#60: "Red is Good" - Why Surfacing Challenges is Critical to Winning Strategic Games

Why things NOT going according to plan can be the magical catalyst you need to achieve more

Jun 20, 2023

Tl;dr — strive for a culture where you can bring up things that aren’t going well without being demonized for it. Positively reinforce bravery when someone highlights a problem, and work with them to enhance whatever solutions they may have brought up. Teams that lack this capability are most likely to achieve mediocre outcomes; not breakthrough ones.

Imagine you’re sitting in a meeting. You’re physically in a conference room with 12 other people, and every one of you is going around reporting out on how your various projects / threads are going.

One lady pipes up and says,

“Well, things are going great for us this week. We finished phase 1 of our research ahead of schedule, we got great feedback from customers on our new concept, the team is working really well together, and we’ve been loving our partnership with everyone around the table here, including product, marketing, and finance. Overall, things are on track.”

And that’s the end of the update.

This is not a good update. This is a mediocre update. I didn’t say it was a bad update, but it’s certainly not an excellent one.

This is not the type of update that will push the group to be better. It’s the kind of update that is meant to be fairly innocuous… to not draw attention, to make others feel good. To reinforce the good feelings you have.

This has been me. It’s been me a lot. It’s been me too many times. Let’s dig into why this type of update isn’t particularly helpful.

When you go to work, are you trying to achieve something differentiated? Are you trying to build something new, to make your team better? Or are you just there collecting your paycheck? Totally fine if you’re in the latter category, but I’m going to assume if you’re reading this, that you’re not someone who shows up, punches in the metaphorical clock, does the bare minimum, and punches out.**

**Eh, sometimes it’s OK to dial back a bit, depending on your situation. Maybe I’m being a bit too hardcore or something here by lambasting the people doing the bare minimum. I acknowledge that there is weakness in my POV, but will charge ahead nonetheless. There’s an old quote I’ve long loved (but haven’t always applied): “if you’re not pissing anyone off, then you’re probably not saying anything.”

So if you want to achieve more, then you probably understand that it requires you to exceed performance in some area. There are three ways you exceed performance targets / expectations:

ONE: You improve or build on a strength. #StrengthToStrength
TWO: You maintain your position in an area
THREE: You address shortcomings and find ways to improve

Here examples:

ONE: Microsoft building on their cloud computing and business software leadership position and layering AI products on top, before other established players. #Improving
TWO: Coca-Cola showing you the same types of advertisements so that you keep consuming their products. #HoldingSteady
THREE: A team admitting that they are so concerned with being nice to each other, that they aren’t giving constructive feedback. #AddressingProblems

I first came across number three above back in 2015 when a colleague of mine, Jeff, mentioned this term Deloitte Nice to me.

To be Deloitte Nice was to just be super positive all the time. To not give the constructive feedback. To not have the tough conversation with that person who keeps bulldozing other people’s POVs in meeting. To not take a moment to stop a meeting and make sure everyone’s on the same page. Etc. etc. This phenomenon was seen as dangerous to higher performance, and so the firm was making a bit of a concerted effort to to dial down the superficial niceness, and dial up the candor (…..annnnnnnd this is where I developed my leadership philosophy around being candid and warm, because candor without warmth or empathy or the ability to listen is a slippery slope to being what some may call an… ahem.. asshole).

Alright, getting back on track here — if we want to exceed our own expectations, we have to be able to hit on each of the above three areas. We need to be able to build on strengths, hold steady where it matters, and shore up weaknesses. This is the foundation of winning any strategic game. It’s these three things, and really nothing else.

The most efficient way to achieve a balance of these three areas is to ensure that your collaborations have elements of all three on a regular basis.

