Start by changing the expectation
If employees are used to bringing problems and receiving answers, they will keep doing it. So make the new expectation clear. When you bring an issue, come with: what happened; what you know; what you think; what options exist; what you recommend. That builds thinking into the conversation.
Do not demand a polished answer every time
The person may genuinely be uncertain. That is okay. You are looking for evidence of engagement. Have they thought? Have they gathered information? Have they considered options? That matters.
Ask for their view first
When someone says:
“We’ve got a problem.”
Do not immediately solve it. Ask:
“What do you think is going on?”
That changes the conversation.
Then ask for evidence
“What do we actually know?”
This prevents the discussion becoming pure opinion.
Ask what they have already tried
This tells you whether they have engaged with the issue. Sometimes they have. Sometimes they have simply brought the first sign of difficulty upward. Useful distinction.
Ask for options
“What are the possible ways forward?”
Now they are moving from problem description into problem-solving.
Ask for a recommendation
Then:
“What do you recommend?”
This is the key step. You are not asking them to guarantee the future. You are asking them to exercise judgement.
Require a reason
“Why do you recommend that?”
Now you hear the thinking. That is more useful than merely hearing the answer.
Build a simple escalation structure
A strong escalation can be:
The issue
What is happening?
The evidence
What do we know?
The impact
Why does it matter?
The options
What could we do?
The recommendation
What do you think we should do?
The help required
What specifically do you need from me? That is a very different conversation from:
“We’ve got a problem.”
Do not make people perform unnecessary analysis
Not every small issue needs a formal business case. Keep it proportionate. A two-minute problem may need a two-minute thought process. The principle matters more than the paperwork.
Ask them to write it down for more complex issues
Writing often improves thinking. For a significant problem, ask for: three bullets; one page; or a short pre-meeting note. Not a thesis. Enough to make the reasoning visible.
Use recommendation-first language
You can say:
“Tell me what you recommend first, then give me the background.”
This forces the person to form a view before getting lost in detail.
Beware the information dump
Some employees bring enormous amounts of detail. But no conclusion. Ask:
“So what do you think we should do?”
Bring the conversation back to judgement.
Do not reward helplessness
If someone repeatedly says: “I don’t know, you tell me,” and you always tell them, that behaviour is efficient for them. Change the pattern. But distinguish genuine inexperience A new employee may genuinely not know. That is normal. Give more context. Teach the reasoning. Then expect more thinking next time.
Development should change the quality of escalation
Earlier:
“What do I do?”
Later:
“I see three options. I recommend option two because…”
That is growth.
Explain how you think
When useful, show the person what you consider. Customer impact. Cost. Risk. Timing. Precedent. That transfers judgement.
Do not keep the logic hidden
If people only hear your final answer, they do not learn much. If they hear your reasoning, they can use it later.
Ask what they are assuming
This is a good thinking question.
“What are you assuming here?”
It often exposes weak reasoning.
Separate fact from interpretation
For example: Fact: customer cancelled order. Interpretation: customer is leaving forever. Not the same. Teach that distinction.
Ask what could make the recommendation wrong
This sharpens judgement.
“What risk sits inside your recommendation?”
Good leaders need to consider downside too.
Ask what happens if nothing is done
This is useful. Sometimes urgency is unclear.
“What is the consequence of waiting?”
That helps prioritise.
Ask whether the issue is theirs to solve
This matters. Some employees escalate because they are not sure whether they have authority. Clarify ownership.
If it is their decision, say so
“This is within your authority. What are you going to do?”
That builds confidence.
If it is genuinely not their decision, still ask for thinking
They may not own the final call. But they can still recommend. That develops business judgement.
Managers should not become vending machines
Employee inserts problem. Manager dispenses answer. That is not scalable. The manager's role is increasingly to improve the quality of thinking below them.
Do not answer too fast
This is hard. You know the answer. The employee is struggling. Silence. Wait.
Use “Humour me”
If they say:
“I’ve got no idea.”
Try:
“Humour me. If you had to make the decision, what would you do?”
Very often they have more judgement than they think.
Make thinking safe
People will not bring recommendations if they believe every imperfect idea will be ridiculed. Challenge the thinking. Do not humiliate the thinker. Say:
“I don’t agree with your recommendation, but I’m glad you brought one.”
That reinforces the behaviour while still coaching judgement.
Do not punish someone for thinking differently
Different recommendation does not automatically mean poor judgement. Explore why.
Look at their reasoning
Maybe their recommendation is actually better. That should be possible.
Be willing to change your mind
If people know recommendations are genuinely considered, they will put more effort into them. If they know the manager has already decided, recommendation culture becomes theatre.
Do not ask for input you will never use
That destroys credibility.
Explain when the final decision differs
“I’m choosing option three because of a risk you didn’t have visibility of.”
Now they learn.
