Spotting problems before your Executive does is one of the most valuable and often the least noticed things an Assistant can do. Every one of us knows the sinking feeling when we don’t spot a problem. Picture the scene, your Executive forwards an email with a short note attached, something like “were we aware of this?”, and your stomach drops a little because the honest answer is no. That clash had been sitting in the diary for a fortnight, and the supplier had gone silent weeks before that. You had even half-noticed the number in the board pack looking slightly off when it first crossed your desk, and then let it go. It was all there to be dealt with, but your Executive noticed it before you did.
It is such a horrible feeling, and most of us have had it more than once. It is frustrating because most EAs work in fast-paced, pressurised environments, and it goes without saying that something will get missed somewhere. Spotting problems before your Executive isn’t detailed in the job description, so no formal training is provided for this crucial skill. And let’s not forget, if you are really good at spotting problems before your Executive does, almost nobody hands you credit for it.
Even so, getting good at it is, in the end, one of the surest ways to become the Assistant who is trusted with the important things rather than kept busy with the obvious ones.
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It helps to be clear about what spotting problems before your Executive does really is, because it is easy to mistake it for nervousness or catastrophising about everything that might go wrong. It really comes down to seeing a small signal early and understanding what it might turn into. A meeting that keeps being rescheduled either by you, your Executive, or the person they are meeting with is not just an annoyance to be tidied away; it is usually telling you something. It could be that a decision is stuck, or that two people are avoiding a conversation they need to have, or that the meeting isn’t that important in the first place. A report that arrives a day late this month and was also late last month is a sign that the person delivering it has time-management issues, motivational challenges, or is incredibly busy. If someone isn’t hitting a deadline for the most senior people in the organisation, it’s usually a sign something is going wrong.
So spotting problems before your Executive does isn’t about predicting the future, which none of us can do anyway (despite what we often see in job postings for EAs). You do it by noticing what’s happening but hasn’t fully fallen into place, and saying something while there is still room to act. Because we know our Executive will eventually see the problem when it becomes impossible to ignore. Catching it before they do is where we want to position ourselves, so we are dealing with the problem at a stage where it is still small, still easy to fix, and still yours to fix before anyone else has to.
This has always been part of the EA job, but spotting problems before your Executive does is becoming a bigger part of it, and the reason is worth talking about.
A great deal of the work Assistants used to be measured on is now work a machine can take on. We know the usual examples – drafting the email, summarising the meeting, pulling the figures into a deck, keeping the schedule tidy; these are all things AI can now do quickly, and increasingly it does, maybe not always as well as you would, but well enough for a first pass. What a machine cannot do, at least not yet and arguably not for a long time, is feel that something isn’t quite working, which is the whole basis of this skill. AI will summarise the meeting beautifully, without ever noticing how someone reacts in the room or on the call, which is the most important thing. It can format the board pack flawlessly without noticing that one figure flatly contradicts what was said three weeks ago. That noticing, knowing which small thing actually matters, is precisely where an Assistant becomes hard to replace.
It is also a reminder that you have never really been defined by the tasks you carry out, but by the value you create for your Executive, and spotting problems before your Executive does is about as valuable as that gets.
So, what does spotting problems before your Executive actually look like, day to day? We could be talking about huge problems, but usually, it is less dramatic than it sounds.
Much of it is simply paying attention to patterns, the recurring behaviours and ways of working that your colleagues demonstrate in their day-to-day work, rather than individual events. Going back to our example, one late report from a colleague is a one-off. The same report, late three months running, is a problem with a cause, and the cause is usually worth a word before it creates a bigger problem or has a greater impact. Again, a diary clash you smooth over is a one-off task we all have to do regularly. A diary clash that keeps reappearing in the same week, with the same two people, is a signal that something underneath needs sorting, and sorting it once saves you a ton of time later.
So, spotting problems before your Executive does usually comes down to noticing a few kinds of signals:
None of these examples requires you to be right every time, because sometimes there actually isn’t a problem, and it will all work out. But spotting problems before your Executive does only means that you flag the thing while it is still small, and that you do it in a way that gives your Executive a head start rather than a fright.
The trouble with all of this, if it stays in your head, is that spotting problems before your Executive does depends entirely on you being alert on the day. Nobody is alert every day – it would be exhausting! The more reliable version of this skill is to build a little structure around it, so that problems surface for you rather than relying on you to be highly vigilant all the time.
So it can be as simple as a standing note of the things you are keeping an eye on, which you review for a few minutes at the start of each day. It might be a habit of scanning the diary a fortnight out rather than a few days out, when most of these clashes are still easy to move. The point is to stop waiting for a problem to jump out at you and instead create a moment when you go looking for it on purpose. It does mean carving out some time in your schedule each day to look for anything that might not be working. Still, it means the difference between getting better at firefighting and removing the conditions that keep starting the fires, and it is almost always the better use of your time.
It is also worth noting that, as with everything, really honing this skill requires a level of trust and open communication with your Executive. Raising a concern that turns out to be nothing, or questioning a figure that turns out to be fine, can feel risky if you are not yet sure you have that relationship with your Executive. You’ve got to start somewhere, though, so start small, and make sure the stakes aren’t too high either way (if it is a problem or not). What you’ll find is that the more you do it, the more often you’ll be right, and your Executive starts to listen. Every time you spot problems before your Executive, you make the case for being trusted with more, and that is a case very much worth making out loud rather than waiting for the work to speak for itself.
The hardest thing about spotting problems before your Executive does is that when you do it well, very little appears to happen. It becomes all just part of the job. The reward for catching a problem early is an uneventful week, and an uneventful week is impossible to put on a list of achievements, despite being a ridiculously valuable skill.
That is exactly why it is worth naming this work for what it is, both to yourself and to the people you support. Too often, it gets written off as luck or being organised. But spotting problems before your Executive does is really the discernment to see what matters before it gets big enough for everyone else to notice, and it is one of the clearest ways an Assistant moves from managing the day to genuinely protecting their Executive.
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