Why We Struggle to Admit Uncertainty in Our Work (And Why We Should)

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Hey folks, 

I'm gearing up for some Nordic adventures with the fam before diving headfirst into fall. But don't worry—I've got some exciting stuff brewing for when I'm back.

First off, a huge thanks to everyone who's been sharing our new book, Who Does What by How Much? A Practical Guide to Customer-Centric OKRs on social media, especially LinkedIn. You folks are amazing! The response has been incredible.

In the newsletter, we dive into a common problem: the difficulty in admitting uncertainty in professional work despite the inevitability of change and adaptation of long-term plans. You’ll find that in the end, embracing uncertainty and flexibility can create more resilient organizations. 

- Jeff

P.S. Don't forget to sign up for our upcoming webinar, "Planning 2025 with OKRs: The Basics." It's free, it's fun, and it might just revolutionize the way you set goals for your organization.

Article: Why is it so hard to admit there’s uncertainty in our work?

Why is it so hard to admit there’s uncertainty in our work? 

We make strategies, roadmaps, plans and budgets that stretch out for years into the future. We inevitably edit, adapt and abandon them along the way yet the push, up front, is for predictions, commitments, and immovable targets. We spend weeks of our lives creating these plans and then base staffing, budgeting, prioritization, and marketing decisions on them. 

Uncertainty is uncomfortable

Humans desire certainty and predictability. We want to know where we’re going and how we’re getting there. We want to know what it will cost and if there will be a return on our investment. That makes sense. 

It’s also not realistic in a world of continuous change.

Not knowing is not only uncomfortable, but it can also be seen as a sign of incompetence: Didn’t I hire you to know how to do this? Isn’t that your job? These are terrifying questions to come from your boss if you admit that while you have strong opinions about where to point the team, you might be wrong. 

Certainty is a fleeting perception

The bulk of our management approaches come from optimization of manufacturing. Certainty is the name of the game in industrial production. Most of us don’t work in that world. We’re building businesses on top of software. Software has become incredibly powerful not insignificantly by its ability to continuously improve. Yet, no matter how much that technology improves to help us sense and respond more quickly, we continue to run up against the consistently risky onslaught of prescriptive certainty.

We have lived experience. We have trained expertise. We’ve practiced our craft for years. We should know exactly how to solve the problems our customers and businesses face. The confidence in prescribing an exact plan is, however, based on what we know right now. And that works for right now. But six months from now? Or 12? Or 36? Does that current lived experience still matter? It probably does, but not nearly as much as it did when you first set out. The world moves forward faster than our lived experience and desire for predictability can keep pace. 

Admitting we’re wrong is avoided and feared

The real reason behind not admitting that our work carries some level of uncertainty in it is because we’d have to admit we were wrong at some point. Admitting we’re wrong is seen as weakness at best and incompetence as worst in many organizations. 

When’s the last time someone, anyone, stood up in front of a team at work and said, “I don’t know how to solve this problem?” 

Certainty gets rewarded—regardless of how right or wrong the prediction ends up being. And round and round we go, year after year, making annual budgets, strategies, and plans that inevitably end up shifting only to make the same demands next “planning season.” 

Embracing uncertainty builds more resilient organizations

Forcing unvalidated uncertainty on a team is demoralizing for teams who know there are better ways to plan. They know that building a bit of humility into our plans, clearly identifying risks to our prescribed plan and setting explicit triggers to revisit the plan increases the organization’s ability to sense and respond to changing market and world conditions. 

These nuanced differences in planning ensure our teams are working towards the most important customer issues right now—even if we didn’t see them coming. They empower and provide the justification for the course correction and true organizational agility demands. 

If you’re looking for a place to try a more “uncertain” approach, start with your mature partnerships. Your long-term clients and partners will take the risk with you. Be up front and clear and shorten your cycles. Check in regularly and adjust the plan based on what you’re learning along the way. Starting here, in a safe place, ensures that the cultural changes needed to more broadly embrace uncertainty—things like psychological safety, for example—take root and grow over time. 

What I’ve been up to

I'm super excited with the incredible workThe OKR Repair Kit, has been helping teams achieve.. Inspired by its success, I've teamed up with my colleague Josh Seiden to bring more free support. Starting this September, we're launching four free monthly webinars to help you master OKRs!

Our first session, "Planning 2025 with OKRs: The Basics," is all about revolutionizing the way we approach goal-setting and planning. 

I've seen firsthand how OKRs can transform organizations. In this webinar, Josh and I will break down what OKRs are, why they're so effective, and how you can use them to create agile, customer-centric plans for 2025. We'll cover everything from the basics of OKRs to practical implementation strategies. 

Watch, Listen, Read

Watch: I've been glued to my TV lately, catching up on a range of good shows. House of the Dragon has me hooked with all its Targaryen drama, while season three of The Bear is serving up more intense kitchen chaos that I’m enjoying. I'm also loving the fresh take on Star Wars with The Acolyte on Disney+.

Listen: I've been on this nostalgia trip lately. Ended up revisiting Siamese Dream by The Smashing Pumpkins. It's wild how that album still holds up, bringing back all those '90s vibes without feeling dated.

Read: I'm currently diving into Build to Sell by my friend Sandrine Olivencia. It's pretty cool to see her ideas on paper, especially since we've chatted about some of this stuff before. I've gotta say, the book's packed with insights that could really help anyone looking to build a business with long-term value in mind.

What’s new on the blog

Can you solve for the business without solving for customers? – I recently received some pushback on our new OKR book for being too customer-centric. It made me think: Aren't we solving for the business by focusing on customers? Using Microsoft's cloud transition as an example, I realized that understanding customer behavior is key to business success. In the end, solving for customers is just good business sense.

Is Agile over? – Agile has been the go-to method for software development and business management for more than 20 years. But recently, I'm noticing signs that its popularity might be fading. Is Agile dead? Not really. It's more like it's evolving. Instead of rigid frameworks, we should focus on outcomes and agility. 

In defense of vanity metrics – While vanity metrics don't show the full picture, they're actually useful in the early stages. Take our book launch—sales numbers might not show impact, but they tell us if we're addressing a real problem. Sometimes, just measuring if an activity is happening is a great start.