Matt Watkinson of Mastering Uncertainty On Five Things You Need To Be A Highly Effective Leader…

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Matt Watkinson of Mastering Uncertainty On Five Things You Need To Be A Highly Effective Leader During Uncertain & Turbulent Times

Get shit done. — What really matters is creating value for customers in the real world. Do not allow people to endlessly pontificate. There are no points for PowerPoint. People need to execute.

As part of our series about the “Five Things You Need To Be A Highly Effective Leader During Turbulent Times”, we had the pleasure of interviewing Matt Watkinson.

Matt is an internationally renowned business author and speaker. He is also the co-founder of the design agency Methodical and a venture partner at the VC fund Tiller Partners.

He won the CMI’s Management Book of the Year for his first book, The Ten Principles Behind Great Customer Experiences, considered by many to be the definitive book on the subject. His second book — The Grid: The Decision-making Tool for Every Business (Including Yours) was published by Random House to critical acclaim. His third book — Mastering Uncertainty — co-authored with the investor and entrepreneur Csaba Konkoly — was recently released, in April 2023.

Thank you so much for your time! I know that you are a very busy person. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

After teaching myself the basics at university, I began my career in the UK, designing websites and software. I was just in the right place at the right time. The UX industry exploded, especially with the iPhone coming out a few years later, and then the whole customer experience movement took off which was the subject of my first book. Ten years ago I emigrated to California where I live now. I co-founded our agency business Methodical five years ago with my best friend Ben.

It has been said that our mistakes can be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I made plenty of mistakes when starting out in my career and continue to do so today, and like most people I have learned far more from my missteps and failures than from my successes.

I have to be honest and say that all of my mistakes have cost me or others time or money, caused us to fail or fall short of the standards we’ve aspired to, or created stress and rework. I do my best to shake it off, learn from it and carry on, but I don’t think I’ve ever found them particularly funny.

The biggest lesson from all of them is that failure is almost always an ingredient of success. We can’t succeed if we don’t try and trying anything — particularly something new — we’re going to face setbacks. Someone once told me that fail stands for “First Attempt In Learning”. So true.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

I am extremely fortunate to have had amazing mentors from day one in my career. I’ve sought them out for every new skill or interest I’ve developed and aspire to be coachable. It is such a huge advantage in life if you can take advice from people — something many of the world’s top performers often mention — but few people seem to be able to do it. I’m especially grateful for the people who gave me a chance early on in my career and showed me the ropes, and of course for Csaba my co-author on Mastering Uncertainty who has taught me so much about entrepreneurship and how to think probabilistically.

Extensive research suggests that “purpose-driven businesses” are more successful in many areas. When your organization started, what was its vision, what was its purpose?

I’m not convinced that purpose driven businesses are more successful. There are plenty of purpose driven businesses that fail, plenty of hugely successful businesses without a societal mission, and many organizations invest insane amounts of time and money coming up with mission statements, brand visions, values, purposes and promises that bear no resemblance to the way they actually behave because it feels good. When we started Methodical it had no purpose beyond giving my friends and I a vehicle to collaborate, and have some fun, and as a means to provide us some income.

Thank you for all that. Let’s now turn to the main focus of our discussion. Can you share with our readers a story from your own experience about how you lead your team during uncertain or difficult times?

I think the more important point here is to recognize that times are always uncertain, and starting or growing a business is always difficult. There are no “uncertain or difficult times”. It is all the time, and we should acknowledge and accept that and make it the basis for how we lead and how we make business decisions.

A huge part of the problem is people thinking making this distinction — as if some times are certain or easy — and thinking that they can predict the future more broadly. Certainty is seductive, but it’s not reflective of reality and the absolutely crucial thing for leaders to recognize is that their attitude to or relationship with uncertainty has profound implications for how they operate their businesses.

Did you ever consider giving up? Where did you get the motivation to continue through your challenges? What sustains your drive?