Teach the commercial context
Employees bring better solutions when they understand the business. Cost. Margin. Customer. Capacity. Timing. Give them enough context. Do not complain about poor judgement while withholding all information That is unfair. Judgement needs context.
Give people access to useful evidence
Dashboards. Customer data. Process information. Whatever they reasonably need.
Define What Success Looks Like
Problem-solving improves when people know the standard. What are we trying to protect? Speed? Quality? Margin? Customer experience? Without clarity, recommendations are weaker.
Teach people to think in trade-offs
Most real business problems do not have perfect answers. Option A may be faster. Option B cheaper. Option C lower risk. Good judgement involves trade-offs. Ask:
“What are we giving up if we choose this?”
That deepens thinking.
Ask who else is affected
This develops business-first thinking. Sales decision. Operations consequence. Customer consequence. Finance consequence. The person learns to think beyond their own function. Ask whether the recommendation solves the problem or merely the symptom Important. If the same issue keeps recurring, ask:
“What would stop this happening again?”
That moves people towards systems thinking.
Do not create endless analysis
At some point, decide. Thinking should improve action. Not replace it.
Use timeboxes
“Take 15 minutes, come back with your recommendation.”
Useful for ordinary issues.
For bigger problems, give more time
Proportionate.
Build recommendation quality into one-on-ones
Ask managers: What decisions did your team bring you? What did they recommend? Where is judgement improving? That makes development visible.
Make it part of What Success Looks Like
For managers especially: raises problems early; brings evidence; offers options; makes recommendations; uses authority sensibly. Now it is part of the role.
Recognise good thinking
Even when the result later proves imperfect.
“You thought that through well.”
That reinforces judgement.
Recognise early escalation too
Do not accidentally create a culture where people wait too long because they are still trying to produce a perfect answer. Say:
“You were right to raise this early.”
Then work on the solution.
Early warning and solution thinking belong together
That is the balance. Raise early. Think actively.
Do not let “bring solutions” become permission to hide
This is the biggest danger. Someone sees a serious risk. Does not yet know the answer. Waits. Bad. Make it explicit:
“If the risk is material, raise it now. We can think together.”
Define immediate-escalation categories
For example: safety; legal; ethical; major financial; serious customer; reputational risk. No waiting for a polished recommendation.
For normal operational issues, expect more thinking
That is where the habit can build safely.
Ask whether the person is throwing the problem ball
They bring issue. Manager absorbs it. Watch what happens. The person should usually leave carrying the next action. End with:
“So what are you going to do?”
That returns ownership.
Do not let the meeting end with the manager owning everything
Classic failure mode. Employee brings problem. Manager leaves with three actions. No.
Support without taking over
Perhaps you need to: approve; connect; give context; remove a blocker. Fine. But keep the main ownership where it belongs.
Ask what help is actually needed
“What do you need from me?”
Very useful. It stops vague upward transfer.
They may need a decision, not rescue
Good. Make the decision if it is yours. Then return execution.
Build a team norm
You could make the expectation:
“Problems are welcome. Problems with no thinking should become less common as your experience grows.”
That is fair.
New people get more support
Experienced people get more expectation. That is reasonable.
Track the progression
Do people bring: more evidence; better options; stronger recommendations? If yes, culture is changing.
Watch whether managers themselves model the behaviour upward
If a manager complains that employees bring problems, but the manager brings raw problems to the CEO, there is a contradiction. The standard must cascade.
CEO to leader
“What do you recommend?”
Leader to manager. Manager to employee. Same principle.
This creates a thinking organisation
That is the real opportunity. Not simply fewer interruptions. More distributed judgement.
Managers become coaches rather than answer machines
That creates capacity.
People become more confident because confidence follows practice
Not because someone told them to “be more confident.” They make decisions. See results. Learn. That builds real confidence.
A practical problem-to-recommendation sequence
When someone raises something, ask: What happened? Clarity. What do you know? Evidence. What have you tried? Effort. What are the options? Thinking. What do you recommend? Judgement. Why? Reasoning. What do you need from me? Support. What are you going to do next? Ownership. That is a powerful management sequence.
A practical team expectation
You might say:
“I want you to raise problems early. Do not sit on something important because you haven’t solved it yet. But where you reasonably can, I also want you to bring me your thinking — what you know, what options you see and what you recommend.”
That is the balance.
One final question
When someone brings you a problem, ask yourself:
“Do they need my answer — or do they need my help to develop a better answer of their own?”
Sometimes they need your answer. Absolutely. But if that is always the answer, you become the thinking bottleneck. The goal is not a business where nobody brings problems. Problems contain useful information. The goal is a business where people bring them:
early; honestly; with evidence; with thought; and increasingly with a recommendation. That is how problem-solving capability spreads beyond the manager. And that is how a team starts bringing you more than problems. It starts bringing you judgement.
