Ask “What if…” Ask it to spur people on to do things they didn’t think was possible. Ask it to help people prepare for contingencies. Ask it to help them improve the way they work.



It happens to all of us and to all of the people working for us. We and they come up against seemingly insurmountable obstacles, lose our forward momentum, stop, and decompose into a pool of self-pitying goop. We worked so hard to get to this point and it’s all for naught.


Unless we can find a way around the obstacles, one obstacle at a time.

Here, “what if…” is about removing constraints or turning them tour advantage.

“We can’t go that way. There’s a boulder on the road.”

“What if we could go around the boulder, over the boulder, under the boulder, through the boulder, move the boulder, leverage the boulder, or find an entirely different route?

“We can’t hire that person. Their salary is too high.”

“What if we compensated them in other ways (like bonus, or equity,) convinced them about the value of the non-monetary rewards, got them fired from their current job?”

“We can’t do that. It’s against the law.”

“What if we got the law changed, changed our approach to be legal, chose to break the law?”

Don’t laugh at the seemingly absurd what ifs. They’re not actually meant to prompt people to do something absurd. They’re meant to prompt different thinking. You’re hoping someone will say, “That’s nuts. But we could….”

Bottom line, ask “What if….?” To help people find ways around the obstacles in their minds.



The opposite happens all too often as well. People charge ahead without thinking about all boulders that could drop in their way.

Here, the “What if…?” question is designed to keep them from getting rattled when things go wrong by preparing in advance.

Preparing in advance is about building general capabilities and capacity – not specific situational knowledge. For the most part, there is a finite set of the most likely, most devastating types of things that are worth preparing for. Think them through. Run the drills. Capture the general lessons so people can apply them flexibly to the specific situations they encounter. Have resources ready to be deployed when those things go wrong.

Threats may be one or more of the following, often in combination:


  • Physical (Top priority. Deal with these first.)
  • Reputational (Second priority. Deal with these after physical but before financial threats.)
  • Financial (Third priority.)



Physical things may be


  • Natural: earthquakes, landslides (with boulders,) volcanic eruptions, floods, cyclones, epidemics etc.
  • Man-made: stampedes, fires, transport accidents, industrial accidents, oil spills, nuclear explosions/radiation, war, deliberate attacks, etc.



Reputational issues may flow from physical things going wrong and how they are handled, or may come from: choices by you or others in your organization, outside interventions, sudden awareness of things already there, etc.


Financial threats come from disruptions in your value chain: supply or product or resources (including cash), manufacturing, selling/demand, distribution, service, etc.

Now, back to three things you should do to prepare. The “What if…?” question helps with all three. Expand the question to:

“What if this happens – what capabilities and capacity do we need to have in place?” Then get people to build them ahead of time.

“What if this happens – what lessons can we apply?” Then get them to apply them.

“What if this happens – what resources do we need to have available?” Then make sure they are available.


Ways of Working

The root cause of most ways of working issues is poor communication – especially around decision rights, hand-offs and touch points. Leaders wait around for their followers to be proactive while their followers are waiting around for their leaders to make and communicate decisions.

Here the “What if…?” question leads to people asking for forgiveness instead of permission.

Ask “What if you started moving on this before you got formal permission from above?”

In many ways, this is the essence of a team’s tactical capacity – high-quality responsiveness under difficult, changing conditions. Teams with strong tactical capacity empower each member, communicate effectively with the team and leader to create critical solutions to the inevitable problems that arise on an ongoing basis, and to implement them quickly. They are constantly asking “What if…?” offensively, defensively and in thinking about they work together.

Click here for a list of my Forbes articles (of which this is #746) and a summary of my book on executive onboarding: The New Leader’s 100-Day Action Plan.

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