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Wes Kao


How to Get Smarter and Sharper Employees

Train your team to think rigorously and systematically

Published: Monday, January 7, 2019 - 12:03

If you’re a leader, you got to where you are because you think strategically and are killer at execution. You simply can’t get far without being good at both.

Now that you’re in charge of people, though, your ability to increase impact depends on how well you manage other people. You need your team to become smarter, sharper, A-players.

Unfortunately, sometimes smart people (like you) accidentally traumatize their teams

You say you want your team to think harder and stop just doing exactly what you say. But every time they have a question, you just answer it. Or worse, you give them a wrist slap for bringing you a new idea.

I get it. You already don’t have time to do your own job, so you definitely don’t have time to clean up everyone else’s mess. But each time you give your team a wrist slap for stepping outside the box, you discourage them from trying new things.

So you have a dilemma: You want your team to think like an owner and bring you fresh ideas — and you want those ideas to be defensible.

What is rigorous thinking?

Rigorous thinking is asking critical questions about tactics and having a systematic way of making decisions. For example, let’s say you manage five to six direct reports.

In a culture where rigorous thinking is expected, the idea is this:

Any idea goes, but each team member should be prepared to advocate for his idea and defend it. You should be prepared to walk through the upside, downside, data points rooted in reality, and how it works given your assets and constraints.

It’s the opposite of lazy thinking. Lazy thinking is making assumptions that you don’t even know are assumptions. It’s having a black box of logic where “suddenly it works, and we have thousands of sign-ups.”

Lazy thinking vs. rigorous thinking

Here are two scenarios of employees coming to you with their ideas. with very different outcomes.

Scenario No. 1: lazy thinking

“Hey boss, can we do [insert random tactic that competitors seem to be doing]?”

Scenario No. 1 result:

You have to think through everything, which leads to decision fatigue. You are constantly correcting your team’s mistakes, which range from minor to major oversights in strategic thinking. Half-baked ideas come across your desk, so you have to think of polite ways to say why this isn’t a good idea without discouraging your team.

Your team doesn’t understand why you always say no to their ideas. You look like the bad guy.

Now here’s a second scenario. Imagine if your team member came to you with this.

Scenario No. 2: rigorous thinking

“Hey boss, I think we should do [insert tactic]. Here’s the upside and why it’s worth the time, budget, and effort: ____. The downside is ____. But we can minimize the downside by testing this out in a small way, like this ____. I’ve seen other organizations like X and Y try this, so I used them as a frame of reference. If you agree, the next step would be ____. I can manage this and report back on how it goes.”

Scenario No. 2 result:

You rarely say no to an idea, because it’s not about saying yes or no. It’s about vetting an idea. You ask strategic questions, so your employees end up realizing the idea won’t work in its current iteration.

They excitedly go back to the drawing board and come back to you with a stronger idea and next steps. They become sharper thinkers over time.

You use less brain power and get better results.

Why this only works if psychological safety is present

To have this type of rigorous thinking and discussion, you need a foundation of psychological safety. Your team has to trust that you care, and you’re asking hard questions because it’s better for them, the team, and the idea itself. No one is trying to make anyone else look bad or feel stupid.

With this understanding, your team is free to rigorously debate with each other to come up with the best possible outcome.

Questions that promote rigorous thinking

Steal these questions for the next time your team member comes to you with an idea:
• “This is a great start. How do you see this working?”
• “Who is this for?”
• “Why would they be excited to do the thing you want them to do?” (For example, the thing could be to sign up, download something, attend an event, share on social media, or make a purchase.)
• “What is this for?”
• “What’s the hard part?”
• “What would success look like?”
• “Who do we need buy-in from in order for this to move forward?”
• “Can we do this ourselves, or do we need to tap in to resources from engineering, sales, or other departments?”
• “How can we experiment with this idea in a way that requires less overhead? And even less overhead? And even less overhead?” (I usually ask this question three times. You’d be surprised how small you can make an experiment while still getting what you need from it.)
• “What models did you look at? What are you using as your frame of reference? This is probably not the first time someone has attempted a tactic like this, so we should learn from what worked or didn’t for them. How is our unique situation different?”
• “How does this tactic play well to our assets and our brand?”
• “What constraints are we working within?”
• “If we decided to move forward with this today, what would you need to make it happen?”

This is not an interrogation

The way you ask matters. Don’t sit back, kick your feet up, and demand to be impressed. That wouldn’t bring out the best in you, and it won’t bring out the best in your team.

Ask hard questions in a way that’s supportive and driven by curiosity, not contempt. When you take this approach as a manager, you empower your team members to figure out and articulate a solution. You show that you’re there with them, and you believe in them.

It’s two people walking through an idea and scenario planning what it could look like, with the goal of finding the best solution. It’s win-win.

Try this tomorrow

The next time a team member approaches you with a question or problem, throw it back at her. Give her a chance to practice thinking rigorously.

Instead of answering her question, say this: What do you think? I want to hear how you would fill in the blanks.”

Then use follow-up questions from the list above.

Many times the person has thought about the scenario but doesn’t feel confident about moving forward yet. This is where the Socratic line of questioning helps you both get a better understanding of the tactic at hand.

Note: Using the Socratic method takes a lot longer than just giving the answer. You might wonder if it’s worth it. But if you keep at it and use self-restraint, in the long run, your employees will get smarter and sharper.

The trade-off

The trade-off is: You either spend the time upfront to train your team well, or you take a few hours every day to correct their work forever. In most cases, training your team to think rigorously eventually takes a load off your plate, so everyone can produce more and better quality work.

I hope you give this a try. It’s worked for many client teams I’ve trained, and I’m curious to hear how it goes for you.

First published Nov. 12, 2018, on Wes Kao’s blog.


About The Author

Wes Kao’s picture

Wes Kao

As a marketing consultant, Wes Kao brings 10+ years of in-house experience at Fortune 500 brands and venture-funded startups. Most recently, Kao was the founding executive director of Seth Godin's altMBA. Under her leadership, the altMBA grew from zero to 550 cities in 45 countries in three years of high-growth. She designed the altMBA’s coaching system, launched the global digital community, oversaw acquisition/retention channels, and built a team of 40 people to support rapid scaling. Prior to this, Kao led digital marketing and brand management at Flite (acquired by Snapchat), Bare Escentuals, L’Oreal, and Gap Inc.