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7 Questions on Leadership with Tom Willmot

Name: Tom Willmot

Title: CEO

Organisation: Human Made

Tom Willmot has 15 years experience leading companies at the intersection of open source, WordPress, and enterprise publishing. He co-founded and is the CEO of Human Made; one of the worlds leading enterprise WordPress agencies, and Altis; an enterprise-grade WordPress hosting platform.

He's also a founding member of the Scale Consortium; a cross-industry group on a mission to grow WordPress as the leading platform for enterprise companies.

He's a passionate people-first leader with a decade+ experience leading globally distributed teams to do the best work of their careers.

He lives in Brittany, France with his wife Leanne, and 2 children.

Thank you to the 2,000 leaders who’ve generously done the 7 Questions on Leadership!

I hope Tom's answers will encourage you in your leadership journey. Enjoy!


Jonno White

1. What have you found most challenging as a leader?

Being a leader is an impact force-multiplier and it's a privilege to be entrusted by others to lead. This comes with a big responsibility as when you make a mistake as a leader the surface area of the impact is usually much larger and people can be hurt.

For me one of the hardest parts of being a leader has been learning how to embrace the seriousness of that responsibility, with the optimism and courage to push forward and aim higher.

2. How did you become a leader? Can you please briefly tell the story?

I started building websites as a teenager, first as a hobby, and then semi-professionally for friends and family. Around 2006 I discovered Open Source and WordPress and left my day job working in special education to strike out as a Freelance WordPress Developer. I was fortunate enough to work on some early examples of large companies building with WordPress and that lead to me founding Human Made with Joe & Noel.

As Human Made grew from just a couple of us to nearly 100 people I've discovered a love to leading, based on a deep belief in the people around me, and an optimism that we can make the future better than today.

3. How do you structure your work days from waking up to going to sleep?

I like to rise early and use the 1-2 hours before my family wakes for reading & writing, often that's a mix of email, internal posts and updates from across the company (we are a globally distributed team and our communication is heavily text based). I find this means I feel on-top of everything that's going on so I can be present and clear-headed throughout the rest of the day.

The rest of my day is usually a mix of internal and external meetings (I try to talk to partners, clients, and peers in the industry every week), and deep work time where I can focus for 2-3 hours at a time on task or project. I find this to be particularly important.

On calls I like to walk and talk and often do 1:1s and some internal meetings walking around the forest near our home in Brittany.

I like to cook and so usually try to cook lunch or dinner each day.

I actually published my "How I work doc" publicly, we use these internally to share how we work with each other

4. What's a recent leadership lesson you've learned for the first time or been reminded of?

That to effectively lead others you must first take care of yourself. I periodically need to re-learn this lesson as I have a tendency to put myself last and push through. But I've been through the cycle enough times now to know that I need to take care of my self in order to show up fully as a leader. I still often feel guilty for doing so though.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

There are several books that have had quite a profound impact on me. I read Maverick by Richard Semler early on, that taught me that you can chart your own path as a leader, that business orthodoxy and best practice can be questioned, and that you can develop your own approach based on your values and 1st-principles thinking.

I found "Reboot: leadership and the art of growing up" by Jerry Colonna to be equally profound, it's central message that compassionate and effective leadership requires a radical level self-responsibility and introspection.

6. If you could only give one piece of advice to a young leader, what would you say to them?

Listen to your heart.

As you start out as a leader it can be tempting to spend most of your time looking outwards as you try to learn how to be a good manager and leader, and how to effectively run a company or a team.

Whilst you can learn the practices of good leadership, great leadership requires heart; it must grounded in your values, your intrinsic motivations to lead, and your belief in the future.

It's often earlier in your career as a leader that these aspects are at their most pure and innocent and so the sooner you can start to tap into them the better. Leading from the heart also requires a lot of courage, best to start early.

7. What is one meaningful story that comes to mind from your time as a leader, so far?

My most meaningful times as a leader are at our annual company meetups (we call them retreats). Every year we do a round of flash talks; each person stands at the front and shares something about themselves or a something they're interested in for 3 minutes. These are rarely directly about work.

Seeing people stand up in-front of their peers and share themselves openly is so humbling and inspiring, the sessions invariably involve tears and laughter in equal measure.

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