I often come across two different schools of thought as it relates to managing high performance organizations: those who prioritize honesty and those who prioritize optimism.
Consider the simple example of a schedule. The honest group favors a schedule that represents our most widely agreed upon expectations. The optimistic group favors an aggressive, if unlikely, schedule that everyone is working towards.
Consider the example of technical hurdles. The honest group indulges open discussions of risks, delays, and challenges. The optimistic group tells teams to do what they need to do to solve problems and deliver on the vision.
Both have issues.
The honest approach can become self fulfilling. Work that might have been done faster almost never is, so it takes upside out of the equation. Setbacks don’t just stall progress for the groups immediately affected but can destabilize other groups. In an industry where shipping is a feature and timing is everything this is a real risk.
The optimistic approach can burn trust between teams and their leadership and also burn people out. It usually entails maintaining a secret schedule of expectations separate from the one shared with teams. It can make leadership look out of touch at best or exploitative at worst.
Of course this is a false dichotomy. We have to do both.
It takes a lot of optimism to ship a product! If we are too “honest” we end up endlessly slipping, compromising instead of solving the hard problems, and constantly reframing the product vision. Sometimes you just have to commit and impress yourself. It also takes a lot of honesty to maintain a team. If we are too optimistic we end up on a death march to nowhere, losing the confidence of the team as we blindly forge ahead in the face of mounting evidence against us.
For a long time at Oculus we were legitimately spinning our wheels trying to advance VR beyond Rift. The hard problems seemed too hard so we would punt on them and land on more conventional approaches. As a team we put a stop to that by really holding ourselves to challenging goals. It worked and we started shipping breakthroughs again. But then we got to a point where when projects really were too challenging people wouldn’t speak up. That makes planning hard and is tough on the team. The key is to find a balance.
If I’m being honest (heh), while I strive for balance between these approaches I lean a little towards the honest approach. I value my credibility as a leader and never want my team to feel like I am keeping things from them. When I joined Microsoft in 2004 as a new college grad I was shocked to find my other new college grad friends already knew Vista was never going to ship as designed. It took a full two years after that for the executive leadership at the company to course correct. This contributed meaningfully to me leaving the company and I never want my teams to feel that way about their work with me.
One practical solution is to instead maintain a probability distribution for the program. It can factor in all the risks identified by honest assessment and still include the potential upside if those risks are navigated successfully. Leadership can pick a percentile to target, allowing everyone to move towards it together confident it isn’t a blind march.