When the quick wins run out

How to spot urgent requests masquerading as quick wins and what to do about them

"We have to do it. We need to get this done so we can close the next deal. It will be a quick win", the CEO declares as you toss another unfinished urgent request into the flaming dumpster of quick wins floating down the flooded street.

Sound familiar? The truth hurts — you're stuck in a vicious cycle of delivering on quick wins. Everyone involved, from those requesting them to those ferociously executing on them knows, these quick wins never materialize. They're not quick. They're also not wins. And they don't stop coming. If you were winning, you wouldn't have to be dropping everything to work on every request that came across the desk.

With everyone in this pressure cooker environment it can be downright impossible to see a way out of it. One day, you think to yourself, we'll switch from being tactical and get more strategic — but you know without a real concerted effort, strategy won't magically come knocking on your door with a basket of muffins and market opportunities.

While I'm trying to take a lighter tone on the situation, this feeling is actually terrible, doing whatever you can to just get to the end of the week.

So what do you do?

Spotting the urgent requests we call quick wins

The first thing to do is to start identifying those dangerous “quick wins”. Because they come in all shapes and sizes. These are just a few examples you might encounter:

Low-hanging fruit

Low hanging fruit opportunities use to exist, perhaps in the early days of your product, but you’ve known for a long time there aren't any left. Nowadays, any seemingly small change requires diving into tech-debt riddled systems. Once you start digging, you reveal massive problems that would need to be addressed before getting to the actual improvement.

The only fruit you'd be reaching for now has long spoiled under the tree and not even the squirrels will touch it.

The feature we need to close the next deal

This is one of the most common and most difficult to fend off as it comes masked as the needs of the customer and has the potential to generate revenue for the company. But you're still in the middle of working on the last urgent request for the last deal... what happens to that?

The sad irony is that teams in your organization start to dread the signing of new customers, because they know another wave of delivering on short term expectations is coming.

These requests break down any hope of a partnership between sales and tech teams. "Sales just wants their commission and doesn't care" gets lobbed from one side, and "the developers aren't working fast enough" from the other.

(Don't even get me started on how the compensation in most organizations works around these sales. Someone got their commission cheque and a bit closer to their quota, others got a massive pile of work that they know they can't deliver on.)

Customer support fire-of-the-day

Drop everything! A super important customer needs us to fix this bug immediately!

Your customers notice when you ship unfinished work. The newly onboarded customer that was demanding a feature to close their deal isn't exactly thrilled to see it was poorly implemented.

Existing customers who rely on your product start to notice cracks in the foundation as more weight is added in the form of one-off additions that were rushed through.

You'll start hearing about these through your support channels, adding additional pressures to your already over-burdened teams.

Common traits

You can see how these are all interconnected, how one leads to the other, and how they can create a vicious cycle.

These requests tend to have definitive due dates but little appreciation for the amount of work needed to get them started or to maintain them. It's no wonder they exhaust teams and lead to low morale.

Prioritization goes out the window too. The statement "we have to get this all done" begins and ends the entire conversation about priority. You don’t even hear people push back anymore because there’s no point, and there’s no win.

If there's something people hate doing, it's setting themselves up for failure which is the constant state you might find yourself in. Is there anything that can be done to turn the tide?

Getting out of the rut of delivering quick wins

Spotting the various forms of these urgent requests is just the beginning. Let's be real. There is no magic trick that can erase these problems overnight.

There's a good chance your entire organization has formed it's procedures and processes around delivering quick wins, rather than lasting long-term value. It's a self-defence and survival mechanism that has organically replaced intentional and deliberate strategy.

For those looking for ways to make a dent in the way things are done, there are some approaches you can start try to help get you to a better place — one that is more strategic, forward-thinking, and helps your business and customers succeed.

With any change, you’ll need to build up the momentum and the support of like-minded individuals from the C-suite and on. It also requires more than what I discuss here, but these are some small tangible ways to get things going in the right direction.

Visually track and discuss the requests

Time and again I've seen conversations about new urgent requests take place without the use of a visualization of all the work already piled up in the queue.

I’m not talking about masterfully created roadmaps, or a backlog filled with minutiae. Write these urgent requests down in a simple list so you can show the organization what you’re expected to deliver on, those in progress, and those at risk of never being completed. Use anything: sticky notes, whiteboard, Trello, a Google Doc.

When people see a growing list, it’s hard to ignore. Without the visualization, on the other hand, we resort to a war of words — he said/she said/they said.

It’s easy to throw more work on an invisible list. Make the list visible.

Start thinking in years

The hard reality is that there are so many small requests that need to be delivered "this quarter" that they quickly approach a time scale of needing years to finish.

When you’re adding another quick win to the pile, but the pile is now spanning multiple quarters and years, the conversation has to shift to determining the priority. Do it all is not a strategy.

As you dive deeper you can start to shift the conversation around common themes or objectives to help focus your the organization’s efforts. It’s hard to do that when everything is a fire for the current quarter. Taking a long view provides the space to have these conversations.

Regroup around who you're here for and why they need you

Reacting to urgent requests is often a symptom of losing sight of why you are here as an organization — the customer you are trying to create value for. While you can get caught up in convincing yourself that each customer request is doing what the customer needs, you are likely spreading yourself so thin that you're no longer holding true to your core value proposition.

Discussing and creating a shared understanding of what the customer needs is something that can easily go by the wayside as day-to-day routines take hold. Re-introduce these critical conversations to ground your organization around what matters most.

Get developers on sales calls so they can hear from customers first hand. Shadow your customer support reps to hear what they’re hearing. Run workshops that help communicate what drives your customers and their common pain points. Get people thinking about your customer.


If you're using the same techniques and are having the same conversations as you did last year when you were in the same grind, then change has to happen now. You can't get yourself out of the barrage of quick wins without doing something different.

Otherwise, retaining customers and employees will become your next big problem.

I'm convinced with the right direction and the right conversations, the cycle can end for the better.

🏁


The Pit Wall Debrief

If this sounds familiar because you’re currently in the middle of it, or had a previous experience, I'd love to chat about what you've tried to get yourself out of the grind. What worked and what didn’t?

If this hasn't happened to you — amazing! Take this as a cautionary tale from the ghost of quarters future. Take opportunities today to make customer needs central to everything you do. If you have a good thing going with this, I’d love to learn more about how you do it!

Let's chat!


Carlos Perez is an Innovation Strategist and Coach at Purple Sector Strategy. He helps product teams get aligned around a shared vision through facilitated workshops and coaching.