The Founder's Paradox: How to Be Agile and Deliver Major New Product Functionality on Time
Shirt sizes. Points budgets. Spikes and a formal PMO. I recently received a thoughtful email from a CTO at a major software company after I spoke at an event on building lovable products in times of crisis. He asked for my thoughts on how best to resolve a constant tension — teams wanting to follow an iterative, agile workflow while the organization needs them to work towards and deliver against firm dates. This experienced executive had tried everything to find that balance between loose iteration and firm delivery. Nothing quite fit. So what is the answer?
It is not simple — because solving complex technical problems and engineering work can be unpredictable. It is hard to know exactly when challenges will be solved and work will be finished.
One line in the email stood out in particular to me. It was the idea that most of his team saw longer-term planning as a "distraction and a mirage" because the future is always unknown. But acting decisively is what product and engineering leaders get paid for. Understanding customers, realizing key insights, and beating others to market with innovative solutions actually matters.
How do you resolve working in a flexible way while getting to market by a set date? It would be easier if time did not matter, but it is an essential variable for success. And delivering value right now is significantly more valuable than bringing it to customers later.
Leaders and companies are rewarded for how quickly they deliver, but meaningful functionality takes precise timing.
Resolving this paradox requires acknowledging that some projects can be flexible and others need to be fixed. There are good reasons for both — but successful businesses are comprised of more than just product and engineering groups and those other groups need to know what is coming when. If you want the organization to move collaboratively and quickly to best serve customers, you often need to deliver by a certain date.
Here are the strategy and roadmap planning steps I recommended the CTO follow to change the mindset and outcomes at his company. You too can follow these steps to successfully become more date-driven:
Step 1: Product management
Map key product initiatives to the high-level business goals so everyone understands the importance and connection. Add loose time frames for when you want to complete major initiatives to meet those goals.
Step 2: Product management and UX
Define the customer needs that support your initiatives as well as the desired timing for solving those needs. Suggest and approximate the solution. (I know the last part is controversial but doing so forces product managers to truly understand the problem, possible solutions, and tradeoffs.)
Step 3: Product management, UX, and engineering
Review what product is suggesting while it is raw and then refine collaboratively. Engineering has the obligation to provide realistic effort estimates as best as they can based on experience. And product must respect what is being explained as a risk and reduce scope (maybe even change the proposed solution) so you can deliver the most value as quickly as possible. Product should also align with cross-functional teams so the entire organization can be ready at launch. This may even include rethinking what functionality can be delivered later on.
Everyone commits to the plan — with the shared understanding that the group will do everything possible to reach the agreed-upon date.
There is also one prerequisite. Product and engineering leaders need to be highly skilled, aligned, committed to the company goals, and completely trusting of one another. If any of those characteristics are not present, the teams will fail and customers will suffer. It is impossible to work against a date with murky strategy at your back, sandbagging, or finger-pointing between groups.
You can set and deliver against firm dates with a group that thrives on achievement, empathizes with users as well as each other, and rejects drama. You will find that each on-time delivery leads to confidence and greater success.
Read more of The Founder's Paradox.