4 Expert Insights

Having an open and honest conversation is very important. The book "Crucial Conversations" will give you some insights as to how to conduct such conversations. From what you wrote, it seems to me that you would consider the conversation with this direct report as crucial.

Sometimes involving an outside person can help you get to the answer without the pain. It has been my experience as a former executive and now a coach and consultant that people have an easy time sharing with me that which they would never share with their boss.

You've received some valid and good advice from fellow mentors above.  And my experience in coaching company leaders tells me that although you have asked about this one particular situation I get curious as to the way you relate to all of the leaders you count on.

The way you present your question and concern comes through as quite detached of any real caring or concern for the person and/or relationship.  It is simply focused on how you keep the person from leaving in order to make it convenient for you and the company.  This is something I would encourage you to examine ... perhaps with a coach ... because it is likely that this will not be the only person to depart if you don't look at this as a 'yellow flag' and willingly examine what might be missing in the way you are relating to your leaders and how you might alter that to enable all to feel valued and appreciated.

As has been said, a discussion with the employee is critical.

I would avoid disclosing that you are aware that he/she is interviewing elsewhere.  You don’t want the employee to feel caught in the act or create any defensiveness.

I would merely affirm to the employee that the she/he is very important to the business, that you appreciate his/her contributions (Be specific about what you value so it doesn’t sound insincere), and ask if he/she has any suggestions on things you could do to help the employee feel happier, more engaged, or more effective.

If the employee has decided to leave, in my experience, it is not effective to try to change his/her mind or negotiate an extended departure time.

Let me suggest that, unless your key employee is working on a time-sensitive (30-60 day) project AND has some critical expertise that no one else in the organization can even approximate, let whatever happens, happen, because delaying someone's departure is rarely as beneficial as one hopes.

Too, the unintended consequences of delaying an employee from leaving, like that, are significant:

>> You're basically training other employees to look outside so that they can get an incentive to stay, too. (Or by not counter-offering, you're basically forcing their hands to leave before they really wanted to.)

>> Your efforts to retain people who have already decided they don't want want to stay helps neither you nor them in anything beyond the shortest of terms.

>> You're diluting any incentive for other employees to want to show their loyalty.

>> You're demotivating that employee's direct reports from striving to learn and perform at a higher level because you just eliminated any opportunity for them to be promoted anytime soon.  

So if a person wants to leave, I say embrace the paradox that every employee is important and no employee is irreplaceable, and let him/her get on with his/her career and see it as an opportunity for you to reinvigorate your organization by filling the position internally, if possible.

An additional note: It's important to also realize that just because a key employee is interviewing, externally, it doesn't mean that s/he WILL leave. Maybe the person is just assessing his/her worth on the open market for year-end salary discussions. Maybe s/he is doing someone a favor by taking the interview. Maybe s/he's doing some research and analysis with the competition so to help you and your company to even greater heights. Maybe s/he's doing it because it's a great way to reconfirm why s/he wants to STAY with you. The possibilities are endless.