How to Prepare for Difficult Conversations with Longtime Employees

You and your longtime employees have gone through a lot together. You’ve developed a special bond as the company evolved, and you might even hang out together on the weekends. What if one of these individuals began underperforming or acting dishonestly? Would you feel uncomfortable confronting him or her about it? As evidenced by Wells Fargo’s recent scandal, company leaders of all types struggle to address this scenario. In fact, more than one-third of managers admit to shrinking away from giving direct feedback to employees when they anticipate a negative reaction. Despite a potentially awkward confrontation, the consequences of letting a longtime employee underperform can be severe. To keep their companies moving in a positive direction, entrepreneurs must learn to address this situation before it turns into something worse.

What Message Are You Sending?

Overlooking a longtime employee’s poor performance demonstrates to the rest of your team that you favor tenure over production, and this can cause resentment.

I went through this dilemma years ago with an employee who was a good friend of mine. Her performance was obviously suffering, and the small nudges I gave her didn’t make a difference. I hoped she’d fix it herself and spare me the confrontation, but that didn’t happen. The more I worried about the situation, the clearer it became I had to take action. Not only would other employees resent her, but newer employees might even follow her bad example and start a trend of underperformance throughout the company.

The decision to have an honest conversation led to a great experience for both of us. We worked out a performance plan, and I got to watch her become a strong contributor again. Since then, I’ve honed a process that makes these situations much smoother and far less nerve-racking to address. Here are its three main steps:

Begin with Yourself

Only 27 percent of employees believes strongly in their companies’ values, often because they don’t see their leaders representing those principles. If your longtime employees don’t see you putting forth a hard, honest effort day in and day out, you won’t have a leg to stand on come discussion time. Instead, lead by example, and show your employees how you expect them to carry themselves.

Schedule Your Feedback

Randomly walking up to a struggling longtime employee and announcing, “It’s time to talk” will only stir up nervousness and negativity. Regular review meetings, on the other hand, provide a great venue for evaluation without the pressure of a spontaneous discussion. At our company, managers and employees hold one-on-one meetings every six months to evaluate progress in a friendly, supportive environment. Many other startups, such as Groove, also believe in the value of recurring, rather than reactionary, progress meetings.

Stay Positive and Future-focused

When you have the talk, remind your tenured employee that this conversation is not a punishment; it’s an opportunity to receive support from a close confidant and to make improvements. Come to the meeting ready to dissect the problematic behavior, and use concrete metrics to support your claims. Then, discuss exactly what changes you want to see, and define what success will look like. Twenty-eight percent of employees say they never discuss future goals during performance reviews, so be sure to talk about next steps, and then follow up at each subsequent meeting.

Your longtime employees have tremendous worth, and you owe it to them (and to your company) to keep them performing at a high level. Honesty always wins, so speak candidly about your expectations, and be ready to offer the ongoing support they need.

If you approach each interaction in a respectful and solution-oriented fashion, you can steer struggling longtime employees back on track and ensure a productive partnership.