Questions to Ask an Underperforming Employee
Questions for a manager holding a performance conversation, designed to separate a skill problem from an unclear brief, a blocked process, or a motivation problem, and to end with something both people can check.
The questions
Open any question for the note
How do you think the last couple of months have gone?
Why ask it
Open with their assessment so you learn whether they already know there is a problem. Someone who says it has gone well has either not been told clearly or does not agree, and those need different conversations.
Talk me through what a normal week looks like, hour by hour.
Why ask it
Time accounting surfaces the real cause more often than any question about motivation: meetings nobody cancelled, work absorbed from a colleague, half the week on a task you thought took a morning. Ask for last week specifically, not a typical one.
Which parts of the job are you clear about, and which are you guessing at?
Why ask it
Giving explicit permission to admit guesswork is the fastest route to a fixable answer. Silence here usually means they do not feel safe saying it, which is information about you.
What did you understand the target to be?
Why ask it
Ask before you restate it. A gap between their number and yours means this is an expectations problem and the previous months of frustration were largely avoidable.
Where do you get stuck, and what do you do when that happens?
Why ask it
The second half matters most. People who stall for days without asking for help need a different intervention from people who ask immediately and get no reply.
What are you waiting on from other people right now?
Why ask it
Underperformance is often a queue problem wearing an individual's name. If there are three named blockers, the fix is yours to make rather than theirs.
Which task takes you much longer than you expected it to?
Why ask it
This locates missing skill without requiring anyone to say they cannot do something. The answer is usually specific and trainable, such as the reporting tool or writing to clients.
What have you already tried to sort this out?
Why ask it
An employee with three attempts to describe is engaged and short of a method. One with none has either not registered the problem or has given up, and you need to know which.
Has any of my feedback not landed, or seemed unfair?
Why ask it
Asking directly is the only way to find out that the message you thought you delivered was heard as encouragement. Expect a delay before an honest answer, and do not argue with the first one.
What do you think I am getting wrong about your work?
Why ask it
This invites the correction they would otherwise take to a colleague or to your manager. If they name something real, such as invisible work or a shifting brief, deal with it before asking for improvement.
Is there anything outside work affecting this that you want me to know about?
Why ask it
The phrasing leaves them in control of how much to say, which is the point: you need to know that something exists, not what it is. If the answer is yes, move to what accommodation is possible before returning to targets.
Do you have the tools, access, and training you need?
Why ask it
Missing system access, an unlicensed tool, or training that was promised and never scheduled shows up as slowness for months. Write down whatever they name and fix it yourself.
Which part of this job do you actually want to be good at?
Why ask it
Answers reveal whether the role and the person are matched at all. Someone who names nothing in the current job is telling you the problem is fit, and that conversation is more useful than a remediation plan.
If you could hand one responsibility to someone else, which would it be?
Why ask it
This finds the task they dread, which is usually the one being quietly deferred and causing the visible failures. Sometimes it can genuinely be reassigned.
What would have to change for the next six weeks to go differently?
Why ask it
Listen for whether the changes are theirs to make or entirely other people's. A list composed only of things others must do tells you where accountability currently sits.
Of the expectations we have just discussed, which will be hardest for you to hit?
Why ask it
This produces a realistic forecast instead of blanket agreement, and it tells you where to put support. Someone who says all of them are fine, after a poor quarter, is not engaging with the plan.
What do you want from me, and how often?
Why ask it
Ask for a concrete arrangement: a weekly fifteen minutes, review of a draft before it goes out, an introduction to someone. Vague requests for more support cannot be delivered or evidenced.
How will we both know in a month whether this is working?
Why ask it
Agree on the specific measure and the date now, in their words, so the next conversation is about evidence rather than impressions. Write it down before either of you leaves the room.
I want to be straight with you: what happens if this does not improve?
Why ask it
Say the consequence plainly rather than implying it, because people who are dismissed months later routinely say nobody told them their job was at risk. Then ask what they heard, so you know it landed.
What have you not said yet that you want to say?
Why ask it
The most important thing in these conversations often arrives after the formal part is finished. Leave the silence open long enough for it.
Running the conversation
Practical guidance for the conversation itself
Before, during, and after
Decide what you are diagnosing
There are four common causes: they do not know what good looks like, they cannot do it yet, something is blocking them, or they are not trying. The questions differ, and treating a clarity problem as a motivation problem is the usual mistake.
Book it properly
A private room, thirty minutes, and a heads-up that you want to talk about how the role is going. Ambushing someone in a corridor or on the way to another meeting guarantees a defensive conversation.
Bring two specific examples, not a characterisation
Name the missed deadline and the report that came back for rework, with dates. Words like unreliable and attitude cannot be discussed, disputed, or improved.
Write the plan the same day
Send a short note covering what you agreed, what you will do, the measure, and the review date. Memory of these conversations diverges quickly, and the note protects both of you.
A twenty-minute structure
In order
- 1Ask how they think it has been going, and listen without correcting yet.
- 2State your two examples plainly, and ask what happened in each.
- 3Work through blockers, clarity, and skill in that order.
- 4Agree the measure, the support, and the date.
- 5Say the consequence if it does not change, and check what they heard.
Common pitfalls
Softening until the message disappears
Wrapping the problem in praise leaves people believing the conversation was positive. Say the difficult sentence once, clearly, and then move to what happens next.
Solving it for them in the room
If you supply the diagnosis and the plan, you also own the outcome. Ask them to propose the fix first, and adjust it.
Having the same conversation a third time
Two rounds without change means the approach is not working. Escalate to a formal process, change the role, or accept the situation, but stop repeating the meeting.
Skipping your own contribution
Unclear briefs, shifting priorities, and unanswered questions are management failures that show up as individual underperformance. Ask about them, and fix what you find.