policy, there have been two people who have taken me up on this, and another eight employees who I had to transition out of the business. What this policy creates is an environment where the transition process becomes much less painful and more of an open environment where our employees feel comfortable talking to me about issues around culture, morale and communication.

The positive effects on the business aren't just limited to conversations around termination; they permeate the day-to-day operations of the business. One of our most talented employees recently told me that about six months ago, she was wondering whether Spotted was going to be the place for her long-term. Instead of harboring those feelings and letting them worsen, she had four or five very open conversations with me about her frustrations working with certain team members, the projects she felt she wasn't succeeding at, the areas she wished she could spend more of her time on and some morale issues she was facing. We talked through these issues one by one and found ways to alleviate them. Now, she feels like Spotted is a place she can see herself at for a long time. It's these types of conversations that make this policy so worthwhile.

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I have brought this policy up in conversation with friends of mine who are senior executives at larger companies or CEOs of early-stage companies themselves. Their counter-argument to this policy is often "That's a huge risk" or "They might steal trade secrets or information from your CRM" or "This is very expensive." I don't believe that any of these responses are warranted because, in my experience, this policy helps breed trust, honesty and loyalty.

By making it known that you, as their manager, have their best interest in mind, you create an environment where employer and employee have faith in one another. They are less likely to do something damaging to your firm. They are also more likely to work hard for those last few months they are working at your company. You are doing them a solid, and they are doing you one as well.

That being said, there are some basic rules of engagement to follow if you are going to adopt this policy:

1. If you sense that an employee is unhappy, bring it up proactively in a 1:1 setting. The more you do this, the more you will condition employees to have open and honest conversations with you. This policy won't be effective if you announce it on an employee's first day and then forget about it until the day it needs to be used.
2. You need to be a leader who genuinely has your employees' best interests in mind. This means that you will sometimes need to have your employees' best interest in mind ahead of your company's own best interest. I had an employee who would talk from time to time about regretting the fact that she didn't study pre-med in undergrad. She joined us one year after graduating from college, and, ultimately, she felt comfortable having an open conversation with me about wanting to do a post-baccalaureate program to fulfill her dream of going to med school. I told her that she should absolutely go ahead and do it. She was a critical part of our team, but the right thing to do was encourage her to pursue her dreams.
3. Once you do have the conversation with the person about the two-month grace period, you need to have a clear plan for those last two months and outline exactly how you expect them to spend the 50 percent of their time on your business. You also have to let everyone at the company know that the two-month period has started so that others don't question why that person is coming and going throughout the work day.

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By creating an environment where leaders and employees are given the permission to have open, honest conversations about the company culture and work conditions, you will ultimately develop a workforce of people who will raise red flags earlier for you, who will make a real effort to help improve the culture on a day-to-day basis, and, in return, will feel secure and trusted. It's a win-win policy for all.