Questions to ask during the ‘stay’ interview

My boss asked me for a meeting to discuss my current projects. This is unusual. He’s not a micromanager and I love his management style. The trouble is my low pay and perks. I wonder if he knows about my plan to leave the company. — Indigo Reef.

​Maybe. He may have received some news about your plan from the grapevine, if you talked about it with your work colleagues. Or your boss may have been assisted by a friendly headhunter to trick you with a lucrative job elsewhere. And you’re the only one who would know that. 

​Aside from those, there are many ways to know about your career plans.

​How would you handle the situation if he asks you to stay? In your case, it’s unusual because your manager is not a micromanager, and you genuinely appreciate his leadership style. So why the sudden one-on-one?

​Naturally, your mind races to some lingering concerns — especially when you think about your dissatisfaction with your compensation. The possibility of the boss knowing your plan adds a layer of tension. Now, would you be honest or offer a tactful white lie to keep options open?

​Navigating this delicate conversation requires balancing transparency with strategy, weighing your loyalty and career ambitions against the realities of compensation and growth. It’s a test not just of negotiation, but of emotional intelligence in action.

​Therefore, be prepared to answer questions, assuming this is a “stay” interview. A “stay” interview is the opposite of an exit interview. If your boss is truly worth his salt, he would know what motivates you to stay.

​Of course, it’s not as simple as that. You should ask thoughtful questions about the progression of your career. If you’re prepared, such a meeting could be an excellent career conversation.

THE BEST QUESTIONS TO ASK
​A “stay” interview is a rare opportunity for employees to pause, reflect, and have an honest conversation with their boss on what keeps them motivated — and what might drive them away. More often than not, a “stay” interview is the best time to discuss compensation.

​Unlike exit interviews, which happen when it’s too late, “stay” interviews focus on engagement and retention. The key is asking the right questions: What challenges can be removed? What opportunities exist for growth, recognition, or skill development? How does your manager see your future in the company? 

​By framing thoughtful questions, employees can uncover actionable insights, strengthen trust, and potentially reshape their work experience — sometimes even improving pay, perks, or responsibilities without changing jobs and while preserving seniority rights.

​Here are some exploratory questions you can ask your boss during a “stay” interview:

​One, performance expectations. This is first on your meeting agenda. Be ready to update the manager on the status of your projects. Review the performance standards and timelines. Ask: “What is needed so I can improve my performance the most?”

​Two, work satisfaction. Find out from the boss how satisfied or dissatisfied he is. Ask: “Which parts of my work do you think add the most value to the team and the whole organization? Are there projects where you think I could contribute more?”

​Three, support and resources. If you’re missing out on certain requirements of the job, then find out those other expectations. Ask: “What support can the organization provide to help me perform better? Are there training programs or learning opportunities you can recommend?”

​Four, organizational direction. You can expect a broad answer from your boss as there could be things that may not be suited for everyone’s consumption. Instead, ask: “Where do you see our team or department in the next two years? How can I best contribute to that direction?”

​Five, career direction. The answer to number four above could give you ideas about your career track. Ask: “What opportunities do you foresee for my growth in this organization? What skills should I develop if I want to take on bigger responsibilities?”​

​Six, communication process. Your boss initiated the meeting. That’s a good sign. But ask this question anyway: “How can we improve our communication and feedback process? How often do you want updates?”

ASKING FOR A RAISE
The above questions may appear intimidating to your boss. Better if you can focus on two to three thoughtful questions, not a dozen. If you do, ensure that you ask them towards the end of the meeting. If not, as soon as the boss asks you if you have questions.

​Asking for a raise can feel awkward. The key is preparation, timing, and a calm, professional approach. If that “stay” interview proved to be well timed, for example when you’ve already proven your worth, then don’t hesitate to ask for a raise while diplomatically touting your track record.

Participate in Rey Elbo’s public workshop on “Smart Strategies for Dealing with Difficult Employees” on April 17, 2026 at The Ascott, Glorietta 4, Makati City. For details or registration, send message via https://reyelbo.com/contact-us.