Negotiations: How to alert the boss about a problematic co-worker


I am one of five directors who report to Ron, the president. Four of us work well as a team and consistently exceed expectations. The fifth colleague, Jenna, is manipulative, operates off her own agenda, takes credit for other people’s work, blames others when she falls short, is passive-aggressive, and it’s getting worse. I am scheduled to meet with Ron to discuss Jenna’s behavior and I don’t want to be confrontational. This negotiation is critical – I want Ron to know that I support his vision but that Jenna’s behavior poses a significant threat to our long-term success. How should I handle this?


You walk a delicate balance. On one hand, you’re frustrated by Jenna’s behavior and wonder why he, the president, hasn’t taken action to rein her in. On the other hand, it is possible that he may not be aware of what’s really happening and will appreciate your insights.

Below are five steps to help you prepare for and manage this conversation with the president:  

1. Define the outcome of this meeting.

Be clear about what you want to happen as a result of this meeting. Do you want the president to know how this colleague undermines the team’s effort? Do you want him to outright fire her? Do you want him to restructure the team and strip her of core responsibilities? Do you simply want to know where he stands on this issue?

The objective you set forth for this meeting will influence what you say and how you say it. Be deliberate with the objective you set and the message you communicate.  

In every negotiation there are “controllables” and “uncontrollables” – the things you can influence and those you cannot. In this negotiation you can control how you position this situation. However, you cannot control the action he takes as a result. It would be unrealistic to expect him to fire her or demote her following your meeting.  The best you can hope for is that he will become more observant, ask more questions and intervene expeditiously when issues arise.

2. Rehearse

How you deliver your message is as important as what you say. The tone of your voice will influence what he hears. If you whine, he may think your complaint is merely a personality clash. As a result, he may downplay the seriousness of the situation and, like a parent, tell you to “go to your room and work it out.” If you become defensive or angry, he may think you question his judgment and retaliate. 

Describe the experiences as almost a third party would. You don’t want your face to flush, your voice to quiver or for you to sound hostile. Rehearse. Rehearse. Rehearse. You want to engage him so he’s curious and wants to fully understand the situation.

3. Speak to what motivates him

You mentioned that you believe in and support his vision, and that your colleague’s behavior poses a challenge in the team’s ability to achieve the vision. Can you provide examples of her behavior that supports how his vision may be at risk? For example could you say something along the lines of, “Ron, I think your vision is right on the mark. And with a focused effort, I am confident this team can deliver. Over the last few months, we’ve been forced to take our eyes off the goal, sometimes at a critical juncture, and it’s cost us valuable time and money. I’d like to eliminate, or at least minimize this in the future and I need your assistance about how to handle this?”    

Have you captured his attention? Hopefully. Have you reinforced your commitment to his vision? Absolutely. Have you challenged or threatened him in any way?  Definitely not. Instead, you’ve let him know you are on his team and need his assistance to better strategize how to win.   

4. Stick to the facts

Describe the situations you have experienced over the last several months. Remain as neutral as possible. Review the facts. Stay away from becoming accusatory or hostile. 

To understand how emotion distracts a listener, compare the two stories below. As you read them, ask yourself, which one is more likely to inspire Ron to want to investigate further, (a) or (b)?

a. “Ron, the day before the Acme project deadline, we received a call from Finance indicating that Jenna had reallocated $20,000 to her department without advance notice. When we approached her, she became very angry.  She screamed and yelled at us saying that we agreed to let her do this back in March. None of us can recall having had this dialogue. What we do know is that she didn’t make the necessary calls nor did she meet with the decision makers like we did, so her numbers were really down. We worked hard and would have exceeded our goal if she hadn’t sabotaged us at the last minute!!!  How can she be allowed to do this? I just don’t trust her and neither does anyone else on the team. She’s not pulling her weight and operates with her own agenda and you’re letting her get away with it!” 

b.  The next six months are going to be intense and last week we had a situation happen that concerns me. I’m not sure how to handle it and so I’m coming to you for advice. Two days before we finished the Acme project, we were told that we were $1,500 shy of our goal. Later that day, Ned called from Finance to tell us that $20,000 had been reallocated to the mid-market division. We had no prior knowledge of that happening. As a result, we were forced to scramble. Jack, Mary, Max and I worked through the night and ultimately we came up short. This is the third time in four months we’ve had something like this happen. We thought we had addressed it, but it doesn’t seem to be the case. We are not equipped to handle these last minute surprises. Would you be willing to meet with us tomorrow to review the Jenkins project? It starts next week and we want to make sure our strategy is solid and leverages our time and talent.”     

If you chose (b), you’re right. You presented enough information so Ron can ask more questions if he wants to know more about the situation. You’re professional and focused on what’s important to him – the goals. Once he meets with the team, reviews the strategy and agrees how to proceed, any unplanned actions by Jenna beyond the scope of the agreement, will become obvious to him.     

5. Don’t tell him how to do his job, ask for help

Pay attention to his body language. Does he roll his eyes in frustration with the situation? Does his look disappointed or angry? Does he act surprised and ask a lot of questions? Is it possible that he really doesn’t know what’s going on? As tempting as it might be to let off some steam and verbally degrade Jenna, resist the temptation and take the high road. Ron is still the president and everything you say and do will leave a lasting impression. Do your job to bring the issue to his attention without coming across as a “tattletale.” Hopefully, he will investigate and once he learns about Jenna’s personal agenda, takes corrective action.   

Regarding his response, ideally, you want Ron to inquire about the $20,000 transfer and the other three situations. If he does, suggest to him that it might be prudent to meet with the team (minus Jenna) so he gathers the information from each team member. Once the other team members validate your message, then he knows he has a weak link. However, you need to be emotionally prepared for him not to ask you a single question and simply agree to meet to review the next project strategy. At the very least he’s more involved, which is a step in the right direction.

To protect yourself moving forward, recap team meetings and all conversations with Jenna via email so there’s a paper trail. Schedule regular debriefing meetings with Ron so he’s up to date on the team’s progress. When Jenna drops the next bomb, he will see for himself the challenges you face. At the very least, Jenna will think twice before she strikes again. With her passive – aggressive behavior, she won’t like being under Ron’s spotlight. 

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