I have often given things up. In fact, I believe that constructive abandonment is a very important skill to develop. If things are not working we should change direction or move on. Tenacity is important in life, no doubt. But so is open-mindedness and adaptability.

In terms of my own work, I am motivated to create useful, beautiful things with people who care. When I know what I am working is has practical value, when I know it can be done to a high standard, and when I know the people I’m collaborating with aspire to do their best work, I have limitless motivation. When any of those three things are missing I cannot motivate myself at all. That’s just how I am.

I’m an author and I believe that books have the power to change lives. Do you have a book in your life that impacted you and inspired you to be an effective leader? Can you share a story?

I agree. Books are incredible because a single paragraph can change your life, and I’ve read hundreds of books over the course of developing my working practice and researching my own. There is no particular book on leadership I’ve read that has inspired me. If I’m honest I just think about the type of leader I would like and try to do that.

I am only ever really involved with managing or leading creative people. Typically what they want is to be in an environment that works for them, to have a very clear brief that sets them up for success, and have the latitude to do the work in the way they see fit.

We also all need to push ourselves to do our best work, which often comes down to taking feedback on board. I try to lead from the front in that regard, showing that I am receptive to any ideas that might improve the work regardless of where or who they come from.

What would you say is the most critical role of a leader during challenging times?

Every organization has some sort of hierarchy, but people often forget that in any system the level above exists to support the level below, not the opposite way around. I think this is always true, but never more so when there is an intense period of upheaval.

When the future seems so uncertain, what is the best way to boost morale? What can a leader do to inspire, motivate and engage their team?

I think creating a psychologically safe environment is absolutely crucial. If people don’t feel like they can contribute, suggest ideas, challenge the status quo or be open and honest about the challenges they’re facing the organization is going to struggle.

What is the best way to communicate difficult news to one’s team and customers?

Promptly and honestly. Set the right expectation, and reset it if it has to change.

How can a leader make plans when the future is so unpredictable?

Any plan is based on our best guess of what we think will happen. Our assumptions might be wrong. Our guesses might be incorrect. This is why Eisenhower famously said “Plans are worthless, but planning is everything.” We need to use the planning process to make our assumptions and expectations explicit, but be willing to adapt as we learn.

Is there a “number one principle” that can help guide a company through the ups and downs of turbulent times?

I’m not sure there is a number one principle, but it is important to take action. In an uncertain environment the only way to know if something will work is to try it and see. This is why the principle of “affordable loss” — trying ideas out at a cost that has no material impact on the business — is so crucial.

Can you share 3 or 4 of the most common mistakes you have seen other businesses make during difficult times? What should one keep in mind to avoid that?

Fixation on narrowly defined metrics and targets almost always ends badly.

Putting too much faith in upfront strategy and analysis — the real-world might have other ideas!

Indecisiveness. You have to make a decision and act. The world is not waiting for you.

Here is the primary question of our discussion. Based on your experience and success, what are the five most important things a business leader should do to lead effectively during uncertain and turbulent times? Please share a story or an example for each.

Keep an open mind.

There might be a better idea out there, or your assumptions might be wrong.

Create a psychologically safe environment.

As I mentioned earlier, to thrive in an uncertain world people need to feel like they can contribute, suggest ideas, challenge the status quo or be open and honest about the challenges they’re facing.

Re-frame failures as learning opportunities.

Punishing people for failing just creates a risk averse environment where innovation becomes impossible. Re-framing failures as learning opportunities sets you up for greater successes in the future.

Spread your bets.

Remember, a big win can more than offset many failures.

Get shit done.

What really matters is creating value for customers in the real world. Do not allow people to endlessly pontificate. There are no points for PowerPoint. People need to execute.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“We plan, God laughs.”

How can our readers further follow your work?

People can connect with me on Linkedin at or check out my website

Thank you so much for sharing these important insights. We wish you continued success and good health!

Matt Watkinson of Mastering Uncertainty On Five Things You Need To Be A Highly Effective Leader… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.