Leadership - Tackle the Monkey First

JJ Bussert | 09/05/2024

This YouTube short was recently shared with me (thanks Frank!), and it brought up a common issue we often face in projects. Stakeholders often prefer to focus on visible wins-what this clip refers to as "the pedestal"-that show immediate progress but often neglect the riskier, foundational work, the "monkey" that needs taming.

So how can we, as the leadership of our teams, avoid falling into this trap?


The Pedestal Trap

We've all been on projects where the pressure is on for the "quick win," the demo, or that flashy feature that can impress stakeholders. The problem is, while everyone's focused on delivering something that looks great on the surface, the real challenges-what I'll call "the monkeys"-are sitting in the background, getting ignored.

These are things like that key system integration no one has ever done before, and the team isn't even sure is possible, or that compliance requirement that has shut down countless projects because it wasn't considered from the start. Maybe it's a legacy system that needs modernization but is too risky to touch, or a security flaw that everyone knows about but doesn't want to deal with because it's not "urgent" enough-or is not visible enough, so stakeholders want to defer it to the end.

Yup, you know those projects. Sure, we got some quick wins that looked great on the surface, but no one was tackling the real problems-unstable architecture, mounting technical debt, and all the risky stuff lurking under the radar. Fast forward a few months, and everything came crashing down. By then, leadership had moved on to the next shiny thing, leaving the dev team to clean up the mess.


The Balance: Pedestal and Monkey

It's tempting to focus on the flashy stuff-the features that grab attention and make stakeholders feel like the project is moving forward. But you can't afford to ignore the risky, foundational work that keeps everything stable. Yes, building the pedestal has its place. Stakeholders need to see progress, and sometimes that visible momentum is what helps secure buy-in and keep the project on track. But that doesn't mean you can keep pushing off the critical tasks-the "monkeys."

As leads of our dev teams, we have a responsibility to guide and advise stakeholders and management. It's up to us to help them see the importance of addressing those foundational risks early on. A successful project strikes a balance between the two: delivering visible progress to maintain confidence, while actively working on the behind-the-scenes tasks that ensure long-term success. It's not about choosing one over the other, but about making sure both are addressed at the right time. Focusing too much on the pedestal will make everything come crashing down when the core issues surface.


Avoiding the Pitfall

So how do you avoid this trap? Don't just chase the visible wins. Yes, sometimes you need to build the pedestal to show stakeholders things are moving forward-but be transparent about the monkeys. Stakeholders would much rather hear upfront about the challenges you're tackling than be blindsided later by a crisis.

I'm not going to say it'll be easy. Depending on how experienced your stakeholders are and how much pressure they're under to produce results, these conversations might be incredibly painful. But as dev leaders, it's our responsibility to be upfront and guide them through these decisions. By tackling the risky, critical work early and keeping stakeholders informed, you're setting the project up for long-term success, even if it requires tough conversations along the way.

Ask yourself in your next planning session:

  • What risky tasks are we avoiding?
  • Are we chasing short-term wins that will hurt us long-term?
  • How can we balance showing progress with solving core issues the team clearly sees?

Focus on taming the monkey before the pedestal is complete, and make sure your stakeholders are along for the ride, knowing what to expect. You'll be glad you did when the project is a success, and you have a well trained Monkey sitting on top of that beautiful Pedestal.


Have you seen this pattern before in your projects? How have you balanced quick wins with addressing risky challenges? What other obstacles have you encountered along the way? Comment below and share your experiences-I'd love to hear your insights!