You’re the CEO of a rapidly growing tech company. You’ve come up with a genius idea and have an internal team of engineers or contractors tasked with bringing it to life.
Everything seems to be going well at first.
But then…
The team starts missing key milestones.
Key features aren’t functioning as expected.
The project seems like it’s gone off track.
As a leader that isn’t in the weeds everyday, how do you discern whether these are ordinary bumps in the road, or an indication of something bigger?
How do you hold your team accountable and ensure that they’re executing at the level you expect?
That’s what this article will help you do.
In my experience mentoring large technical teams, leaving engineers to figure out how to implement features of a product without giving them a clear roadmap rarely works.
Engineering teams need guidance, but they also need to be held accountable for results. It’s the only way to ensure progress is being made.
But on the executive side, visibility into the project is just as important. Whether I’m working with founders at startups or when I was managing projects at large enterprises, I see a recurring theme of leaders not knowing what’s happening on the ground.
They hear about delays, new requirements, and unexpected requests — all of which impact the quality, schedule, and budget of the project.
Sometimes the problems are attributed to talent/skills issues. Sometimes it’s a time management issue. Sometimes it’s because of unforeseen changes in the market.
Since they have no way to discern the root cause of the issue, they have no choice but to accept the requests at face value.
Having a roadmap that tracks progress adds transparency to the process. If a feature was supposed to be delivered but keeps getting kicked down the road, it reveals problems that can be investigated
No matter how (in)experienced your team is, every project needs three key elements to keep it on track:
1). Project Roadmap: Your roadmap is your engine and maps to your project milestones. It helps you align how difficult you think your tasks are to how well your team is performing. The roadmap is the macro view that tells you what milestones you should be hitting, and when you should be hitting them.
Your roadmap focuses the team on getting results sooner than later — even if it’s ugly and doesn’t work. The goal is to err toward the side of action and deliver something that people can touch.
It’s the blueprint of what you’re building, which gives your team a vision and provides transparency if things don’t go according to plan.
Lastly, your roadmap serves as a de facto agreement between the business side of the house and your engineering team, allowing each other to set expectations and ask the right questions around delays and errors.
2). Established Sprint Cycles: A sprint cycle is the heartbeat of your project. It’s your delivery process, calibrated to a predictable, rhythmic cadence. Items enter the sprint cycle in a “to be done” state, are worked on, and come out the other end as complete. If your roadmap is your engine, your sprints are your micro gears, making sure that the engine of your project is running like a well-oiled machine.
The roadmap guides your sprints from a macro perspective. The sprints/delivery cycles are the smaller gears that break down the big tasks into smaller tasks that your team is responsible for delivering at the end of that cycle.
Typical sprint cycles are two to three weeks long, which is just enough time for your team to make progress, and short enough for you to spot problems before they take the project too far off course.
The most important thing is to create a delivery cadence. That way you know that you won’t go more than three weeks without making progress. It keeps the everyone accountable to producing results within a specific timeframe.
3). Structured Feedback: Even the best managed projects sometimes miss the mark. The key is to be able to understand what happened and how to prevent it in the future.
From a leadership perspective, it’s your job to ask the technical folks to explain what’s happening. Since you’ve created a roadmap and defined sprint cycles, you will be checking in with your team regularly. You want to make sure that you understand what’s happening with the project.
Your engineering lead should be able to explain delays or issues in layman’s terms.
One of the most sophisticated tactics we’ve seen to align expectations between the product and engineering teams is to collaboratively agree to expectations and timeframes. That way deadlines aren’t a “top down” imperative, rather they were mutually agreed upon in an environment of trust and cooperation.
Coming to agreements creates commitments that were borne out of introspection. That way, even if a deadline is missed, or a task doesn’t turn out as expected, the team can learn from it and move on.
This nips blaming, negativity, and scapegoating at the bud and creates a culture based on accountability, rapid learning, and improvement — all in service of the end goal.
Structured feedback loops aren’t designed to hold anyone’s feet to the fire, rather, they’re a way to check in on the health of the project and correct course as necessary.
Product and engineering need to have clear agreements between each other to develop a successful product. Trust and accountability on both sides is important. This is a guide to help bridge those gaps and ensure that everyone is in alignment.
If you do it right, you’ll build an accountable, collaborative culture with a team that’s committed to delivering the best outcome.
