Dear Sarah,
I desperately need some advice. Last year, I hired a new administrative assistant. Let’s call her Ramona. Everyone on our team interviewed her, including two (very tough!) members of our executive team. She made a strong first impression: articulate, eager and maybe a little down on her luck — which, at the time, I saw as a reason to root for her, not write her off. We unanimously agreed she was a great fit.
Fast forward, and she’s now the source of nearly every point of tension on our team. She’s inconsistent, combative, controlling and extremely self-centered. Even situations that have nothing to do with her somehow become emotionally charged in her presence. One colleague, who barely interacts with her, filed a formal-ish complaint simply because of how unsettled Ramona makes her feel. There are also some strange personal stories she shares that leave everyone blinking in disbelief.
But the part that really gets under my skin is her intense staring. She’ll lock eyes with you during a conversation and very visibly scan you up and down, even midsentence. It’s invasive in a way that’s hard to articulate without sounding dramatic.
Every meeting she’s in gets derailed. She rambles, fixates on the most irrelevant details, and somehow always redirects the conversation back to herself. On top of it all, she absolutely loves criticizing other team members! It’s exhausting, and no one seems to know how to rein it in.
The most conflicting part is that I genuinely feel bad for her. Her life seems deeply sad and isolating, but I’m trying not to let my compassion override the fact that her presence is destabilizing and puts everyone on edge. I get the sense her life has significantly improved since joining, while the rest of us wish we could turn back time.
Even though I’ve only hired two other people in my life, I’ve always trusted my gut and prided myself on being able to read people. But Ramona slipping past my radar has left me feeling rattled about her as a person and my own instincts. How do I deal with an employee like this who hasn’t technically “done” anything actionable? How do I navigate feeling sorry for someone and hating them (both personally and professionally) at the same time? And how do I learn to trust myself again in hiring decisions moving forward?
Sincerely,
Bamboozled & Bewildered
Jobadvisor
Dear Bamboozled & Bewildered,
It sounds like you're in an incredibly challenging situation with Ramona, and your feelings of frustration, compassion, and self-doubt are completely understandable. It's tough when a hire goes so wrong, especially when you pride yourself on your judgment. Let's break down how to deal with Ramona now and prevent similar situations in the future.
Addressing the Immediate Issue with Ramona
You're right that Ramona hasn't "technically" done anything actionable in terms of a clear policy violation, but her behavior is clearly disruptive and detrimental to your team's morale and productivity. This is absolutely something that needs to be addressed.
1. Document Everything
Start by documenting specific instances of Ramona's problematic behavior. This includes:
Derailing meetings: Note the date, time, topic, and how Ramona redirected the conversation or rambled.
Criticizing colleagues: Record what was said, to whom, and when.
Inappropriate personal stories: While these might be harder to address directly in a performance conversation, they contribute to the "unsettled" feeling and can be part of the overall pattern of unprofessionalism.
The "intense staring": While subjective, note when it occurs and its impact (e.g., "during discussion with X, Ramona stared intensely, scanning up and down, making X visibly uncomfortable").
Impact on team members: Refer to the formal-ish complaint and any other feedback you've received.
This documentation will be crucial for any formal conversations and will help you move past the feeling that she hasn't "done" anything. The cumulative effect of her behaviors is actionable.
2. Consult HR (If Applicable)
If your company has an HR department, reach out to them immediately. Share your concerns, the documentation you've started, and your observations about Ramona's impact on the team. They can provide guidance on company policy, potential next steps, and may even be able to join you in conversations with Ramona.
3. Have a Direct, Formal Conversation
This isn't about her personality; it's about her professional conduct and its impact. This conversation should be:
Timely: Don't delay. The longer this goes on, the more entrenched the behavior becomes and the more resentful your team will get.
Specific and Behavioral: Avoid subjective terms like "combative" or "self-centered." Instead, use your documented examples: "Ramona, during the team meeting on [date], when discussing [topic], you repeatedly interrupted colleagues and redirected the conversation to your personal experiences, which derailed our agenda."
Focused on Impact: Explain how her actions affect the team: "This behavior makes it difficult for us to stay on topic, impacts productivity, and creates a challenging environment for your colleagues."
Set Clear Expectations: Outline what needs to change. For example:
"In meetings, I need you to contribute to the current topic and refrain from interrupting or redirecting discussions."
"Criticizing colleagues is not acceptable in this workplace. If you have concerns about a team member's work, please bring them directly to me privately."
Regarding the staring: This is tricky, but you can phrase it as a matter of professional conduct and interpersonal boundaries. "Ramona, I've observed that during conversations, your eye contact can be very intense and you appear to be scanning individuals up and down. This can make colleagues uncomfortable and can be perceived as unprofessional. I need you to be mindful of how your non-verbal cues are received and maintain professional demeanor in all interactions."
