Senior leaders in Silicon Valley are among the best-educated, most sophisticated, and savviest executives you’ll find anywhere. Yet over the course of placing senior high-tech leaders in new positions over the past 14 years, I’ve seen far too many make fundamental mistakes that cast a cloud over their leaving their old employers. The consequences range from the distasteful to the disastrous: hurt feelings, lasting resentment from former colleagues, blame for harming the company, and — worst of all — a reputation for thoughtlessness that can damage a career. It’s painful to witness, and it begs the question: If they can’t get it right, who can?
Other than the admonition to resign diplomatically, little detailed advice has been available about how to leave one’s current company the right way. Even less research has been done on leaving well. To close that gap, my firm undertook a national survey of more than 700 senior executives and human resources officers. Only 16% of the senior executives reported that they would have done nothing differently the last time they voluntarily resigned. Here are their top three regrets and what you can do to avoid their mistakes:
Being unprepared to be fired on the spot.You never know how much resentment your departure might evoke, or how harsh the response might be. In the worst-case scenario, you could be fired on the spot and escorted from the building immediately. Especially if you’re going to a competitor, don’t be surprised if your resignation turns into a termination. Almost all of a representative sample of senior executives and chief human resources officers we interviewed to supplement our survey said that someone leaving for a competitor would be terminated immediately.
Nevertheless, if you are going to a competitor, say so. Being less than forthright will only compound the resentment when you’re inevitably found out and saddle you with a reputation for evasiveness. Tell your current company that you are crystal clear about your obligations to them and that you have already talked about the issues with your new company.
Take every precaution to avoid the suspicion that you might be taking valuable data, technical information, or customer information with you. That means resisting the natural inclination to transfer or delete files from your computer that you regard as personal or of no consequence to the business. If you want to transfer some personal files, do it in front of an HR person. And don’t erase company files, because under forensic examination (if it comes to that) it can look fishy.
Neglecting to rehearse.The second most frequently cited regret was failing to confidentially rehearse the explanation for departure with a trusted advisor. It’s not just a matter of being tongue-tied. The inability to explain clearly and reasonably to a boss or colleague why you’re leaving can lead to hurt feelings and misunderstandings, and it can open the door to protracted and painful attempts to talk you into staying when your mind is made up.
Before springing your decision on your boss, go first to a trusted advisor to get coaching and another perspective. This critical initial conversation will give you the opportunity to talk through your personal and professional reasons for leaving and how you plan to mitigate the effects on colleagues and the company. It will also give you an initial reaction to your decision. Your mentor may make you aware of implications you had not considered, such as timing or the reaction of a key colleague you had overlooked. Your mentor may also be able to suggest the best way to approach your boss with the news.
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Not having a plan for the fallout.The effects of resignation ripple outward from your boss to your colleagues and the company as a whole. Foreseeing all of those effects can be challenging, so it’s not surprising that shortsightedness in that respect was the third most frequently cited regret in our survey.
In looking at our data, we found that when it comes to analyzing the likely effects of their resignations, executives typically fall into one of three categories: those who focus on the optimal timing of their departures (38%), those who focus on relationships (31%), and those who take an unsystematic, scattershot approach, improvising as they go (30%).
Those who focus on timing believe that you must understand the larger context in which the announcement of your departure will take place: the signal it might send to the market and the effect on projects or processes (such as budgeting, strategy formulation, and compliance activities) that a departure will disrupt.
Those who focus on relationships are inclined to think most carefully about the many people their leaving will affect. The list often turns out to be surprisingly long — superiors, peers, direct reports, high-potential mentees, customers and clients, analysts, industry observers, and others. Both groups are right — you should think carefully about timing and about relationships.
Those who take a scattershot approach are asking for trouble. They checked off significantly fewer adverse effects of a clumsy departure. And while 95% of the executives who focused on timing and 98% of those who focused on relationships identified reputational damage as an adverse effect, only 65% of the improvisers did so. The improvisers were also far less likely to indicate that they had transitioned out of their last job gracefully (and were more likely to be dissatisfied with their current job and actively looking for a new one). They also more frequently cited regret about being unprepared for the worst-case scenario, which suggests that their carelessness may have contributed to such unfortunate outcomes in the past.
These aren’t rookie mistakes. In fact, the respondents in our survey who were most likely to say that they had spent too little time thinking through their departures were CEOs. With a challenging role ahead, it’s easy for even the most seasoned executives to regard their current role as already behind them and to neglect the nuances of a successful departure. Don’t — or you might very well regret it.