UpTrajectory Review

Susan Thompson's piece in Small Business Trends lays out a five-question framework for conducting employee annual reviews, and the timing is no accident. As the calendar year closes, small business owners everywhere are either scrambling to complete reviews they have been putting off or dreading the awkward, box-checking conversations that often result. Thompson's approach is deliberately simple: ask what the employee accomplished, what challenges they faced, what skills they developed, what their future aspirations are, and how communication can improve. The framework itself is not revolutionary, but that is precisely the point. For owners who have been winging it or skipping reviews entirely, having a structured set of prompts is genuinely useful scaffolding.

The real value here for a small-business operator is not the questions themselves but the discipline they impose. Most small business owners conduct reviews informally, if at all, and when they do happen, the conversation tends to be one-directional: here is what I think of your performance, here is your raise, see you next year. Thompson's framework flips that dynamic by front-loading employee self-reflection. When you ask an employee what they accomplished and what challenges they faced before offering your own assessment, you get a more honest picture and reduce the defensiveness that plagues so many review conversations. That matters enormously in a small business where every hire carries outsized weight and a bad review experience can poison a working relationship for months.

Where we are somewhat skeptical is the framing that these five questions alone will transform your review process. The article gestures at the importance of ongoing feedback but does not fully reckon with the reality that an annual review, however well-structured, cannot compensate for eleven months of silence. Research consistently shows that employees respond better to frequent, informal check-ins than to a single high-stakes annual conversation. Thompson's questions work best as a capstone to continuous dialogue, not a substitute for it. Owners who treat this as a once-a-year ritual will likely find the conversations stilted and the insights surface-level. The framework is a floor, not a ceiling.

There is also a second-order effect worth considering: the questions about skills development and future aspirations implicitly signal to employees that growth is possible within your organization. In a tight labor market where small businesses often lose talent to larger competitors offering clearer career ladders, that signal carries real retention value. However, it also creates an obligation. If you ask employees where they want to go and then do nothing to support those goals, the question becomes hollow and can actually accelerate disengagement. Owners need to be prepared to act on what they hear, whether that means adjusting responsibilities, investing in training, or having honest conversations about limitations.

Our advice: use Thompson's five questions as your starting structure, but pair them with at least quarterly informal check-ins throughout the year. Before the review, send the questions to employees in advance so they can reflect rather than improvise. During the conversation, take notes not just on performance but on what support the employee requests, and follow up in writing within a week. The owners who get the most from annual reviews are not the ones with the best questions; they are the ones who treat the answers as commitments rather than pleasantries.

“Performance appraisal questions for employees should focus on specific achievements, challenges faced, and how their work contributes to team goals.” — Small Business Trends

Takeaway: Send these five questions to employees before their annual review and follow up on their answers in writing, or the conversation becomes an empty ritual.