Leaders teach others to think past hope

If your team is showing up to meetings with plans that have them working off the best (or worst) case scenario, they’re not thinking effectively enough. Our job as leaders is to teach others to think past hope. One outcome just isn’t enough – even if it’s really conservative. We need people considering a variety of outcomes.

Hope is not a strategy.

I used to work at a company where the CEO had to approve the hiring of every employee. Initially I worried that I would bring him a candidate that didn’t impress him. Soon enough I realized that his approval process was more about the conversation we were going to have than about the conversation he had with the candidate.

After a bit of back and forth about how I saw the role structured and when the candidate might start, the conversation always moved to the same spot – three questions that used to stress me out to no end.

  1. How will you know if they’re a good fit or not working out?
  2. How long will it take to know if they’re working out?
  3. What will you do if they’re not working out?

What he was saying was that I needed to move beyond the hope that the candidate would be a perfect fit – no matter how much I wanted that to be the case.

think past hopeConservative estimates are just as bad as wild ones.

I helped run another company where we were responsible for creating the timelines for every major software release of our flagship product. These were the big dates that would be announced to the tons of large companies that were our clients.

So I would gather all the right folks into a boardroom and get estimates from each. They would focus on what we were trying to do, what we had left to do, and what kinds of efforts would be involved, in terms of time, to get our product out the door.

Invariably, one person at the table would tell me that we’d be done in the next week or two. He knew that everyone else would take longer. He just wanted to claim that he wasn’t holding anyone up. We both knew that he wouldn’t be done in a pair of weeks.

Others would tell me they needed a couple of quarters – which was way too long. More importantly, their estimates were wrong too. Just because they were super conservative didn’t help any.

What I wanted was accuracy. Not hope. Not ridiculousness.

Single outcome predictions

Whether you’re working to hire someone, working on a budget, or working on effort estimates, the reality is that most of our teams are filled with people who are making predictions on a single outcome trajectory.

Some people on your team are always hoping for the best. Their single outcome expectation is that everything goes great.

Other folks on your team never see the sun. Everything will always go wrong. And they feel helpful by preparing for that single outcome.

It doesn’t matter what side they’re on. They can’t get themselves to consider multiple outcomes.

Ever heard of multivariate analysis? Sound like it’s too tough to consider? I feel your pain. And because even the phrase sounds frightening, we don’t teach our staff or teams to think in this way.

Four questions to help your teams think in multiple directions

The four questions I’m going to show you here are not rocket science. They’re all “what if” questions. But I find that they’re helpful in causing people to think in more than just one direction.

1. What if I didn’t exist?

In other words, instead of counting on me to make a final call, what would you do if the final call were yours? Or what additional information were you hoping that I could give you will you need to now go get on your own? Or what if I wasn’t holding you back at all?

2. What if I wanted to cut the time in half?

In other words, what if I didn’t want to just incrementally adjust your concept, proposal or budget? What if I wanted to carve it in half? Cut its resources and/or timeline? What would you do? What could you do? What would you be willing to do?

3. What if you were given 30% more resources (time and/or money)?

In other words, if I wanted to accelerate things and I gave you more time or money, what would the result be? Would you be done more quickly? Would you improve your plan? How would additional resources change the nature of what you thought was possible?

4. What if you discover this will fail in the next couple of weeks?

In other words, if this budget, effort, estimate, or expectation were to fall apart quickly – what would you do? Would you double down? Would you skip it entirely? Would you need different folks to help you?

When put together in a single conversation, they can make the person on the other side of the table injured from whiplash. They don’t know if you’re coming or going. But that’s not the point.

The point is to teach people to think in multiple directions.

When you do that, you’ve taught them real contingency planning. And that’s what it means when I say leaders teach others to think past hope.

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