Creating great strategy feels bad.

Being strategic isn’t about being nice.

A friend of mine asked me for one lesson I wish I’d learned earlier in my career helping Boards, investors, and management teams build winning strategies. There are many, but that one stood out from our conversation – in part because it mirrored so much of what he taught me from his experience helping some of the world’s best sales leaders:

Sure, sometimes it can be nice, but in my experience, if no one got uncomfortable, then the team probably wasn’t being very strategic.

This can be an especially tricky position for any external third party in charge of helping a group develop a single, optimal, unified strategy. This external third party can have an endless amount of titles and be as experienced as a multi-decade strategy consultant working at break-neck speed in industry or as inexperienced as the guy down the hall who says he says he is “amazing at strategy” (bless his heart).

There is considerable pressure for the third party to accept a narrative that emphasizes likability.  The third party wants to be asked to do this work again. To be asked to do this work again, it stands to reason that the team must want to see you again, which means they must like you, which means they need to feel good during their time with you. Whether you are a strategy consultant doing this for money, the guy down the hall doing it for glory, or the team member unknowingly sacrificed by the team to play facilitator, the pressure feels real.

But it isn’t. Great strategy rarely feels good in the birthing of it. Instead, it forces teams and individuals to examine the truths, possibilities, and implications that they most fear. If you’re playing the role of third party, you likely know you are helping the team most in those moments it feels the worst. The team needs your help doing the hard things.

People don’t naturally want to explore a world of uncertainty that implies the future is potentially uncertain and unsafe. We are hard-wired to seek out comfort, not chasms of ambiguity and potential disaster. When someone is excited about the potential of a new product they don’t naturally love hearing someone ask, I hear a lot of compelling reasons why the market may buy this product from us, but can someone tell me the reasons the market wouldn’t? But you, third party, must lead them into the void, because we don’t know the wisdom that waits there until we seek it.

People don’t naturally love realizing that they had, at least in part or collectively, bad ideas. It feels bad, and we are hard-wired to want to feel good. But if a strategy isn’t at least internally consistent, it stands no realistic chance of being successful. No one wants to hear that’s a great point about how customers are increasingly seeking cheaper options to solve basic problems, can you help me reconcile that with the current proposal to add a bunch of cool new features that will significantly drive up our prices? But you, third party, must hold up the mirror, because no one wants to walk out of a strategy session and into the marketplace with food in their teeth.

People don’t naturally want to give up whatever they think is theirs (either already theirs or should be theirs). We are hard-wired to look out for ourselves and our tribes. We want our budgets increased, our status elevated, our careers fast tracked, our people taken care of. No one wants to hear that sounds like a very important initiative for the company, looking at the work that will need to be done, it seems like most of it is really about people change across the org. Should this work roll up to ops or HR? But you, third party, must help the team create a strategy that creates the most value for the team, not some subset of individuals.

Perhaps most of all, most people simply don’t want to disagree publicly. It’s unpleasant. People don’t want to have to voice their disagreements with each other to each other in front of others over and over. Most people dislike telling someone they are wrong almost as much as they dislike hearing that someone thinks they are wrong. But the whole point of a strategic planning conversation is the acknowledgement that the collective, with great facilitation, can come up with and align around a significantly better strategy than if it were all owned by any one individual. When someone with wisdom is hesitant to share it, you, third party, must help them find their voice.

All of the above makes obvious sense, when you think about the goal of great business strategy, which is typically some version of, to create the most possible value, not to make people feel great. And you know what, former self? Once you do that, people may be a little sore in or after the meeting, but once the strategy starts working, everyone will claim it was their idea, feel great about it, and want to work with you again.

I talk about what I’ve learned from two decades studying and practicing strategy at the intersection of Boards, investors, and management teams of high growth businesses. Any identifying details of companies I’ve worked with have been changed to protect their identities, but the experiences and insights (when that’s what they are) are true. I’m always looking to hear and learn from others, so please ping me directly or leave a comment to keep the conversation going.