What to Do Before Saying “This Isn’t Working”
By Sophie Makonnen
Feeling stuck at work doesn’t always mean you’re lost—it might just mean you need a better map or a different one. Before you escalate a problem or stay silent too long, here are six questions that can help you move forward with clarity and credibility.
What have I already tried?
This question isn’t just about being active instead of passive. Take the time to list what you’ve actually done, not just in your head, but clearly and in writing.
What actions have you taken?
Who have you spoken to?
What steps did you attempt, and what was the result?
What alternatives did you consider but not pursue and why?
This isn’t just for your own clarity. It prepares you to speak confidently if you need to brief others. You’re showing that you’ve taken initiative, even if the problem is unresolved. You’re not passing along confusion; you’re passing along a situation that has been worked on and now requires a new level of input.
If the honest answer is, “I haven’t done anything yet,” name that. Avoiding reality doesn’t help you prepare. Acknowledging it lets you ask: Why not? Are you unsure? Avoiding conflict? Waiting for permission?
This question isn’t about solving the problem—it’s about owning what you’ve already done
What exactly is getting in the way?
Sometimes, the hardest part of being stuck is not knowing why. This step is about slowing down and pinpointing what’s blocking progress.
Start by scanning for both internal and external factors:
Is it missing information?
Is there unclear ownership, you’re not sure who’s responsible for what?
Are you waiting for input or approval from someone else?
Are you hesitating, maybe because the environment makes it hard to act without getting permission first? Are there unspoken rules ? Do you need that permission ?
It’s about identifying whether you’re facing something solvable or structural. Once you know that, you can engage more strategically and decide whether the next step is a conversation, a workaround, or a shift in expectations
Try and identify immediate next steps that could get things moving:
“To move this forward, I would need input from [X team]”
“This step typically requires [Y]’s signoff.”
“In this context, I don’t have the authority to proceed alone.”
“This isn’t something I’ve seen handled at my level in the past, so I’ve paused.”
Who else might be able to help?
Support doesn’t have to come from your manager. In fact, some of the most effective problem-solving happens when you build laterally—not just upward.
Before you escalate, ask yourself:
Have I consulted a colleague who might have dealt with something similar?
Have I reached out to the team or department that’s part of the solution?
Have I looked for a precedent, template, or past case that might guide the next step?
This isn’t about doing someone else’s job, it’s about widening the lens. Sometimes people become accustomed to working in silos. Its about connecting the dots, even if those dots lie outside your immediate scope. Reaching across to another team or peer shows initiative. It signals you know how to engage the system, not just wait for decisions. Lateral problem-solving like this often reflects the kind of initiative that builds trust and leadership credibility.
If you try reaching out and run into a dead end, that’s still useful to share with your manager in due time. It shows you kept trying and helps them understand what hasn’t worked. It also proves you’ve done your homework and aren’t just passing the problem along. You can say: Here’s what I’ve checked, here’s who I’ve asked, and here’s where I got stuck.
In some organizations, reaching laterally can be sensitive. If that’s the case, evaluate the context carefully and be transparent about your approach so it’s clear you’re building support, not bypassing hierarchy.
What would I recommend if I were my boss?
This is a shift in perspective. It means stepping out of your usual role and looking at the problem from the wider system—30,000 feet up.
Ask yourself:
If I were responsible for making the final call, what would I do?
What trade-offs would I need to weigh?
What implications might this have across teams, timelines, or priorities?
What resources would be available at that level that I may not be able to see from my current perspective?
This approach offers two key benefits. First, it strengthens your strategic thinking by encouraging you to consider the broader impact of decisions and to think like a leader.
Second, it prepares you to engage leadership more effectively. Rather than simply presenting a problem, you can offer well-considered solutions and actively contribute to decision-making.
Adopting a new perspective does not require having all the answers. Focus on understanding the broader context and share your ideas thoughtfully.
What’s the minimum I can do to stabilize the situation (so it doesn’t get worse)?
Sometimes, what you try doesn’t work. The issue may be crosscutting, bigger than your role, or dependent on actors who aren’t responding. Still, a small action can often keep things from escalating.
Ask yourself:
Is there a short-term action I can take to contain risk or limit confusion?
Can I put in a temporary measure, clarify something, or document an issue ?
Is there a way to preserve trust or keep communication open that is reasonable—even if resolution isn’t possible yet?
They buy time, reduce harm, and can invite others to engage when they see a thoughtful first step.
Do I need to act—or just inform? (Are there red flags I shouldn’t ignore?)
Not every situation needs escalation. But not every situation should stay quiet, either. What matters most is your judgment.
Ask yourself:
Is this something I can manage, or is it something that could become a reputational, operational, or relational risk if left unaddressed?
Am I flagging this because I see early warning signs—not because I want someone else to take over, but because leadership should be aware of them?
Am I pausing because I don’t want to surprise my manager later? And is that a good instinct to follow here?
In these situations, you are not asking your manager to step in. Instead, you are communicating early and clearly. For example, you might say:
“I’m managing this for now, but I want you to be aware that [X] could evolve quickly or touch on areas that need higher-level alignment.”
Or:
“This seems manageable today, but there are signals it could shift beyond my role—just flagging now so we can track it together if needed.”
This builds trust. You’re showing that you’re not hiding problems, but you’re also not handing them off when you don’t need to. You’re keeping others in the loop, instead of making it their problem. It shows you are part of the solution. You may not solve everything, but you are a steady and reliable contributor.
These six questions aren’t about doing it all yourself. They’re about staying engaged to understand the shape of the problem by breaking it down and being prepared, whether you solve it solo or bring others in.
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