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Are you struggling with a hard problem? You may be asking the wrong question.

I recently spoke with a client—let’s call him John—who asked me a very dangerous question.

 

A question that could have wasted hours of his time and tens of thousands of dollars of his budget, as well as created conflict and confusion within his team.

 

John had a challenging mandate. A technology leader in a high-profile role at a major manufacturer, he needed to improve the way three separate teams worked together in order to delight their customers with a new generation of connected devices.

 

It was an exciting opportunity for John and his company. But different operating philosophies had created simmering tension that made it hard for the teams to collaborate—which they had to do to succeed. He also needed to overcome the historical culture of blame, so that issues didn’t linger as they had with his predecessor.

 

After describing his situation, John asked me, “What do you think we should do?”

 

Now, I like to be helpful. My instinct was to ask clarifying questions and respond with thoughtful suggestions.

 

But I stopped myself. His question was well-meaning. And it seemed like a good question. Most of us have asked a variation of it at some point in our lives. But it threatened to lead us down a treacherous path.

 

Because to solve a thorny problem, you have to start with the right question. If you don’t, you’re in danger of spinning your wheels, wasting time and resources, and making the problem worse.

 

The “What do you think I should do?” question, in particular, carries a lot of baggage. It creates two new problems that can further stymie teams. Luckily, there is one small yet powerful tweak to the question that will supercharge your effectiveness.

 

First, let’s dig into why it’s wise to avoid the “Should do” question.

 

The “Should do” question focuses on the wrong thing. 

 

It puts us on a quest for certainty that is at odds with the challenge of solving hard problems.

 

I get the desire for certainty. I feel it—like all of us. It’s nice to imagine a future state where things… just work. Where you’ve arrived, as if the solution is your favorite meal waiting for you at the end of a long day. You can look back, satisfied, at a job well done.

 

But that’s not how complex problems work. After all, if there were a “Should do” just hanging around, waiting to be scooped up, you and your team would have figured things out already!

 

As you push toward certainty, you’ll stop being curious. You’ll fixate on an early solution, discarding other ideas (and contradictory data) that come in later.

 

You’ll charge forward like an angry bull running through the streets of Pamplona. Only to find yourself trapped in the bullfighting ring.

 

The “Should do” question creates resistance.

 

You—your team, your division, your organization, your industry—have all arrived, together, at this particular moment in time. You’ve gotten here with some luck and by developing a set of skills that help you solve your problems very effectively.

 

Consider a team of sophisticated engineers I recently worked with in a high-risk industry. They, along with their company, had spent decades honing their skills to keep things from falling apart. Maintenance. Safety. Planning and executing complex work.

 

To support this, they were incredibly good at creating long, intricate procedures.

 

But, over time, operations grew more complex. Line employees became frustrated at the bloated requirements. “Corporate just doesn’t get it.”

 

The leader I worked with understood this problem, but both he and his team struggled to influence the rest of the company.

 

At this point, it was tempting to play with a “What should we do?” question. There were some pretty interesting answers: we should trim our procedures. We should let people apply for waivers. We should create a process to reassess the risks of all our procedures.

 

Many of these are good ideas. But they all required a change from business as usual and would have created resistance—not just within the team of engineers I worked with but across the organization.

 

“Should do” questions emerge when something isn’t going quite right—when you need to move in a different direction. But the question itself encourages rigid, definitive answers that create resistance.

 

People don’t like being made to change, but they’re often excited to be invited to take part in a change. But that’s just not possible with a “Should do” question.

 

Ask this question instead.

 

At this point, you might be feeling frustrated. If you can’t ask people what they think, how can you move forward when you’re stuck?

 

It turns out there’s a simple tweak that makes all the difference. Instead of asking a “Should do” question, ask “What can we try next?”

 

This question embraces uncertainty by acknowledging that the solutions to your thorniest problems aren’t out there in neat packages to be found.

 

The solutions emerge from a series of small steps that you discover over time. Asking a “What can we try?” question gets us moving. And the word “next” means that it doesn’t matter if we’re moving in the right or the wrong direction, because we’ve chosen a small enough step to experiment with.

 

“What can we try next?” also avoids the wrong kind of resistance. By working through a series of experiments, you get people engaged in defining the problem and testing solutions as you go. You transform resistance into creativity. And where you do get resistance, it’s a good indication that you’re probably moving too fast, that you’re missing something.

 

In the SimplerTimes™, asking the right question would not have mattered so much. There were lots of problems that could be solved with hard work and by implementing basic approaches like procedures or checklists. The answers were out there, we just needed to figure out what we should do.

 

But that’s not the world we live in anymore.

 

So, we need a new question.

 

As John and I talked, we came up with his very own “Try next” strategy. Instead of picking a direction and moving toward it, his first step was to meet individually with the leaders of his three teams, describe what he was seeing, and ask them what they thought they could try next.

 

So, dear reader, what problem will you try this approach on next? Comment below and let me know.

 

P.S. If you’re interested in how the modern world creates thorny problems, listen to my podcast with my friend and Harvard Business School professor Amy Edmondson for an in-depth discussion of these issues.

 

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I’m curious… can you help me?

I’ve got a bit of a different newsletter for you today.

 

I’ve got something that’s on the tip of my tongue that I’m trying to articulate. A thought that’s in the process of crystallizing—and I could use your input to solidify it.

 

Recently, I’ve been thinking a lot about the way that work has changed over the last 20 to 30 years. I think that that’s the time frame in which the world really shifted from being complicated (lots of things to keep track of) to being complex (driven by systems and interactions).

 

In a complicated world, we can improve things with better procedures. We can consider what needs to be done and, if we make sure we do the right things at the right time, we’ll mostly be OK. (Think Atul Gawande’s Checklist Manifesto).

 

But, in a complex world, we improve by learning from the system itself. We gather data about what works and what doesn’t. We need people to speak up. Managers to listen. And feedback loops that capture both positive lessons and cautionary tales and distribute them throughout an organization or company.

 

As many of you know, my book Meltdown was all about the way that things go wrong in complex systems. Complexity can push systems toward catastrophic outcomes where the system behaves in ways that designers and operators never foresaw.

 

That brings us to the theory I’m developing now.

 

In addition to the ways that complexity creates opportunities for failure, I think it makes day-to-day work harder.

 

We have to process more information and manage more connections than ever before. Complexity obscures the solutions to problems. And even when we come up with solutions, we have to implement them within a system where we may only be able to influence a slice of things.

 

I’m hoping to gather some data on people’s experiences. Whether you’ve been in the workforce for decades or just started your career, I suspect each and every one of you have insights on this.

 

So, please tag me on social media (handles below) and let me know:

  • How has your industry or discipline gotten more complex over time?

  • How has that affected your day-to-day work?

 

Thanks. It’s a big help.

 

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