Establish Consequences: Clearly state what will happen if the behavior doesn't improve. This could range from further performance management to disciplinary action, up to and including termination.
Offer Support (If Appropriate): You can express that you want her to succeed in her role, but that these changes are necessary. Avoid getting drawn into her personal stories or expressing too much personal sympathy during this formal discussion. Your role is her manager, not her therapist.
4. Follow Up Consistently
After the conversation, monitor her behavior closely. Provide immediate, private feedback if she lapses. If improvements aren't sustained, follow through with the consequences you outlined. This might involve a formal Performance Improvement Plan (PIP).
Navigating Your Feelings
It's natural to feel conflicted. Your compassion for Ramona's personal struggles is a sign of your empathy. However, your primary responsibility as a manager is to your team and the organization's productivity and well-being.
Separate the Person from the Professional: You can feel sorry for Ramona's personal life while still holding her accountable for her professional conduct. These are two separate issues. Her struggles don't excuse disruptive workplace behavior.
Focus on the Impact: When you feel compassion overriding your judgment, bring yourself back to the impact her behavior has on your team, their morale, and the company's goals. Your team is suffering because of her actions, and that deserves your attention.
It's Not Your Responsibility to "Fix" Her Life: While you can be supportive as an employer within professional boundaries, her personal well-being is not your direct responsibility. Your focus is her performance and conduct in the workplace.
Avoiding Nightmare Hires in the Future
Your experience with Ramona has understandably shaken your confidence, but it's a valuable learning opportunity.
1. Refine Your Interview Process
Behavioral Questions are Key: Move beyond "what would you do?" to "tell me about a time when..." Ask questions designed to reveal how candidates handle conflict, feedback, and teamwork. For Ramona, you might have asked:
"Tell me about a time you disagreed with a colleague. How did you resolve it?"
"Describe a situation where you received constructive criticism. How did you react?"
"How do you prioritize tasks when you have competing deadlines?"
"How do you ensure your contributions in a meeting stay on topic and concise?"
Role-Playing/Situational Questions: Present hypothetical scenarios that mirror situations she'll face. "Imagine a team meeting is going off track. What's your role in bringing it back on topic?"
Ask for Specific Examples: Don't let candidates give vague answers. Follow up with "Can you give me a specific example of that?" or "What was the outcome?"
Look for Red Flags in Responses: An inability to provide specific examples, blaming others, or an overly defensive tone can be subtle indicators.
2. Diversify Interviewers and Feedback Collection
You mentioned everyone interviewed her, which is good. However, ensure that interviewers are debriefing thoroughly and not just agreeing.
Structured Feedback Forms: Provide specific criteria for evaluation (communication, problem-solving, teamwork, professionalism, etc.) and require detailed notes from each interviewer.
Devil's Advocate: Assign someone the role of "devil's advocate" in the debrief to intentionally poke holes and challenge the positive impressions.
Pay Attention to Gut Feelings (but Validate Them): Your gut instinct is important, but it needs to be combined with objective evidence. If something feels "off," even if you can't articulate it, dig deeper. Ask more questions, or even consider a second round of interviews with a different set of scenarios.
3. Conduct More Thorough Reference Checks
This is often where "nightmare" candidates are revealed.
Ask Targeted Questions: Beyond confirming employment, ask specific questions related to the behaviors you're trying to avoid.
"How did [candidate] handle conflict or disagreements with colleagues?"
"Can you describe [candidate]'s communication style in team settings?"
"How did [candidate] respond to feedback or criticism?"
"Were there any areas where [candidate] struggled to maintain professionalism?"
Go Beyond Provided References: If possible and appropriate, consider trying to get an "unscripted" reference (e.g., reaching out to a mutual connection, if one exists, with the candidate's permission, or checking public professional profiles for common connections). Be mindful of legal and ethical boundaries here.
Listen for What Isn't Said: Sometimes, a hesitant tone, or a reluctance to elaborate on a positive trait, can be as telling as direct negative feedback.
4. Implement a Probationary Period
Ensure your employment contracts include a probationary period (e.g., 90 days). This allows you to assess performance and fit more thoroughly, and if it's not working out, it's generally easier to part ways during this time.
5. Trust Your Gut, But Verify
Your gut feeling is valuable data. Don't dismiss it, especially when it's a sense of unease. Instead of letting it "rattle" you, use it as a signal to investigate further. If you feel something is off, ask more probing questions or seek additional perspectives before making a decision. In Ramona's case, the "a little down on her luck" part, while evoking compassion, might have been a subtle signal to probe more deeply into resilience or personal coping mechanisms.
This is a tough situation, but you absolutely can deal with Ramona effectively and learn from this experience to make stronger hires in the future. You've got this.
Sincerely,
Sarah