Why Does Your Best Employee Keep Bringing You Problems?
Because they can see the tradeoff and have no way to know how you would weigh it. Most of what they bring is a choice between two goods, such as speed and margin, and your answers to those choices have never been written down anywhere they can read. Until they are, asking you is the safest move they have.
"Don't bring me problems, bring me solutions" is some of the worst management advice still in circulation, and I say that as someone who repeated it for years.
Think about who actually brings you problems. It's rarely the person who has stopped paying attention. It's the one who noticed the supplier's delivery window has crept, who saw that two customers were promised the same Thursday, who realized the new intake form loses a field every time it's saved from a phone.
Your best employee finds problems because they care enough to look. The ones who never bring you anything are either not looking or have learned that it isn't worth the trouble. A steady flow of problems from your strongest person is a good sign about them. What deserves a second look is why all of those problems end up at your door.
I've watched this pattern in a lot of owner-run businesses, and I've made every mistake available in trying to fix it. Here is the post-mortem, because the failures are more useful than the fix.
Why doesn't asking for a recommendation fix it?
The first thing I tried was the polite version of the slogan. Bring me the problem, but come with what you'd do about it. It sounded reasonable, and it did change the shape of the messages. They became "Here's the situation, I'd suggest X, okay?"
The trouble was that I said okay nearly every time, and that made me an approver, a role I'd just created for myself. The question had moved from "what should we do?" to "may I?" That's arguably worse, because it dresses dependence up as initiative, and I felt better about it for about six weeks without anything having changed.
Does being less available force them to decide?
The next idea was that if I weren't around to answer, she would have to decide. For a week or two I was slower to reply, took calls less often, and left the building more. What happened is that a pricing question for a long-standing customer sat for three days. She was waiting on me, I was out of reach, and by the time we talked the customer had lost patience and the issue had grown.
Being unavailable when no authority has been transferred doesn't produce decisions. It produces delay, and the person who delays pays for it in the customer's eyes even though the cause was mine.
What's wrong with answering fast and moving on?
I was good at this one, and it made things worse in a quiet way. I'd give a fast, sensible answer in a text message, and we'd both go back to work. Three weeks later the same underlying question would return wearing different clothes. A different customer, a different product, the same tradeoff between keeping a promise and protecting margin. Because my answers lived in a text thread, nothing accumulated. She had no precedent to point to, so she had to ask again.
Why do the same problems keep reaching you?
When I lined up the problems she had brought me over a couple of months, they turned out to be about the same four or five things. Almost every one was a tradeoff between two goods: speed against margin, a loyal customer against a fair schedule, doing a job properly against finishing it on time. She understood the facts perfectly. What she couldn't tell was which side I'd choose, and the only way to learn was to ask. I had resolved these tradeoffs for years without ever stating the exchange rate, because it had always lived in my head and had never needed to be said.
That changes the diagnosis. She wasn't lacking judgment or confidence. She was lacking my preferences, and no amount of encouragement transfers those. They have to be written down somewhere she can read them.
What is a ruling log?
What helped was embarrassingly simple. A shared document, one line per entry, with four columns:
- the situation
- what I decided
- the reason
- the date
Each time she brought me a problem, I answered as before, and the entry went into the log with the reason in one sentence. The reason matters more than the ruling. "Gave the customer the Thursday slot, because they've been with us six years and the delay would cost us more than the overtime" will help with a dozen later situations that don't resemble it at all.
Writing the reason down is the same move as replacing policies with the why, applied one decision at a time.
After the third or fourth entry that pointed the same way, we turned the pattern into a limit, in plain words: "You can decide anything like this up to $300 or half a day of rescheduling. Tell me after." I chose that figure by asking what a wrong call would cost, and whether I'd lose sleep if she used the authority every day for a week. At $300 the answer was no. At $2,000 it was probably yes.
I'd rather start slightly lower than I'm comfortable with and raise it than start high and take it back, because retracting authority is far more damaging than granting it slowly.
Each limit gets a review date, usually two months out. When we review, I look at how the authority has been used. If she's used it ten times and I wouldn't have changed any of them, the limit goes up. If she's used it twice with one decision I'd have made differently, we talk about that one, and the limit usually stays.
If several kinds of question compete for the first limit, start with the ones that hold up a quote, a booking or an invoice, since those cost money every day they wait.
Who should write the ruling log?
My first version of the log failed. I'd asked her to write the entries, since she was the one who'd learn from them. By the third week she had stopped. Writing up a ruling is a small tax, and she was under pressure with real customers. The log went stale, and we were back to texting.
What fixed it was moving the effort onto me. We now spend fifteen minutes on Friday going through the week's questions, and I write the entries while we talk. It takes me less time than the scattered texting did. It also surfaced something I hadn't expected: in a few cases, while explaining the reason aloud, I realized I didn't have one, and that I had been deciding the same way out of habit. Those rulings changed.
Not everything moved. Staffing questions, pricing changes beyond a certain size, and anything involving a customer dispute that might become a legal matter still come to me, and I think that's right. She still brings me a handful of problems each week. I'd say the volume is noticeably lower, but I never counted properly before we started, so I can't give you a number I trust.
For a fuller list of what to hand over and what to keep, see when to delegate work to your team.
How do you start a ruling log this week?
You can start without any of this infrastructure. The next time your best person brings you a problem, answer it, then add one sentence about why, and write it down somewhere shared, with the date. Don't ask them to maintain it. When the same kind of problem arrives a second time, ask them what the earlier ruling would suggest. By the third, offer the limit.
The measure I'd watch is how often they arrive with the answer already worked out against what you've said before. That is the point where the log has become their judgment as well as yours, and it tells you more than the raw count of problems does. And if what keeps reaching you turns out to be a decision only you can make, that's worth knowing too.
Frequently asked questions
Should I ask my team to bring solutions along with their problems?
Ask for their read on the tradeoff instead: which two goods are in tension and which way they lean. You still get a recommendation, but you stay out of the approver seat, and once the reason goes into the log, their lean becomes something they can act on the next time without asking.
What if two entries in the log seem to contradict each other?
Read them side by side and find what split them. Usually the situations differed in a way the written reasons didn't capture, so add a sentence naming that difference. If they didn't differ, one ruling was a mistake or a habit, and the newer entry should say plainly which one now stands.
Does a ruling log work with more than one employee?
Yes, and it pays off faster, because one ruling answers the same question for everyone who would have asked it. Keep one log per area, such as scheduling or pricing, rather than one per person, and let each lead read the others. Limits can still differ by person, written beside each name.
Which decisions on your team still need you?
If you'd like help building this kind of decision structure around your own team, that's the work we do at Systems to Scale Group.