So let’s revisit that update I gave above. Here’s a better version:

New Addition:

…Although we are on track overall and there are some bright spots to call attention to, there are also some potential warning signs hiding underneath the surface. We’re already thinking of how to address these points, and I would love to invite you all to an optional “workroom” where we think through how to make sure we address these points of potential concern:

First off, while we’ve gotten positive customer feedback, no customers have followed up on their positivity with action. We’re not seeing them taking any meaningful actions after we show them this concept. People aren’t even signing up. This might imply that maybe we’re not addressing a problem that is mission critical for customers.

Secondly, while we finished our research phase ahead of schedule, we realized halfway through that we weren’t tracking a potentially super valuable dimension of study. We’re considering opening phase 1 back up and going back over to layer in this new dimension of data, but doing so will take an extra week.

Thirdly, while our partnerships around this table have been really positive, we’re still having some challenges getting approval from Legal on a fast timeline. I know they’re bogged down with our enterprise contract review processes, but I would love if we could find a way to get just a little more time per week from them — maybe even just 2-3 hours

Yes, these additions made the update longer, but it also made it far more actually valuable. While the first version made everything seem positive, the second version actually starts to tease out the truth, and to also tee up actions to take to improve. This is the foundation of shoring up weaknesses, and achieving more. It’s this. It’s this moment when you have the bravery to admit that your on track according to your project plan but not on track as it pertains to helping the business achieve more.

Why am I choosing to write about this?

Well, I’m a pretty positive dude. I’ve gotten tons of feedback over the years that I’m positive and energetic and kind. All things I appreciate, and certainly strengths that I want to keep building on. But all those comments mask something I’ve been practicing for many years: the art of bringing out the truth in a way that: (1) doesn’t throw people under the bus, (2) keeps outcomes top of mind for everyone, and (3) helps improve the functioning of an entire group.

…Because when you give an update like the one I just typed out above, you’re telling others around you that it’s OK to surface challenges.

But critically, the most senior leaders need to positively reinforce this! That three-point candor onslaught isn’t going to do anything positive if the senior leader of the group demonizes you or applies a ton of pressure to you.

The people who bring up problems should be rewarded for their bravery, because it is not easy to be the person to bring up problems, and yet it’s the underpinning of a high-performing team and organization. Yes, ideally you’ll bring up problems and have at least some aspect of a solution to said problems / areas of concern, but it’s perfectly OK to say, “We’ve put some thought into this, but could benefit from some focus from the braintrust here as we improve our plans going forward.”

I chose to write about this today because I’ve been reflecting a bunch on the skills I’ve picked up in the last few years, and undoubtedly the most important one has been the topic of this letter: being willing to surface problems or areas of concern.

As my startup team and I have been diving into what we’re building, we are actively surfacing areas of potential concern. We’re quickly calling out when we might not agree, when there might be a better way, when we might not be on the same page, and it is freaking.excellent. It feels so good, because we know that with each conversation where we listen carefully + respond thoughtfully, we move closer to powerful realizations about how to bring an incredible experience to market, and how to actually achieve our north star outcomes.

So what does this mean for you?

You should strive to improve your culture. Your team’s culture…your company’s
You should strive to create an environment where problems can be surfaced, where the red “Off Track” indicator on a status report doesn’t lead to people getting shat on, but leads to the group swarming around the problem and ideating thoughtfully.
If you don’t have this, you should talk to your peers / managers about it
If they don’t listen, you should ask a senior leader how they think about this
And if you’re still stuck, leave a comment here or reply to my e-mail (many of you do, and it’s SO FUN to hear your thoughts) with why you feel like this can’t be done. I will personally respond to you and/or I’ll update this letter with additional tactics for how you can achieve this

And is this possible in every work environment? No. It definitely isn’t. I’ve definitely been on teams/cultures where what I’ve outlined would’ve never flown. … And I’ve learned to keep as far away from those cultures as I can, because the only thing those places will achieve is mediocrity.

See you next week!

(P.S. Would also love to hear anything else that has worked for others as they’ve dealt with this challenge in their teams. While some situations aren’t tenable, many are… What have you done to create an environment where you can surface shortcomings/risks proactively?)

Exonomist by Michael Davis

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