Jagged, not Smooth.

Smooth is good. Or so it goes. It's common to tell someone, "I hope it goes smoothly" before an important test, interview, or, in our case, during discussions and reviews. However, there are times when you wish things wouldn't go so smoothly—when the jagged edges of a project cut and hurt. Ironically, that might be the very reason your project ultimately goes smoothly. Why jagged, not smooth? Read on...

Back when I was at Amazon, we would regularly conduct product risk reviews with senior leadership. Preparing the risk review document was a significant task, requiring input from various cross-functional leads. Each of them wanted their respective workstreams to be portrayed positively to our leadership. Once I (the PM) created the initial draft, the "color battles" would begin, lasting until five minutes before the actual review. Thankfully, the leadership team at Amazon was incredibly experienced and with the support of deep data-driven documents were able to focus the conversation on the hard topics and get to the desired outcomes.

What I learned was that the less "risky" the document made the program appear—with lots of greens and the occasional yellow—the more likely it was to slip or encounter major last-minute problems. Conversely, the more jagged the document felt, with plenty of yellows and a healthy dose of reds, the better the actual program outcomes were. The more we smoothed out the edges early on, the more it hurt later.

And jagged is not just about risks and colors. Gaps in strategy, scope creep, lack of shared vision among partner teams and an unclear understanding of the big picture - all of these are meant to stay jagged and rough until leadership acknowledges the challenges and is forced to act on it. Smoothing these sharp edges will most certainly result in “cordial reviews” but not necessarily in “the best outcomes”.

So how can we do better? Here are some ways that I have seen work well.

1. Verbalize and agree on the vision. Without aligning on a shared vision for success, all other discussions are moot. Insist on complete alignment before moving ahead to the actual strategy.

2. Let not opinions get in the way of data. It is often convenient to find excuses to brush off data.

3. Dont avoid the hard conversations. It is sometimes natural to keep going and avoid the painful discussion as long as possible. While forcing the hard discussion will make things uncomfortable in the near term, it will also allow for a honest conversation to happen before it is too late.

4. Dont make it personal. The jagged edges are about the goals and strategy. They are not about you or anyone else in the room. Hard conversations can get gnarly if they don’t stay objective.

5. To that effect, spend the effort on a good doc that clearly articulates the problems, the gaps and opportunities. Well written docs can anchor the conversation on the real issues.

Building ambitious new things is hard. It is on us to make sure we don’t make it harder on ourselves and on everyone else by avoiding the hard discussions. Sharper edges help focus attention and facilitate a concerted effort to meaningfully fix them. Together, as a team.